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Advice / Succeeding at Work / Work Relationships

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

boss and employee in one-on-one meeting
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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. (Reading this article and realizing you don’t even have these on your calendar regularly? Here’s how to ask your boss to set up weekly check-ins.)

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— you can use this template to create one and send it to your boss before you meet.

Share Important Updates (But Keep Them Quick)

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 Slack, or in passing over lunch.

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.

Ask a Lot of Questions

The best use of one-on-ones is spent here—debugging a problem, thinking through an obstacle, or gathering feedback or guidance on how to take the next step forward.

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?”

It’s important to note that your role as an individual is not only to surface questions but also to provide some initial thoughts on how you might solve these problems. It’s okay if your ideas aren’t fully baked, but make sure you’ve thought through potential solutions, rather than rely fully on your manager to solve those issues for you.

Make Commitments Out Loud

What next steps will you and your manager both agree to? What tasks will your manager commit to taking on, and what’s on you to carry forward?

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.

Discuss the Long Term

Not every one-on-one needs to be about the short-term—remember to discuss long-term goals every now and then.

Think about how your manager can help you grow in your career, and ask for feedback to help guide the way.

For instance, ask yourself and your boss: “What am I good at and how can I get to the next level?” “What are my strengths?” “What are some gaps in my experience, and what help do I need to get there?”

You should send these questions along in advance (a.k.a., in your agenda) so your manager can prepare thoughtful feedback. This also gives you time to self-reflect and prepare for your part of the conversation.

These simple changes will help your one-on-ones be more productive and show your manager that you’re proactive about managing your work and your career—and confident in your abilities to do so.

one-on-one with boss

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