Soft Skills Engineering

In this episode, Dave and Jamison answer these questions:

Dave and Jamison, long time listener first time caller. I appreciate everything you do, I look forward to my Monday morning commute because of this podcast.

I’ve been a software developer for about 4 years. I’m a career changer and graduated from a boot camp. I was fortunate enough to earn a junior developer position at a non software company and have been promoted during my tenure. I work on a small team and enjoy what I do and the level of impact I have. I am one of the most senior developers. My only concern is that I do not receive direct mentorship from more experienced developers.

Am I limiting my future prospects by not job hopping? When is the right time to leave a company and seek new opportunities?

Hello Mr. 💃 and Mr. Smith. I’ve been working in software ~6 years. In the same company (don’t judge). And about a year ago I advanced in the position of a team lead of 4 developers. I would actually like to attribute this advancement, at least partially, to listening to your podcast. Although luck was involved as well. ANYWAY. There were quite a few questions on how to keep your soul intact while working with Claude. And your advice was to focus on product side, and\or to focus on improving the processes. Now my question is - how can I help my teammates to not lose their soul? How can I help them to not turn into meat proxies? We work in the startup, so tasks are not defined in details. Which does give them some agency over whatever they are building. But I don’t think it’s enough anymore. I think one specific teammate leans toward copying the task description, throwing it at Claude and making a PR out of it. With very few iteration over the quality of the code. Can i blame them? Not really. But how can I help? It’s like the ownership of the code was taken from them. And from me, but at least i can do other stuff. For the context - I am reviewing the PRs manually. Please spam me with idea. Saying to the team - just don’t use AI is not an option, because the speed will go down. A lot. Plus we all are 100% addicted.

PS Most of my developers have experience of +2 years in the field. One is completely fresh and started half a year ago. Maybe for him the approach should be different? He is pretty good at not generating complete slop. But I think for him it’s even harder to learn and to read all this code.

In this episode, Dave and Jamison answer these questions:

Listener Random Listener asks,

You guys talk a lot about externalities, which helped me understand a lot about how my manager works. He wants to do things fast, but he does not follow good and standardized processes, even the ones he tries to push onto us. This adds a lot of work for us because now his mess becomes our mess. How can I give him this feedback in way he will both understand and not feel resentment? Thanks

Hello. I am individual contributor and have been with this team for 2 years.

About a year ago a manager and a lead joined the team to fill in the growing positions. They came in with their preferences for code design, architecture, and ideologies.

But they were all different from how we worked before. Their ways are not bad, but they add unnecessary complexities, taking away energy from just doing my pick-up - code - ship way.

I shared my concerns, but they never get accepted as they just want to exercise their manager and lead powers. My teammates share similar opinions as me.

Is it a worthy fight showing resistance to these changes or should I just suck it up adapt to their preferences?

Each time I show any bit of resistance, it is being taken by them personally to their ego and discussions go on for tens of minutes and ends with either of us pissed off.

Won’t quit my job for these petty people. Should I just say yes, adapt my work for good or bad and blame them when things don’t work? Do I even need to care about these workflow and operational changes as an individual contributor? Would there be any benefit resisting bad decisions at the cost of my mental peace?

Thanks. You guys make me look forward to Mondays.

In this episode, Dave and Jamison answer these questions:

Hi Soft Skills Engineering, I’m a senior software engineer with over 20 years of experience. I’m hoping you can help with with a problem where I’m dumb, weird and bad at my job!

There is a recurring problem where, despite all my experience and graybearding, despite my big words, I sometimes just miss very important details, and ways that are very consequential and cause time and feature gaps.

Sometimes I make a faulty assumption and gloss over initial errors, and later I get big errors that require big fixes. For example, sometimes I just miss random lines from a product spec or whole parts of the UI, like a blind spot, or like a Mandela situation where I could’ve sworn it was different where I read it. Sometimes, I read the docs on some library but didn’t really *read* the docs and missed the important line that I needed before things get broken.

It’s a soft skill, sorta, because it’s about how I go about my work, and I don’t know what I can do about it. It’s almost an intrinsic trait, isn’t it? But I’d love any idea about how I can improve or how I can adjust how I can work to compensate. Or possibly here how this is normal and it’s a process issue - but I don’t need excuses and am willing to improve.

Thanks for your great wisdom and advice!

So it has happened, a massive codebase written entirely by Claude via prompts from my non-technical PM.

And now I’m tasked with “make it work, integrate it into all these other services and tools we have. Thanks!”

How do I even begin approaching a massive codebase written entirely by AI with no actual software engineer validating/overlooking it at any point until it became this monster and now it’s my problem? I am also an L2 engineer that got prematurely promoted to L3 and now I just want to prove myself and work on a cool project (10000s of requests, many bottlenecks that need to be fixed, scaled, design docs put together… the whole shabang#)

Help. Urgent. 911. I want to cry.

Thank you, love the podcast!

In this episode, Dave and Jamison answer these questions:

Hey Dave and Jamison.

I don’t know what to do with the amount of the AI slop I have to review and I’m getting close to burnout.

I have a lot of context on my project, so my colleagues see me as a point of reference. Additionally, at a past job, I was a tech lead and could easily cover for TL if I wanted to (which I don’t) and I feel like the TL of my project and some of my teammates are taking advantage of this.

Every day I receive a lot of low quality documents to review. For example, our TL creates sloppy project planning documents and tickets and sends them to me for comments. Since they contain so many errors, sometimes including obvious security or data compatibility issues, or just text that is unrelated to the project, I end up basically rewriting everything.

The same thing happens with code reviews. Some code is obviously AI-generated slop with lots of duplication and errors, that in many cases misses acceptance criteria or has doc strings filled with buzzwords and adjectives. I usually add a lot of comments per PR and I know the author sends them directly to their LLM and then pastes back a verbose answer. As a result, I end up in endless conversation loops.

I’ve tried talking to my colleagues one-on-one, explaining how much work they are delegating to me. I’ve asked them to review their own work first and explained how exhausted I am, hoping they would show some compassion. But nothing has changed, because everyone seems to be in survival mode in this era of layoffs and I feel like they have become comfortable with me doing their work. I’ve also tried talking about this in retrospectives and tech team meetings, but the TL and tech directors did not support me because AI usage is encouraged. Instead, they said that they really appreciate my feedback because I have so much experience and thanked me for doing such excellent code reviews.

I also end up making most of the project’s tech decisions, I am the sole contributor to the project’s documentation and my vacation is mapped out in the roadmap as low delivery period. 😢

I like the project and I’m terrified to switch jobs in these times. But every day, it gets harder and harder to comment on obvious slop written without care without sounding rude or sarcastic. Sometimes I find myself still angry after work.

Is it too late to set the boundaries?

In this episode, Dave and Jamison answer these questions:

Hi Dave and Jamison,

I’ve been a Java backend dev for over 10 years. After getting laid off from a job I loved, I spent 3 tough months job hunting. I eventually landed a full-stack role at a non-tech company where I am the entire front-end department.

The team is a mess:

A CTO who hasn’t coded in years and calls me directly to assign tasks, all labeled “highest priority.” When I asked the CTO and CEO if we had QA, they literally laughed at me. Prod releases are “tested” by the CTO before telling me to push immediately.

I’m at a crossroads:

Stick it out for 6–12 months to gain AI experience, then quit? Try to move into management, and rebuild this mess into a functioning engineering organization.

What should I do?

Hey, Dave and Jamison.

I’m a non-native Japanese speaker working in Tokyo with about 6 years of experience in backend(3 years in Tokyo) and haven’t used English in work.

I started listening to this podcast for learning English. And I soon found this podcast is very funny and I found a lot of problems actually exist around the world, like AI hype, why people hate HR, low-performing team members, useless product managers, etc.

For some reason, I want to leave Japan and find a job using English. I think the best approach is to find an English job in Tokyo first. And then transfer to an English-speaking country.

I want to know as a non-native English-speaking engineer, what English level I need to get a senior engineer job using English.

What would you consider if you were the manager who is interviewing a non-native English speaker?

Thank you guys, I love this podcast, I can learn English, get some answers to the questions I’m confused about too, and laugh every week.

In this episode, Dave and Jamison answer these questions:

Listener Jame ain’t no dance asks,!

Hey Space Therapists, I am a consultant that helps big companies to fix all kind of stuff. It’s ridiculous how many different hats I wear. One day I’m the interim PM, the other day I am telling SAP devs how to use a coding agent, next day I gather stakeholder requirements for a customer self service portal. I do all of these tasks on a fairly shallow level and all of that work is happening without much coordination from my company. I think I do a good, but it’s hard gathering feedback on my work, since no colleagues are involved and I can’t simply ask the customer without revealing insecurity. Send sophisticated tips and don’t make me quit. Cheers!

Can I tell a coworker to stop using Claude?

I work on a small team at a midsized company, and a coworker keeps dropping overly verbose pull requests that are full of AI jargon. These are increasingly hard to understand, and then when I ask for design intent clarification I often get sent a long document that is even harder to understand!

And the code sucks! misleading docstrings, overly complicated functions, and weird places where the AI has convinced them that something needs to be backwards.

And often times I end up having to fix failing tests (that my coworker probably didn’t run), or report back later that their changes have degraded something in prod or is causing a lot of logging noise.

I worry that I’m doing the same thing and just not noticing. Code is starting to pile up in review and I don’t want to be rude and comment “ai slop” on 50% of the code! What can i do?

In this episode, Dave and Jamison answer these questions:

Listener Myamax myamax says,

I just listened to episode 527 and could really use some advice on being good at interviews.

I was recently laid off with a decent severance package, so I have some breathing space. I’ve had several interviews, and I usually get past the initial screenings, but I don’t shine in technical rounds.

I’m a career switcher, and most of my tech career has been in analytics at a big company. I’m good at distilling things, very good at debugging and navigating mazes of corporate legacy, but I haven’t really built things from scratch. I’m not a pure individual contributor, not a product manager but some technical-product hybrid, and it was a fun place to be. I stole good ideas from different teams and stitched them together adding common sense on top. I spent a lot of time with users and stakeholders to understand their data and their processes. Most of the time they needed common sense and decent data foundations. Only in rare cases it came to fancy algorithms.

How can I sell myself better? Should I be looking for more product-oriented roles? Maybe spending my severance building tiny end-to-end systems to get better at take home assignments is a good idea?

I’d be grateful for any thoughts and your general interview advice for the software folk!

Hi, this is Mental Mario from Episode 395, where i was asking about being “the new hotshot in town”, as you put it. I took your advice, performed to the best of my abilities while trying to stump on my collegues work, and two years in think it worked out pretty well! I got my raises and will become the second in command after my boss. But wait- there is trouble in paradise!

With more money obviously comes more responsibilities, but i can’t shake the feeling that recently I’m doing the majority of the work in my team of five. From refinements to troubleshooting, from code reviews to releases, tasks just come hurling to me.

The team has a lot of confidence in me, but this leads to situations where they don’t challenge my ideas and approaches, which causes problems since obviously I make mistakes too- but I don’t have the teams safety net any more.

This dynamic feels unhealthy to me. Is this feeling justified, or is this just the way it is when moving up the corporate ladder? Given that I’ll be the senior of the team, do i need to delegate more task and supervise them, when I’m feeling overwhelmed with tasks?

Thank you so much for the show!

In this episode, Dave and Jamison answer these questions:

Hi Jamison and Dave, jesters of my daily commute. I’m a *mechanical* engineer at a megacorp, and since people are people, I find most of your advice transfers pretty well.

I’m the tech lead within a small-ish org of about 25 people. We’re in-office, and split between two locations (in a similar time zone), and multiple different projects. This means that there are a lot of Zoom meetings between locations. Lately, I’ve been having an issue with engineers deciding to take these meetings from their desks in our open office plan rather than finding a phone or conference room. I find this practice to be maddening! It’s really distracting because there will often be background noise that makes it hard to clearly understand them, and it also means that my workplace is a cacophony of people yelling into their AirPods, competing to overcome the background noise of their colleagues’ yelling into their AirPods.

How do I make this stop and get my coworkers to hop into a phone or conference room for their meetings?! Oh btw, my manager is one of the worst offenders.

Listener bootersket says,

I have 3 years of experience, all at this same company and team. My team has one staff software engineer who really knows the codebase well. When I have questions about why such and such thing is the way it is, I ask him. I’ve noticed his answers are unhelpful. Often they are short, with very little detail. I can’t tell if thinks they’re sufficient, doesn’t know how to explain himself clearly, is mad at me, or if I am just don’t know enough to understand them.

For example, once I asked about two different variables that seemed ambiguously named and to refer to the same thing. His response was short and sweet. Quote: “almost the same thing”.

Am I the problem? Is he? When I get responses like that I don’t feel compelled to keep asking questions in different ways because it doesn’t feel like he cares about mentoring juniors with dumb questions like myself. What do I do?

In this episode, Dave and Jamison answer these questions:

A listener named “Will angel answer my question?” asks,

Hi, I recently joined a new company about 1.5 months ago. It is the technology arm of a family-owned business group that has existed for over 30 years, providing technology services to all the other companies in the group.

After a one-week onboarding, I was assigned to a team. After 2–3 days, I still had no tasks, so I asked a coworker to pair program with me so I could learn more about the processes and continue learning. The task was easy, and we finished it in less than a day. For the next 2 days I did nothing, asked my boss for tasks but he just told me to wait.

Two days later, we finally had a planning meeting, and they assigned me three tasks for the upcoming two weeks. I finished the first one in 25 minutes and other ones in not much more time. It has been like this ever since. I’m really enjoying all the free time, but I’m also feeling anxious that I may eventually be part of a layoff.

Apparently, the company is doing well, and they’re hiring a lot of people. Should I ask my manager what’s going on? Maybe everyone on my team is pretending to work and going to the gym at 3 p.m.? What might be happening? What would you do?

I’m a staff software engineer at a fully remote, 300-employee US SaaS startup. It was just announced that we are being acquired in an all-cash deal by a publicly traded tech company more than 10 times our size.

I’ve been here for 8 years and absolutely love this job. Over my tenure, I’ve risen from a junior to a staff engineer, built critical customer-facing features, and developed internal tools used company-wide. I’ve also renegotiated my salary such that LinkedIn recruiters can rarely match it. While my stock options aren’t enough to let me retire early or fund Jamison’s yacht, I know I’m ludicrously lucky to be getting a six-figure payout.

But what comes next? Leadership says we will operate as a standalone division for at least a few quarters, meaning no massive backend migrations immediately. However, I’ve never worked at a publicly traded company—only at consultancies and startups. My pessimistic expectation is that corporate bureaucracy will sanitize the culture I helped build.

Should I lean in, try to hold on to some of the startup magic, and lead the inevitable integration work to ingratiate myself with the senior engineers at the parent company? Or should I take advantage of my golden handcuffs being unlocked and finally move on?

In this episode, Dave and Jamison answer these questions:

Hello Dave and Jamison!

I’m a longtime listener going back to the early days of the podcast, and I’ve listened to every episode since. When I started listening, I was beginning my career as a software engineer. Your advice has truly helped shape how I think about work, engineering, leadership, and all the weird human stuff that comes with building software.

Now I’m more than 10 years into my career, and I’ve run into a problem that I suspect many experienced engineers are dealing with right now.

In episode 521, you talked about how brutal the current job market is, and the question asker from that episode had been unemployed for a year. I’m thankfully not there yet, but I recently lost my job in a large layoff, and the first couple of months of searching have been pretty discouraging.

I’m applying to roughly 10–20 jobs a day. I tailor my resume to each role, ensuring it accurately reflects the skills and terminology in the job description. I usually include a cover letter too; AI gets the privilege of writing the mediocre first draft, and then I rewrite it into something I would actually say.

Despite all of that, I’ve only made it past the resume screen three times so far, one of those was through a referral, and several other referral applications have gone nowhere.

The strange part is that I’ve tried applying across the whole spectrum:

Roles that would be a step up, where I think I could do the job but haven’t held that exact title before Roles at roughly my current level, where I can honestly check almost every box in the job description Roles that would technically be a step down, but that I’d happily take and feel extremely confident I could do well

So my question is: How do you get companies to actually interview you when you’re an experienced engineer in a market overwhelmed with qualified candidates?

At this point, I’m starting to wonder whether there’s such a thing as an awkward career middle age: too experienced for some jobs, not obviously senior enough for others, and competing with hundreds of people for everything in between.

If you were in this situation, what would you change? More networking? Fewer but more focused applications? Different positioning? Showing up at the hiring manager’s house with a fruit basket and a printed copy of my GitHub profile?

Would love to hear how you’d approach it from the other side of the hiring table.

Dave and Jamison,

Hit me with your dumbest, funniest, most brutally honest advice because I need it.

So here’s the deal: I’m a software engineer with 30+ year in the industry, a dinosaur who’s already reinvented himself like a half-dozen times, network, dev, infra consultant, back to dev. Now I’m having a midlife-ish (okay, late-life) crisis and I’ve fallen in love with security and compliance. Like, actually excited about compliance, which I’m told is a red flag in itself.

Problem is: I’m less than 10 years from retirement and my brain doesn’t bounce back from “starting over” the way it used to when I was a spry young whippersnapper.

So, am I an idiot for even considering torching my comfy expertise to go be a security newbie this close to the finish line? Or is this exactly the kind of chaotic energy I need before retirement?

In this episode, Dave and Jamison answer these questions:

Hi Dave & Jamison! I’ve been listening for almost a year now and have worked through nearly your entire back catalog in reverse. The podcast has genuinely helped me become a better engineer, so thank you!

I’m two years into my software engineer career at a large infrastructure company. I was promoted to SWE II last year, and this year my manager told me she felt my work was promotion-worthy, but because I’d just been promoted and she had others on the team to consider, she wants to target me for next year’s cycle instead. She gave me a spot bonus and said she’d try to make up for it in my raise.

I understand and appreciate the honesty, but I’m also a little disappointed because I’ve worked hard to hit every milestone on the roadmap she gave me, and career progression does matter to me.

My question is: How should I navigate the next year? What should I focus my 1:1s on? Should I push for a mid-year promotion if that’s an option, or instead focus on building an undeniable case for next year? How would you approach this if you were in my shoes?

Hey Dave and Jamison,

Long time listener. First time question asker :).

I recently joined a major tech company. Before this, I worked at a mid-sized company with about 200 engineers. In my old role, I built customer-facing products. The work was challenging and exciting, and I genuinely enjoyed it. I ended up moving to a new city to be closer to family and started looking for a job. The job search was brutal. Honestly, by the end of it, I would have accepted just about anything. Luckily, a major tech company extended an offer. The money was great, and I thought it would be a huge plus to have a major tech name on my resume. It is a fully remote role, but they did mention that they could go hybrid in the future.

I knew ahead of time that the team built internal tools instead of customer-facing products. But after joining, I realized most of what we do is closer to operations than actual software engineering. I know I should have screened the team better. I was just so relieved to get a good offer from a top company that I accepted without thinking twice. I am not enjoying the work at all.

I am not planning to quit immediately. However, I want to be ready to leave in about a year or earlier if they decide to lay us all off. I want to make sure I utilize my time here as best as possible. Do you have any suggestions on how I can best position myself for an internal transfer or an eventual external move?

Also, I have been in this role for close to 2 months now. I did a 1-1 with the manager in my first week, but after that, have not had any 1-1s. He has not scheduled anything. I was thinking of scheduling it myself but not sure if that can be seen as too forward.

Btw this is outside US, if that matters :)

Thanks again for your advice and laughs.

In this episode, Dave and Jamison answer these questions:

Hey Dave and Jamison, First, I love your show and it has now been part of my Monday evening routine for many years to listen to your podcast while cooking dinner.

I recently joined a mid-sized software company (500 people) as a senior data engineer. The salary is a significant bump from my previous job and I really like the team on a personal level. Three months after I joined, the company laid off half its employees and announced a strategic pivot away from their previous core business to become an “AI-first company” and develop new products in novel, more profitable sectors. The product that my team had been working on until that point was scrapped and there are no new projects coming from the business side. In subsequent communications, it was revealed why: Management has no concrete ideas for the future strategy, neither on what products to develop nor on which sectors to target. Instead, our team (among others) is now tasked with coming up with new product ideas to “save the company”. I’m a data engineer, not a business development manager, and while I have dealt with high ambiguity from the business side in previous roles, it was never this extreme.

