Soft Skills Engineering

In this episode, Dave and Jamison answer these questions: Dave and Jamison, long time listener first time caller. I appreciate everything you do, I look forward to my Monday morning commute because of this podcast. I’ve been a software developer for about 4 years. I’m a career changer and graduated from a boot camp. I was fortunate enough to earn a junior developer position at a non software company and have been promoted during my tenure. I work on a small team and enjoy what I do and the level of impact I have. I am one of the most senior developers. My only concern is that I do not receive direct mentorship from more experienced developers. Am I limiting my future prospects by not job hopping? When is the right time to leave a company and seek new opportunities? Hello Mr. 💃 and Mr. Smith. I’ve been working in software ~6 years. In the same company (don’t judge). And about a year ago I advanced in the position of a team lead of 4 developers. I would actually like to attribute this advancement, at least…

In this episode, Dave and Jamison answer these questions: Listener Random Listener asks, You guys talk a lot about externalities, which helped me understand a lot about how my manager works. He wants to do things fast, but he does not follow good and standardized processes, even the ones he tries to push onto us. This adds a lot of work for us because now his mess becomes our mess. How can I give him this feedback in way he will both understand and not feel resentment? Thanks Hello. I am individual contributor and have been with this team for 2 years. About a year ago a manager and a lead joined the team to fill in the growing positions. They came in with their preferences for code design, architecture, and ideologies. But they were all different from how we worked before. Their ways are not bad, but they add unnecessary complexities, taking away energy from just doing my pick-up - code - ship way. I shared my concerns, but they never get accepted as they just want to exercise their manager and lead powers.…

In this episode, Dave and Jamison answer these questions: Hi Soft Skills Engineering, I’m a senior software engineer with over 20 years of experience. I’m hoping you can help with with a problem where I’m dumb, weird and bad at my job! There is a recurring problem where, despite all my experience and graybearding, despite my big words, I sometimes just miss very important details, and ways that are very consequential and cause time and feature gaps. Sometimes I make a faulty assumption and gloss over initial errors, and later I get big errors that require big fixes. For example, sometimes I just miss random lines from a product spec or whole parts of the UI, like a blind spot, or like a Mandela situation where I could’ve sworn it was different where I read it. Sometimes, I read the docs on some library but didn’t really *read* the docs and missed the important line that I needed before things get broken. It’s a soft skill, sorta, because it’s about how I go about my work, and I don’t know what I can do about…

In this episode, Dave and Jamison answer these questions: Hey Dave and Jamison. I don’t know what to do with the amount of the AI slop I have to review and I’m getting close to burnout. I have a lot of context on my project, so my colleagues see me as a point of reference. Additionally, at a past job, I was a tech lead and could easily cover for TL if I wanted to (which I don’t) and I feel like the TL of my project and some of my teammates are taking advantage of this. Every day I receive a lot of low quality documents to review. For example, our TL creates sloppy project planning documents and tickets and sends them to me for comments. Since they contain so many errors, sometimes including obvious security or data compatibility issues, or just text that is unrelated to the project, I end up basically rewriting everything. The same thing happens with code reviews. Some code is obviously AI-generated slop with lots of duplication and errors, that in many cases misses acceptance criteria or has doc strings…

In this episode, Dave and Jamison answer these questions: Hi Dave and Jamison, I’ve been a Java backend dev for over 10 years. After getting laid off from a job I loved, I spent 3 tough months job hunting. I eventually landed a full-stack role at a non-tech company where I am the entire front-end department. The team is a mess: A CTO who hasn’t coded in years and calls me directly to assign tasks, all labeled “highest priority.” When I asked the CTO and CEO if we had QA, they literally laughed at me. Prod releases are “tested” by the CTO before telling me to push immediately. I’m at a crossroads: Stick it out for 6–12 months to gain AI experience, then quit? Try to move into management, and rebuild this mess into a functioning engineering organization. What should I do? Hey, Dave and Jamison. I’m a non-native Japanese speaker working in Tokyo with about 6 years of experience in backend(3 years in Tokyo) and haven’t used English in work. I started listening to this podcast for learning English. And I soon…

