Do more 1:1s!
(This post is essentially a linkpost for Ben Kuhn's excellent article, The unreasonable effectiveness of one-on-ones. I suggest you read that if you haven't already!)
It's hard to ignore problems when you regularly have someone gently and supportively bringing them to your attention. The power of one-one-ones is that you solve these problems by default instead of letting them fall by the wayside. 1:1s have the additional benefit of surfacing problems that you did not know were there; everyone has fundamental blindspots, and having a spotter helps you see things that you structurally could not have seen before.
In my life, I've experienced a number of 1:1 formats. Here's how I approach each of them.
Manager / Report Relationships
There is a prolific amount of literature on this, so I won't spend long here. If you read one thing, consider this summary of "Managing to Change the World".
If you're the report, remember that the goal of the 1:1 is to support you, and you should approach them with that in mind. Make it as easy as possible for your manager to help you; your manager is most likely time-poor, so make your problems legible and have a suggested plan-of-action for all of them. For the fuzzy problems where you are stuck on a solution, be prepared to share all the relevant context so your manager can best advise you.
In her book Scaling People, Claire Hughes Johnson discusses her four operating principles. The one I remember the most is "say the thing you cannot say," and I think the one-on-one provides a unique default space to bring up weird, uncertain, fuzzy items.
Of course, it's also the space to bring up more concrete items. When giving feedback, a framework I use is the "diamonds and spades" method, which basically encourages you to be specific:

I've also seen the EEC method used. When giving negative feedback, provide an Example of the behavior, its Effect on others, and instructions on how to Change it in the future.
Peer Relationships
I'm currently implementing this with my friend Matt. I think finding the right person to do this with is more than half the battle; Matt brings such clarity, focus, emotional awareness, and growth-mindset to these meetings that I find energizing.
Currently, we have a blocked-out 2 and a half hours on Saturday. We independently do the preparation for the meeting before this block. We spend some portion of the block on me, an equal portion on him, and the rest of the time executing on the first thing that we've identified.
Here's an overview of what we do, in no particular order:
- We start the voice recording of the meeting.
- We review the goals that were set at the last session, and we set goals for the upcoming week.
- We review each other's long-running goals and check in on how those are going.
- If the blocker is an emotional one, we open the space to digest and process that. Matt and I have a shared language here in Circling, Gendlin's Focusing, and IFS.
- Norm: If at any point during the session we find something that takes less than two minutes to complete, we do that thing.
- Perhaps this is just with Matt, but we are extremely meta. "I notice that I'm not listening because I'm distracted." "I'm sorry, can you repeat the last thing you said?" "I notice that I want to say something, but don't feel comfortable saying it yet." "I suggest we pause for five minutes and speed-write on this topic." "What is the purpose behind you asking that question? I believe it's X, and I'm going to answer X instead of Y, does that seem good with you?"
Romantic Relationships?
It's early days yet, but I find the 1:1 format incredibly exciting for my current relationship. I look forward to them every week. Having a "default time" to discuss problems or fuzzy uncertainties in the relationship is wonderful, and certain topics are more easily discussed when one has time to think and put words to paper. You can also use this time to co-plan out long-run adventures or life events.
Believe it or not, you can also do some version of a 1:1 with someone that you're not in an established relationship with yet. See this post on "Agile Dating" by Jessica Fan.
Extras: I previously wrote a memo called My playbook for one-on-ones, though this gestures at walk-and-talks rather than sit-down-and-prep meetings.