I was looking forward to working on interesting technical challenges within a great, experienced team, but now I feel like I’m expected to become an “idea guy”, a role that doesn’t really match my personality. My question is: Should I be patient and try to turn this situation into “an opportunity for growth”, or should I start applying elsewhere? I’m a bit worried that the short length of stay at this company will leave a stain on my CV.

Many thanks to my favorite space lawyers, an anonymous listener.

Hi!

My current job is at a 10k+ large risk-adverse company that currently has nil, none, nada, nichts ai tools available for coding. I of course did the only reasonable thing. I’ve gotten a new job at a middle-sized fintech company that’s going ”AI first”.

I’m really excited about finally using ai outside hobby projects. I worry however, that my future colleagues will go too quickly ahead while vibecoding, vibearchitecting, vibetesting… leaving a mountain of tech debt behind. A lazy colleague would actually be better than an intellectually lazy colleague in this scenario. (I sincerely hope that I won’t be that coworker)

Are my worries overblown or sane? Any gotch’as to avoid? Maybe you can give a brief survival guide to the brave new AI world?

In this episode, Dave and Jamison answer these questions:

I work for a small software company on a team of about 7 or 8 engineers. I like working here. I like the people, the autonomy, the pay, my boss, and the stack among other things. I try to remind myself of this regularly so I don’t take it for granted. I’ve been here for about 2.5 years and would love to continue working here.

Our CTO, like many, has become a big AI cowboy coder. Every few months, he vibe codes a new project and then decides to interrupt the full workloads that we have a limited number of engineers to do to hand his project off to be cleaned up, worked into the product, and solve all of the problems that remain once actually put into practice. This usually ends up going to a different engineer per project, who is then tied up with the CTO’s whims and is no longer available to do the work planned by product. Our EM knows this and knows the frustration and lost velocity, but what can he do? (rhetorical, not the question)

Most recently, I was tasked with implementing some reporting dashboards he did into the product, but he specifically asked me to make it in such a way that he can continue to work on and add to because he can’t be bothered to run the actual product. This is very concerning to several of us. He has no clue what he’s writing or how bad it is. We’ve talked about perhaps making him do PRs, but a) who can make him, he’s the CTO, and b) he’ll have no clue what to do with PR pushback given that he has no clue what he wrote. And again, who can make him actually fix it if he asks us to rubber stamp it? (rhetorical, not the question)

I’ve been listening to the show for years and I’ve talked to friends at other companies, so I know this is everywhere. Is it as everywhere as it seems? Is it worth finding a new place to work where the CTO isn’t running so rampant? As I stated before, I’d rather not leave, but if I talked about that as a concern, I don’t want it to sound like an ultimatum, even if maybe it is at some level. Is this just the new reality for us, or is there something that can be done?

I am a senior software engineer at a big tech company. I live in central Europe but my team is in the US and I’m 9 hours ahead. I have 7:30 pm meetings and sometimes take an hour before and/or after this meeting to prep or follow up. Previously I slept in later and started later to deal with these meetings. However, now my daughter is starting kindergarten and I wake up early (5-6AM) to be with her, drop her off, etc. Now in the evening meetings my brain is fried and I can’t even articulate myself well. The next day I think about so many things I wish I had said in those meetings.

I can’t quit as I make 160K right now and I would only be making 60-80K tops in my country and have some financial commitments. Relocation to the US is also not an option because I have kids and don’t want them to move.

So far I have been skipping meetings and my manager has not expressed concern but I feel so detached from my team. I don’t even know what most of my peers are working on.

It feels like I am out of ideas to make this better. Please share your space wisdom with me :)

This is a rerun of episode 331.

In this episode, Dave and Jamison answer these questions:

Listener ninjamonkey says,

I am a new grad who is half a year into the role now at a very large company. Recently, a senior engineer on my team asked me to create a ticket for an infra team for a problem with a service. I provided logs and steps to reproduce the issue and did a health check before submitting.

Right after, the manager of the team put me into a group chat with their team, asked why I created the ticket and told me to start doing my job and they can’t debug for me.

From these interactions and comments on the ticket, it feels the infra team will likely not work on the tickets I report or de-prioritize them. This has left me discouraged and hesitant.

I will have to do lots of this kind of infrastructure work in the future. Additionally, one of the goals my manager set for me is to work with more external teams for the upcoming year.

What do I do here? Do I tell my manager about these interactions? Do I tell my team lead, staff/seniors to swap out for different kind of story?

I work for a small startup. I was the first employee other than the 2 founders.

Being the first developer hired, naturally means I have the most knowledge about our application. I also have good organisational skills, which has led to me becoming and being referred to as the “Lead Developer”.

I have recruited 2 of the 3 new developers, and have trained both of them and got them up to speed.

At first I was pleased with the progression and was keen to grow into the position, and told the founders so.

Since then, I have changed my mind, I don’t want to be the lead - due to the following:

The communication is absolutely pitiful. Any questions we ask of the founders we get about a 30% reply rate no matter the form of communication. We get poorly defined tasks and requirements The CTO will just blast through some of our features over the weekend and say here I fixed it for you

I don’t want to quit my job (just yet… its a comin though).

I have actually discussed the above points with them, but I know these 2 founders will never change their ways.

How do I tell them I just want to go back to being an Individual Contributor like my Employment contract states?

In this episode, Dave and Jamison answer these questions:

I stayed too long at my first company and now my career is ruined?

Hi both, long time listener. (Since I graduated university 4 years ago actually and felt I could never find a job but listening to you guys made me feel not like such an outcast in our field.)

I graduated in 2022. Didn’t really apply around much and almost immediately accepted the full time offer from the company I did my internship with during my degree. And fast forward to middle of 2026… I am still here.

I’ve long stopped growing as an engineer and have actually been stuck on a simple CLI tool for almost 4 years now with little to no cloud/backend/etcetera experience to show in my 5 year career. I don’t feel I am desirable in the job market at all due to this and waited way too long to look for a job because I was comfortable and happy. I feel paralyzed (no need to put on your space therapist hats BUT some career advice would be wonderful!)

(Also did I mention I am in Canada and want to move to Europe and live the rest of my life there but visa sponsorship with my level of experience is impossible? Maybe that’ll be for my next question…)

Thanks for all you do, cheers!

I have a non-CS engineering degree, and am looking to transition into Software Engineering. I have the option of pursuing a degree with Tuition Reimbursement from my job, but am in a bit of a strange situation deciding which degree. Basically, I’ve figured that with my current Engineering background I could pursue either a second Bachelor’s degree through Universities offering a “Post-Baccalaureate” program in Computer Science, or a Master’s degree, with maybe only a slightly longer program to get the Master’s as opposed to the Bachelor’s. Otherwise the total length/cost of the programs would be roughly the same.

I have heard though that it might not be a great idea to go into a Master’s program unless you know what specifically you want to study.

I am curious what you think would be more “hire-able” between the two options for someone pursuing the career change into Software Engineering?

In this episode, Dave and Jamison answer these questions:

Dwill Ainghell asks,

During the golden era of software development, it was commonly stated that you should always negotiate job offers. The argument was that the company has invested significant time and resources into you as a candidate and there is always some wiggle room for negotiations. A popular article / podcast by Patrick McKenzie likened it to doing something slightly uncomfortable like “reciting poetry while simultaneously standing on one foot” with almost no downside. (https://www.complexsystemspodcast.com/episodes/how-to-negotiate-your-salary-package/)

Does this still hold true in today’s environment? I’m a SWE with 10 years of experience and I’ve been unemployed for close to a year. I’m expecting an offer from a large company and I fear that I will look like a fool trying to negotiate in my current position and the current job market dynamics. Even worse, I fear that they might retract the offer and give it to someone else. That being said, I don’t want to leave money on the table.

What’s the correct course of action in today’s environment?

Listener Stu says,

In episode 500, you said something to the effect of “working hard and doing a great job with the work you’ve been assigned is not the promotion track”. I’d love to hear you discuss what it does take to get promoted and how to do that.

In my job, we have a jira queue and engineers are tasked with taking from the top of the queue and executing work. There’s also an expectation to lead pre-defined projects (define the scope, write the tickets, and shepherd it along).

All of these projects have deadlines, so how do you recommend people get the defined work done, lead projects, and still find time to do whatever it is to get promoted?

Why is doing an excellent job not enough?

In this episode, Dave and Jamison answer these questions:

Hey Dave & Jamison,

Long time listener. Love the podcast.

I recently rejoined a remote team that I worked with in the past. I was super stoked to rejoin this team because they were collectively one of the most competent and technically excellent teams I’ve ever worked with. And they’re all genuinely nice people as well.

I left the team before AI coding had really caught on, but coming back to the team has been a huge shock to me. Almost everyone now exclusively writes code with AI. PR descriptions are all AI generated, and code review has become copy-pasting AI-generated comments into GitHub.

Being a remote team it was already hard to connect, but now it feels like almost all interactions are their AI assistant talking to my AI assistant.

I’m not anti-AI, and I get that writing code with AI can be much quicker. But I’m struggling with the loss of what made the team feel good to work on, specifically the craftsmanship, level of engagement, and the learning from eachother. The product itself is still high quality (even if the codebase is less-so), but the process itself is a lot less enjoyable now.

I don’t want to be the person who shows up after being away and immediately makes it everyone else’s problem that I miss the old way of doing things. But I’m having doubts if I want to be a part of this team.

Is this just what software engineering looks like in remote organisations now? And should I expect most teams are now operating like this?

Hi Jamison and Dave,

Love your podcast.

I was recently hired as a mid-level full-stack developer with the promise of leading a new squad. On day one, I discovered management scrapped the squad idea and promoted an existing developer to sole lead instead.

The team consists of this new lead, two 20-year VB6 veterans, and me. The codebase is lawless: direct DB access, fat controllers, 1-2K+ LOC classes everywhere (copy/pasted boilerplate) and severe Broken Access Control (OWASP #1) where authenticated users can extract anyone’s PII (full name, home address, phone number) via a simple email query string.

My coworkers rely heavily on generative AI but do not review the output. They constantly commit “AI slop” that barely functions and introduces endless bugs. I used to clean it up, but I recently realized they care so little about the codebase that no one even notices if I stop. Add in a “Senior Product Manager” whose entire UX background is a three-month internship, who invents customer requirements to defend her inconsistent designs.

I am already applying elsewhere.

My questions:

How do you handle a bait-and-switch of this magnitude?

When the team cares so little that no one notices if you stop cleaning up their AI-generated bugs, how do you stay sane and professionally sharp while riding out the clock?

Show Notes

In this episode, Dave and Jamison answer these questions:

Hi D&J! Question from Sweden!

I’m a senior dev that have seen a lot of orgs without tech lead and/or staff engineer roles. I know some companies have them, but mostly newer more techy companies. Bigger older less techy companies usually have non-coding “architects”. Though that’s one title I have no good experience of, just neutral ones or worse :)

In particular I’ve been in many teams without a tech lead (all developers are equal, no tiebreaker vote). It’s often successful due to a leader and/or consensus emerging organically and peacefully. I loathe the failure modes however: consensus abuse through veto (we can’t move discussion forward because someone explicitly actively disagrees, a “keeping the meeting hostage” situation), disagreement on technical priorities and choices (lowest common denominator it is…) or that the team is bickering and bikeshedding during technical discussions.

Is this just a regional/cultural thing, or is it more about the type of org? Also would you say it’s to the detriment of these orgs to not have these “technical leadership hierarchies”?

Thanks!

Hey Dave and Jameson, love the show. I’m a Software Engineer at a major tech company. The org is non technical. I consider myself pretty well rounded. I consistently hit my sprint goals, crush my story points, and even put in weekend commits when needed as well as talk but I dont look for conversations into work im too far away involved in. My direct manager thinks my output is good. He told me to work on communication, but the work and my drive is good.

I have a relaxed demeanor in a high stress environment. Recently, I learned there are concerns that my “vibe” seems lazy and unengaged, and those concerns may have been shared with my skip-level manager. When my friend literally pulled up my raw metrics and story points to defend me, the friend had no answer, but just reiterated that it’s a “vibe thing.”

It feels like a political target has been placed on my back by business people who don’t understand my work but hold corporate influence. I told my manager and he says im doing fine, and people will say what they say. Everyone talks, etc, and just to focus on his feedback.

My question is: How do I fight a “vibe” complaint when the data says I’m crushing it? Should I cave and alter my lifestyle to play the corporate theater game, or do I double down on my metrics, lean on my manager, or dare them to try and figure out how valuable I am?

Thanks, An Engineer Who Refuses to Look Bored

In this episode, Dave and Jamison answer these questions:

I have been at a small startup company for 5 years now. It’s a very small technical team, 4 devs and a tech lead that contributes code & architecture. I am getting a small raise this week for my 5 years but it’s a smaller raise than I was expecting. We’re an all remote team across the globe but I had a dev co worker in the same city as me just leave the company. This has put more pressure on me as I’m the only dev in the primary time zone we operate in, everyone else is east coast or opposite side of the world. With the added pressure and some forward comments from me in one on ones with my tech lead I expected much more that I’m being offered.

I think I’m supposed to quit my job but I’m terrified of that idea. This is my first job in the field and I love the work. The full stack startup experience is fun and I’ve learned so much, and I like my team a lot. I’ve never even applied to another position in tech yet, I got this one with the first application I sent out. That’s not even considering the current state of the field rapidly changing with AI and the general lack of jobs I am constantly hearing about in tech.

Is there a world where I should tell my boss I’m thinking about leaving? I’ve become an integral part of the team I think that would result in movement upwards, but that sounds so risky if I haven’t even put in an application anywhere else. Should I take the old quit your job advice even when the field is so shaky?

Thanks guys! And you reading the patreon names is the best part of my week too.

Hi there, I’m about 4 years into my career. I’m at my second job after leaving university. The first was at a firm under 50 employees and the current is at a firm with a global footprint and several thousand employees. Both are in Europe.

I moved to Europe on a work visa as a pathway to citizenship. I’ve never felt like either my past or current employer has taken advantage of my situation, but it’s important that I keep my job.

At both employers, I generally work one weekend day a week to meet expectations and keep on the promotion train. I’m not the only one; several of my colleagues do the same.

For now I have the time to work late, as my significant other is back home. Soon they’ll be moving over, however, and they have made clear they will not be okay with me going into work every Saturday.

Maybe I’m paranoid. Maybe the expectations at work aren’t clear. Maybe this is part of software. But basically, how do I get to a point where I can checkout on weekends and not feel guilty or like I’m falling behind?

Do I need to work longer weekdays? Do I need to sacrifice promotions? Do I need to get better at saying no?

In this episode, Dave and Jamison answer these questions:

Hey guys. This question comes all the way from New Zealand. Recently discovered your podcast about a month ago, and have been catching up with older episodes on morning walks ever since - you guys are awesome. Anyway - the question: Is it more beneficial to work for a company where the software itself is the product (SaaS etc) or does it no longer matter given the rise of the robots anyway? For context - I’ve been working for a telco/internet company for just over five year. Initially when I joined there was a huge roadmap of software to develop internally - things like customer facing portals, diagnostic tools, and of course internal tooling. However over the past couple of years, it has just been cost cutting and downsizing. Given that the company is not in the business of selling software, our department has been stripped to skeletal level just to ‘keep the lights on’. So, I’ve started applying for jobs at SaaS companies on the basis that even with AI, there will at least be a continuous roadmap to work on. Or, is this a case of ‘snakes in the greener grass’… or whatever the idiom is. Keen to hear your thoughts!

I’m an EM about 7 months into a role at a larger private software company. When I joined, the explicit expectation was 1 team (~8 direct reports). I’m happy to say my team has crushed it: award-winning product launch, clear monetization path, company IPO positioning. I made some bold headcount decisions, reduced spend, built the team’s trust back up, and things are now actually quite great. I’m generally a cynical person and so I don’t say that lightly :)

Last week my boss told me I’m taking on a second team, bringing me to 16 direct reports. When I asked if this was a promotion track, he said no. Apparently the expectation is now ALL EMs manage 2+ teams.

Problem: the internal HR leveling rubric still says 2+ teams is a Sr. EM expectation, which I didn’t apply for… precisely because I didn’t want it. When I pointed this out, he said “that’s out of date, and you’re behind your peers because you only have been running one team”. I did the job I was hired to do, did it well, and the goalposts moved without anyone telling me.

The kicker: the team I’m absorbing used to be run by a Sr. EM, who now has just one team!!

So a Sr. EM is shrinking scope while I’m handed their struggling team and told I’m behind. It wasn’t framed as a vote of confidence. It felt like a quiet reassignment.

Three questions: Am I being oversensitive to just poor communication (it’s possible the senior EM is being managed out and I shouldn’t use that as a benchmark)? Should I push for a comp increase since I’m now doing 2x the scope I was hired for? And how hard do I push back?

One constraint: I’m a couple months from planned medical leave and can’t afford to leave before then, so I have limited leverage.

In this episode, Dave and Jamison answer these questions:

My company follows scrum, with daily standups. We got a new scrum master. He is very formal and procedural and I struggle with our daily meetings.

He goes through a long list of assigned tickets, asking each ticket owner about status and info on progress. We are all engineers with many years of experience but it feels like we are in the kindergarten. We don’t have deep expertise about each others work. It is important to know what each of us is doing more or less, but going deep in these issues makes me disconnect, and I think these meetings are above all very good to signal blocking points and ask for help. A recitation of tickets and work being done is not their purpose. On top of that, most days it takes 25-30 mins to go through all the issues.

Am I being difficult complaining about this? I tried to be polite when I raised the issue but I was told more or less that this way is better for the company. Is it common in the industry to go through dailys like this?

Thanks a lot, guys, you do great work and I look forward to the SW/industry podcast that makes me laugh the most!

Hi! Long-time listener here, I remember Jamison mentioning this podcast on JS Jabber and I’ve been listening ever since. Best part of my week!

In my current organisation I have a tech lead role on a small, internal platform team. Our “customers” are mainly other engineers. Due to several re-orgs, I have over the years worked with a number of Product Managers and Engineering Managers who have all had one thing in common: they don’t understand the technical domain we work in very well. You could say we have “Product Managers” who do not understand the “Product”.

At the same time, these people are expected to interact with stakeholders, set the platform vision, manage the roadmap and backlog, prioritise risks, write documentation, do demos, etc. In the end, a lot of this work falls through to me. I do the work, but have also received negative feedback from my skip level that I need to do a better job keeping the product manager and engineering manager in the loop.

I just got a new EM and am heading into our first expectations setting meeting. How can best express that my expectation is that the roadmap for a technical platform team should be managed by someone technical? Do you think product managers have a role on internal platform teams?

In this episode, Dave and Jamison answer these questions:

Hi from a long-time listener and first-time caller. I need some advice on a toxic workplace situation.

I’m currently unhappy with my job due to a difficult dynamic with a colleague. My manager put us on the same team, meaning we share responsibility for our output. Although this colleague is technically a level below me, they act as though they have seniority. This creates significant friction: they’re resistant to advice, insist they’re always right, and refuse to accept reality even when they can’t deliver what’s required. They’re incredibly stubborn, and arguing with them about what’s feasible takes an excessive amount of effort.

The situation is particularly frustrating because I’m held accountable for the shared results. If I weren’t responsible for the final outcome, I could probably just ignore their behaviour. Instead, they frequently talk a big game while contributing very little actual work. People unfamiliar with our domain are easily misled by their confidence, even though they are incompetent. Consequently, I’m forced to clean up their mess; otherwise, I’d be the one bearing the blame for the failure.

I tried discussing this with my manager, but unfortunately, it made me look bad rather than resolving the issue. If I were the manager, I’d fire this person immediately, but my manager is clearly one of those people who get fooled by their smooth talk. I’m very close to handing in my notice, and let the manager know how incompetent this person is. But I’m furious that I feel I have to give up a role I enjoy just because of someone who makes my life miserable.

My question is: Should I stick it out and try to navigate this politics-heavy environment, or is walking away the only option left? How do I leave without burning bridges or letting them win?

Hello gentlemen, long time listener of the show and finally getting around to asking my first question (how exciting!)

I’m going to be joining a new company in a few months and am wondering how to best handle the transition in order to make an excellent first impression and maybe set myself up for career growth… while not biting off more than I can chew.

For context: I’m joining a company that builds QUANTUM COMPUTERS 🤯 after a background in working in completely different, non-scientific fields. To be fair I’m just joining as a Senior Software Engineer on the Cloud team, I won’t be building the actual computers.