In this episode, Dave and Jamison answer these questions: Listener Jame ain’t no dance asks,! Hey Space Therapists, I am a consultant that helps big companies to fix all kind of stuff. It’s ridiculous how many different hats I wear. One day I’m the interim PM, the other day I am telling SAP devs how to use a coding agent, next day I gather stakeholder requirements for a customer self service portal. I do all of these tasks on a fairly shallow level and all of that work is happening without much coordination from my company. I think I do a good, but it’s hard gathering feedback on my work, since no colleagues are involved and I can’t simply ask the customer without revealing insecurity. Send sophisticated tips and don’t make me quit. Cheers! Can I tell a coworker to stop using Claude? I work on a small team at a midsized company, and a coworker keeps dropping overly verbose pull requests that are full of AI jargon. These are increasingly hard to understand, and then when I ask for design intent clarification…

In this episode, Dave and Jamison answer these questions: Listener Myamax myamax says, I just listened to episode 527 and could really use some advice on being good at interviews. I was recently laid off with a decent severance package, so I have some breathing space. I’ve had several interviews, and I usually get past the initial screenings, but I don’t shine in technical rounds. I’m a career switcher, and most of my tech career has been in analytics at a big company. I’m good at distilling things, very good at debugging and navigating mazes of corporate legacy, but I haven’t really built things from scratch. I’m not a pure individual contributor, not a product manager but some technical-product hybrid, and it was a fun place to be. I stole good ideas from different teams and stitched them together adding common sense on top. I spent a lot of time with users and stakeholders to understand their data and their processes. Most of the time they needed common sense and decent data foundations. Only in rare…

In this episode, Dave and Jamison answer these questions: Hi Jamison and Dave, jesters of my daily commute. I’m a *mechanical* engineer at a megacorp, and since people are people, I find most of your advice transfers pretty well. I’m the tech lead within a small-ish org of about 25 people. We’re in-office, and split between two locations (in a similar time zone), and multiple different projects. This means that there are a lot of Zoom meetings between locations. Lately, I’ve been having an issue with engineers deciding to take these meetings from their desks in our open office plan rather than finding a phone or conference room. I find this practice to be maddening! It’s really distracting because there will often be background noise that makes it hard to clearly understand them, and it also means that my workplace is a cacophony of people yelling into their AirPods, competing to overcome the background noise of their colleagues’ yelling into their AirPods. How do I make this stop and get my coworkers to hop…

In this episode, Dave and Jamison answer these questions: A listener named “Will angel answer my question?” asks, Hi, I recently joined a new company about 1.5 months ago. It is the technology arm of a family-owned business group that has existed for over 30 years, providing technology services to all the other companies in the group. After a one-week onboarding, I was assigned to a team. After 2–3 days, I still had no tasks, so I asked a coworker to pair program with me so I could learn more about the processes and continue learning. The task was easy, and we finished it in less than a day. For the next 2 days I did nothing, asked my boss for tasks but he just told me to wait. Two days later, we finally had a planning meeting, and they assigned me three tasks for the upcoming two weeks. I finished the first one in 25 minutes and other ones in not much more time. It has been like this ever since. I’m really enjoying all the free time, but I’m also feeling anxious that I may eventually be part of a layoff.…

In this episode, Dave and Jamison answer these questions: Hello Dave and Jamison! I’m a longtime listener going back to the early days of the podcast, and I’ve listened to every episode since. When I started listening, I was beginning my career as a software engineer. Your advice has truly helped shape how I think about work, engineering, leadership, and all the weird human stuff that comes with building software. Now I’m more than 10 years into my career, and I’ve run into a problem that I suspect many experienced engineers are dealing with right now. In episode 521, you talked about how brutal the current job market is, and the question asker from that episode had been unemployed for a year. I’m thankfully not there yet, but I recently lost my job in a large layoff, and the first couple of months of searching have been pretty discouraging. I’m applying to roughly 10–20 jobs a day. I tailor my resume to each role, ensuring it accurately reflects the skills and terminology in the job description. I usually…

In this episode, Dave and Jamison answer these questions: Hi Dave & Jamison! I’ve been listening for almost a year now and have worked through nearly your entire back catalog in reverse. The podcast has genuinely helped me become a better engineer, so thank you! I’m two years into my software engineer career at a large infrastructure company. I was promoted to SWE II last year, and this year my manager told me she felt my work was promotion-worthy, but because I’d just been promoted and she had others on the team to consider, she wants to target me for next year’s cycle instead. She gave me a spot bonus and said she’d try to make up for it in my raise. I understand and appreciate the honesty, but I’m also a little disappointed because I’ve worked hard to hit every milestone on the roadmap she gave me, and career progression does matter to me. My question is: How should I navigate the next year? What should I focus my 1:1s on? Should I push for a mid-year promotion if that’s an option, or instead focus on…

