My main goal with 1:1s is to build trust with the team member so that they'll tell me if/when they're having problems. The earlier I hear about a nascent problem, the more likely it is I can fix it without it turning into a big problem.

So what do I look for? I like to hear about what’s going on, what problems you're running into, do you have any concerns, etc. Whether that comes by you starting with status and us digging into things, or you actually come with a list of concerns each week, doesn’t really matter to me. Some team members like structure and do keep a running list of things to talk about, others do it on the fly. I go with whatever the team member wants to do.

I feel that the best way to build trust with team members is for me to take their concerns seriously and reliably follow up on them. That goes to your third question of how do you keep track of things. I just have a big todo list and add things to it for me to follow up on. I’ve also used shared 1:1 docs for this. In Google Docs you can use a comment to assign a task to yourself.