I have some experience in leadership, but not nearly as much as I wish I had, this is something I’d love to try and get into a little bit more (and couldn’t at my last company which was too small). I’m also a little intimidated at the idea of stepping into the “big leagues”, but want to use this opportunity to show that, I too, can ball.

However, I am worried that everyone is going to be waaay smarter than me and that I’ve actually been playing in the ball pit for years.

I’m a little scared of attempting to ball too hard and fumbling, causing dissapointment on their end, and impostor syndrome on mine.

How would you go about joining a new company with the excitement of a new start and the drive to be the best I can be, while also remaining humble and grounded in reality?

Should I “fake it t’ill I make it” and be super confident? Or take a more reserved approach?

In France we call this a “rich person problem”, everything is great because I have a cool new job, but I don’t want to mess it up! HELP!

In this episode, Dave and Jamison answer these questions:

My parent organization has trust issues: we registered on a recent survey as one of the lowest across the bigger software org (thousands of employees).

There are two groups: functional, trustworthy people who get stuff done, and people who are behind, stuck, or just not working. Those struggling say they need better emotional support, but there is consistent, documented evidence that they cannot keep up.

I’m perpetually frustrated that there are only two or three people in an org of 30 who can effectively complete tasks and manage the insane workload. I am biased: those in whom I have no trust have repeatedly demonstrated that they cannot be trusted. I believe that the organization would be able to go faster without them.

Whats the right answer here? Should I start my own company to abandon this mess? Do we cut scope super aggressively to allow underperformers to be reasonable contributors?

One example: one of these contributors was walked through the process, given written documentation of the process, verbally confirmed an understanding of the process, and committed to starting that day. And then two days later identified they hadn’t started for those two days because they were blocked by something that was explicitly captured in the document and discussed in the recorded meeting. They do not raise this until they were asked for their progress multiple days beyond the critical start date.

Hi Dave and Jamison,

First, thank you for the podcast. As someone on the spectrum, it really helps me analyze social situations I struggle with.

My question: I work at a software company where management is pushing the use of LLMs for coding, and my team recently started using Spec-Driven Development. SDD often requires strong upfront planning, which has quietly split my small team between developers who plan well and those who get lost in “vibe-coding” loops.

One of those people is a close coworker I consider a friend (we hang out after work and have honest chats about everything). He’s not strong at planning, so I end up explaining each ticket to him in detail. But he’s really great in other ways: communicative, asks a lot of questions in refinement sessions that set a good example for others, does thorough handoffs with the QA team, always responsive in chat, always trying to help. He’s also one of the rare people who actually pay attention to alerts.

Since we started using SDD, the gap in our speed and output quality has become very visible. One of our tech directors noticed and asked me to teach him planning. We spent several days drawing schemas and working through small features together, and it was clearly painful for him. The TD also had his own sessions with him, but eventually gave up because my friend seemed so discouraged, and the TD decided to “stop the torture” and leave him alone. The hard part is that after all these teaching sessions, he actually seems even slower than before and also more discouraged and down.

Since then, our friendship has changed. He stopped talking to me outside work, and I think he now feels jealous or bothered by the difference in our performance. I’m okay with continuing to explain tickets and outlining detailed execution plans for him, but I worry that I’m keeping him in his comfort zone and not really helping his career. And I also miss how things used to be between us 💔

What should I do?

P.S. I’m not an LLM fan or enthusiast, I take a practical approach to using them. But I hate how they’re taking jobs away from devs who really love coding but are weak at planning or not interested in it. It doesn’t feel fair.

In this episode, Dave and Jamison answer these questions:

How long until I am ethically obligated to let my company know I’m doing no work? There was a big re-org at the company I recently joined. It’s a huge financial company, so there’s a lot of bureaucracy. Somehow in this mess I was kicked off the first team I joined so that I was pending re-assignment. It’s been a month and I haven’t been re-assigned. Instead of being in between jobs not working, I am currently in between teams, but still getting paid! This feels unintentional on the part of the company as no one has followed up with me. I’ve been happily using the time to catch up on hobbies, but I’m starting to get concerned about what will happen when the other shoe drops. At what point do I start to venture into irreversible reputational harm? For some added context, teams at this company are about 6 people and the manager handles several teams, so I’ve never talked to my manager since I joined. I got the message about the re-org from a screenshot of an email that my scrum master shared in my last stand-up.

AI changes how software is build. Actual coding is mostly done by LLMs now (I hate it, but it is what it is). What do you think should I focus on learning now to not become obsolete in 1-2 years? I am a senior dev with 13yoe, and loved coding, but now I find it hard what my role will be in the next years (still have 30+ before retirement). I do not want to go to the EM track, at least not in the near future. So is it more architecture knowledge, security, AI internals, …? What do you think?

In this episode, Dave and Jamison answer these questions:

Should I declare my struggle with this AI world we live in here? Nah. I mean, I’d like the hype to die down, a lot, but we keep getting new tools and I get to experiment, so here we are.

My real struggle, and this podcast is implicated in it, is around non-technical people contributing to production systems. Why are we so obsessed with this idea?

COBOL tried it. Low-code and no-code tried it. BDD and Gherkin aspire to it. Yet time and again the field demonstrates that you need people who know their stuff.

To “democratize” software engineering implies that all people have the desire and ability to become software engineers. That premise is false. You democratize access to education or financial systems, the stock market say. You don’t democratize skill. Skills are earned. We would never, I hope, democratize bridge engineering or piloting an aircraft. Software engineers are just as critical as either. When our software breaks, money goes missing, electrical grids fail, information stops flowing.

What I do think is great: now more than ever, as long as tokens stay cheap, people have more ability to build useful tools for themselves. But here is how I think about it. We have done tremendous work on literacy, and most people can read, but not everyone is an author. The same applies to code.

anon e mouse asks,

Should I share my tools?

I keep building small local software tools to better test and debug the application I’m working on. The problem is that whenever I go “above and beyond” the assigned and expected work and try and responsible check it into version control and share it with the rest of the team, it gets bogged down in code reviews because it doesn’t meet the team lead’s vision because it wasn’t part of the vision! Once I go through that process though, it’s mostly appreciated, but the team lead is under a lot of business pressure and often mentions that we need to focus.

Maybe I’m not focused enough, but many of these little tools are things that making verification and delivery much smoother! Like local testing utilities to verify and sample api endpoints that otherwise could only be called after prod deployments due to a lack of test data. Our partners like when we’re able to show the output before deployment, and the rest of the team usually struggles with that.

I feel a pressure to hide my tools, but then I feel sloppy for having a bunch of useful tools outside of version control. These are things like formatting output, running experiments, testing data for variations. Am I unfocused or just bad at articulating the value of these tools?

In this episode, Dave and Jamison answer these questions:

I’m approaching 15 years of experience with the last 7 years at fang. About a year ago I was promoted to staff engineer (thanks to the podcast) and switched to an adjacent team under the same director. I have never actively pursued a management role but I’ve been starting to think about it more.

A colleague of mine just announced they need to take extended medical leave (1-2 months) and I was asked to fill in as a temporary manager while they are out. How do I go about managing a team if everyone knows it’s short lived? Should I just try to keep the team alive or aim higher? Is 1-2 months enough for me to get a sense of whether I’d enjoy management? I feel like I’ve dived into the deep end and it’s scary but also exciting.

I love the podcast, I’ve listened to every episode! I’ll take whatever comedy or advice you have to offer.

Bobby Drop Tables asks,

Recently came out of a salary negotiation where HR blocked a payrise because they said I was already the highest paid non-management position dev. While I’m getting paid well for the market, I wouldn’t say it’s a ridiculous amount. HR said they wanted a fairly flat salary range across the organisation, with pay differences being dealt with via performance bonuses.

On paper this sounds good for most departments (sales, engineering etc), but I’m really struggling to figure out what metrics management could use to assess the software team. It feels like any metric that could be dreamt up could/would be gamed and would likely have negative consequences.

Have you ever come across any decent metrics or methods for assessing software performance when it comes to performance bonuses? Especially when the team lead might not have a say in who gets what or how much?

In this episode, Dave and Jamison answer these questions:

I work at a large remote company. We meet up once or twice a year. I don’t really know much about my engineering coworkers aside from the 5 people on my team, so the in person meet ups seem like a good place for me to get to know people from the other teams.

I am a career switcher, and am currently a mid level IC (borderline junior) in my late 30s and a youthful appearance. At these meetups, my position and appearance (and honestly, possibly my demeanour) makes me feel like I am expected to socialize with other ICs in their 20s. Although they are nice people I find it hard to relate to them when talking about non work related topics since I am much older and in a different stage in life than all of them, (married with a mortgage and kids).

I want to socialize with coworkers closer to my age and stage in life but most of them are team leads or manager. I feel like socializizing with them would be seen as brown nosing. I’ve also heard that once someone is a manager, it is very hard for them to befriend ICs because they are now their boss, and that they mostly befriend other managers. My previous career had little management/corporate politics type stuff, so I don’t know if this is true. Would I be hurting myself by doing this?

Am I over thinking this? Would I be fine socializing with whomever I want? Do you have any words or advice regarding my situation? Thanks!

Hi Dave and Jamison,

Before you tell me to quit my job, hear me out. I have worked in technology for about 30 years. I’ve been at the same company for the past 20 years, but I’ve changed roles many times to keep work interesting. I have enjoyed learning new technologies while working in development, architecture, system administration, management, vendor relations, and more. This has been very beneficial to my career, and I appreciate all the opportunities to grow. I’ve earned a good reputation and am well respected by my peers. I’ve proven my worth to leadership many times over by reducing expenses by many millions and creating innovative solutions to improve efficiencies. I work for corporate America in the insurance/finance industry, which is generally considered to be led by cold, heartless, power-hungry mongers, a stereotype that probably has a few exceptions but is generally not incorrect. I’ve never appreciated this industry’s business practices, but I’ve had to make a living over the years, so here I am.

I am finally at my breaking point and am absolutely fed up with how employees, customers, and communities are treated by my industry. Because of this, I just cannot find value in my work. I’ve been beaten down over the years and am tired of being exploited by management. I no longer volunteer to take on big projects, and instead of being someone who outshines others, I have decided to settle for mediocrity. I’m planning to retire in a few years and honestly don’t have the energy or desire to search for another, potentially more meaningful, industry to work in, especially in the current job market.

I genuinely care about many of the people I work with. Very few of them are in it to climb the corporate ladder. Most are just trying to earn enough money to pay the mortgage, feed their children, care for aging parents, and hope to have enough leftover for their own retirement.

How do I not leave a wake of malaise for my peers when I leave but also not help feed the beast until then?

In this episode, Dave and Jamison answer these questions:

I am a senior software engineer at big tech and need a career change. With the rise of AI, I no longer enjoy this profession and panic everyday just waiting for a huge round of layoffs. At this point I feel like I am on some assembly line hitting enter like a monkey. Therefore I have been thinking of changing lanes and would like to get into engineering management. On the one hand I have enjoyed mentoring, strategic planning and coordinating projects across vendors and across teams, but besides that I don’t have clear evidence that this profession would fit me. In my current job there is no immediate opportunity to step up and manage a cross team project at the moment, so I am not sure how I can figure out if engineering management is the right choice for me. How do I figure this out without doing the job and how does one transition into it, probably as an external hire or transfer hire?

Paolo asks,

I’ve stepped into a senior role recently. I’m no longer the primary driver on projects. I’m supposed to create space for junior developers to lead, make decisions, and own outcomes. My job is to mentor and support, not to take the wheel.

But I’m seeing projects drag because of passivity. Sometimes the solutions are inefficient. Other times it feels like the core problem isn’t fully understood before execution starts. In a few cases, momentum just stalls, and weeks go by without real progress because no one is pushing the work forward. It’s worth mentioning that I check in multiple times to offer help yet these problems keep happening.

I believe people grow by struggling, so I don’t want to jump in at the first sign of friction. But if a project slips or fails, that responsibility ultimately rolls up to me.

So how do you strike the balance? How do you give someone real ownership, not just symbolic ownership, while still maintaining standards and accountability? And how do you avoid becoming either the micromanager who swoops in too quickly or the absentee leader who lets things drift?

In this episode, Dave and Jamison answer these questions:

How can I get our company to follow the law and stop sending SPAM without being regarded as negative?

We’re sending out emails that don’t comply with CAN-SPAM, and I think we should comply due to the risks, but I don’t want to risk any blowback! People want the emails to look more ‘human’ sent, and putting your mailing address at the end of an email is not very human, so we’re not doing that… It’s a medium startup (500 people), but I’m close enough to the marketing work that they might know it was me! Should I send an email to our general consul? How can I raise concerns and do the right thing without being regarded as not a team player??

How do I stay motivated on a team that’s always sick?

I’m on a team of 3 ICs and one manager. The other two ICs are plagued by health issues. I am trying to be empathetic, but this has been going on for the at least a year. One of them regularly takes sick days, often turning into sick weeks. The other has a long term issue and regularly does half days. This affects our ability to produce results, but we don’t have a PM and don’t really have deadlines given the nature of our work, so it’s not really noticed. I feel like we are moving a lot slower than we could be, and when we do check-ins on our goals at the end of each quarter, we maybe only hit like 50% of our goals.

To me it’s quite obvious why we don’t hit our goals, but everyone else seems to be surprised by it. My manager can’t manage with enough rigor to produce results. I’ve brought this up to them before (our goal misses, not teammates being sick), but nothing seems to change. As the only seemingly-healthy member of the team, there’s no incentive to work more than the bare minimum. I feel like I should be taking more sick days! This is very demotivating and I feel like I’m stagnating. How would you all approach this situation? Should I also suddenly have health issues? Is this actually a blessing in disguise and I should make the most of it?

Show Notes

https://overcast.fm/+ABLmzfhZxak

In this episode, Dave and Jamison answer these questions:

Hey there, I started a new job in August at a large European retailer. There were ups & downs, but long story short, my weekly one-on-ones with my manager was either positive or neutral. This was my second job after graduating, so the firm factored in, I’d like to think, when setting expectations this was my first time switching codebases and tech stacks.

On January 3rd, I was fired in the last month of my 6 month probation. This was a total surprise. My tech lead told me I required too much assistance from others to finish my tasks.

Some part of me doubted the sincerity of my boss, since I asked for example pull requests or tickets where this was the case and he was unable to provide a single example, but obviously, like every dev, technical insecurities are a big part of my life.

I’ll be starting a new job at a prestigious newspaper in May, so here’s my question. In a remote first environment, how do I determine if I’m meeting expectations? How do I gauge my standing in my team? How do I avoid a repeat? How do I effectively integrate myself into a codebase?

Disclaimer: At the end of January, everyone in my department was hauled into a meeting and was told the retailer hired 11 external, Portuguese developers to ‘finish the job’ since management wasn’t happy with the output of the 9 internal developers (aka nearshoring) and no internal would get a pay increase this year. My tech’s boss was also fired/forced out/quit before he could be fired.

Trevor asks,

How do I balance depth with breadth? At my current job, I am moved around projects/code bases all the time and I am exposed to a variety of technologies and subareas. That’s cool but I feel like I only manage to face the consequences of our choices for a couple months until I am moved again. I think I need more time to really become an expert in any one area. At the same time, I dread getting stuck in maintenance work. It seems like most people around me (at my company or outside) find it boring and soul-sucking, and are only excited about major projects from scratch. Does a job that has a good balance of both exist and if so, how do I find it?

In this episode, Dave and Jamison answer these questions:

Hi Djavison,

I’ve heard y’all say something along the lines of “this is the most exciting time to build software” in a few recent episodes.

I’m glad that has been your experience and seems to be the experience of many others.

But for me as someone 5 years into the career who is, thankfully, employed—I can’t help mourning a job that no longer exists. Obviously, there are still lots of us with the job title “software engineer” that create software. But, what I originally fell in love with doesn’t really seem like a thing you can get paid to do anymore.

I now spend most of my development time reviewing code and making sure things work. Which feels way less rewarding and way more soul-sucking.

Maybe I’m just nostalgic for being a more junior developer, but it’s obvious that our jobs have changed forever and will continue to evolve.

So, my question is: How can I get excited and feel passionate about this new way of doing things?

I am a senior team lead with 10+ years of experience. This is the first time I’ve had a team mate that clearly disrespects me.

I have a Middle+ teammate who is technically perfectionistic and openly says I’m doing a poor job and that basically he doesn’t see me as an authority. He says I am not as devoted to technical excellency and improving the project as he is, and that I ignore his opinions, which is his term for not having the same opinion about tech stuff as he does.

He doesn’t see the big picture and thinks he’s the only person on the team trying to make the code better. But the worst part is he never admits he’s wrong. I had to scramble to fix a bug he created when we caught it right before release, and he accused ME of introducing it!

My manager know what’s going on, but I feel terrible about it. I have many different projects and responsibilities. I can not be as devoted to the codebase as he wants. Plus, I am not the architect and nor should I be. I see that it demotivates him (like the person in the 499th episode), only in this question I am the senior.

I know my weaknesses and I am working on them, I don’t think I can address his feedback. More than that, I’ve always tried to maintain a good relationship with him and always gave him the freedom to work on tech stuff and develop his skills. But what to do when your child has grown and is now unthankful? 😂

Thanks for your advice!

In this episode, Dave and Jamison answer these questions:

I’m a senior software engineer at a remote company (~500–700 people), and over the last year a new HR org replaced our old people team. They’ve spent six months building a new goals/leveling framework. During a public meeting I asked in slack: “We’ve had goals before and then stopped using them. How will these be different?” Nobody answered directly.

The next day I was pulled into a meeting. The new VP of HR had screenshotted my question and sent it up my management chain. My manager told me they were on my side but leadership didn’t appreciate it. Days later I was pulled in again and told the problem was my “tone.” I didn’t argue because we were at an impasse. It felt like tone policing and like being sent to the principal’s office. I didn’t feel like they were treating me like an adult. In yet another 1:1, my manager said leadership wanted it raised again and that they don’t want questions like that in public. I told him the meeting should’ve been an email and that would’ve avoided this problem.

Is this normal? What should I do? It’s upsetting enough that every time this gets brought up, it wrecks the rest of my workday. I’ve already been passively job searching for about three years because of broader issues, and now I feel like leadership might be pushing me out. This also follows being labeled a “dissident” by our product director after I raised roadmap concerns in another all-hands. Most of the leaders involved are newer (2 years or less), while I’ve been here 4+ years, so I’m wondering if the culture is changing right in front of me. Thanks for the show! Y’all have helped my career a lot.

Hi Softskillets! Love the show, thanks for making me laugh every walk break I take!

I’m in an org where the Frontend Platform Team has adopted a fairly rigid rule—forcing all domain logic into pure functions—to prevent “bad code.” I see value in for the big picture, but the rule is enforced at every level, even within my own team modules. It feels incredibly unnatural and cumbersome. I see our team is often leaking logic into our UI layer to avoid boilerplate that usually come “out of the box.” (in this React(ive) framework).

I’ve tried to address this a few times, but I always get shut down with “theoretically correct” answers that don’t actually acknowledge the pain we feel on the ground. Most of the feature engineers have tried to bring this up, felt unheard, and eventually just stopped trying.

Recently, I used AI to help me synthesize these conversations and better understand the bottleneck. I wrote a long markdown file to validate with my teammates if they felt the same. The Platform Team got wind of it, and I shared it. This triggered a lot of frustration (understandably they felt it was AI slop sent their way).

I eventually got a meeting with one of the platform engineers. I tried to stay focused purely on the problems, knowing my solution (allowing state management in the domain layer) would be pushed away. The meeting went poorly. I didn’t feel like the weight of our frustration was understood, and when I mentioned potentially allowing some optionality for senior engineers, I was literally laughed at.

It feels like this rule is now followed like a religion. How do I rebuild this relationship and actually be taken seriously? How can I change a culture where the “builders” feel like the “gatekeepers” are limiting them instead of helping them?

In this episode, Dave and Jamison answer these questions:

Hi Jamison and Dave. Eight years into my software engineering career, all of it at Series B and C startups, I’ve been craving two things: a recognizable brand name on my resume and the chance to work on real scale problems. After a long search, I finally got both. The catch? I got them in the wrong order.

I accepted an offer at one of the hottest and fastest-growing AI companies in the application layer space. Exciting work, smart people, real momentum, but not quite a household name yet, and not quite facing the kind of scaling challenges that come with a billion users yet either. Two weeks later, I finally heard that I cleared the interviews from a big brand name tech company. I’ll be honest: it wasn’t my first choice brand name. I bombed interviews at a few others and this was basically my consolation prize.