In this episode, Dave and Jamison answer these questions: Hey Dave and Jamison, First, I love your show and it has now been part of my Monday evening routine for many years to listen to your podcast while cooking dinner. I recently joined a mid-sized software company (500 people) as a senior data engineer. The salary is a significant bump from my previous job and I really like the team on a personal level. Three months after I joined, the company laid off half its employees and announced a strategic pivot away from their previous core business to become an “AI-first company” and develop new products in novel, more profitable sectors. The product that my team had been working on until that point was scrapped and there are no new projects coming from the business side. In subsequent communications, it was revealed why: Management has no concrete ideas for the future strategy, neither on what products to develop nor on which sectors to target. Instead, our team (among others) is now tasked with coming up with…

In this episode, Dave and Jamison answer these questions: I work for a small software company on a team of about 7 or 8 engineers. I like working here. I like the people, the autonomy, the pay, my boss, and the stack among other things. I try to remind myself of this regularly so I don’t take it for granted. I’ve been here for about 2.5 years and would love to continue working here. Our CTO, like many, has become a big AI cowboy coder. Every few months, he vibe codes a new project and then decides to interrupt the full workloads that we have a limited number of engineers to do to hand his project off to be cleaned up, worked into the product, and solve all of the problems that remain once actually put into practice. This usually ends up going to a different engineer per project, who is then tied up with the CTO’s whims and is no longer available to do the work planned by product. Our EM knows this and knows the frustration and lost velocity, but what can he do? (rhetorical, not the question) Most recently, I…

This is a rerun of episode 331. In this episode, Dave and Jamison answer these questions: Listener ninjamonkey says, I am a new grad who is half a year into the role now at a very large company. Recently, a senior engineer on my team asked me to create a ticket for an infra team for a problem with a service. I provided logs and steps to reproduce the issue and did a health check before submitting. Right after, the manager of the team put me into a group chat with their team, asked why I created the ticket and told me to start doing my job and they can’t debug for me. From these interactions and comments on the ticket, it feels the infra team will likely not work on the tickets I report or de-prioritize them. This has left me discouraged and hesitant. I will have to do lots of this kind of infrastructure work in the future. Additionally, one of the goals my manager set for me is to work with more external teams for the upcoming year. What do I do here? Do I tell my manager about these interactions? Do I tell…

In this episode, Dave and Jamison answer these questions: I stayed too long at my first company and now my career is ruined? Hi both, long time listener. (Since I graduated university 4 years ago actually and felt I could never find a job but listening to you guys made me feel not like such an outcast in our field.) I graduated in 2022. Didn’t really apply around much and almost immediately accepted the full time offer from the company I did my internship with during my degree. And fast forward to middle of 2026… I am still here. I’ve long stopped growing as an engineer and have actually been stuck on a simple CLI tool for almost 4 years now with little to no cloud/backend/etcetera experience to show in my 5 year career. I don’t feel I am desirable in the job market at all due to this and waited way too long to look for a job because I was comfortable and happy. I feel paralyzed (no need to put on your space therapist hats BUT some career advice would be wonderful!) (Also did I mention I am in Canada and…

In this episode, Dave and Jamison answer these questions: Dwill Ainghell asks, During the golden era of software development, it was commonly stated that you should always negotiate job offers. The argument was that the company has invested significant time and resources into you as a candidate and there is always some wiggle room for negotiations. A popular article / podcast by Patrick McKenzie likened it to doing something slightly uncomfortable like “reciting poetry while simultaneously standing on one foot” with almost no downside. (https://www.complexsystemspodcast.com/episodes/how-to-negotiate-your-salary-package/) Does this still hold true in today’s environment? I’m a SWE with 10 years of experience and I’ve been unemployed for close to a year. I’m expecting an offer from a large company and I fear that I will look like a fool trying to negotiate in my current position and the current job market dynamics. Even worse, I fear that they might retract the offer and give it to someone else. That being…

