In this episode, Dave and Jamison answer these questions:

1. 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 AI, there will at least be a continuous roadmap to work on. Or, is this a case of ‘snakes in the greener grass’… or whatever the idiom is. Keen to hear your thoughts!

2. I’m an EM about 7 months into a role at a larger private software company. When I joined, the explicit expectation was 1 team (~8 direct reports). I’m happy to say my team has crushed it: award-winning product launch, clear monetization path, company IPO positioning. I made some bold headcount decisions, reduced spend, built the team’s trust back up, and things are now actually quite great. I’m generally a cynical person and so I don’t say that lightly :)

   Last week my boss told me I’m taking on a second team, bringing me to 16 direct reports. When I asked if this was a promotion track, he said no. Apparently the expectation is now ALL EMs manage 2+ teams.

   Problem: the internal HR leveling rubric still says 2+ teams is a Sr. EM expectation, which I didn’t apply for… precisely because I didn’t want it. When I pointed this out, he said “that’s out of date, and you’re behind your peers because you only have been running one team”. I did the job I was hired to do, did it well, and the goalposts moved without anyone telling me.

   The kicker: the team I’m absorbing used to be run by a Sr. EM, who now has just one team!!

   So a Sr. EM is shrinking scope while I’m handed their struggling team and told I’m behind. It wasn’t framed as a vote of confidence. It felt like a quiet reassignment.

   Three questions: Am I being oversensitive to just poor communication (it’s possible the senior EM is being managed out and I shouldn’t use that as a benchmark)? Should I push for a comp increase since I’m now doing 2x the scope I was hired for? And how hard do I push back?

   One constraint: I’m a couple months from planned medical leave and can’t afford to leave before then, so I have limited leverage.

In this episode, Dave and Jamison answer these questions:

1. 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 dailys like this?

   Thanks a lot, guys, you do great work and I look forward to the SW/industry podcast that makes me laugh the most!

2. Hi! Long-time listener here, I remember Jamison mentioning this podcast on JS Jabber and I’ve been listening ever since. Best part of my week!

   In my current organisation I have a tech lead role on a small, internal platform team. Our “customers” are mainly other engineers. Due to several re-orgs, I have over the years worked with a number of Product Managers and Engineering Managers who have all had one thing in common: they don’t understand the technical domain we work in very well. You could say we have “Product Managers” who do not understand the “Product”.

   At the same time, these people are expected to interact with stakeholders, set the platform vision, manage the roadmap and backlog, prioritise risks, write documentation, do demos, etc. In the end, a lot of this work falls through to me. I do the work, but have also received negative feedback from my skip level that I need to do a better job keeping the product manager and engineering manager in the loop.

   I just got a new EM and am heading into our first expectations setting meeting. How can best express that my expectation is that the roadmap for a technical platform team should be managed by someone technical? Do you think product managers have a role on internal platform teams?

In this episode, Dave and Jamison answer these questions:

1. 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 misled by their confidence, even though they are incompetent. Consequently, I’m forced to clean up their mess; otherwise, I’d be the one bearing the blame for the failure.

   I tried discussing this with my manager, but unfortunately, it made me look bad rather than resolving the issue. If I were the manager, I’d fire this person immediately, but my manager is clearly one of those people who get fooled by their smooth talk. I’m very close to handing in my notice, and let the manager know how incompetent this person is. But I’m furious that I feel I have to give up a role I enjoy just because of someone who makes my life miserable.

   My question is: Should I stick it out and try to navigate this politics-heavy environment, or is walking away the only option left? How do I leave without burning bridges or letting them win?

2. Hello gentlemen, long time listener of the show and finally getting around to asking my first question (how exciting!)

   I’m going to be joining a new company in a few months and am wondering how to best handle the transition in order to make an excellent first impression and maybe set myself up for career growth… while not biting off more than I can chew.

   For context: I’m joining a company that builds QUANTUM COMPUTERS 🤯 after a background in working in completely different, non-scientific fields. To be fair I’m just joining as a Senior Software Engineer on the Cloud team, I won’t be building the actual computers.

   I have some experience in leadership, but not nearly as much as I wish I had, this is something I’d love to try and get into a little bit more (and couldn’t at my last company which was too small). I’m also a little intimidated at the idea of stepping into the “big leagues”, but want to use this opportunity to show that, I too, can ball.

   However, I am worried that everyone is going to be waaay smarter than me and that I’ve actually been playing in the ball pit for years.

   I’m a little scared of attempting to ball too hard and fumbling, causing dissapointment on their end, and impostor syndrome on mine.

   How would you go about joining a new company with the excitement of a new start and the drive to be the best I can be, while also remaining humble and grounded in reality?

   Should I “fake it t’ill I make it” and be super confident? Or take a more reserved approach?

   In France we call this a “rich person problem”, everything is great because I have a cool new job, but I don’t want to mess it up! HELP!