In this episode, Dave and Jamison answer these questions:

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

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

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

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

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

Thanks so much for your thoughts!

In this episode, Dave and Jamison answer these questions:

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

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

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

I had my first day yesterday as a senior developer and dozed off at an hour meeting at the end of the day today. The meeting was about planning the next year on a zoom call with the leadership I was following in the beginning but at some point they started to talk in something I can‘t really understand(to excuse myself, I had had mant meetings throughout the day and still new to their product). I should’ve turned off my camera but I kept it on while I was definitely zoning out and got my eyes closed few times.

In this episode, Dave and Jamison answer these questions:

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

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

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

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

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

In this episode, Dave and Jamison answer these questions:

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

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

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

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

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

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

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

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

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

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

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

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

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

In this episode, Dave and Jamison answer these questions:

Hi Dave and Jamison,

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

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

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

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

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

Thanks again for everything you put out into the world.

Hi Soft Skills Engineering Team,

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

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

My question is:

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

Warmest regards,

In this episode, Dave and Jamison answer these questions:

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

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

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

A listener named Bob says,

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

In this episode, Dave and Jamison answer these questions:

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

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

Listener Michael Q asks,

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

In this episode, Dave and Jamison answer these questions:

A listener named Mike says,

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

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

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

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

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

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

In this episode, Dave and Jamison answer these questions:

Mr A. N. Onymous says,

Hi Dave and Jamison,

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

In this episode, Dave and Jamison answer these questions:

Albert Nonymous asks,

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

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

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

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

It has been hell.

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

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

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

What do I do next?