In this episode, Dave and Jamison answer these questions: Hey Dave & Jamison, Long time listener. Love the podcast. I recently rejoined a remote team that I worked with in the past. I was super stoked to rejoin this team because they were collectively one of the most competent and technically excellent teams I’ve ever worked with. And they’re all genuinely nice people as well. I left the team before AI coding had really caught on, but coming back to the team has been a huge shock to me. Almost everyone now exclusively writes code with AI. PR descriptions are all AI generated, and code review has become copy-pasting AI-generated comments into GitHub. Being a remote team it was already hard to connect, but now it feels like almost all interactions are their AI assistant talking to my AI assistant. I’m not anti-AI, and I get that writing code with AI can be much quicker. But I’m struggling with the loss of what made the team feel good to work on, specifically the craftsmanship, level of engagement, and the…

In this episode, Dave and Jamison answer these questions: Hi D&J! Question from Sweden! I’m a senior dev that have seen a lot of orgs without tech lead and/or staff engineer roles. I know some companies have them, but mostly newer more techy companies. Bigger older less techy companies usually have non-coding “architects”. Though that’s one title I have no good experience of, just neutral ones or worse :) In particular I’ve been in many teams without a tech lead (all developers are equal, no tiebreaker vote). It’s often successful due to a leader and/or consensus emerging organically and peacefully. I loathe the failure modes however: consensus abuse through veto (we can’t move discussion forward because someone explicitly actively disagrees, a “keeping the meeting hostage” situation), disagreement on technical priorities and choices (lowest common denominator it is…) or that the team is bickering and bikeshedding during technical discussions. Is this just a regional/cultural thing, or is it more about the…

In this episode, Dave and Jamison answer these questions: I have been at a small startup company for 5 years now. It’s a very small technical team, 4 devs and a tech lead that contributes code & architecture. I am getting a small raise this week for my 5 years but it’s a smaller raise than I was expecting. We’re an all remote team across the globe but I had a dev co worker in the same city as me just leave the company. This has put more pressure on me as I’m the only dev in the primary time zone we operate in, everyone else is east coast or opposite side of the world. With the added pressure and some forward comments from me in one on ones with my tech lead I expected much more that I’m being offered. I think I’m supposed to quit my job but I’m terrified of that idea. This is my first job in the field and I love the work. The full stack startup experience is fun and I’ve learned so much, and I like my team a lot. I’ve never even applied to another position in tech yet, I got this one with the first…

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

In this episode, Dave and Jamison answer these questions: My company follows scrum, with daily standups. We got a new scrum master. He is very formal and procedural and I struggle with our daily meetings. He goes through a long list of assigned tickets, asking each ticket owner about status and info on progress. We are all engineers with many years of experience but it feels like we are in the kindergarten. We don’t have deep expertise about each others work. It is important to know what each of us is doing more or less, but going deep in these issues makes me disconnect, and I think these meetings are above all very good to signal blocking points and ask for help. A recitation of tickets and work being done is not their purpose. On top of that, most days it takes 25-30 mins to go through all the issues. Am I being difficult complaining about this? I tried to be polite when I raised the issue but I was told more or less that this way is better for the company. Is it common in the industry to go through…

In this episode, Dave and Jamison answer these questions: Hi from a long-time listener and first-time caller. I need some advice on a toxic workplace situation. I’m currently unhappy with my job due to a difficult dynamic with a colleague. My manager put us on the same team, meaning we share responsibility for our output. Although this colleague is technically a level below me, they act as though they have seniority. This creates significant friction: they’re resistant to advice, insist they’re always right, and refuse to accept reality even when they can’t deliver what’s required. They’re incredibly stubborn, and arguing with them about what’s feasible takes an excessive amount of effort. The situation is particularly frustrating because I’m held accountable for the shared results. If I weren’t responsible for the final outcome, I could probably just ignore their behaviour. Instead, they frequently talk a big game while contributing very little actual work. People unfamiliar with our domain are easily…

In this episode, Dave and Jamison answer these questions: My parent organization has trust issues: we registered on a recent survey as one of the lowest across the bigger software org (thousands of employees). There are two groups: functional, trustworthy people who get stuff done, and people who are behind, stuck, or just not working. Those struggling say they need better emotional support, but there is consistent, documented evidence that they cannot keep up. I’m perpetually frustrated that there are only two or three people in an org of 30 who can effectively complete tasks and manage the insane workload. I am biased: those in whom I have no trust have repeatedly demonstrated that they cannot be trusted. I believe that the organization would be able to go faster without them. Whats the right answer here? Should I start my own company to abandon this mess? Do we cut scope super aggressively to allow underperformers to be reasonable contributors? One example: one of these contributors was walked through the…

