In this episode, Dave and Jamison answer these questions:

1. 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?

2. Paolo asks,

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

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

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

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

In this episode, Dave and Jamison answer these questions:

1. 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??

2. 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?

https://overcast.fm/+ABLmzfhZxak

In this episode, Dave and Jamison answer these questions:

1. 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.

2. 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?