How to Have a Successful One-on-One With Your Boss (Even if You Don't Get Along)

Updated: Dec 14, 2020




Whether you’ve been working for years or are just starting out, you know that having good one-on-one meetings with your boss is crucial for your success.


At best, these meetings can leave both you and your manager feeling productive, energized, and prepared for the week and work ahead. At worst, they can leave you feeling confused, drained, or even hopeless about the path forward. Send an email to your boss requesting a weekly catch up and which day of the week suits them best. Then send the calendar invite yourself, don't wait for them or their secretary to do it for you.


Here’s how to make the most of this time so you get what you need to get ahead.


Set an Agenda

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. Have a clear agenda— and send it to your boss before you meet.


Share Important Updates

It’s key to share any important updates with your manager—here’s what I did last week, here’s what I’m doing this week, here’s the result of X project—but be careful of spending too much time discussing these.


Prior to your one-on-one, consider what you want to get out of sharing updates. Remember that you don’t have to share everything in person—many things can be explained over email or in an informal conversation.


Instead, prioritize them. Here are some questions to ask yourself to do this:

  • 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.


Whenever I have a meeting, I always have a document (in powerpoint or word) that covers the following items:

  • What am I discussing in the meeting? What am I trying to achieve? What are the gaols of the meeting? Will attendees find it useful ?

  • Who’s attending

  • What you’ll talk about, who will talk about what, and how much time each topic will take to discuss

  • Next steps you want to take after meeting - follow up with meeting notes (if applicable) that clearly states what is expected from individuals .. I also name the individual. You may have a large team that report directly to you, or be a single contributor working with other teams in order to deliver, I think that it's important to name these people to provide clarity and direction and what next steps need to be actioned.

161 views

Recent Posts

See All