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

In this episode, Dave and Jamison answer these questions: Should I declare my struggle with this AI world we live in here? Nah. I mean, I’d like the hype to die down, a lot, but we keep getting new tools and I get to experiment, so here we are. My real struggle, and this podcast is implicated in it, is around non-technical people contributing to production systems. Why are we so obsessed with this idea? COBOL tried it. Low-code and no-code tried it. BDD and Gherkin aspire to it. Yet time and again the field demonstrates that you need people who know their stuff. To “democratize” software engineering implies that all people have the desire and ability to become software engineers. That premise is false. You democratize access to education or financial systems, the stock market say. You don’t democratize skill. Skills are earned. We would never, I hope, democratize bridge engineering or piloting an aircraft. Software engineers are just as critical as either. When our software breaks, money goes missing,…

In this episode, Dave and Jamison answer these questions: I’m approaching 15 years of experience with the last 7 years at fang. About a year ago I was promoted to staff engineer (thanks to the podcast) and switched to an adjacent team under the same director. I have never actively pursued a management role but I’ve been starting to think about it more. A colleague of mine just announced they need to take extended medical leave (1-2 months) and I was asked to fill in as a temporary manager while they are out. How do I go about managing a team if everyone knows it’s short lived? Should I just try to keep the team alive or aim higher? Is 1-2 months enough for me to get a sense of whether I’d enjoy management? I feel like I’ve dived into the deep end and it’s scary but also exciting. I love the podcast, I’ve listened to every episode! I’ll take whatever comedy or advice you have to offer. Bobby Drop Tables asks, Recently came out of a salary negotiation where HR blocked a payrise because they said I was already…

In this episode, Dave and Jamison answer these questions: I work at a large remote company. We meet up once or twice a year. I don’t really know much about my engineering coworkers aside from the 5 people on my team, so the in person meet ups seem like a good place for me to get to know people from the other teams. I am a career switcher, and am currently a mid level IC (borderline junior) in my late 30s and a youthful appearance. At these meetups, my position and appearance (and honestly, possibly my demeanour) makes me feel like I am expected to socialize with other ICs in their 20s. Although they are nice people I find it hard to relate to them when talking about non work related topics since I am much older and in a different stage in life than all of them, (married with a mortgage and kids). I want to socialize with coworkers closer to my age and stage in life but most of them are team leads or manager. I feel like socializizing with them would be seen as brown nosing. I’ve also heard that once someone…

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

In this episode, Dave and Jamison answer these questions: How can I get our company to follow the law and stop sending SPAM without being regarded as negative? We’re sending out emails that don’t comply with CAN-SPAM, and I think we should comply due to the risks, but I don’t want to risk any blowback! People want the emails to look more ‘human’ sent, and putting your mailing address at the end of an email is not very human, so we’re not doing that… It’s a medium startup (500 people), but I’m close enough to the marketing work that they might know it was me! Should I send an email to our general consul? How can I raise concerns and do the right thing without being regarded as not a team player?? How do I stay motivated on a team that’s always sick? I’m on a team of 3 ICs and one manager. The other two ICs are plagued by health issues. I am trying to be empathetic, but this has been going on for the at least a year. One of them regularly takes sick days, often turning into sick weeks. The other has a long…

In this episode, Dave and Jamison answer these questions: Hey there, I started a new job in August at a large European retailer. There were ups & downs, but long story short, my weekly one-on-ones with my manager was either positive or neutral. This was my second job after graduating, so the firm factored in, I’d like to think, when setting expectations this was my first time switching codebases and tech stacks. On January 3rd, I was fired in the last month of my 6 month probation. This was a total surprise. My tech lead told me I required too much assistance from others to finish my tasks. Some part of me doubted the sincerity of my boss, since I asked for example pull requests or tickets where this was the case and he was unable to provide a single example, but obviously, like every dev, technical insecurities are a big part of my life. I’ll be starting a new job at a prestigious newspaper in May, so here’s my question. In a remote first environment, how do I determine if I’m meeting expectations? How do I…

In this episode, Dave and Jamison answer these questions: Hi Djavison, I’ve heard y’all say something along the lines of “this is the most exciting time to build software” in a few recent episodes. I’m glad that has been your experience and seems to be the experience of many others. But for me as someone 5 years into the career who is, thankfully, employed—I can’t help mourning a job that no longer exists. Obviously, there are still lots of us with the job title “software engineer” that create software. But, what I originally fell in love with doesn’t really seem like a thing you can get paid to do anymore. I now spend most of my development time reviewing code and making sure things work. Which feels way less rewarding and way more soul-sucking. Maybe I’m just nostalgic for being a more junior developer, but it’s obvious that our jobs have changed forever and will continue to evolve. So, my question is: How can I get excited and feel passionate about this new way of doing things? I am a senior team lead…