Here’s the thing about this mega tech company right now: the culture has … shifted. It feels less like a tech company and more like a social experiment with a $1.5 trillion market cap.

So now I’m torn and the clock is ticking. My start date at the AI company is in a few weeks and I’m currently in team matching at the mega tech co. Do I renege before I even badge in? Do I start, survive team matching, and then quit? Or do I just honor my commitment and forget about the brand name for now?

More broadly: under what circumstances is it ever okay to renege or quit shortly after starting? Have either of you been in this situation or been on the receiving end? I need stories, I need wisdom, and honestly I need someone to just tell me what to do.

I’ve changed from a java developer role to OIC integration on oracle cloud. I’m not sure if that was a good move as it doesn’t feel like I’m doing much coding but lots of clicking. I was thinking that having cloud experience would benefit me but now I’m not sure. I’m not sure if I should run back to a java developer job or give it a chance and how much time would be a fair chance?

In this episode, Dave and Jamison answer these questions:

I’m a software developer with about 15 years in the industry, and I am soon starting as the CTO of a robotics company with about 50 employees.

Though I have years of experience and an academic background within the field of robotics, I have always been focused on the software side of things. In my new role, I am ultimately responsible for the hardware team as well.

How do I go about earning the respect, and becoming an effective leader, of my new colleagues working in a field in which I am not an expert myself?

Hi, I’m meowmeow, and I’ve enjoyed your podcast for a long time.

I’m working at a small engineering company which don’t have lots of profit.

Recently, the PMs at my company(including the CEO) have started “vibe coding” directly on our product. They’ve even added PMs to the project planning list as contributors.

Whenever they open a PR, the code is AI-generated and reflects their personal working style. The code quality is fairly low and engineers end up spending a lot of time reviewing and fixing it, even though we’re already under a heavy workload.

Our CEO comes from a product management background. He believes PMs should write code and deploy their own implementations, and that engineers are not fast enough and should simply move faster.

I’ve already been feeling stressed due to the workload, and this situation seems to be making it worse. Engineering leadership doesn’t seem able to push back effectively.

What should I do?

In this episode, Dave and Jamison answer these questions:

Hi, thank you for the podcast, I am long time listener, first time asker. Something weird is going on at my company. A colleague of my always wanted to get promoted to management, he got the opportunity, but after multiple preparatory meeting for this new promotion, HE QUIT! He did not tell what happened there, only that “it was time for something new”. Now several months later my skip level declared that he wants to be a developer again. Another manager was offered his position, which is a significant promotion (basically head of engineering), which he accepted, but after being included into high level meetings he declared that he is also QUITTING! We now have an interim Head of engineering, who declared that he is only doing this until a replacement is found. Why does no one wants to be in the management? What is happening at these meetings that people leave? Btw. the financial state of the company is not great, but not horrible, the CEO even declared that there won’t be layoffs this year. So what’s going on? I really like working at this company, but I can’t shake the feeling after these events that I am up for a big surprise soon.

Hi,

I’m a senior dev at a megacorp. I’m struggling with AI. We’ve got a lot of initiatives around it and are expected to be using it with our work. The problem is every time I try to use it I get really frustrated. It feels like working with a junior dev who doesn’t know the codebase well but knows lots of language/framework trivia. I also feel displeasure in my work turning into just reviewing some generated code and fixing it up. Especially, when you have to be very thorough because we all know that a single line of code can cause an outage. I just find no joy in this kind of work and am starting to have an aversion to it even when I just try to learn more about it.

I’m also having a hard time teasing apart the hype from the reality. I’m either hearing that “the models are so great, this is the future, coding isn’t a career anymore” or “this is hype, the bubble will burst soon and ruin everything.” Both of these outcomes seem kinda catastrophic but I have no idea which one to believe in (or maybe there’s a 3rd option?).

So, how do I overcome this aversion? How do I make sense of the hype vs. reality? How do I learn to stop worrying and love the slop?

Thanks, Dr. Strangecode

In this episode, Dave and Jamison answer these questions:

A listener named Derek asks,

I am the CTO and cofounder of a startup. Now that vibecoding is a thing, our CEO has kind of gone rogue, and and he’s vibecoding a bunch of random stuff, one of which he bought a domain for and has pushed a potential customer to pay for, without talking to our team. I feel like this is fragmenting our focus, but I don’t want to ban our CEO from vibecoding and being creative. how should I handle this without damaging relationships?

AdmiralFox asks,

Hi Dave and Jamison!

Longtime listener, first-time question asker here.

After 14 years at a consultancy firm, I’m moving to a major retailer to become their Java Learning and Community Lead. Instead of shipping code, my new role will be shipping knowledge. I will be managing learning paths, organizing internal knowledge sharing events, and help managers screen candidates. Basically, I’m moving from a ‘Maker’ role to a ‘Multiplier’ role.

I have 13 weeks of notice period (Standard European “I’m not leaving yet after 14 years” protocol) and I want to use my free evenings to prepare.

My questions for you:

How do I transition from “the guy with the technical answers” to “the guy who helps everyone else find the answers”?

How can I use the remaining time of my notice period to prepare for the people side of this role?

Love the show! Keep up the ‘quit-your-job’ advice coming (although I’ve already taken it!)

In this episode, Dave and Jamison answer these questions:

I have been with my current organization for 5+ years. I like the company and have generally had a good experience working here. However, the last several years I have not really gotten a raise except for the standard “merit raise”, which does not cover inflation, so effectively the last several years I have made less money than the year before. I brought this up to my EM who said there is no chance of the company increasing the merit raises to meet inflation, unless I get a promotion. However, my EM also said there are no promotions available.

I don’t know if this means the company knows the job market is tough and they don’t have to pay us as much, or if the company is in dire financial straits and unable to keep salaries up with inflation.

This job market is tough and I don’t know how long it would take me to find a new job, but certainly I will look. My question is basically, how can I go about getting my manager to help me level up to make myself a more attractive candidate for a future job without necessarily tipping my hand that I am job searching.

On one hand I assume he knows that I might be looking. On the other hand if the company is in a bad position and we have another round of layoffs (we have had several over the past few years), I don’t want to be first on the chopping block because it looks like I have my foot out the door.

I’m just wondering how much I should make it clear what my goals are to have my EM work with me, or play it close to the vest.

I am a Software Engineering Manager with about 12 years of experience. I am a few months into a new role at a medium sized private company. The day I joined I found out that all ICs under Staff-level are international contractors! Surprise!

My team is mostly contracted “Senior developers”. Nobody is anywhere near what I consider “Senior”. The company has a culture of aggressive performance reviews. However, I’m seeing ICs and other Managers around me who are all seriously below the bar compared to other places I’ve worked in the tech industry. I get a lot of vague pressure from the Director/CTO level to “raise the bar” and quickly exit people who aren’t meeting it. I already fired one person for performance and behavior issues, but I feel like I’m between a rock and a hard place.

If I’m truly going to hold my team accountable to my and the company’s own published performance metrics, I should fire the whole team. That’s probably not good. Alternately, I can pad performance evaluations to convince my boss that everyone is meeting expectations. This also isn’t good, but feels like what everyone else is doing.

Also, I’m a little queasy doing aggressive firing and performance reviews for contractors. The company treats them as full time employees (after hours on call expectations, etc) and I’m not sure how Earth lawyers would look at this situation.

Help!

Final wrinkle - my last two jobs I’ve lasted less than a year. I wasn’t fired but just haven’t been able to find a good fit for a little while. I’m worried that if I just leave this job 6 months in, it’ll start to look suspicious on my resume.

In this episode, Dave and Jamison answer these questions:

I’m a new listener to the podcast and work as the sole developer for a sports team, which is the only company I’ve worked for since graduating from university 8 years ago. I listened to episode 493 while clenching my teeth as you told a listener to absolutely not take the job with the European football club as a solo developer. Yikes! While I feel I have continued to grow my skillset in my role, I’m now feeling vulnerable about having no professional experience working alongside other developers or on large-scale applications.

I feel very conflicted about leaving my current company. I have a respectable developer salary for the (non-American) low cost of living area I’m in, have a great manager, and have built up a ton of good will and trust within the organization. I get all the freedom I could ask for to make design decisions, implement devops practices, try out new technologies, and make mistakes. I also find the work interesting and there’s always something else to do! I’m a little scared of the horror stories that I hear about the real dev world and don’t want to take my current situation for granted.

I would really appreciate guidance on what you think I should do. I have clear skill deficits in certain areas, but would have to give up a lot of liberties with a role change.

Listener Brian asks,

My job is mostly okay, but could be better because of the people in it. I joined a greenfield project a few years ago as my first software engineer role after transitioning from other data work. I grew up with the project and improved my engineering skills. A year ago we hired two new people. They had relevant experience and seemed to know what they were talking about in the interview, and had five & ten years of experience (aka, more than me).

Onboarding the first few months was whatever, BUT they’ve never really improved afterwards. They turn in work that has clearly not been tested or does not meet the ticket’s requirements, barely review PRs and have never (!) left any comments/feedback, and despite their level (senior+). I don’t really trust them to work on anything more than the smallest, simplest stories.

I’ve provided specific feedback in PRs and in performance reviews (sometimes very low-level and specific, and sometimes very high-level about guiding questions or principles), but nothing’s changed. I’ve felt frustrated, drained, and confused - why is it such a struggle to get someone with an entire decade of development experience to turn in a straightforward PR? One other teammate has admitted (privately) that some work was sloppily done, which is consoling but otherwise I’m not sure if it’s bothering others as much as it does me.

They’re offshore so maybe it’s just a communication thing? The rest of the team has been on the project since the beginning so maybe we’re poorly set up for new devs. I have high standards for myself and others and I’ve always been the most junior developer on the team and am new to the senior role.

Am I just being a perfectionistic jerk? Is that a bad match for (essentially) junior teammates? Should I just reset my expectations and accept that their level and years of experience don’t translate into high performance? Thanks for any insights.

In this episode, Dave and Jamison answer these questions:

‌

Hi Dave and Jamison,

Internal dev asker from the second half of Episode 441 checking back in. Your “ask what scared the previous dev” advice in particular has paid off handsomely; I now carry around a little book of eldritch warnings and, somehow, people keep bringing me their unknowable monsters to interpret. It’s almost as though the previous dev knew these sorts of things would happen! I didn’t set out to acquire Lovecraftian knowledge, but here we are, still in one piece.

Today’s puzzle: getting busy humans to test our stuff early, while feedback can still make it into production. We’re trying to build a culture where people will poke at a rough prototype now, instead of filing a Very Concerned Ticket three hours before release. How do we get people to test and provide feedback earlier? Do we stay disarmingly warm, promise tiny time boxes, and make a public show of “you said / we changed” until participation feels like the default? Or do we wave our terminal windows around threateningly on a screen share and promise doom (and minor annoyances) until they comply?

Thanks for lending sanity to the abyss, —An increasingly arcane internal apps dev

I have been listening to your podcast regularly and am inspired by how the podcast and the community have grown.

I am a developer with over 10 years of experience and have moved to Sweden from a country outside Europe, with the ambition to build my long-term life and career here.

For several years, I have tried to take that step myself, but often encounter the same obstacle: I am told I need experience as an engineering manager — but without the role, I can’t get the experience, and without the experience, I can’t get the role.

I have invested a lot of time and energy in developing myself: learning about leadership, coaching, communication, and team dynamics.

Despite this, I find it difficult to see a clear path forward. With everything happening in tech right now, I sometimes feel stuck and uncertain how to break this cycle.

My question is: how did you take your first step? How can one realistically enter an engineering manager role when the door seems closed without prior experience?

Thank you for creating such an honest and inspiring podcast. It already means a lot to me — and to many others, I am sure.

In this episode, Dave and Jamison answer these questions:

I’m a relatively new people manager and I really struggle when it comes time for performance reviews, or even regular praise or critical feedback in one-on-ones, because I can’t help feeling like an adult “talking down” to another adult, regardless of whether the feedback is generally positive or critical and instructive. Something about it all seems so patronizing to me. How can I approach this stuff with a different mindset?

Hello D & J! Quick one from your biggest fan!! This week (Tuesday 6th Jan 2k26) I was promoted to Tech Lead of our team. In my new role, I have done no work *cries*, I’ve spent all my time assisting team members, unblocking QA, dealing with ad hoc requests from product/stakeholders…. I asked the previous tech lead is this what they did? They did! And they said spent their personal time to complete stories assigned to them.

Is this really what a tech lead does?!?!! Helpppp

In this episode, Dave and Jamison answer these questions:

Listener Tom says,

I’m a software developer with six years experience, mostly at small startups with engineering teams anywhere between 2 and 10 developers.

Because these startups have been small, most of the interviews were really casual. I’d speak to either the CEO, or CTO about my past experience, and we would talk about the direction the company was heading, and whether I’d be interested in joining. They felt less like interviews, and more like free-flowing conversations.

I’m now back on the market, and I’m looking at larger, more established tech companies. I can get past the tech interviews just fine, but I’m struggling with the soft-skills interviews. Compared to what I’m used to they’re a lot more structured and it feels like they’re looking for answers that fit a certain criteria and format.

What advice would you give to someone used to interviewing at small startups, but now interviewing at larger companies?

I took an unpaid full stack internship role at a new non-profit, and it turned out to be a team completely made of other interns. There isn’t a single experienced engineer on the team. I have gone way deeper than originally intended and am now functionally a founding engineer where the founder pretends I’m a lead engineer and calls me an intern. The founder is also hellbent on having the highest development velocity, and sometimes will contribute their own AI-generated code, often bypassing the review process especially for things I’m not comfortable signing off on like an AI-generated TOS and user agreement.

I recently learned that the founder is not viewed highly in their local area after a scandal where they were accused of scamming a large sum of money, which is likely why they are doing their free community projects they started now in order to save face. This has backfired, and now people are calling their projects “AI generated schemes” despite the services being completely free.

I’m not sure if I should continue contributing to these projects anymore. Since the founder rushes things to get done, walks through legal areas with their AI “lawyer,” and has a bad image, I’m worried about whether my resume will be taken seriously by potential future employers.

Should I continue working for this person or is the experience not worth it?

In this episode, Dave and Jamison answer these questions:

Hello gentlemen, long-time listener here, and I’d love your take on something that’s been keeping me up at night.

The high powered boss that I report to is someone I genuinely like and respect.This manager is smart, kind, honest, and overall great to work with. We have a solid relationship. I also come from big tech, so I sometimes feel I have better experience around managing projects and keeping teams organized. However she recently shared in confidence that there’s a chance of resigning in the next few months. and when I asked what keeps her up at night, the headache did not seem so big of a deal to me.

But ever since hearing this news, I’ve been catastrophizing the next few months. I’m not ready to job-hunt. At the same time, if this manager does leave, it could be a really good opportunity for me to step up.

So here’s what I’m struggling with: 1.How do I position myself for a potential promotion without making it seem like I’m going behind my manager’s back or trying to undermine them? 2.Should I quietly start looking for an job anyways, just in case? 3.And how do I stay sane when this might all be for nothing and the manager might actually stay?

Would really appreciate your wisdom on how to navigate this without losing more sleep.

Thanks for everything you do!

I’ve worked as an engineering manager in a few big companies in Berlin, but after too much corporate politics bs, I flipped the fingers and quit. In the 2025 economy, that wasn’t the smartest move — finding a new job has been harder than ever.

I’ve been focusing on smaller companies, ideally under 100 people. Ideally less politics, more autonomy. But now I’ve got an offer from Google in Bucharest — nearly double the compensation what I could get in Germany. The catch? I’d have to leave my strong circle of friends in Berlin and start over in a new city, new country.

What would you do in my place? Brainstorm with me please 🥺

In this episode, Dave and Jamison answer these questions:

Dear Damison and Javison, I work at a very small startup (<10 engineers) and am trying to hire 2 engineers. I’m doing the intro/screener interview for these roles & am working with a recruiting firm to source candidates. My problem is that sometimes my intuition tells me that a candidate is not going to make it through our hiring process, but I can’t articulate why. Our hiring process is neither cruel nor unusual, and on paper these candidates have the skills and experience we’re looking for. But I feel a duty to let the hiring process do its work; I want to be principled about this. For reference, I’d say I screen out 2/3 of recruiter-screened candidates, and of those remaining, 2/5 of the candidates have the je ne sais quoi for which I should be saying non, merci. One made it all the way to reference checks! Do I need to do a better job rejecting these nice, smart people instead of wasting our time? Also note that I am not a manager, and although I have a lot of experience interviewing candidates, this is the first time I’ve done the *first* interview with candidates (first-ish; the recruiting firm interviews them first).

Listener Jeppe says,

Hi Soft Skills nation,

What’s the accepted practice with staying or leaving the private chat channels of my previous team?

I work at a large company and recent switched teams internally. I helped establish the team and got along really well with them. The transfer was on good terms (they invited to their Christmas dinner after the transfer!) and my managers agreed that I could always help my old team in case something came up.

I’m still in the internal chat channels for my old team. I love hearing what they’re up to and catching up. They explicitly told me not to be a stranger, so I’m not! However, I don’t think there’s much business value in being in their channels. Sometimes we have more technical chats about internal tools, and it would probably be better if I had those discussion with my new team.

What should I do? Should I just stay until their manager decides to kick me out? Should I be proactive and talk with the manager about it? Should I leave a teary message about how I’m going to miss them all (even if I see them regularly at lunch and outside work sometimes)?

In this episode, Dave and Jamison answer these questions:

Hey Guys, long time listener, first time asker!

At my BigCorp Co., whenever I talk to my skip level about my concerns, it seems we are playing the ‘Gloom Olympics’ every time we meet. I’ll mention I worked late, and he’ll counter with, ‘That’s nothing, I haven’t slept in three days!’

This repeated lack of empathy is demotivating and I don’t think I have had a fruitful discussion with him.

How can I tackle this? How can I feel heard?

I’ve decided to leave my current job as a software engineer at a large retail chain. This is my first out of university, and I’ve been here three years.

I’m interviewing for two other jobs: one as an engineer at another large retail chain on a team, and another at a world renowned European football club.

That job would be very different. I’d be the first internal dev hire ever, and I was told I should expect no other devs to get hired for 2+ years. I’d write my own tickets and review my own prs. The project would be to build a dashboard to manage the players - drug testing, injuries, rosters - internally.

What should I do? Feedback & mentorship were central to my growth at my current job. I won’t have that at the sports club. My concern is I go to the football team, drink a lot of beer & have a great time, but after 3 years of being my own boss, I’ll think I’m the greatest dev ever but really not have kept up to date with modern trends, forgotten how to take feedback, and written a lot of 💩 code.

In this episode, Dave and Jamison answer these questions:

Listener AWS multi-region is not real multi-region, ask me how I know asks,

We’ve recently acquired some bright-eyed and bushy-tailed new grads. What have you found to be the most effective way to onboard new grads into development roles? How has it changed (if at all) since the advent of LLMs? I want to make sure my new-grad crushing machine is operating as smoothly as possible considering the recent advancements in developer tooling. Those new grads won’t crush themselves!

Listener Taso asks,

Early in my career I was all-in on startups. Then I spent seven years in big companies in leadership roles. I learned a lot, but the politics and the pace were so slow that at some point I’m pretty sure geological processes were moving faster than our release cycles. So I finally flipped some metaphorical fingers and quit. Since then I’ve been interviewing almost exclusively with startups… except Google, where I somehow ended up with an offer on a team I’d genuinely enjoy. You’ve both bounced between big tech and startups—if you were in my shoes, how would you think about choosing between the two?

In this episode, Dave and Jamison answer these questions:

I handed in my resignation this past Monday. During the conversation, my manager confided in me that this coming Wednesday, 25% of the workforce is being laid off.

For context, this is the second round of layoffs. The first round happened a year ago and was a disaster. It was announced via an internal video the night before, but the CEO forgot to mention that the affected employees had already been notified privately. This caused mass panic; thinking they were next, many experienced engineers immediately brushed up their resumes and jumped ship voluntarily. Even my skip-level manager was in the dark. Shortly after that chaos, we were acquired by an American Private Equity firm.

Morale has been at an all-time low ever since, and the writing has been on the wall all year.

Now I am in the awkward position of serving my three-month notice period while walking through the ruins of my company. I am the “lucky one” who quit voluntarily two days before the hammer dropped to join a different company for a massive raise and promotion, while my colleagues are about to lose their jobs.

