Do One-on-Ones, Like a Boss

Are you getting the most out of your one-on-one meetings?

Adam Prescott
6 min readNov 13, 2020

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Photo by Brooke Lark on Unsplash

There are millions of articles and books about the importance of one-on-ones for managers and leaders. When I was a new manager, it’s something I read about and put a lot of effort into. I didn’t feel like I was good at them, and I didn’t look forward to them.

But — like many things — the more you do them, the better you get. This is the story of things I’ve learned with time and experience.

Make Time to Prepare

This is the piece of the puzzle that I was missing for too long. The secret to good one-on-ones is preparation. Make it part of your morning routine to prepare for each one-on-on you have that day. Eliminate distractions and dedicate focus to each person you’re meeting with.

The secret to good one-on-ones is preparation.

How do you prepare for these meetings, though? It’s a combination of looking back and looking forward. Review notes from the previous meeting, reflect on interactions and contributions, and think about the person’s life outside of work.

First, you need to make sure you’ve dealt with anything you signed-up for last time to demonstrate accountability and build trust. If you missed something, that’s okay — there’s still value in bringing it up as something you couldn’t get to, provided that you don’t lose track of things and deliver more times than you don’t.

Next, think about the person and how they’ve been since you last met. Have they completed important work? Has there been conflict? Have they raised complaints? Have they been engaged? Have they been visible? As part of your preparation, identify positive and negative things to call out. These can be individual or team items, too.

Finally, look ahead to the future. What short and long-term goals does the person have, and are there things you can do to help them make progress? Some examples would be to follow-up on a commitment they made last time, give feedback on a instance where they exhibited a specific positive or negative behavior, or provide advice or reference materials that could help them.

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