In this episode, Dave and Jamison answer these questions: I’m a senior software engineer at a remote company (~500–700 people), and over the last year a new HR org replaced our old people team. They’ve spent six months building a new goals/leveling framework. During a public meeting I asked in slack: “We’ve had goals before and then stopped using them. How will these be different?” Nobody answered directly. The next day I was pulled into a meeting. The new VP of HR had screenshotted my question and sent it up my management chain. My manager told me they were on my side but leadership didn’t appreciate it. Days later I was pulled in again and told the problem was my “tone.” I didn’t argue because we were at an impasse. It felt like tone policing and like being sent to the principal’s office. I didn’t feel like they were treating me like an adult. In yet another 1:1, my manager said leadership wanted it raised again and that they don’t want questions like that in public. I told him the meeting should’ve been…

In this episode, Dave and Jamison answer these questions: Hi Jamison and Dave. Eight years into my software engineering career, all of it at Series B and C startups, I’ve been craving two things: a recognizable brand name on my resume and the chance to work on real scale problems. After a long search, I finally got both. The catch? I got them in the wrong order. I accepted an offer at one of the hottest and fastest-growing AI companies in the application layer space. Exciting work, smart people, real momentum, but not quite a household name yet, and not quite facing the kind of scaling challenges that come with a billion users yet either. Two weeks later, I finally heard that I cleared the interviews from a big brand name tech company. I’ll be honest: it wasn’t my first choice brand name. I bombed interviews at a few others and this was basically my consolation prize. Here’s the thing about this mega tech company right now: the culture has … shifted. It feels less like a tech company and more like a social…

In this episode, Dave and Jamison answer these questions: I’m a software developer with about 15 years in the industry, and I am soon starting as the CTO of a robotics company with about 50 employees. Though I have years of experience and an academic background within the field of robotics, I have always been focused on the software side of things. In my new role, I am ultimately responsible for the hardware team as well. How do I go about earning the respect, and becoming an effective leader, of my new colleagues working in a field in which I am not an expert myself? Hi, I’m meowmeow, and I’ve enjoyed your podcast for a long time. I’m working at a small engineering company which don’t have lots of profit. Recently, the PMs at my company(including the CEO) have started “vibe coding” directly on our product. They’ve even added PMs to the project planning list as contributors. Whenever they open a PR, the code is AI-generated and reflects their personal working style. The code quality is fairly low and…

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

In this episode, Dave and Jamison answer these questions: A listener named Derek asks, I am the CTO and cofounder of a startup. Now that vibecoding is a thing, our CEO has kind of gone rogue, and and he’s vibecoding a bunch of random stuff, one of which he bought a domain for and has pushed a potential customer to pay for, without talking to our team. I feel like this is fragmenting our focus, but I don’t want to ban our CEO from vibecoding and being creative. how should I handle this without damaging relationships? AdmiralFox asks, Hi Dave and Jamison! Longtime listener, first-time question asker here. After 14 years at a consultancy firm, I’m moving to a major retailer to become their Java Learning and Community Lead. Instead of shipping code, my new role will be shipping knowledge. I will be managing learning paths, organizing internal knowledge sharing events, and help managers screen candidates. Basically, I’m moving from a ‘Maker’ role to a ‘Multiplier’ role. I have 13 weeks of notice period (Standard…

In this episode, Dave and Jamison answer these questions: I have been with my current organization for 5+ years. I like the company and have generally had a good experience working here. However, the last several years I have not really gotten a raise except for the standard “merit raise”, which does not cover inflation, so effectively the last several years I have made less money than the year before. I brought this up to my EM who said there is no chance of the company increasing the merit raises to meet inflation, unless I get a promotion. However, my EM also said there are no promotions available. I don’t know if this means the company knows the job market is tough and they don’t have to pay us as much, or if the company is in dire financial straits and unable to keep salaries up with inflation. This job market is tough and I don’t know how long it would take me to find a new job, but certainly I will look. My question is basically, how can I go about getting my manager to help me level up to make myself…

