One-on-ones are a management tradition at lots of tech companies, perhaps popularized by High Output Management,1 in which a manager regularly schedules time with a direct report to discuss whatever the report

Alignment—that is, talking through the root causes of any disagreements that have come up. This matters for two reasons. The obvious one is that whoever is wrong about the disagreement will improve their models of the world. The less obvious one is that both participants in the one-on-one get better at imagining what the other person would think about something, which is critical for building a high-trust working

Uncertainties. The founders always encouraged me to use 1-on-1s to ask about anything I was uncertain about, even if it didn’t affect my day-to-day work. If anything, I spend more attention worrying about things that don’t affect my day-to-day work (because those are the things I can’t control), so I’d often end up a lot less stressed after these discussions. For the founders, I think these discussions helped them discover problems with internal communication—for instance, occasionally I’d get worried about some strategically important project elsewhere in the company because they’d forgotten to announce progress reports on

I also now think the “caring a lot” qualification is way more important than I used to. Lots of people (including Eve) try having “accountability buddies” that they meet with to discuss progress on their goals, and accountability buddies are rarely this effective. The main difference is that most accountability buddies don’t care about each other in the same way that managers/reports, or significant others, do: for me, Eve’s progress was the top idea in my mind in a way that I doubt it was for anyone else. Because of that, I ended up having more insightful feedback for her than a random “accountability buddy”