Last Monday was my first day as an official employee of Microsoft where I’ll be working on web components as part of the Fluent design system team. As longtime readers already know, I’ve had a long term relationship with Microsoft – from Paravel’s 2012 responsive redesign of the Microsoft homepage to the five year #davegoeswindows stunt –  it feels like a new chapter in the career story arc to finally acquire one of the famous blue badges. I’m still new and have barely setup my computer but so far my team of peers, the larger group, the project itself, and the other folks across Microsoft I’ve connected with are all great.

Going from a company with two coworkers to a company with 200K coworkers is certainly an adjustment. It’s my first job in 18 years where I’m not working for myself but by far the biggest eye-opener throughout this process was doing tech interviews! I learned a lot about myself; like how after decades of coding in a room by myself, performing in front of someone else isn’t natural for me. Weirdly for me, a live demo in front of thousands of people… no problem. A random generated coding challenge in front of one person… palms sweaty, mom’s spaghetti levels of difficult. I also learned that too much caffeine and the panic-flavored adrenaline of interviewing is a lot of chemistry for my active brain to process.

I eventually figured out how to interview and I had a lot of great conversations with great people at great companies. That said, this experience left me with lingering qualms about the tech interview process. A lot of it comes down to the information asymmetry where the seller (the hiring company) has more information than the buyer (the job candidate) and it’s hard to get any feedback for self-improvement. Even in my limited experience, it’s not uncommon to sink 15+ hours into a take home coding test and interview loop only to receive a terse rejection. Granted there’s promise of a six figure salary at the end of the rainbow, these jobs don’t fall out of the sky so you need to put in work, but I think that situation needs to be a bit more equitable to candidates – a Newtonian dynamic of matching effort.

One question they ask you at interviews is “What are you looking for in your next role?” and while that sparks thousands of ideas, I boiled my needs and wants down to two core concepts:

  • Be a part of a larger team of engineers - I’d like to work on a larger team of developers. I want to be in a situation where I can actively and passively learn from other engineers who are subject matter experts in different subjects. As a life-long learner, I’d like to take myself out of the “lone developer” paradigm and absorb as much as I can.
  • Be tangential to the money machine - When you run your own business there’s a tight coupling between how much you work and how much money you make and you’re constantly aware of that fact. After 18 years of running my own business and two particularly intense years of startup burnout, I’d like to try something different and play a more supportive operational role for a bit.

I think I found that in Microsoft. There’s a multitude of people I can ping about niche technology choices. There’s even access to a library of research papers. And already I can see how operating in a product support role seems to provide more opportunity for strategy to the broader needs of the organization as opposed to reactivity to the needs du jour that happen in Productland.

I’m sure throughput will be a bit slower without direct access to the publish to production button. I’m sure there’s topics I won’t be able to talk about on this here blog (but I tend not to blog about specific work-related activities here anyways so that won’t change). And I’m sure I’ll have to put a disclaimer here and there that these ideas are my own and not reflective of my employer. Henceforth and furthermore all bad ideas are copyright of Dave Rupert LLC®.

It’s the end of an era for sure but also the beginning of a new one and potentially the beginning of lots of new ones, who knows. Thanks to Trent and Reagan. Thanks to everyone who provided emotional support on this journey. Thanks to esteemed friends who provided referrals. Given the current macroeconomic situation, I feel lucky to have landed somewhere familiar with great opportunities and many Dave Rupert-shaped problems.