Soft Skills Engineering

Episodes

• Episode 512: Can non-engineers really contribute code with AI and not sharingMay 11, 2026 · 42 minIn 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?PlayPlay Episode 512: Can non-engineers really contribute code with AI and not sharing
• Episode 511: Should I take a temporary management position and performance-based bonusesMay 4, 2026 · 35 minIn 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?PlayPlay Episode 511: Should I take a temporary management position and performance-based bonuses
• Episode 510: Old and behind and how do I hang on for the last few years until retirement?Apr 27, 2026 · 33 minIn 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 planningPlayPlay Episode 510: Old and behind and how do I hang on for the last few years until retirement?
• Episode 509: I hate AI software dev, so should I become a manager and leading, not doingApr 20, 2026 · 36 minIn 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?PlayPlay Episode 509: I hate AI software dev, so should I become a manager and leading, not doing
• Episode 508: My company is an unethical spammer and my coworkers take so much sick timeApr 13, 2026 · 32 minIn 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/+ABLmzfhZxakPlayPlay Episode 508: My company is an unethical spammer and my coworkers take so much sick time
• Episode 507: I got fired unexpectedly and breadth and depthApr 6, 2026 · 33 minIn 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?PlayPlay Episode 507: I got fired unexpectedly and breadth and depth
• Episode 506: I hate my job with AI and my team-mate thinks I suckMar 30, 2026 · 40 minIn 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!PlayPlay Episode 506: I hate my job with AI and my team-mate thinks I suck
• Episode 505: Called to the principal's office and my team leads are super dogmaticMar 23, 2026 · 45 minIn 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. IPlayPlay Episode 505: Called to the principal's office and my team leads are super dogmatic
• Episode 504: Should I quit my AI job before my first day and professional button-clickerMar 16, 2026 · 32 minIn 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?PlayPlay Episode 504: Should I quit my AI job before my first day and professional button-clicker
• Episode 503: Hardware is hard and my PMs are pushing AI slop codeMar 9, 2026 · 36 minIn 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?PlayPlay Episode 503: Hardware is hard and my PMs are pushing AI slop code
• Episode 502: Management keeps leaving and I hate using AI to codeMar 2, 2026 · 41 minIn 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. StrangecodePlayPlay Episode 502: Management keeps leaving and I hate using AI to code
• Episode 501: Vibecoding CEO and doing to teachingFeb 23, 2026 · 29 minIn 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!)PlayPlay Episode 501: Vibecoding CEO and doing to teaching
• Episode 500: Am I the only one not getting raises and firing my whole teamFeb 16, 2026 · 36 minIn 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 howPlayPlay Episode 500: Am I the only one not getting raises and firing my whole team
• Episode 499: Should I quit my solo dev job with a sports team and senile seniorsFeb 9, 2026 · 33 minIn 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’rePlayPlay Episode 499: Should I quit my solo dev job with a sports team and senile seniors
• Episode 498: Testing in big corporations and how to get my first management jobFeb 2, 2026 · 31 minIn 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.PlayPlay Episode 498: Testing in big corporations and how to get my first management job
• Episode 497: Patronizing perf reviews and can't get anything done as a tech leadJan 26, 2026 · 27 minIn 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?!?!! HelppppPlayPlay Episode 497: Patronizing perf reviews and can't get anything done as a tech lead
• Episode 496: Passing non-technical interviews and my internship with only other internsJan 19, 2026 · 26 minIn 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?PlayPlay Episode 496: Passing non-technical interviews and my internship with only other interns
• Episode 495: What to do when my boss quits and moving to Romania?Jan 12, 2026 · 32 minIn 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 🥺PlayPlay Episode 495: What to do when my boss quits and moving to Romania?
• Episode 494: Am I interviewing all wrong and leaving old team chatsJan 5, 2026 · 26 minIn this episode, Dave and Jamison answer these questions: Dear Damison and Javison, I work at a very small startup ( 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)?PlayPlay Episode 494: Am I interviewing all wrong and leaving old team chats
• Episode 493: My boss one-ups my negativity and football engineeringDec 29, 2025 · 21 minIn 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.PlayPlay Episode 493: My boss one-ups my negativity and football engineering
• Episode 492: Fresh grads and startups or the googDec 22, 2025 · 33 minIn 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?PlayPlay Episode 492: Fresh grads and startups or the goog
• Episode 491: Re-arranging deck chairs on the Titantic and my boss leaks private infoDec 15, 2025 · 36 minIn 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!PlayPlay Episode 491: Re-arranging deck chairs on the Titantic and my boss leaks private info
• Episode 490: How do I break into software dev from QA automation and undersellingDec 8, 2025 · 26 minIn 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?PlayPlay Episode 490: How do I break into software dev from QA automation and underselling
• Episode 489: Ethical dilemma for a gambling app dev and ethical employersDec 1, 2025 · 34 minIn 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?PlayPlay Episode 489: Ethical dilemma for a gambling app dev and ethical employers
• Episode 488: How do I survive in a culture of optics and jira slackerNov 24, 2025 · 30 minIn 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 😩PlayPlay Episode 488: How do I survive in a culture of optics and jira slacker
• Episode 487: My manager ignores me during 1:1's and I am required to work in an empty officeNov 17, 2025 · 36 minIn 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?”PlayPlay Episode 487: My manager ignores me during 1:1's and I am required to work in an empty office
• Episode 486: No one on my team talks and skip level meetingsNov 10, 2025 · 29 minIn 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?PlayPlay Episode 486: No one on my team talks and skip level meetings
• Episode 485: I'm terrible at hiring decisions and my coworker spams us with AI-generated memesNov 3, 2025 · 43 minIn 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!PlayPlay Episode 485: I'm terrible at hiring decisions and my coworker spams us with AI-generated memes
• Episode 484: How to get a raise after slacking off for YEARS and my PM won't stop DM'ing meOct 27, 2025 · 29 minIn 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 DMsPlayPlay Episode 484: How to get a raise after slacking off for YEARS and my PM won't stop DM'ing me
• Episode 483: My team hated me from day one and should I stack PTO before my resignationOct 20, 2025 · 38 minIn 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.PlayPlay Episode 483: My team hated me from day one and should I stack PTO before my resignation
• Episode 482: I got a promotion, but a tiny raise and an imposter interviewed for my teamOct 13, 2025 · 31 minIn 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.PlayPlay Episode 482: I got a promotion, but a tiny raise and an imposter interviewed for my team
• Episode 481: I'm bored and will I ever find out why I was fired?Oct 6, 2025 · 29 minIn 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?</PlayPlay Episode 481: I'm bored and will I ever find out why I was fired?
