In this episode, Dave and Jamison answer these questions:

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

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

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

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

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

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

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

In this episode, Dave and Jamison answer these questions:

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

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

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

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

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

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

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

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

In this episode, Dave and Jamison answer these questions:

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

2. Hi!

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

   Thank you for your precious advice!