In this episode, Dave and Jamison answer these questions: I’m a new listener to the podcast and work as the sole developer for a sports team, which is the only company I’ve worked for since graduating from university 8 years ago. I listened to episode 493 while clenching my teeth as you told a listener to absolutely not take the job with the European football club as a solo developer. Yikes! While I feel I have continued to grow my skillset in my role, I’m now feeling vulnerable about having no professional experience working alongside other developers or on large-scale applications. I feel very conflicted about leaving my current company. I have a respectable developer salary for the (non-American) low cost of living area I’m in, have a great manager, and have built up a ton of good will and trust within the organization. I get all the freedom I could ask for to make design decisions, implement devops practices, try out new technologies, and make mistakes. I also find the work interesting and there’s always…

In this episode, Dave and Jamison answer these questions: ‌ Hi Dave and Jamison, Internal dev asker from the second half of Episode 441 checking back in. Your “ask what scared the previous dev” advice in particular has paid off handsomely; I now carry around a little book of eldritch warnings and, somehow, people keep bringing me their unknowable monsters to interpret. It’s almost as though the previous dev knew these sorts of things would happen! I didn’t set out to acquire Lovecraftian knowledge, but here we are, still in one piece. Today’s puzzle: getting busy humans to test our stuff early, while feedback can still make it into production. We’re trying to build a culture where people will poke at a rough prototype now, instead of filing a Very Concerned Ticket three hours before release. How do we get people to test and provide feedback earlier? Do we stay disarmingly warm, promise tiny time boxes, and make a public show of “you said / we changed” until participation feels like the default? Or do we wave…

In this episode, Dave and Jamison answer these questions: I’m a relatively new people manager and I really struggle when it comes time for performance reviews, or even regular praise or critical feedback in one-on-ones, because I can’t help feeling like an adult “talking down” to another adult, regardless of whether the feedback is generally positive or critical and instructive. Something about it all seems so patronizing to me. How can I approach this stuff with a different mindset? Hello D & J! Quick one from your biggest fan!! This week (Tuesday 6th Jan 2k26) I was promoted to Tech Lead of our team. In my new role, I have done no work *cries*, I’ve spent all my time assisting team members, unblocking QA, dealing with ad hoc requests from product/stakeholders…. I asked the previous tech lead is this what they did? They did! And they said spent their personal time to complete stories assigned to them. Is this really what a tech lead does?!?!! Helpppp

In this episode, Dave and Jamison answer these questions: Listener Tom says, I’m a software developer with six years experience, mostly at small startups with engineering teams anywhere between 2 and 10 developers. Because these startups have been small, most of the interviews were really casual. I’d speak to either the CEO, or CTO about my past experience, and we would talk about the direction the company was heading, and whether I’d be interested in joining. They felt less like interviews, and more like free-flowing conversations. I’m now back on the market, and I’m looking at larger, more established tech companies. I can get past the tech interviews just fine, but I’m struggling with the soft-skills interviews. Compared to what I’m used to they’re a lot more structured and it feels like they’re looking for answers that fit a certain criteria and format. What advice would you give to someone used to interviewing at small startups, but now interviewing at larger companies? I took an unpaid full stack…

In this episode, Dave and Jamison answer these questions: Hello gentlemen, long-time listener here, and I’d love your take on something that’s been keeping me up at night. The high powered boss that I report to is someone I genuinely like and respect.This manager is smart, kind, honest, and overall great to work with. We have a solid relationship. I also come from big tech, so I sometimes feel I have better experience around managing projects and keeping teams organized. However she recently shared in confidence that there’s a chance of resigning in the next few months. and when I asked what keeps her up at night, the headache did not seem so big of a deal to me. But ever since hearing this news, I’ve been catastrophizing the next few months. I’m not ready to job-hunt. At the same time, if this manager does leave, it could be a really good opportunity for me to step up. So here’s what I’m struggling with: 1.How do I position myself for a potential promotion without making it seem like I’m going behind my…

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

In this episode, Dave and Jamison answer these questions: Hey Guys, long time listener, first time asker! At my BigCorp Co., whenever I talk to my skip level about my concerns, it seems we are playing the ‘Gloom Olympics’ every time we meet. I’ll mention I worked late, and he’ll counter with, ‘That’s nothing, I haven’t slept in three days!’ This repeated lack of empathy is demotivating and I don’t think I have had a fruitful discussion with him. How can I tackle this? How can I feel heard? I’ve decided to leave my current job as a software engineer at a large retail chain. This is my first out of university, and I’ve been here three years. I’m interviewing for two other jobs: one as an engineer at another large retail chain on a team, and another at a world renowned European football club. That job would be very different. I’d be the first internal dev hire ever, and I was told I should expect no other devs to get hired for 2+ years. I’d write my own tickets and review my own prs. The project would be to…