How do I navigate the next 90 days? How do I interact with the survivors who are likely furious and overworked, knowing I’m already checking out?

Sincerely,

Rearranging Deckchairs on the Titanic

Hello!

I have a bad manager, like really bad. She gets the whole team together to say “so and so is getting laid off tomorrow, or in a month, don’t say anything”. She openly shares employee compensation in 1-1’s, gossips about her boss and team members and takes feedback as personal attacks.

Would you believe me if I said that no one trusts her?

What should I do? I want to contact HR but I have never talked to HR before in my career. I know I can’t tell her because engineers who have offered feedback on team dynamics, or general professionalism, get yelled in 1-1’s. Is this something worth taking to HR or do I just live with it until… I get a new job? If I do say something what do I say? Do I bring up the distrust she has created amongst the team or do I keep it to the poor judgement and unprofessionalism? Do you want to write the letter for me? Yes!? Thanks!

In this episode, Dave and Jamison answer these questions:

Hi Dave and Jamison, I’ve been in QA/QA automation for 13 years now with a CS degree, and I’ve been trying to change my role to a software developer for a while. My only issue is that every time I brought my career aspirations to my managers they seemed to “not care” or give vague answers to “kick the can down the road”. In the past I fully demonstrated I can do the work by submitting bug fixes, writing and deploying a few microservices by myself (all product feature work), on top of performing my QA duties. I get high marks in my performance reviews, but that doesn’t seem to be enough! I also seem to attract some resentment from my team (silently but it’s noticed) as they see a QA trying to soak up their dev work and I get a strong “stay in your lane” vibe. I do it to help them, not take all of their work. Any advice? Am I approaching this the wrong way? And what would you do in my situation? Thanks and all the best!

Hi!

Three years ago, I relocated from a third-world country to Europe for work. I tend to undersell myself a lot. I know I am a competent, hard-working, and smart engineer. I have strong opinions and can evaluate trade-offs. I can participate in discussions about complex systems, and I have experience managing projects.

But sometimes I’m afraid of looking dumb and scared of confrontation. This means I rarely voice my opinions or suggestions. I often let go of them at the slightest objection, even if I believe the other person is mistaken. Whenever I speak or comment on a subject in Slack, I always use phrases like “I’m not 100% sure”, “as far as I remember”, or “I have to look it up but I think … “. These would not matter If I was showing my confidence through other means like participating in discussions confidently, but these all add up to create an image of someone reliable in getting things done, but not reliable at taking more responsibility.

I was not like this before moving. Occasionally I struggle with the language when in big meetings or talking about complex matters, but I’m comfortable with English. It has an effect for sure, but it is not the cause.

I’m going to start a new position and I want to have a longer career there. But I’m afraid that I can not give myself the head start I know I’m capable of. How can I improve my own personal onboarding process and let my new colleagues and manager know how lucky they are to have me on their team?

In this episode, Dave and Jamison answer these questions:

Hey Jamison and Dave, love your show!

A question for you guys coming all the way from the Netherlands 🧀

I’ve started as a software engineer in a gambling company lately and the moral aspect of it bothers me a bit.

And while listening to you talking about the importance of accessibility in the last episode (#488) I came up with this moral dilemma: should a developer push for making a gambling app more accessible for users with disabilities or better not to? 😅

Thank you 🖤

Listener Arie Marie asks,

What are some good ways to research prospective employers to see if they have a strong commitment to ethical and human values? What are good questions to ask prospective employers during an interview? How can I be a developer and do what I love, and know that I’m not making the income inequality greater? How do you develop a lens to look at a company and discern it’s positive impact? How do you know if you’re making the world a better place?

In this episode, Dave and Jamison answer these questions:

Hey Dave and Jamison,

Big fan of the show — listening from Portugal! (Proof that even across the Atlantic, software politics are universal.)

I’m a tech lead, and lately I’ve noticed a culture where people seem to care way more about how things look than what actually gets done. It’s like the appearance of productivity matters more than real impact. Honestly, it drives me nuts!!

I know politics are part of any organization, and way more in a leadership role, but this feels excessive. As someone who values substance and solid engineering, how do I deal with or influence this kind of culture without losing my sanity (or turning into one of those “optics-first” people myself)?

Thanks for all the insights and laughs. Kudos from Portugal!

Listener Charlie says,

I’m fresh out of college at my first software engineering job. Several months ago I was appointed the accessibility champion for my team. I proposed a few items in the quarterly planning session, but I think it wasn’t enough. My project manager called out our whole team, but I think it was mostly aimed at me.

I’ve been struggling with creating Jira cards, shaping with the team, writing a11y guidelines, etc. It’s tedious and I’m not really familiar with this kind of work. How can I get better at the “other stuff” besides just writing code?

P.S. I volunteered for this responsibility 😩

In this episode, Dave and Jamison answer these questions:

“My manager insists on a weekly 1:1 with me, but he rarely pays attention. He’s often on his laptop, texting, checking email — basically anything but listening. I’ve tried sending agendas, rescheduling, reducing frequency, waiting until he’s less busy — nothing helps. I’ve even started sitting in silence until he notices I’ve stopped talking, but that only works for a minute. This has caused real problems. For example, he almost had me cancel a million-dollar project because he misheard me say “Java” instead of “JavaScript.” When he finally realized I was right, he said, “Every time I heard Java I automatically tuned out.” How do I handle a 1:1 with a manager who won’t pay attention, without risking my work or my relationship with him?”

“I’ve worked for a big retailer for 10 years now and I used to really enjoy it. I liked my team a lot, problems we worked on, technologies we used. Unfortunately the last few yours brought a few rounds of layoffs and my old team doesn’t exist anymore and the new team is pretty much awful. They’re all on the East Coast, while I’m on the West Coast. I’m required to work EST hours but also to commute to the office 5 days a week and sit there alone and talk to my team on zoom. I’m a staff software engineer and I haven’t been programming much for the past year. Most of my time is spent in calls, I start every day with the same 3 calls. I live 50 miles from the office and I take a company shuttle that leaves at 7am. I’m required to join the calls from my phone. I leave for work at 6:30am, I’m back at home at 6:30pm. A few times a week I need to do deployment at 10pm. I tried speaking to my manager and to my director. They don’t care. My every attempt to improve our processes is met with opposition. My manager is afraid of changes. I can’t believe this is where I am but I’m too tired to prepare for job hunting. I can’t afford to quit. I don’t know how to get myself on track and dust off my programming and interviewing skills. I’m praying they’ll lay me off so that I can use the severance to do all those things. But this isn’t really a plan, it’s wishful thinking, and I’m afraid that my career options are getting worse by the minute. Do you have any advice on how to get myself out of this hell hole?”

In this episode, Dave and Jamison answer these questions:

I work at a big tech company on a remote team of about 10 people, and most of them have been here for 5+ years. I’m in the “newer” half of the team with 4 years here. My problem is, in group meetings, absolutely NO ONE talks. I mean zero small talk, they have trouble responding to simple yes or no questions. Everyone participates thoroughly when it’s a technical discussion, but it’s clear no one has any interest in speaking more than necessary. We used to have one super talkative guy on our team, and even then it was mostly silence to his chats about his weekend. Is there anything I can do to get these people to speak at least a little bit? It feels insane how little I know about these people after 4 years.

P.S. even in one on one chats, almost all of them shut down small talk

A coworker told me that I should be having quarterly one-on-one’s with my skip to make sure they’re aware of all the good stuff I’ve been up to and my goal of promotion. This sounds correct, but feels weird when I think about setting this up. I haven’t had much direct communication with my skip, just a few responses to his questions during design meetings, but nothing else really. How do I feel less weird about this?

In this episode, Dave and Jamison answer these questions:

What signals do you look for when interviewing candidates? I’ve helped interview many people at this point and almost all of the engineers that I marked as “hire” that we brought on board ended up being low performers and were eventually managed out. I wasn’t the only one who approved them either, so not all the blame falls on me, but I’m really doubting my ability to assess talent.

Is hiring inherently just this difficult? Is there anything I can do to improve my judgement or screening approach?

Hi Dave and Jamison,

A coworker on my team won’t stop creating AI generated memes.

We’re a remote team and every meeting he shares memes in the chat whilst we’re trying to have productive conversations. He does this in any type of meeting, including all-hands meetings with C-level execs. On smaller calls he often hijacks it to share his screen and show us a meme he just created about something that was just said.

It started off funny at first. But it’s now a constant distraction.

I find it frustrating because I don’t see how he can be paying attention and contributing to discussions when he’s busy making memes. And, I also don’t appreciate seeing AI versions of my own face being shared into public Slack channels.

How can I address this without sounding like I am anti-fun?

Love the show, been listening for many years, keep up the good work!

In this episode, Dave and Jamison answer these questions:

Hi! Love your show and how casually you talk and make fun of everything! I started my career as a freelancer and then joined a mid-size software development company to learn how the sausage is really made, salary wasn’t that important back then. A few kids and a lot more expensive lifestyle later the compensation has become more motivating, but I’m not sure how to sell myself to my manager if I don’t feel like I deserve a high salary myself. (The manager decides the salaries for all our team members.) For years I’ve been focusing on my family and other life stuff, so I’ve spent a looot of working hours not working and basically doing the minimum progress acceptable. Slow progress has come up once with my manager, from which I wiggled out of with various excuses. I’ve realised that this way of working isn’t really fair for the company and my teammates and I’ve started to take this job and my career seriously in the last few months. The company and everyone working there are super supportive and it’s been a terrific experience for all of those years. I’ve gotten a raise multiple times with always me initiating that conversation. There aren’t any clear metrics to improve that directly ties to the salary: I’ve asked my manager about it and the answer was vague like “we have this local salary survey that we take as the base and work from there”. So long story short: how to ask for a raise while not feeling like a criminal since I feel like I haven’t earned the salary I had thus far?

I’m a team lead who’s growing increasingly frustrated with my project manager. Every planning conversation ends up in my private DMs, no matter how many times I’ve asked him to move these discussions to the team chat.

When he messages me one-on-one, my team loses visibility into decisions, questions don’t get addressed openly, and important context just evaporates. It’s not only slowing us down, it also makes me feel like the burden of relaying everything falls squarely on me.

I’ve tried gently redirecting him back to the shared space, but he keeps defaulting to my DMs. How can I get him to respect the boundaries of team communication without damaging our working relationship?

Sincerely, Lost in the PM’s DMs

In this episode, Dave and Jamison answer these questions:

How would you handle a situation where a team forms a negative opinion about you from day one — without any clear reason and without ever giving you a real chance to prove yourself?

Even when you contribute technically, your suggestions are ignored… until someone else repeats the same thing and suddenly it’s considered valid.

Is it possible to stay in that kind of environment without becoming bitter or burned out?

Can you keep contributing professionally — or is it healthier to just walk away?

You guys are awesome. Jamison, I interviewed with you and it was lots of fun and productive. Which is really rad.

Now… I just landed a 12-month contract in big tech role. It’s perfectly aligned with my long-term career goals. My current fintech FTE is perfectly opposed to my long-term career goals.

The question — how unethical / despicable would it be to start one week of PTO at my FTE on the same day as Day One at my contract role so that I can onboard without distractions and then put in my resignation upon returning to my FTE? What about two, three, or four weeks of PTO?

Also… are two-week notices still the default still in 2025?

Also also… I promise I’m not AI — I’ve been using em dashes since the 20th century.

In this episode, Dave and Jamison answer these questions:

After a year of trying, I recently got promoted to staff engineer!

It’s great to receive recognition for my work, but i’m not actually very happy, because I only got a 4% raise! I spoke with a former coworker about how much a staff engineer in my role should expect, and he said that he would be insulted by less than . My comp is now slightly below !

In addition to this, times are tough for the business, so it seems unlikely that we’ll get annual bonuses, meaning I likely won’t even get to appreciate the larger target staff bonus! What a bummer!

How should I approach this? A year and a half ago after getting a below inflation raise, I was told I was at the top of my level’s pay band and would need to get promoted if I wanted to go much higher. Now that I’ve gotten promoted, it seems like that wasn’t true! I should be grateful that I still have a job and got promoted and got any increase, but I feel like I’m being short changed! How can I talk to my manager to see about getting more money?

My company does not address complaints. Here are two examples.

On my first day, the lead engineer told me not to participate in the project. He was impossible to work with: He’d hold up PR’s for 3 months because of linting and prettier rules. Eventually, I figured out he was exceptionally insecure and wanted no feedback or anyone to expose his technical weaknesses. I conflicted with him a lot and got shuffled to another department.

My 2nd example comes from a trainee. I helped him out everyday after standup for 30 minutes. How he passed his interview, I don’t know. He didn’t know what a semicolon was after a 4 years bachelor in computer science and 6 months of being a trainee. I complained to a friend at work who had, I didn’t know, interviewed the trainee. My friend was surprised, and so we hopped on a call with the trainee who didn’t recognize my friend. After snooping around on social media, we found the guy who had done the interview, the trainee’s brother. I told HR & my department head. Nothing happened.

Here’s the question: Getting kicked out of a department ruined my confidence. I have a safe, secure job where there’s no pressure. But my firm doesn’t address complaints properly. Time and time again, people will complain about the linting/prettier guy or other issues like the trainee and nothing is done. Should I leave? I work on a greenfield project here. Switching to a (likely) legacy codebase I didn’t build and dealing with higher pay/expectations is very daunting.

In this episode, Dave and Jamison answer these questions:

Hi Dave and Jamison,

After fleeing a sinking ship of a startup, I became a solo developer at a medium sized college. This role has really allowed me to expand and grow in ways that I haven’t imagined, but I have encountered an interesting issue I didn’t have in the startup world: there isn’t much to do.

At my one year mark, I was promoted into a management position, but with no direct report. I will soon have an employee under me doing data integrations. My manager has been reluctant to give me data integrations work despite knowing that I want to understand what my employee will be working with.

I’ve found some of my own projects, but I’ve completed them all. I’m getting bored. I’m a competent developer, learn fast, and get things done quickly. Recently I’ve been planning an upgrade to some of our legacy code, but it will take probably a year or more to complete.

Some former colleagues reached out about working with them for a substantial pay bump, but I don’t like the idea of leaving after just over a year and a half. Do I keep riding it out here, or is it time to start looking else where?

Thank you both for this wonderful podcast. Its a joy to listen to on my walks. I’m sure I get stared at when I try to hide a laugh or grin from the amazing list of Patron names and your commentary.

I was recently terminated a few months before my 1 year vesting cliff as an IC2 for being days (not weeks) late on 3 or 4 stories. The late ones were defined incorrectly by management, or were for paying technical debt created by senior engineers, and my manager knew this. I had no IC2 or IC1 peers on my team for comparison. My performance review for the first half of 2025 was not released to me, I was fired when I would have seen it. This means the only reasoning that management has shared with me was my late work. In 1 on 1s before, my lateness has been something my manager has mentioned, but never a warning of termination (or a “pip” as some call it) and no indication that it’s anything more than an area to improve. The org has made poor decisions that left them tight on funds, and I feel the most financially responsible thing for them to do was fire me rather than give me a warning which would let me hit my cliff or lay me off where they’d give more on my way out.

Had I been pipped or laid off, I would not be asking about this. Should I go with the confusing justification that my boss was truthful in his attribution of my firing without warning to my lateness (and can you help me understand why that’s professionally justified)? Should I go with the disheartening approach and brainstorm other shortcomings that would better justify an unwarned firing, possibly spurring professional growth or a career change? Or should I say I got instafired because of penny pinching and opaque management?

In this episode, Dave and Jamison answer these questions:

(follow-up from question 449)

Hello. Return question asker here. You answered my question from episode 449 “my tech lead ignored my warnings”. I want to give a follow up. I sat by and did not say anything else, he shipped the broken feature, and it broke in production. Instead of fixing it he rose the threshold on the datadog alert so high no one would ever get alerted. Then he left the company. When talking to my manager about the bug we agreed it was part of that refactor and I said “I warned him” and they shrugged it off.

I assume he is also a long time listener of this podcast and took the age old “leave your job” advice. Kudos.

(question below)

I am here for more than just an update though. I am starting to think I understand why he left. It sucks here. I am the lowest level engineer on my team and have not been promoted for the last 2 years because “there is no money”. Ok, fine, I understand that the economy is tough. However I have increased the revenue of my department by 4x, have lead the development of our flagship product this entire year, have been teaching engineers new technology and have been working 60 hour weeks. On a team of 6 I do 33% of the work. 2x what is expected of any one engineer. This last week I received a “meets expectations” performance review. And I am mad. In 1-1’s with my boss they explicitly tell me “I am not saying to sandbag but just do less work. Your teammates are getting compared to you and its making everyone look bad.”

Don’t worry Dave and Jamison, I am going to quit this job so I don’t need that advice, however you can throw it in if you like, but I’m wondering how do I handle this? Do I confront my manager in the next 1-1 with the data and say I am underleveled and underpaid or do I just take the advice to do less and coast til I find another job? Do I share with HR in the eventual exit interview that this was the straw that broke the camels back?

I’m returning to work after a very long absence due to personal issues. How can I ramp back up quickly? It’s a weird situation because I’m not exactly joining a new job, but it’s been so long that it basically is. I haven’t even opened a code editor in months!

In this episode, Dave and Jamison answer these questions:

Hey skillet nation, long time skilletee first time skilleter here. I started at a scale up about 6 months ago and recently, I was asked to help with a project that was greatly behind schedule. The folks responsible for the original system are no longer at the company, and the team currently attempting to get it over the finish line have struggled greatly. The codebase is full of performance issues and the infrastructure was not set up to scale. Basically things are bad.

Since joining, I’ve helped draft a plan to fix most of the performance issues, and then incrementally improve the architecture. Things are going great, except for the fact that we’re 6 weeks out from our deadline with a burnt out dev team.

To resolve this, our CTO hast started to rapidly hire contractors to “help out”. As one might expect, this has only slowed us down. But our CTO, lacking trust in the previous team, has found the promises of the contractors very alluring. I, on the other hand, don’t love the idea of building this greenfield system with temporary workers and then dropping it on an already burnt out team to maintain.

Am I overreacting? How would yall handle this scenario? How can I convince our CTO that “the mythical man month” still applies here, regardless of what the contracting company says?

Listener k pop demon hunters asks,

Hello! I’m a senior engineer in a big tech company. I recently got a bad annual review from my manager due to the fact that I caused a delay happened in my last project. It was a compliance process involving multiple stakeholders and one of them didn’t give me an immediate approval for the step they owned. I promptly updated my submission for review after I got the initial feedback, pinged them in a messenger and sent a reminder mail every day until I got an approval from them. I feel absurd that I got a bad review due to the delay of external process. What could I have done this better?

Thanks for the great show. It’s making my commute more enjoyable. Keep it up!

In this episode, Dave and Jamison answer these questions:

Can you coach self-awareness? I manage someone who seems to believe their skill set is on par with their teammates, regardless of their constant PR feedback regarding the same issues over and over, the extra attention they are regularly given to help them overcome coding challenges, and the PIP they are currently on to address these issues (and others). What are some approaches I could take to help steer them to better understand their areas for growth when explicit measures don’t seem to get through?

I work at a small 10-person startup. The company has absolutely nothing to do with AI, but one of the founders has gone full evangelist. He genuinely believes AGI is arriving this year and that there isn’t a single job, task, or process where an LLM isn’t the obvious tool.

Day in, day out, he’s posting links to random AI products with captions like “looks interesting 👀”. It’s like Clippy got a16z funding, moved to Shoreditch, and now spends his days flogging us apps we didn’t ask for. He also insists we “use AI more in development,” despite not understanding development in the slightest.

The routine is always the same:

He asks the engineering team how to achieve some goal (always involving an LLM). We give a sensible answer, weighing complexity, cost, feasibility. He comes back with a massive pasted transcript: “here’s what ChatGPT thinks.” We pick out what’s actually useful, quietly bin the nonsense. He takes our response, shoves it straight back into ChatGPT, and returns with another transcript: “here’s what ChatGPT thinks.”

This has been going on for months. At this point, he’s basically a human middleware layer for ChatGPT — no analysis, no original thought, just endless copy-paste recursion. I’m genuinely worried he’s outsourcing his entire thinking process to a chatbot and slowly losing the ability to engage with ideas on his own.

How do I tell him — politely but firmly — that this is both rude and a bit tragic? And, half-serious: is there a prompt injection I can use to jailbreak my founder back into being an actual founder rather than a ChatGPT relay bot?

