In this episode, Dave and Jamison answer these questions:

1. 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?

2. 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!

In this episode, Dave and Jamison answer these questions:

1. 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?

2. 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 DMs

In this episode, Dave and Jamison answer these questions:

1. 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?

2. 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.