Whenever I’ve had a team, I’ve made sure I schedule at least bi-weekly (preferably weekly) 1:1s with each person I manage.
These would always follow the same general agenda:
Current Project status. This would be a basic top-level green/yellow/red style update. Most of the time I know this already, but it’s good to triple-check things.
Things I need to communicate. These are all the things I’ve learned that affect them. Most of the time I’ll cover these items in the weekly team meeting, but I’d try to reinforce them here.
What’s on their mind. Open time for them to bring up big issues on their mind.
Big working topic for the session. I liked to have at least one thing we could talk about in-depth, usually around the whiteboard. This usually ended up displacing at least one other meeting that week.
Rumors and Gossip. Rumors and gossip time is critical. It’s important to have a dedicated time to talk about everything that’s going on: what they’re hearing and what they’re thinking. It’s less critical at a startup, much more critical at a place like NPR, a distributed, complicated and highly-social organization.
Don’t talk about any topic that you could discuss in the open, among your team desks or in the cafe. If it’s safe enough to be overheard — it’s not the right content for a 1:1. Email it, send it in Slack, discuss among the desks, say it at a meeting, anything but a 1:1.
Commit to saying one rather awkward thing every 1:1, and get the other person to commit too. Agreeing in advance and getting permission makes it feel way more safe. Committing creates peer pressure to be real. It works.
You should read that whole article. Lots of good ideas.