In this episode, Dave and Jamison answer these questions:

Hey guys,

I have been working for four months at my job and I already don’t like it.

This is my first job out of college and I work as a C# backend engineer for a small B2B SaaS company. I really think this company is a dead end. There is a lot of technical debt and antipatterns and we have no automated testing whatsoever. Most of our time is spent manually debugging but no one wants to refactor.

I’m already thinking about working somewhere else. However, it took me a while to get this job, and I don’t think the market has gotten any better since. I’m trying to decide whether I should focus on applying to jobs again or if I should work on a bunch of side projects and open source to stand out better. On one hand, I can learn new technologies on my own to make me stand out for my next job, but on the other hand, I feel like as long as I stay at this company I am wasting time, since I’m not learning from my job. I want to switch to more distributed backend engineering in Java anyways, but I’m not sure how to go about it.

Listener Ghani asks,

“I’m a mid-level software engineer who has trouble communicating with my engineering manager and product manager when there is unclear or missing information about an assignment/story/project.

They answer with hostile/dismissive tone/non-answer (e.g it’s on the jira-card, epic, etc). They course correct when they have the information later, harshly

my impressions were

they don’t have the information at the time they expect engineers to make decision they expect engineers to know something they don’t (e.g architecture, infrastructure, past decision, plans, etc)

I really want to look for where we can have a safe exchange of information. How can I do this?

In this episode, Dave and Jamison answer these questions:

Two junior engineers recently joined my team, and I’ve been tasked with onboarding them. This is the first time I’ve been responsible for junior devs, and I’m struggling with how to coach them up. For context, we’re a small engineering team where self-sufficiency is highly valued; processes/overhead is minimal, and we have a real bias for action. As such, when they ask me for help, my intuition is often to respond “Keep looking, figure it out!”; in my mind, walking them to the answer would be anthithetical to our culture and set the wrong expectation for how they should go about solving problems. This is especially the case when they throw their hands up and say “Help, I’m stuck, what do I do”. Though, I don’t want to be so unhelpful that it frustrates them or legitimately impedes their progress. I’ve also noticed them sometimes going “behind” me to ask others engineers for help, which makes me think that I am being too unhelpful. The number one question I ask myself is: How much help should I be giving them? How do I find the right balance here?

I’m seeing more and more AI slop in my org’s code base that I fear will have meaningful impact on the integrity and maintainability of the application we deliver to customers. Everyone talks the talk of “Ultimately, it’s the implementer’s responsibility to audit and understand the code they ship,” but few seem to walk the walk. How can I best work with my team to address this, especially in a context where leadership is prioritizing velocity?

In this episode, Dave and Jamison answer these questions:

Hi!

I’m currently working for a big tech company and I’ve just accepted an internal transfer to another team. At the same time, an external company reached out, offering me a job for a role I’m interested in and twice my current compensation.

I’m not sure what to do. The offer from the new company is very interesting and I wouldn’t think twice at accepting it if I still was in my old team. But now that I’ve accepted the internal transfer, I don’t know what’s best for my career: stay with my current company and lose out on a great offer, or go with the new company but likely burn bridges with my current manager, possibly closing off future opportunities to return to my current company (something that I’m open to in the future)?

How do I politely but firmly stop a project manager colleague, who has vast open plains in their calendar compared to my Tetris-stacked week as a senior software engineer, from parking themselves at my desk for 45-minute vent sessions about everything that’s frustrating them about our project? It’s never just the weather; it’s a full-blown TED Talk on their annoyances, which makes me feel defensive and frustrated in return. I’ve tried the headphones-on-and-look-intently-at-the-screen-approach, and sitting on the other side of the office, booking a smaller meeting room to hide, and carrying on working as they tell me about their troubles with both leadership and members of my team. Nothing seems to work. They find me every time. Is there a way to escape without faking my own death or staging an office fire drill? Thanks!

In this episode, Dave and Jamison answer these questions:

Hi Dave & Jamison,

Long time listener, first time google-form filler outer!

I work in a hybrid role as a lead developer and manager of a small team (less than 5). I’m new to management and most of ny experience so far has been with smart, motivated engineers. . .

UNTIL! My new recruit is driving me crazy, they are clearly very capable, but just do not do the work. They are frequently late for work, frequently sign off early, and constantly evasive when I ask for updates. I have spoken to them about these issues a bunch, and everytime they are apologetic and say they “have some personal issues but are working on it” - and nothing changes. Urgh!

I am pretty sure I will have to fire them, but I feel terrible about it! I know I can’t keep them on and pay them to do nothing, but what’s the best way to let somebody go? How do I break the news to the rest of the team? How do I avoid feeling bad for the rest of my life?

Yours guiltily,

Anon

A listener named “erm what the sigma” asks,

Do you have any advice on how to reduce the ramp-up time when context switching? I’ve always felt like context switching comes at a high cost for me—it just takes so long for me to mentally shift between tasks. This wasn’t much of a problem before, but I’ve recently become a tech lead and now my calendar is cluttered with meetings (why did I ask for this again??). I’m struggling to complete my coding stories because just as I hit my stride, I get pinged by someone on my team to help them or have to jump into yet another meeting. pls send help

In this episode, Dave and Jamison answer these questions:

Hi Jamison and Dave!

I am not a developer, but my question is hopefully transferable. I sit in between lawyers and developers. I advise on technology that can be applied to legal processes and I support our teams in using a range of platforms and AI tools to be more efficient across their work.

I have ADHD (late diagnosis at 22) and often have trouble with executive function, remembering details, progressing large projects with no deadlines, and remembering verbal instructions.

Have either of you ever had a neurodivergent person on your team? If so, how did you support them? What environment helped them to work best? Also, what frustrations did you have and how could they have mitigated them?

Any help would be appreciated to help me avoid driving my manager insane (I live in constant fear that one day she will snap and I’ll be fired even multiple years in). 😂

Hi Dave and Jamison, you’ve made my runs very enjoyable over the last years, thank you so much for that - even though I doubt that laughing out all the time is great for my performance.

I’ve been in web development for 7 years now and a Lead Fullstack Engineer at a consulting firm. Being a “lead” currently only means that my team mates seek my opinion and guidance on topics, without me having any increased responsibility. In September, I’ll move countries (Europe to Australia) and will be on parental leave until mid ‘26 when I’ll have to look for a new job down under. I feel quite stressed by recent developments (AI), already have the feeling of not being able to keep up with all the new things (ask my 300 open tabs of articles I want to read), and fear that I could loose touch in my time off. How can I deal with this FOMO? And which topics would you look into in the upcoming months if you were in my place?

Show Notes

In this episode, Dave and Jamison answer these questions:

I’m the CTO of a small startup. We’re 3 devs including me and one of them is a junior developer. My current policy is to discourage the use of AI tools for the junior dev to make sure they build actual skills and don’t just prompt their way through tasks. However I’m more and more questioning my stance as AI skills will be in demand for jobs to come and I want to prepare this junior dev for a life after my startup. How would you do this? What’s the AI coding assistant policy in your companies. Is it the same for all seniority levels?

Hi everyone! Long-time listener here, and I really appreciate all the insights you share. Greetings from Brazil!

I recently joined a large company (5,000 employees) that hired around 500 developers in a short time. It seems like they didn’t have enough projects aligned with everyone’s expertise, so many of us, myself included, were placed in roles that don’t match our skill sets.

I’m a web developer with experience in Java and TypeScript, but I was assigned to a data-focused project involving Python and ETL pipelines, which is far from my area of interest or strength. I’ve already mentioned to my manager that I don’t have experience in this stack, but the response was that the priority is to place people in projects. He told me to “keep [him] in the loop if you don’t feel comfortable”, but I’m not sure that should I do.

The company culture is chill, and I don’t want to come across as unwilling to work or ungrateful. But I also want to grow in the right direction for my career. How can I ask for a project change, ideally one that aligns with my web development background, without sounding negative or uncooperative? Maybe wait for like 3 months inside of this project and then ask for a change?

Thanks so much for your thoughts!

In this episode, Dave and Jamison answer these questions:

I’m a senior developer on a small team, and I’m feeling frustrated with a junior developer I work with. They’re smart and perfectly capable, but they stick very strictly to the confines of their assigned work. They’ll finish their tickets, but unless they’re directly asked, they don’t offer to help with other areas, pitch in on shared responsibilities, or step up when the team is trying to work cross functionally.

This engineer seems content to stay in their lane and do “just enough.” I know they’re junior, so I don’t expect miracles, but I expect some initiative. This is most frustrating because it’s a small team and it often feels like we’re working with half of an engineer when they disappear into a corner and leave the pressing issues for the senior developers to handle.

How can I encourage them (or maybe push them a bit) to see the bigger picture and contribute more to the team’s success without coming across as bossy or micromanaging? Is this really my responsibility to fix, and am I expecting too much of a junior?

I had my first day yesterday as a senior developer and dozed off at an hour meeting at the end of the day today. The meeting was about planning the next year on a zoom call with the leadership I was following in the beginning but at some point they started to talk in something I can‘t really understand(to excuse myself, I had had mant meetings throughout the day and still new to their product). I should’ve turned off my camera but I kept it on while I was definitely zoning out and got my eyes closed few times. I am so embarrassed and don’t know what should I do and feel. I like this new workplace and people so far but should I already look for another job? Help!!!

In this episode, Dave and Jamison answer these questions:

I was on a meeting with a team generally regarded to be pretty annoying to deal with and not particularly useful. The meeting was pretty annoying and not particularly useful. I audibly said to myself after leaving “holy crap what a waste of time.” Turns out I hadn’t left and may not have been muted (?) but I’m really not sure. I left immediately without checking due to cringe overload, so I have no way of knowing.

How do I even go about this? I have to meet with this team regularly. My spirit has left my body, this question was typed by the husk that remained.

I am almost 2 years into my software development career. A few months ago, I was moved to a team where I was the only frontend developer. My team responsible for maintaining a large, legacy angular project and building a new internal in React tool to support the ML engineers at our organization. Our organization hired some contractors to help with building the new tool, all of which have the same or less dev experience as me.

Our project manager is not engaged in our project. He is on multiple teams. I have to communicate with our customer, gather requirements, create user stories, and QA the contractors’ work. This is not the type of work I am particularly good at or enjoy. This is on top of me being the de-facto frontend tech lead. I am STRUGGLING to keep up. I can only do a little bit of work on our project each iteration and doing required maintenance of the legacy application has become very difficult to do because of how little attention I am able to give it.

I don’t want to do all the other stuff, I just want to write code. What should I do?

In this episode, Dave and Jamison answer these questions:

I’m a long time listener to the podcast. Thanks for reading and answering my question!

I have over 20+ yrs experience as a manual QA and 6+ yrs experience as a SDET. I’m in a new role as a hybrid manual QA / SDET for a company that hasn’t had QA for a few years. After a couple of months a new hire was added to support a new project in non-development or QA tasks. While waiting for the launch of the new project, senior leadership decided to have this new hire to help me with QA. They have no experience in QA or coding. I spent a considerable amount of time training them, and found it difficult.

After a few months my manager told me the hire will transition to lead QA. They will NOT be my supervisor or manager. I will be answering directly to the manager as before. I feel sidelined since I didn’t get hired on as a Sr. or Lead role. I’ve already been left out of numerous meetings catered to team leads only.

The new hire is very vocal in meetings. They repeat my ideas as their own, and speak for me when I don’t agree. It’s exhausting to hold back ideas from the new hire or correct them and add context to the rest of the team when I disagree.

I’m worried I’m training this new QA lead to be my replacement. What are your thoughts? I feel like the company culture is chaotic for the long term. Any thoughts what I should do in the short term and long term?

Hi Dave and Jamison (as a unit would you answer to Davison?). Long time listener, first time caller.

I recently joined a data-engineering team at chill 90s multi-national tech company. My boss and I are based in the UK, and two more junior engineers who do the bulk of the IC work are based in India. These two engineers seem to work hard, have far more domain knowledge and technical ability than me, and generally seem to do most of the work. There’s also a senior engineer who’s kind of absent.

My boss is a ‘red personality’ who’s been at the org for at least a decade, who doesn’t seem as close to the technical detail. He cares about the destination and wants to get there yesterday, but discussions about ‘ways of working’ or the specifics of achieving the output seem to bore him. He characterizes such talk as risk-aversion.

I’m shocked by some of the technical details. Tooling chosen specifically to bypass version control, editing Jupyter Notebooks to deploy changes to ‘production’, dashboards that seem to have totally wrong data, etc.

It seems like they will do the minimum required to make things ‘work’ and then move on. Scalability or making things interpret-able for others just doesn’t seem to weigh on their mind. It’s then me as the new-joiner navigating their hacky code who inevitably wanders into all the pitfalls and gotchas.

I’ve tried to advocate for better practices and lead by example. They nod along, but ultimately seem resistant to change. I need their help and experience with the codebase, but I also have this creeping sense that their working style is too sloppy and unprofessional. They don’t report to me, and our mutual boss seems happy with the work. I feel a bit like the guy in Twilight Zone: I can see a gremlin wrecking the plane, but nobody else can see it, and my attempts to address the situation just seem a bit hysterical.

What’s worse, my gentle attempts at flagging the issues with my boss haven’t gone down well. In my first performance review my boss mentioned something about a ‘us versus them attitude’ and ‘assuming good intent’.

What do you make of this situation? Am I the a-hole? Have you faced this sort of thing in the past? Is it time to consider old-reliable? Is 4 months too soon to quit a job?

In this episode, Dave and Jamison answer these questions:

Hi Dave and Jamison,

Long-time listener, first-time question asker. Thank you both for the wisdom, perspective, and jokes you bring to the podcast.

I recently received an inheritance of around $500,000. It’s not “quit your job and buy a yacht” money, but it is enough to reshape my life. I’m in my late 30s, currently working in a senior engineering role. I’ve had a solid run in the world of code, but I’m ready to walk away from it, zero regrets, just done. What’s pulling me now is UX and product design: more creative, human-centered, systems-aware work.

I’ve applied for a one year master’s program in UX design, starting in 2026. I’m planning a sabbatical before that to travel, reset, and explore - think trains across Canada, a design conference in Vienna, a food tour in Greece. I’m also investing in short courses and portfolio work during that time.

Financially, I’ve been careful: I paid off my mortgage, invested part of the inheritance, and set up a buffer. So I’m not winging it… but I am stepping away from a six-figure salary, a career my friends and family have supported me to build, and am will have no income for the next 18 months, and that’s a little scary. I want to use this opportunity well, not just coast, or panic-spend, or accidentally put myself in a worse position five years from now.

How would you approach this kind of mid-career pivot with a windfall cushion? Any mental models, risk assessments, or “soft skills” wisdom to help me stay brave and smart?

Thanks again for everything you put out into the world.

Hi Soft Skills Engineering Team,

I’m the oldest person on my team (by a respectable margin), and I’ve been taking great delight in gently baffling my younger colleagues with expressions like “I’ll get that done in two ticks,” “give me a bell if you need help,” and “stay on the line after stand-up” (even though we’re on Teams, not a landline).

It has become a bit of a sport for me to see how many retro, obscure, or regionally-specific phrases I can sneak into our chats and meetings before someone finally asks, “What are you even saying?”

My question is: What other delightfully old-school and vaguely professional expressions can I deploy to maintain my status as the team’s resident linguistic cryptid?

Thanks for all the great advice you give, and for validating my mission to keep corporate life interesting!

Warmest regards, Resident Old Person

In this episode, Dave and Jamison answer these questions:

I am a data scientist and was recently passed over for promotion to senior because my projects weren’t “senior level” enough, and I do too many ad hoc requests that delay delivery of my bigger projects.

I am a go to for VP and C suite level execs in my company and am commonly asked to help with incidents, all of which are main reasons my projects get delayed. At the same time, I am told by my manager that requests from these stakeholders/incidents are more important than my projects. Every time I try to push back and let stakeholders know that a project will be pushed back due to incidents, they all agree it’s the right prioritization. And yet, every single performance review I get the same feedback about too much as hoc work.

I would really like to try again for promotion but I feel like I haven’t been able to change my balance of ad hoc work at all (this is actually getting worse), and support from my manager is lackluster - I don’t feel like it’s even worth trying again in a few months. What can I do to change this dynamic? (Besides quitting!) or is this a poor management/process problem that I cannot solve myself?

A listener named Bob says,

I want to transition into web development at the least. I have been teaching myself, but I also know that the dev world is more about connections than anything else. I have reached out to multiple people but really have not gotten far. I really want a career transition. I have found a Bachelor of Science degree in web development at Full Sail University. I would graduate in 2.5 years. Is it worth it to take this program or keep self-learning and building out projects? I would be taking this degree all while making time for my family.

In this episode, Dave and Jamison answer these questions:

I had my performance review two months ago where I scored a “Does not meet expectations”, which I definitely understand, and my manager told me that some of my coworkers had been complaining about me. I’ve been working hard on improving ever since and my manager told me that they were really impressed with my progress and told me that some of my coworkers had expressed similar sentiments.

I have now gotten a really good job offer but I’m reluctant to take it. I’m still working on improving myself with the help of my manager and I don’t want to stop working on this. I would also like some more time to show my coworkers that I really have grown before leaving, feels like that would leave behind a more positive image of me. I’m fairly junior still so contacts seem good to have, and better performance does too, and a better job does too. What should I do? :D

Listener Michael Q asks,

‌

Hello! I only recently discovered this podcast but it has quickly become a daily ritual in my commute to and from work. Although I am more of a mechanical and data focused engineer, I find the lessons extremely applicable! I work at a midsized biotech company. I have been in my current role for about three years as a product engineer. Because I’m on the commercial side, my contributions have been very visible to the higher ups and have gotten a lot of recognition, which has been great. I am now transitioning to the more hardcore engineering team. Although I admire this team and think they are the most innovative group on site, I think their work goes largely unrecognized as behind the scenes magic. I think they deserve more recognition and accolades for the work they do. How can I bring them into the spotlight? Or am I naive in assuming that just because I am motivated by recognition, everyone else would appreciate it too? Note: I do not want to quit my job.

In this episode, Dave and Jamison answer these questions:

A listener named Mike says,

To what degree do you think it’s appropriate to talk with your peer managers about people that have moved from their team to yours? How much weight do you give their criticisms of an IC that they used to manage that is working out just fine under your leadership? How do you know if it was mostly due to a conflict in their relationship, or if there’s a nugget of truth you need to look out for?

Hi, thanks for a great show. I’ve listened to 400 episodes in a year - thanks for making my commute fun!

I’ve been at my current job as a software developer for a year. It’s a great company overall, but we rely on a 30-year-old in-house ticket system that also doubles as a time reporting tool. It lacks many basic features, and project managers often resort to SQL and Excel just to get an overview. As you can imagine, things get forgotten and lost easily. Everyone dislikes it, but the old-timers are used to it.

They want any replacement to be cheap and also handle time reporting, which really limits our options. I suggested to keep using the old system for time reporting only for now, but the reaction made me feel like I’d suggested going back to pen and paper.

While the company is old and set in its ways in some areas, it has made big changes in others, so I’m not ready to give up hope just yet. How can I at least nudge the company toward adopting a more modern ticket system to improve visibility and planning? I’ve shown examples that save time and offer better overviews, but it hasn’t made much impact. Where should I focus my efforts—or do I just have to learn to live with it?

Some more context: This is in Europe and the culture at the company is generally open to feedback and discussions from anyone. I have 10+ years experience and a relatively good influence. My manager is driving change successfully to make the company more modern but I suspect he might have given up on this one.

In this episode, Dave and Jamison answer these questions:

Mr A. N. Onymous says,

Hi Dave and Jamison,

Long time listened, second time caller! I wrote a little while back with a common new-manager question about how to handle one of my reports who was at the lower end performance wise, but at the top end on the pay scale. I’d been trying to manage it by getting raises for the rest of the team in order to balance things out a bit (and make the rest of the team happy). I did consider Limogeage but having them on the team was better than a vacancy.

Fast forward a year or so, and the problem resolved itself when this team member left - or so I thought. We’ve had a few months gap before opening recruitment again, and it turns out this team member wasn’t happy at their new role and has applied to come back. Given they negotiated well with us the first time I’m guessing they’ve had a healthy pay bump at their new role. What should I do?

On the one hand I know their performance, they do deliver well and I’m happy working with them and managing them. Would it be rude to offer them to come back at their previous salary (assuming they’re the “best” person when we interview)? Will they be offended if we don’t offer them the role?

