Michael Wolfe has a great article about 1:1s and the benefits they provide at a startup.
I wasn’t familiar with this being an established concept when we were starting Contactually, but we started doing it, and it’s been pretty helpful.
At the moment, I have a few different types of standing 1:1 meetings, outside of the ad-hoc meetings to discuss a particular issue.
We have other touchpoints (weekly metrics meetings, OKRs, etc) where status updates are given and tasks are delegated, so when I meet with each team lead weekly, I take a purely servant leadership attitude. I may come in with certain discussion points, but my general focus is to help them identify and remove blockers. We have recurring times blocked in our calendars, but, to avoid it being a burden on them, my team leads + VPs can always cancel or move if they have something more urgent.
This is one of those cliche “we’re always talking but we never… talk” occurrences. Every week or two, I have standing meetings with my co-founders. These are usually unstructured, but it ends up being focused around our shared concerns, or bringing up issues we’ve noticed. I’ve found that the longer we go without connecting, the more friction and tension develops.
In addition to board meetings and ad-hoc topic discussions, having standing meetings also ensures that we’re aligned on major issues, they’re aware of what we’re working on, and know exactly where to help.
This is one of the more enjoyable things I do in the company. As we’ve grown, my facetime with each employee has diminished. So I have a standing meeting once a quarter with every full time employee. Beyond a general “how’s it going,” I’ve found it helpful to come in with a set of standard questions, which I’ve adopted from the 12 questions Gallup’s research has yielded (highly recommend you read Good to Great). I take careful notes which remain private, but I may have clear next steps to bring up with other people. Quarterly may seem like a long time, but I’ve found the time to fly by, and be just long enough that we can track issues to resolution.