In this episode, Dave and Jamison answer these questions: Listener AWS multi-region is not real multi-region, ask me how I know asks, We’ve recently acquired some bright-eyed and bushy-tailed new grads. What have you found to be the most effective way to onboard new grads into development roles? How has it changed (if at all) since the advent of LLMs? I want to make sure my new-grad crushing machine is operating as smoothly as possible considering the recent advancements in developer tooling. Those new grads won’t crush themselves! Listener Taso asks, Early in my career I was all-in on startups. Then I spent seven years in big companies in leadership roles. I learned a lot, but the politics and the pace were so slow that at some point I’m pretty sure geological processes were moving faster than our release cycles. So I finally flipped some metaphorical fingers and quit. Since then I’ve been interviewing almost exclusively with startups… except Google, where I somehow ended up with an offer on a team I’d…

In this episode, Dave and Jamison answer these questions: I handed in my resignation this past Monday. During the conversation, my manager confided in me that this coming Wednesday, 25% of the workforce is being laid off. For context, this is the second round of layoffs. The first round happened a year ago and was a disaster. It was announced via an internal video the night before, but the CEO forgot to mention that the affected employees had already been notified privately. This caused mass panic; thinking they were next, many experienced engineers immediately brushed up their resumes and jumped ship voluntarily. Even my skip-level manager was in the dark. Shortly after that chaos, we were acquired by an American Private Equity firm. Morale has been at an all-time low ever since, and the writing has been on the wall all year. Now I am in the awkward position of serving my three-month notice period while walking through the ruins of my company. I am the “lucky one” who quit voluntarily two days before the…

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

In this episode, Dave and Jamison answer these questions: Hey Jamison and Dave, love your show! A question for you guys coming all the way from the Netherlands 🧀 I’ve started as a software engineer in a gambling company lately and the moral aspect of it bothers me a bit. And while listening to you talking about the importance of accessibility in the last episode (#488) I came up with this moral dilemma: should a developer push for making a gambling app more accessible for users with disabilities or better not to? 😅 Thank you 🖤 Listener Arie Marie asks, What are some good ways to research prospective employers to see if they have a strong commitment to ethical and human values? What are good questions to ask prospective employers during an interview? How can I be a developer and do what I love, and know that I’m not making the income inequality greater? How do you develop a lens to look at a company and discern it’s positive impact? How do you know if you’re making the world a better place?

In this episode, Dave and Jamison answer these questions: Hey Dave and Jamison, Big fan of the show — listening from Portugal! (Proof that even across the Atlantic, software politics are universal.) I’m a tech lead, and lately I’ve noticed a culture where people seem to care way more about how things look than what actually gets done. It’s like the appearance of productivity matters more than real impact. Honestly, it drives me nuts!! I know politics are part of any organization, and way more in a leadership role, but this feels excessive. As someone who values substance and solid engineering, how do I deal with or influence this kind of culture without losing my sanity (or turning into one of those “optics-first” people myself)? Thanks for all the insights and laughs. Kudos from Portugal! Listener Charlie says, I’m fresh out of college at my first software engineering job. Several months ago I was appointed the accessibility champion for my team. I proposed a few items in the quarterly planning session, but…

In this episode, Dave and Jamison answer these questions: “My manager insists on a weekly 1:1 with me, but he rarely pays attention. He’s often on his laptop, texting, checking email — basically anything but listening. I’ve tried sending agendas, rescheduling, reducing frequency, waiting until he’s less busy — nothing helps. I’ve even started sitting in silence until he notices I’ve stopped talking, but that only works for a minute. This has caused real problems. For example, he almost had me cancel a million-dollar project because he misheard me say “Java” instead of “JavaScript.” When he finally realized I was right, he said, “Every time I heard Java I automatically tuned out.” How do I handle a 1:1 with a manager who won’t pay attention, without risking my work or my relationship with him?” “I’ve worked for a big retailer for 10 years now and I used to really enjoy it. I liked my team a lot, problems we worked on, technologies we used. Unfortunately the last few yours brought a few rounds of layoffs and…