We haven’t had interviews yet - so help me Dave and Jamison, you’re my only hope!

AI has taken over my team mate’s brain. HELP!

I work for a ~10ish or so team building a B2B finances related app for several platforms (mobile, web, backend, etc). On the Web team, there’s only two of us.

I’ve been on this team for around 4 years now, and during this times I’ve had several coworkers (the previous ones have either left the company voluntarily or involuntarily, moved to other teams, or completely left the field). I’m 100% convinced it’s not because of me, so let’s take that out of the question right away :-). All of this to say is that I tend to be the person that knows the most about our (quite large) codebase.

We work on a ten-year-old React application with some technical debt, but overall I think it’s pretty good.

My coworker comes from Android development. While he’s a great developer and has AMAZING soft skills (probably a listener of this podcast!, or maybe not because he has not quit yet?) he’s a little bit lacking on the general “Web Stuff (TM)” knowledge and many of the specifics details of our codebase.

A bigger problem is that he seems to have totally given up on learning web skills or understanding our codebase and is instead just tab-tab-tab-ing autocompleted AI crap all over the codebase.

His code works as expected, but when reviewing his PRs I feel like a slave of the AI. I’m not reviewing another human’s work, but just what some AI model is doing. While it works, it’s terrible code for another human to maintain. For example, there’s lots of “inline” crap that we already have utility functions or libraries for, regexes everywhere, custom CSS all over the place instead of using our design system, abuse of the CSS cascade instead of using our CSS-inJS solution, large files with lots of code repeating existing logic that’s already somewhere else, and code comments every 2 lines or so which provide no value, but that’s what AI does to explain things.

I’m not against AI (I also have explicitly to say this to prevent it killing me in the future). I use it for explaining things to me, writing utility functions, suggesting improvements, or as a google search replacement that saves a lot of time.

But leaving AI to do your work mindlessly while you sip orange juice and watch how it codes is wrong. We’re not there yet. These PRs work and are difficult to reject because management wants to ship fast. However, they are harming the codebase. We’ll get to the point where only AI will be able to touch it due to the amount of repetition, duplication and overall non-human friendly code.

How do I tell this person “Please stop doing this and instead learn things properly, and use AI as a tool and stop you being the tool of the AI” without hurting any feelings, and without being seen as the AI grinch?

Thanks for your help! Love the podcast, and why scroll keeps jumping up when writing on this form? Seems like AI is boycotting me.

In this episode, Dave and Jamison answer these questions:

Albert Nonymous asks,

I am the CTO at a small (5 engineers) tech start-up with non-technical founders. I was their first full-time employee and as such have been able to fully form this company the way I want. I’ve worked here for 9 years now and own 10% of the company. I enjoy the tech and the job itself. The pay is ok, not crazy Silicon Valley numbers but pretty good for a country with free health care.

However, I started here while still in university. This is still the only job I’ve ever had. I am afraid that my resume will become less valuable the longer I stay here. I still keep up with current trends with hobby projects, but I’m worried that my resume will become less valuable if I ever need to look for another job.

Also, I don’t believe this company will succeed in the long run. I am still the only person on the board who knows how our tech even works and I have found myself slacking off quite a bit during the last year since having my first child. In the meantime, I also feel like I can’t just quit this job since that will almost certainly spell the end for this company and all its employees (some of which I count among my friends after all these years). What do I do? Am I overthinking things? Can I just keep working here until it eventually goes under? Or do I absolutely need to bite the bullet and pull the Jamison and Dave Time-Honoured Special™ and quit my job before I become totally un-hirable?

For much of my 9 years as a software engineer, I wanted to be a leader. I just really enjoyed mentoring, training, improving workflows, working with stakeholders and co-ordinating on projects. Leadership seemed like a natural fit and so I was super psyched to be finally made a team leader last year.

It has been hell.

It has been like falling backwards out of a tree and hitting every branch on the way down, meanwhile it’s literally raining anvils and sabre toothed tigers. The constant pressure to have work lined up for the team and be able to report on the activities of the team at a moment’s notice is unbearable. I can’t stand being responsible for the delivery of other people’s work, writing up reports that no one reads or painstakingly de-noising pointless metrics. I dread having to pull eager young developers out of refactoring rabbit holes.

Fortunately, as I took this ‘promotion’ with no raise, I’ve easily been able to get myself busted back down to IC. Happy days 😎

The problem now is that I have no idea what to do with my career. My core experience is with dot net as a mid level engineer but honestly I’m what I would call a ‘hyphen’ shaped developer - I’ve seen and done a lot things but not to an expert level. Front end, back end, BI, and everything in between. That felt ok when I was aiming for leadership but now I feel lost. I honestly feel ready to go full goose farmer 🪿.

What do I do next?

In this episode, Dave and Jamison answer these questions:

One of my employees is probably getting laid off, what do I do!?!

I’m a tech lead / manager for a consultancy and a contract reduction means that one of the people I supervise is likely going to get laid off soon! We’ve found new roles for most of my people, but it’s likely that at least one will get laid off.

I want to help this person out. How much support is typical for a manager / ex-manager to provide in a job search, and how can I go above and beyond without doing too much?

Over the last year, my company has gone through 3 rounds of layoff. The engineering culture has changed dramatically. With the fraction of engineers remaining, I am increasingly concerned that it’s going to be me next. The company’s posture is that everything is “business as usual” and there is nothing to be worried about, but this is what has been said all along. Morale seems to be low with low engagement in department initiatives.

I am looking for some advice here, if I stay with the company – what is a healthy way to engage with the current culture to build it back up (or evolve it into something new)? If I decide to leave the company – how can I set proper boundaries to prepare for leaving, but remain engaged until a new opportunity arises?

In this episode, Dave and Jamison answer these questions:

Hey, long-time listener, listened to almost all episodes now and have been loving it since day 1!!

I am a senior engineer at FAANG and work 45-50 hours a week and have a lot of cross-org responsibilities. I am lucky to have a beautiful wife and two wonderful young children. I guess, you can imagine how difficult it already is to manage work/life; especially because I am working remote from a different timezone with large dilation.

I did lots of side projects before I had a family. But I was totally okay leaving all that behind for a great family life. Now, I have been struck by a really cool idea for an AI-based product that intersects with static analysis and my day-to-day work, which I cannot stop thinking about. I am sure that this project would be more than I could handle at the moment without cutting back on anything else.

The question now really is, how do people with families and FAANG jobs do side projects? Or do they even? Do they have more than 24 hours in one day?

Hello! Love the show, one-time contributor :p

I’m in agony about my recent compensation change regarding my promotion and I am looking for some wise guidance (and if not that, some funny jokes will do).

Context: I work at a big tech company. I got promoted to a senior engineer, but. I didn’t get a bump to my salary. Instead, the company “indicated” that the raise would happen in six months, at the next performance review, which happened last week.

What did I end up getting? Nothing :)

Why? Apparently they have not been giving salary bumps to people who get promoted, and it has enraged people.

It hurts my pride. I consistently get good performance reviews & peer feedback. People go out of their way to say how good my work is. I have every evidence to say I am a strong performer.

My manager is very supportive and tried escalating my case. But the company didn’t budge. They did say that “there’s a chance” to “make it right” in 6 months.

On the one hand it feels petty to leave a company because I didn’t get the raise I wanted, especially when I do really enjoy working here. On the other hand…I am very disappointed.

What do I do? Do I stick it out for another six months and see what happens? Are there options left other than start prepping myself for interviews?

You are amazing people. Cheers.

In this episode, Dave and Jamison answer these questions:

I have managed a product for some months now. My previous manager split their team in to mini-teams of 2-3 people. They gave me a small team and plenty of autonomy to own the product and go crazy on it. I had the time of my life as the team lead. I learned a ton and was really developing management skills. My new manager is more hands-on. They want to do things my old manager left space for me to do, like project planning and quarterly planning. Now I feel micro managed when they get involved. I become territorial. It feels like he doesn’t recognize the independence of the mini team. I feel like I’m going backwards and and undoing all the management growth I’ve had, becoming just a software eng who should just keep their head down and work on a task. I don’t know what to do. How do I keep my independence and keep growing, but also get along with the new lead and learn from them in the process?

I work as a senior engineer in a large team alongside a few other senior technical leaders. I’ve consistently received positive feedback from my manager about my impact — improving engineering quality, operational excellence, and team communication patterns.

At the same time, there have been challenges in collaboration and teamwork between other senior leaders and the teams they work closely with.

My manager has been highly supportive of the projects and changes I propose, and many improvements have been implemented based on my suggestions. However, during the recent promotion cycle, despite this positive feedback, I was not promoted, while another senior engineer — who is known to have collaboration challenges — was promoted instead.

When I asked for feedback, I was told that while my contributions are appreciated and my time will come, they couldn’t explain the specific factors behind the promotion decision.

I now feel a bit demotivated, as it seems engineering excellence and team impact may not be the primary factors considered for growth here.

My question is: How should I think about my next steps? Should I keep investing in this team or start considering other opportunities?

In this episode, Dave and Jamison answer these questions:

I work for a B2C fintech startup as a senior engineer. Our onboarding funnel has a lot of moving parts due to regulatory compliance and a litany of requirements from various parts of the business. As a startup, we also live and die by optimizing for and demonstrating growth, so we need to gather data from our product and pipe it to various analytics platforms. Finally, we need to offer customer support for high-touch edge cases. All of this is connected together in a very patchwork way between our own code and various secondary and tertiary systems (CRMs, CDPs, data warehouses, etc).

I am torn between two ideas. One is that we may very well be doing something “state of the art” in terms of integrating all of this together. The other is that we are engaging in wheel reinvention on a massive and incredibly wasteful scale. I have no way of knowing though, because I am having such a hard time finding holistic accounts from anyone who has done something like this. My gut says that this is something dozens, if not hundreds of companies have had to build at some point, but I don’t know where to find people talking about it.

How do I find documented, real-world case studies for how to build a complete package like this? Everything resource I can find online is a myopic, narrow slice of the entire pie focused on only one aspect of the problem. No one is talking about how you integrate e.g. a sane and scalable analytics stack with a fast evolving product. All they want to talk about is how to make a “webscale backend” or “do growth hacking” while assuming someone else is going to draw the rest of the owl.

Where do I go to find these people or these resources? Maybe these constitute some form of “trade secrets” - does anyone even want to give this information up freely? If my higher-ups saw me go outside the company for resources, would _they_ think I’m leaking important secret sauce?

Sorry that got so long. I love the show! Keep being awesome.

I’ve been at my company for about four years, and I’m currently a senior engineer. When I first joined as a mid-level engineer, there was a certain tech lead who wasn’t exactly known for his warm personality. On my very first day, I joined a Zoom call and witnessed him verbally berating someone. This type of behavior was fairly common at the time and earned him quite the reputation as a jerk, though thankfully it became less frequent over the years.

Fast forward to today, and he’s genuinely transformed. The intensity has dialed way down; he’s now approachable, supportive, and even recently earned a promotion to engineering manager. It’s honestly been impressive to watch.

We have a friendly relationship, and I’d like to acknowledge his growth because I genuinely admire it. But here’s the catch: How do I, as someone junior to him, respectfully bring this up without accidentally implying, “Hey, congrats on no longer scaring everyone at work”?

In this episode, Dave and Jamison answer these questions:

Nearly every time certain developers on the team want to address technical debt, they end up just adding more technical debt. Of course, after one round of addressing technical debt, the developers in question believe that yet another round of redesigning and refactoring is in order. This stresses me out for many reasons, as you can imagine, and has led to my productivity dropping to an abysmal rate. I spend a large chunk my time resolving merge conflicts and re-orienting myself in an ever-changing codebase. Do you have any suggestions for me?

Hi!

I’m a software engineer at a big tech company, and I’m starting to feel siloed in my IC role. I’m getting my work done, but I’m often lost when it comes to the bigger picture. I can’t keep up with what our internal customer teams are doing, what they need, or even what my own team’s priorities are. I’m feeling siloed, and it’s starting to worry me. I know that just being a good IC isn’t enough to advance my career here. To get promoted, I need to understand the impact of my work, be aligned with the team and customer goals, and show that I can contribute to the overall success of the company. But how can I do it? How do I stay informed about customer needs and team priorities and position myself for career growth without getting completely overwhelmed?

Thank you for your precious advice!

In this episode, Dave and Jamison answer these questions:

I am a senior software engineer in a big tech/faang company and this week is my first ever on call rotation. My team is doing a lot of CI work, monitoring pipelines and support queues during on call. It is probably not as much of a hassle as on call for product teams, but for me personally on call was the nearest I have ever been to hell.

Our on call is not the regular getting pinged when something goes wrong, instead we have to manually monitor a dashboard 12 hours constantly for 7 days as the alarming is quite fuzzy.

I am the only EU remote worker that has to adopt to the on call PST timezone. That means, my on call shift goes from 3pm-3am in my timezone. It is day 5/7 and I am down 24 energy drinks already, cause this was the only way to stay wake. Knowingly, that this would be just a short-term tradeoff against health, I am now living through the most explosive diarrhea I have ever had. On top, I am sleep derived, dizzy and every body part hurts.

That would already be terrible on its own, yet I additionally have a young family, with a 4 year old and a toddler. The on call week, has not only been though on me, but especially also on my children and wife. I don’t have time for the kids at all and my wife is doing 100% of everything at the moment, including waking up, breakfast, bringing our son to kindergarten, cooking, cleaning, playing, everything. She is also quite exhausted therefore.

Besides On Call, my job has been great and a huge monetary opportunity that is very rare in the EU, therefore quitting just because of 4-5weeks/year is not an option I am considering. Yet, I am wondering if there could be any way of smuggling myself out of the on call rotation. I have seen, that a staff level engineer on our team is not participating in the rotation, but that might be because he got a lot going on with other teams as well.

A listener named bebop asks,

Is your average “Big Tech” dev “better” than a random dev selected from a large non-technology company? I can’t help but feel that if I want to level up my career, I’m going to have to either move into big tech or some unicorn startup.

In this episode, Dave and Jamison answer these questions:

Hey, I am a web developer getting bored of the regular development work. I am interested in finance and the monetary system and due to the overlap of finance and engineering I feel down the Bitcoin rabbit hole and even spiked interest in crypto like Solana and Sui. I am pretty sure most of crypto is a FUD, delulu or straight up scam, yet the technology looks appealing and interesting to learn. So that said, I am still really interested in learning more about crypto and dabbling in the development space of that. Yet, I am hesitant because I fear that this could reflect negatively on me. What do you think? Is a bit of crypto okay or really that bad?

Hi Dave and Jamison

After five years as an engineering manager, I want to return to coding. But I’m facing a few challenges:

First, I worry about leaving my current team. It feels like I’m abandoning the people I’ve been supporting. Should I make this transition elsewhere to avoid this awkwardness?

Second, I’m struggling to find time and energy to rebuild my technical skills. After a full day of management work, it’s hard to open the laptop again for coding practice.

Finally, I’ve been humbled by how rusty my coding skills have become. Tasks that would take a practiced engineer minutes are taking me days, which is frustrating and denting my confidence.

How have others successfully navigated this pendulum swing back to an IC role without burning bridges or burning out?

Thanks, a rubber duck

In this episode, Dave and Jamison answer these questions:

A listener named Dakota asks,

I’m a UX designer, and I’m constantly looking for growth opportunities. I’m having trouble finding mentors to help challenge me, as every time my boss/senior designer leaves the company, I assume their work and we don’t backfill their spot or my old position.

This leads me towards podcasts like this as I’m trying up-skill and to learn how to be a better team member and support other roles.

I’d love your perspective on working with product/ux designers. What have the challenges been? What makes you love working with a designer? Have there been times where you’re both arguing for the best user experience, but fail to agree on what experience is best?

Hey guys!

It seems like lately, I only work in two modes:

Stressed and tired Bored and disengaged

I often get to own large, urgent initiatives. I spend weeks or months on them. This work is fascinating! I end up being stressed, tired, and counting days until my next vacation.

When they finish, I go back to regular tickets - ones that take a day or two, maybe a week to complete.

And its great! For a few days. Then the boredom sets in. I pick through the tickets, trying to find something interesting. I finish a ticket and realize there are another 4 hours before the end of the day. I start to miss the rush of working on a complex puzzle, even though it’s terrible for my work/life balance.

A month or two pass, and a new complex and urgent initiative comes in. The cycle continues.

So my question is: Is this a common feeling? Are there ways to find a “easy-work/hard-work” balance? Do you have any advice on not overworking when urgent tasks come in, and not dying from boredom when there is no interesting work?

In this episode, Dave and Jamison answer these questions:

I’m a manager on a Product team. I’ve been asked by upper management to measure “story points completed per developer per sprint” and display the results publicly each sprint to motivate lower-performing employees. I explained why, according to Scrum, I don’t think this is a good idea. But I think my explanations came across as me not wanting to make my team accountable for performance.

For some context, I currently track productivity by reading daily updates, PRs, and tickets, from each developer.

I worry that “story points” is easily game-able as a performance target, and will make the team want to modify the points after the fact to reflect actual time spent. Then story points will become a less useful tool for project planning.

I’d like to satisfy the higher-up ask to measure productivity, but in a way that is good for the team, the company, and my career.

Any thoughts on how to approach this?

A listener named Mike asks,

I work for a company with 30 employees. Our CEO is trying to be our CTO by prompting all our issues to ChatGPT. This week we had a discussion about changes needed to comply with specific certifications requested by one of our customers. 15 minutes later I got an email containing a chatGPT conversation giving ‘advice’ that I debunked just 20 minutes beforehand. I have been vocal about my concerns of over-use of LLM’s before and think it’s dangerous for our CEO to keep sending large chunks of factually incorrect text across the org. He did finally stop talking about story point burn down because chatGPT told him it’s a bad metric though. So maybe this is salvageable?

In this episode, Dave and Jamison answer these questions:

Greetings! I work at a research company with ~500 engineers and scientists. My company started promoting this new portal they setup that is like a private linkedin. You can fill up the profile they setup for you and apply for positions within the company. Why is my company doing this? They even offer meetings with Talent Acquisition team and they give you feed back on your resume etc. Thank you!

As someone who’s been a developer for a while, how can I ensure that I’m continually be exposed to and learning topics outside my purview? The further I get from school, the more laser-focused my knowledge seems to become. It’s easy to concentrate solely on my day-to-day tech stack and the architecture I work with, but how can I make sure I stay up to date with recent advancements in the field? Is there an RSS feed that I can stream directly into my frontal cortex to keep me up to date?

Also, I understand this query may not be ‘soft’ enough, so if it must be cast into the void, banished to the land of unanswered questions – I accept my fate

In this episode, Dave and Jamison answer these questions:

I’ve been a developer for about 1.5 years. I work for a large consultancy. we provide services to big clients. I’m working on a front-end codebase that has been through three consulting companies already.

Tired of just moving tickets and fixing bugs, I decided to refactor the front end of the entire application we support. Touching the codebase to add features gave me a pit in my stomach. No integration tests, no staging environment, huge functions with tons of parameters, etc.

The client provided technical guidelines that were pretty solid, but the code just didn’t follow them at all. In the time left on the contract, I refactored the codebase to fix the biggest problems to align with the client’s technical guidelines. I did all this without my manager/PO/PM asking me to.

But now, how do I communicate what I’ve done to the client and my manager? Can I get any recognition for it?

A listener named Mike asks,

I’ve been in my role for about 1.5 years in a dev team of 7. I really like the job, it has a good culture and I’m learning. Sometimes I channel my desire to learn into improving our projects with small, self directed changes on my own time. I these changes are useful but aren’t high enough priority to make it into planned sprint work. I don’t inundate the team with these requests, it happens maybe 1-2 times a month.

We make a point of working in small steps, usually submitting several PRs per day each. I really like this approach, and I also keep my occasional self-directed bits of work small in scale. However, I’ve noticed these PRs receive more scrutiny and more “whataboutism” that our regular on-the-books PRs.

For example, for regular sprint tickets there’s an understanding that we’re making progressive improvements or building small pieces of features that exist within the constraints of our systems. We might flag broader improvements to consider, but there’s no expectation to re-boil the ocean every time we want to merge code.

