How to Have a Successful One-on-One With Your Boss

The most productive one-on-ones have some kind of structure, which requires you to do some prep beforehand. Basically, don’t just show up and chat—you’ll lose precious time in rambling conversations.

• Is this time-sensitive? If it’s urgent, don’t wait for your next meeting to provide an update. Mention anything urgent in real time so your manager can quickly help you before the going gets too tough.
• How complicated is my update? If you find yourself drafting an essay-length email to your manager, that’s a good sign your update is better suited for in person. On the other hand, if it’s short and sweet, go on and send over an email, but don’t let it cut into precious one-on-one time.
• Is this an opportunity to share a win? Don’t be afraid to share and celebrate your wins. Help your manager see your progress and acknowledge your good work. This also helps your manager share your work with leadership who you might not interact with you on a regular basis.

Ask questions that get to the heart of your concerns. For instance, if you’re stuck on a potential strategy, you can ask your manager: “How would you approach X? My proposed solution is Y, any feedback on this?”

Articulate and agree on these commitments in the last part of your one-on-one so you’re crystal clear on what’s expected between now and your next check-in. This could be as simple as your manager agreeing to send over a report that might be helpful for you, or as complex as you agreeing to have a difficult conversation with a client.