• Episode 480: Do I just coast until I quit and going back to work after a long timeSep 29, 2025 · 27 minIn 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!PlayPlay Episode 480: Do I just coast until I quit and going back to work after a long time
• Episode 479: Contractors to the rescue and dinged for delaySep 22, 2025 · 34 minIn 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!PlayPlay Episode 479: Contractors to the rescue and dinged for delay
• Episode 478: Can you coach self-awareness and my boss is an llmSep 15, 2025 · 38 minIn 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?PlayPlay Episode 478: Can you coach self-awareness and my boss is an llm
• Episode 477: Four months and I already hate my job and grumpy and fuzzySep 8, 2025 · 37 minIn 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?PlayPlay Episode 477: Four months and I already hate my job and grumpy and fuzzy
• Episode 476: How much help is too much help and guarding against slopSep 1, 2025 · 37 minIn 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?PlayPlay Episode 476: How much help is too much help and guarding against slop
• Episode 475: Am I too loyal to my big tech job and politely preserving timeAug 25, 2025 · 33 minIn 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!PlayPlay Episode 475: Am I too loyal to my big tech job and politely preserving time
• Episode 474: I hate the idea of firing a low performer and cheaper context switchingAug 18, 2025 · 38 minIn 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 helpPlayPlay Episode 474: I hate the idea of firing a low performer and cheaper context switching
• Episode 473: Mental health support and overcoming FOMO of taking a break from workAug 11, 2025 · 35 minIn 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 https://blog.jsbarretto.com/post/software-is-joy https://medium.com/@djsmith42/the-3-highest-roi-technical-skills-for-software-developers-21b412d79affPlayPlay Episode 473: Mental health support and overcoming FOMO of taking a break from work
• Episode 472: Should my junior dev use AI and thrown in to ETLAug 4, 2025 · 26 minIn 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!PlayPlay Episode 472: Should my junior dev use AI and thrown in to ETL
• Episode 471: Why does my junior engineer do so little and I fell asleep in a Zoom meetingJul 28, 2025 · 28 minIn 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!!!PlayPlay Episode 471: Why does my junior engineer do so little and I fell asleep in a Zoom meeting
• Episode 470: I said something stupid in a meeting and just want to codeJul 21, 2025 · 30 minIn 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?PlayPlay Episode 470: I said something stupid in a meeting and just want to code
• Episode 469: Passed over for lead role and perhaps I'm the jerkJul 14, 2025 · 35 minIn 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. TheyPlayPlay Episode 469: Passed over for lead role and perhaps I'm the jerk
• Episode 468: Should I take a mini-retirement and doubling down on anachronismsJul 7, 2025 · 31 minIn 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 PersonPlayPlay Episode 468: Should I take a mini-retirement and doubling down on anachronisms
• Episode 467: I can't get promoted if I do my job and should I get a degree to get a job in this economyJun 30, 2025 · 40 minIn 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.PlayPlay Episode 467: I can't get promoted if I do my job and should I get a degree to get a job in this economy
• Episode 466: Bad performance review and moving in to the cavesJun 23, 2025 · 29 minIn 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.PlayPlay Episode 466: Bad performance review and moving in to the caves
• Episode 465: Talking to your report's previous manager and how to replace a 30-year-old ticketing systemJun 16, 2025 · 29 minIn 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.PlayPlay Episode 465: Talking to your report's previous manager and how to replace a 30-year-old ticketing system
• Episode 464: Rehiring an overpaid boomerang and AI has taken over my teammate's brainJun 9, 2025 · 49 minIn 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” crPlayPlay Episode 464: Rehiring an overpaid boomerang and AI has taken over my teammate's brain
• Episode 463: CTO w/ weak resume and I tried management and it was TERRIBLEJun 2, 2025 · 27 minIn 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 goPlayPlay Episode 463: CTO w/ weak resume and I tried management and it was TERRIBLE