When I submit a self initiated piece of work there can be a long back and forth of suggestions that can involve changing other dependent code, changing internal APIs which may have side- effects, and generally a level of defensiveness in the code that we never normally expect. I understand that by submitting off the books PRs I am requiring some work-time from reviewers, but there is more pushback than I’d expect. It feels like because I get the ball rolling on my own time the normal cost-benefit constraints go out the window, and the code purists come out to play.

Could I be annoying the team with these submissions? Have you experienced team members doing the same thing? Is there a way I can scratch my own itch by learning against our systems without creating this resistance?

In this episode, Dave and Jamison answer these questions:

A listener named Scot asks,

A new architect was hired at my company 6 months ago. I’m an engineer one rung lower on the hierarchy and have been here for 3.5 years. He hasn’t done much to learn about any of us who have been here for a while, so he is constantly undermining my skills and suggestions and assuming he’s smarter than me. On our most recent project we had a lot of issues due to his design, which departed from our best practices. He’s still acting like he knows best and is getting under my skin. Our company usually hires more collaborative people so I’ve not had to deal with this before. How can I stay calm, professional, and confident in my skills while working with this guy?

Who is my boss? No, really. I need answers.

I’m a Principal Developer with so many bosses, I’m starting to wonder if this is a multi-level marketing scheme. My team lead gives me work. His boss gives me work. Every project lead crashes into my inbox like the Kool-Aid Man screaming that their thing is the most urgent. My calendar is a cursed artifact, filled with 20+ hours of meetings a week, where I nod knowingly while my soul quietly exits my body.

My team lead is a Designer and has no idea what I actually do or the expectations of a Principal Developer, which is convenient, because neither do I.

When I asked his boss to help me prioritize, I was told, “It’s all important—just make sure mine is done first, and don’t tell the project leads.” Our product owner wants to be anything but a product owner, and our scrum master is treated like the office secretary, not a blocker remover.

Top it off, I’m now being asked to weigh in on architecture decisions for our tech stack while not being invited to architecture meetings and being told to “just figure it out” when I asked how to structure the documents and diagrams they want. So now I’m behind on doing dev work, pretending to be an architect, and the team I’m meant to be mentoring never see me unless they’re in one of the same meetings I’m trapped in.

How do I set boundaries and prioritize without causing a nuclear meltdown? Or should I just consult a Magic 8-Ball and let fate decide? Because honestly, I’m one email away from faking my own disappearance and leaving an out-of-office message that says, “No.”

In this episode, Dave and Jamison answer these questions:

I struggle with behavioral interviews. I’ve gotten a little bit better as I’ve done more interviews, but it’s still a major pain point for me.

I have some common behavioral question answers written out in a spreadsheet in SAR format, but I feel that not all of them are good examples for a mid-level developer. The main problem is that I can’t remember in detail all the things I’ve done at work in the past few years. For example, I can think of one time I had a small conflict with a coworker, but I can’t remember the details of what happened. I have a work diary of sorts, but unfortunately, I haven’t been regularly writing things down. Also, I usually just write down accomplishments and notable things that happened. Should I start writing down experiences that match up with these types of behavioral questions?? Do you have any advice on how I can jog my memory and reflect on all the things I’ve done during my career to craft good answers to behavioral questions?

I also freeze up when I’m asked a “tell me about a time when…” question that I’ve never experienced. I’ve heard advice like “come up with a hypothetical scenario and explain what you would do” or “just lie and make up a story”. I’m the type of person who has a very hard time lying and making stuff up on the fly.

I am one year into being promoted to a team lead at my company. We are made up of 4 devs, 2 QA, and a product owner. One challenge for our team has been differing time zones. Our 2 QA engineers are east coast while the rest of the team is on the west coast. Currently one of them signs off at 5pm EST and the other at 4pm EST. This means that if there’s any communication that needs to happen between dev and QA it has to happen in the morning since by 1pm PST they are headed out the door. This also constrains the times that I’m able to schedule meetings that involve QA.

I’ve been thinking for awhile establishing a set of core hours from 9am-2pm PST but have been afraid of the pushback from our QA. I feel like making this adjustment is reasonable and other people I’ve asked have echoed that sentiment but my desire to people please and be looked at favorably is preventing me from making a change. In all honesty we can get by with the current set up, but I find myself getting bitter about not being able to schedule meetings in the afternoon and stories getting held up because QA is off the clock so early. What do?

In this episode, Dave and Jamison answer these questions:

Hello, long time listener first time question asker. I work for a medium sized tech company and I recently moved teams. Right now my old team is attempting to refactor a bunch of code I wrote to use a library that’ll make life easier. I don’t blame them, I tried to do the same thing. It does not work. I asked the tech lead “did you run into the same framework bug I did when I tried this refactor”… “nope” he said. So out of curiosity I pulled down the branch and guess what I saw, the same bug when I tried this refactor 3 months ago. Now I am in a weird position. Do I tell the tech lead again (he was the tech lead when I tried this same refactor) that this does not work or do I ignore it because I am no longer on that team? I don’t want to overstep my bounds but I also know its a lot of work to refactor all this code, so much work they’d need to stop delivering features and add this to their roadmap.

I have been interviewing for leadership roles and I keep getting asked “What is your Leadership Style”? I am honestly not quite sure how to answer this as I don’t really understand what they are asking. I have searched the internet for a clean, 5th normal form database that lists the available styles to no avail with no definitive tables. It seems this is truly a soft skill. From your experience, what is the interviewer really asking in this case, how can I better identify common styles, and what can I do to grow my skills in this area?

In this episode, Dave and Jamison answer these questions:

A listener named Steven says,

Long-time listener of the podcast here—it always brings me so much joy!

Should I prioritize title over salary?

I’m currently based in Europe, working as a Senior Engineer at a big company that pays really well. The problem is, there’s almost no chance for promotion due to the economy and budget constraints. Plus, because of the organizational structure, I’m stuck solving small problems that don’t have a big impact. It’s frustrating—but again, the pay is great.

Recently, I got an offer for a Staff Engineer position at another company. The catch is, the pay isn’t as good (30%+ cut), and I’m not sure about their culture or structure yet. However, the title could potentially open more doors for me in the future.

Should I take the offer, accept the pay cut, and hope it’s a step forward for my career?

Hello! Long time listener, first-time caller :-) I’m on the final stretch of classes to finish my BS in computer science at WGU, most of which I’ve done while working. I’m now 40, and I have had 3 previous occupations and employers: aircraft mechanic for 5 years at a small shop, figure skater with Disney on Ice for 6 years, and most recently a partner at an environmental remediation/heavy construction firm for 10 years where my primary responsibilities were field crew management and technical writing for ecology reports. I would love your advice on how I could use these experiences to stand out on a resume or in a job interview. How can I indicate that I’m a hard worker and that I know just enough to know that I know nothing and am ready to learn? Thank you for your time, keep up the good work!

In this episode, Dave and Jamison answer these questions:

I am a mid level engineer overleveled as a senior engineer in a FAANG company. I got super lucky landing this high paying remote job, but dang… I did underestimate the expectations for my senior level. I had no FAANG experience before, just working at startups, flat hierarchies, just doing the heavy lifting coding.

Now it is all about impact and multiplying impact across the team. I am told I should do less IC work and more leading of projects and owning initiatives.

Can you give me some general advice on what actions I can take to get from the mid-level to senior-level? I am not really sure, what taking ownership really means in practice… These just seem like empty phrases to me without a meaning…

I have had a bit of time, while running a 40 minute build, so I looked into open pull requests. One PR caught my eye and I started to read through it and left a comment with a suggestion for a small change. All in all sounds good probably, but the caveat to this is, that the PR was marked as Draft.

I was thinking that it would be useful for the author of the PR to already get some suggestions during development, but the response got me thinking. The author passive aggressively mentioned that the PR is in Draft and that there is more work to do.

Am I the jerk for commenting on a draft PR? Second question, what other things should I pay attention to in code reviews to not be a jerk?

In this episode, Dave and Jamison answer these questions:

A listener named Matthias (mah-TEA-as) asks,

In episode 444 you’re talking about the problems when hiring in the age of AI. I’m a manager who’s trying to hire right now and frankly I’m at a loss. If feels like I’m wading through a sea of AI slop. What tips do you have to cut through the slop and reach actually good candidates?

Where I work the developers do not seem to “get” source code control systems like git. I’m not a developer but have worked with developers at previous jobs and usually the developers instituted good source control practices themselves.

Our developers know they should push their code to the repo but only do it weekly/monthly, treating it as a “backup”. Some back up their laptops using tools like Time Machine so think have taken care of safeguarding their source code that way.

How can I convince them that working in git, committing their code as they go, pushing regularly, branching/merging, tying code updates to tickets, etc will benefit them far more in the long run?

In this episode, Dave and Jamison answer these questions:

A listener named Kevin asks,

Hey, found the show and really enjoy it! Been listening from the beginning and have noticed that one of the pieces of advice given is that you should not stay at your first job for too long, because it’s more likely that you’ve not found the best job for you. I think The Secretary Problem is the closest thing being cited.

I tend to agree with the math, but I’m still at my first software engineering job after 5 years and don’t really want to leave. There are obviously things I don’t particularly like or people I find challenging, but for the most part, I work on interesting projects with smart people, it’s fully remote, the benefits are great, and my salary is comfortable. There have been times where I started to look for another job, only to have my current circumstances improve enough that I stopped the search.

What advice do you have for someone like me?

I don’t know if it’s relevant, but I’ve managed to get married, buy a house, and just recently had our first baby. The pressure to provide and be conservative with my career is building.

Again, love the show and I hope you’ll get to answering this before I catch up. I started from the beginning in late 2024, and in mid Jan 2025, I’m just past episode 50. I’ll let you do the math.

As a tech lead, I joined a project two years in the making which had only one engineer doing everything, including management. In the two years, only a POC has been completed and a “pre MVP-MVP” build is in progress. There is a hangup though, the funding for the project is supposed to come from another departments budget that doesn’t want it, and work was committed by the department I am in, and a third department intended to be completed by the end of the quarter.

I have been trying to finesse my teammate into cancelling the project or at least allow a resetting of expectations. My manager agrees with me. There seems to be a tug of war between AVPs and Directors. This has led my teammate to make some corporate aggressive comments. These are being directed in many directions, including department heads opposing the project.

In your professional space experience, how can I help my teammate with understanding that his tactics are potentially damaging to his reputation and the project?

In this episode, Dave and Jamison answer these questions:

After a decade as a Senior front-end engineer in companies stuck in legacy ways of working—paying lip service to true agility while clinging to control-heavy, waterfall practices—I’m frustrated and exhausted by meetings and largely apathetic, outsourced teams who don’t match my enthusiasm for product-thinking or improving things. It seems allowed and normalised everywhere I go.

How can I escape this cycle of big tech, unfulfilled as an engineer, and find a team with a strong product engineering culture where I can do high-impact work with similarly empowered teams? Thank you, and sorry if this is a bit verbose! Thanks guys. Martin

‌

How do you judge your competency in a technical skill and when should you include it on your resume? Should you include a skills that you haven’t used in a while, skills you’ve only used in personal projects, or skills that you feel you only have a basic understanding of?

I’m a frontend developer and I’ve seen some job descriptions include requirements (not nice-to-haves) like backend experience, Java, CI/CD, and UI/UX design using tools like Figma and Photoshop. I could make designs or write the backend code for a basic CRUD app, but it would take me some time, especially if I’m building things from scratch. I’ve seen some resumes where the writer lists a bunch of programming languages and technical skills, and I often wonder if they truly are competent in all of those skills.

In this episode, Dave and Jamison answer these questions:

I think my team’s PM might hate me. Hate is exaggerating, but they often will give public praise to other members of my team on work they’ve done, and seem to be pretty friendly with others, but I have never gotten the same treatment. I have also not gotten negative feedback from them in the 3 years we’ve worked together, so I don’t really have any information to go off of here.

I don’t need everyone to like me, but it feels weird to see someone act nice with everyone else and relatively cold with me. I get along pretty well with everyone else on the team, too. Would you do anything in this situation or just try to ignore it?

I’m a newly minted senior engineer and frequently pair with other more junior engineers to help them when they run into issues. Along with my company-provided senior engineer hat, my manager has asked me to try to take on more of a vested role in mentoring other engineers.

One engineer I regularly assist seems to have anxiety issues. When I start reviewing their code or ask them about their debugging steps, they almost always start the conversation by telling me they’re nervous. I usually reassure them that we’re all teammates, we have a shared goal and there’s no judgement - only a desire to help them resolve whatever issue they’re encountering. While this does help somewhat, they continue to show clear signs of anxiety. I’ve also noticed the same behavior during team code reviews.

They’ve been here for over a year, and I feel bad that they still seem to be struggling. I’d like to offer some sort of suggestion or guidance. What’s the best way to approach this? Would recommending therapy be out of line? Should I talk to my manager, or would it be better to leave it alone entirely?

In this episode, Dave and Jamison answer these questions:

I would like your advice on how I can improve my communication skills. I realize that practicing is usually the best way, but I am interested in taking online courses or learning more on becoming a better communicator. However, I am currently taking courses in CS and would like to primarily focus on that. I’m wondering what your thought are, especially when it comes to investing time in either a community college or online extension course.

I have to make a confession. I am a job hopper, never staying longer at a job than a year. I am getting bored quickly, I always get the feeling of the grass is greener on the other side and I keep finding myself distracted from my current job always thinking of the next step, the next job, the next big thing.

This feeling is a double edged sword. On the one hand I know that I am aware that this repeated behaviour is not sustainable and healthy. On the other hand it helped me progress extremely in my career and climb the ladder quickly and now after five years of experience I landed at big tech in my dream job role. But I still get this old feeling of planning the next thing, finding myself distracted and losing interest and not being satisfied.

I want to stay at the job and keep earning the big bucks for my family. What can I do to get rid of the grass is greener syndrome?

In this episode, Dave and Jamison answer these questions:

I’m currently in the interviewing pipeline for an engineering position at a fairly large healthcare company. In light of the recent events surrounding UnitedHealthcare, there’s been renewed criticism towards the insurance industry as whole. I was interested in this position and the work culture seems good, but now I’m having second thoughts. If I were to accept an offer from this company, could it somehow negatively affect my career or reputation? I feel like I’m worrying over nothing, but let me know your thoughts. Also, hypothetically speaking, what would you do if you received a job offer at a company that recently had negative press?

Hi! I’m an internal applications engineer, and after a couple of years of propping up a couple of different small and midsized companys’ intranets with duct tape and cardboard, digging through old, unmaintained code that nonetheless runs the business, and trying to decipher the intentions and reasonings of the Developers Who Came Before, I have landed what is perhaps the dream position: the primary internal applications developer at my new company is retiring, and the business has hired me on such that we have a few months for said senior developer to catch me up and hand things off.

I’ve been brought through the basics; how to troubleshoot day-to-day misshaps, which clients need to be handled with care, and I’ve been shown the excel workbook that will make the finance department explode if it’s edited incorrectly. What other non-technical questions should I ask my senior before he leaves?

Thanks and thanks also for an awesome show!

In this episode, Dave and Jamison answer these questions:

Stefan

Help! Most of the time people ask questions about issues that already happened. I however, would like to prevent one.

I am a young Tech Lead and really love my responsibilities, team and especially my manager. With the help of your podcast I could even resolve my last issue regarding compensation. Of course I dutifully did my part and reallocated some of my payment increase to finance Jamisons yacht.

My very awesome manager “Bob” is so great that he has to manage 4 teams. Naturally, because Bob and those 4 teams are doing great, Bob gets rewarded with even more work. In his “free time” Bob is a parent of two teenagers which is also not necessarily known for being a stress free environment.

Lately I noticed that Bob is more stressed than usual. Bob told me that he wakes up in the middle of the night because he remembers missed TODOs in the job. I also see this change in his body language and general demeanour.

Now that a very critical project is coming up, Bob, as the go to person for more work has to allocate a significant time of his day to support this project.

I fear that Bob is on a path to burnout and this new project might be the last drop. I would really hate to get a different manager. Statistics claim it will probably be worse… Also I really wish for Bob to be well and health, too. ;)

How can I help Bob in his situation? How do I address those concerns with him without looking condescending? We have a good and open but not close relationship, that I would not like to ruin by overstepping my bounds.

Thank you very much. I love the podcast. You make me laugh and learn with every single episode. You rock!

I am a very young senior engineer at a big tech company and I think nobody really knows how young I actually am. I just turned 24 and usually in prior jobs other developers started hating me once they found out that I am this young and already in a senior role. Here at the current place, I have the feeling that all of the engineers in levels below me are already a lot older and have more years of experience under their belt. Also, I think they do not know about my age, because I never shared that in the recruiting process, nor later on. Usually people assume I am in my early 30’s and have a baby face, but when I tell them that I am a baby face because I am actually young, they become envious and things go south from there. Should I keep this a secret or am I playing too much into this?

PS: I am also already married and have kids, so that could make them assume that I am older.

In this episode, Dave and Jamison answer these questions:

What advice would you give for working with an ineffective leader whose input is crucial to your work? I’m a senior developer for a mid-sized non-tech company with probably 60-80 devs, and in the past year I’ve been working more with a VP of software who seems to still be involved in code details, getting pulled in to production issues, in-person code reviews, etc.

He’s a nice guy, but he seems like he’s being pulled in too many directions at once. When he schedules a meeting, there’s a 50% chance it happens on that day and time, and when we do have meetings, if we bring up questions and high level issues we need feedback on he’s quick to “take ownership” and say he’ll do X and Y. Inevitably, X and Y slip down the priority list because production issues and who knows what else, and we’re stuck waiting weeks on end for something that if he’d just delegated the work to someone else, we’d have long since moved on. But we still need his input to shape our work. How can we as lower-level developers (with a manager who isn’t involved in this project at all) help mitigate these delays?

I’ve recently accepted a new position after spending more than three years at my first job out of college. Currently, I’m a Senior Engineer at a large, corporate-like company (300+ people), but my new role will be at a much smaller startup (20-30 people).

I’m excited about the change but also a bit nervous, as I know startups can be fast-paced, and I’ll need to get up to speed quickly.

What advice do you have for setting myself up for success in this new role—both before I start and after I begin? I have a couple of weeks before my start date and want to use that time to prepare effectively.

In this episode, Dave and Jamison answer these questions:

I am a first time caller and full time listener of your show.

I was released from prison a year ago and I coded for 18 years straight on all sorts of stacks as part of my job requirements in the pen. Imagine the irony when I discovered what codepen was.

A dev told me about an opening for full remote/full stack web dev at their company. I’ve used the tech stack before but I have a non-traditional background to say the least. I’m not worried about being qualified but I have never worked in a team and I have always been responsible for production.

I work for a large retailer in a non-coding role. I’m also doing some freelancing on upwork/fiverr, but the pay is low and the jobs are not fulfilling. I was self-employed before I was incarcerated and I know how to beat the pavement and get small time work, but this is an opportunity to work at a real software house. I don’t even care if it’s a feature factory, I just have loved coding since I was 14.

What do I do? I am confident in my skills and ability to deliver under pressure (in a place that has pressures you can’t imagine). I have a cover letter, but a bad resume and no open source projects from this millennium. I do have a reference - a Captain I worked for said he was willing. However, the opportunity was unexpected and I have not prepared anything.

The dev who brought me the offer was a casual friend in IRC and he told me that my resume was mentioned in some meeting. I know you have suggested in previous shows that having someone get your foot in the door is the best way but I really think that feels gross to me.

Anyways, longtime listener of your show and first time caller. In fact, when I was in prison, a few years before I was released we finally got tablets with an incredibly limited amount of content. Your show was one of a few on coding but I really enjoy your take on the soft skills because even though I worked in a non-traditional environment, teamwork was always the focus and I listened to everything from square one (took me a long time to get there).

So thank you for your podcast you don’t know how many times I could sit in my cell listening to your show and disappear from my cage.

Sincerely, Names have been change to protect the guilty

Second time caller from NYC! I previously wrote in as an 18-year-old CS graduate (Episode 332).

I’ve focused intensely on work for the past 4 years, consistently working 60+ hours per week.

I always assumed that this approach to life would eventually bear fruit, but a couple months into turning 20, I’m realizing that I haven’t really done anything memorable besides work (which is a scary realization at 20).

While I like working hard and want to ensure the success of the company I work for, I also want to feel like I am living. How have you struck the balance between work and non-work in your lives, and how has that related to the culture of the company you were working for at the time? I should also mention the company I work for (early stage, well funded) does have a culture where it’s expected to work everyday, and 60 hours is approximately the minimum expected.