Sep 10, 2026
How to level up orgs:
- when you first join, ppl will be nervous. They know you're there to make changes but don't know which ones or when. So you'll have to contend with some ambient tension for a while
- your demeanor must reflect (1) appreciation for the immense work done before you even got there, (2) humility because you'll rely on your team for basically everything, and (3) readiness to make decisions ppl may not like that will benefit the group in the long run
- all three ^^ are necessary, skipping any one of these comes with its own special kind of pain
- you'll go through two phases-- learning phase and changes phase. (Of course you never stop learning, and like cold/hot days you don't know where one ends and the other begins. But it's still a useful way to think about things.)
Learning phase:
- meet everybody. Managers, ICs, junior, senior, customers, product, critical path, periphery-- everybody. Each group carries information, and you need all the signals you can get to triangulate a good course of action
- other than relationships, meeting ppl has two goals: (a) learning all you can, and (b) assessing the org's capabilities
- learn learn learn. Ask newbie questions. Learn about architecture, code, product, customers, user experience, security, cost structure, reliability, whatever. A lot of this you won't be able to absorb right away. That's ok, let the information wash over you. (I personally adore being a beginner again)
- throughout all this you'll be forming opinions about ppl. Almost everyone does this adhoc, but that's bad for the same reasons doing interviews adhoc is bad
- so know what you want to learn about each person. This should roughly be a softer version of the interview process for their role. Do they think clearly? Communicate well? If they're an engineer, can they program? If product, how structured are they about assessing customer needs? How well do they use data? etc.
- as people answer your questions, there will be parts you don't understand that seem so simple you'll feel embarrassed to ask. You MUST ask about those!!
- either they'll disabuse you of your naiveté, or you're thinking about smtg in a new way that never occurred to anyone, or they don't have an answer because the question isn't important, or they don't have an answer they should have and there is a gap. Either way you learn something
Changes phase:
- at some point you'll feel confident about a decision to make a change. Could be big or small, but you know it will make everything better
- you'll typically get one of four reactions-- (1) we can't do this for a vague inarticulable reason you can't understand yet, or (2) we're still adjusting to you and don't understand what you're asking so we can't do this, or (3) omg thank heavens someone is finally fixing this, or (4) we can't do this for a clear articulable reason
- reactions 1-3 you should politely acknowledge and safely ignore. Reaction 4 is tricky. Sometimes you really can't do the thing. But sometimes people just don't want change and are very good at rationalizing it. You need to intuit which situation you're in
- generally if you're competent and thorough, ~99.9% of your intuitions will eventually prove right. If you have ~100 intuitions a day, which isn't an overstatement, you'll be wrong roughly every week or two. For sure account for that but don't let it stop you. You'll make mistakes and fix them, it's ok
People:
- once you start making changes people will either adjust or they will not. In my experience the "won't work for vague reasons" people and "I don't understand what you’re asking" people never work out. Most "rationalize convincingly" people usually work out super well after they see some successes (though a few will self-select out)
- you'll make new hires, but keep in mind every org has superstars working deep in its bowels who for whatever reason aren't recognized. Too young, too old, too shy, too aggressive, too inexperienced, too set in their ways, too this, too that, too whatever. Find these people and elevate them
- this will make the old guard confused and uneasy. "Why is Jenny who's only a year out of college suddenly in all the important meetings?" But having everyone ask this question is what you want. Elevate the ppl you want the team to emulate
- visualize what the org looks like in six months once you've fixed all the immediate problems. Keep that vision in your mind's eye; don't get too bogged down by the current state