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You’ve got your first one-on-one meeting with an employee: How to prepare?

If you’re a new manager, here are the exact 1-on-1 meeting questions, agenda template, and approach you can take for your first 1:1 meeting with an employee.

first one-on-one meeting with an employee

If there’s anything you should be supremely focused on as a new manager, it’s your first 1-on-1 meeting with an employee. That first encounter might seem like a formality to you. But in reality, it’s formative.

The first 1-on-1 meeting with an employee sets the tone for your relationship with this person who’ll you’ll work with every day. It’s the one opportunity you have to set a groove, a pattern, for what you want your interactions to be like, and the standard for what feels good going forward. As a result, investing time in preparing for your first 1-on-1 meeting with an employee is a wise use of your time.

But how exactly should you hold this first one-on-one meeting with an employee? Have no fear 🙂 I’ll share what we’ve learned from over six years of research and working with 15,000+ managers and employees…

#1: Tell your new hire why you’d like to start holding one-on-one meetings with them.

One-on-one meetings are not status updates. One-on-one meetings are not for brainstorming projects. You can talk “the latest” about a project or “what’s next” in another meeting, via email, or even Slack. One-on-one meetings are rare, invaluable time purely to uncover potential issues and share feedback with one another. When else do you ever get the opportunity to do this, face-to-face?

Making this purpose clear is paramount because your employee may have never had one-on-one meetings at their previous job(s) where this was true. Orienting them to this particular purpose of the one-on-one meeting is therefore essential.

Here’s an example of an email you can write explaining this…


I was thinking it’d be useful to have regular one-on-one meetings every week or so. I view these meetings as a time for me to really listen to you — to hear what’s on your mind and what you think can be better in the team. It’s also chance for us to both get on the same page, share feedback with one another, and discuss how we can both grow in our respective roles.

We can co-write the agendas ahead of time using this (insert tool of your choice here)  — so we together are ensuring we’re talking about the things that matter most.

Might you be up for it? Let me know what you think!



Looking for more detailed guidance on one-on-one meetings? Make sure to check out our 1:1 module in Canopy.
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#2: Ask your new hire what frequency and duration of one-on-one meetings they prefer.

For these first one-on-one meetings, for how long and how often should you hold them? If the new hire directly reports to you, I recommend weekly one-on-one meetings for 1-hour long for the first 90 days or so. If the new hire doesn’t directly report to you, either a biweekly or monthly one-on-one meeting for 1-hour is likely sufficient.

Regardless, the most important part here is to get input from them on the frequency and duration, in the first place. This way there’s greater buy-in on these meetings happening — it’s not just something you’re demanding and imposing on them.

Here’s more information on how often you should be holding one-on-one meetings with your employees, depending on your team size.

Are your one-on-one meetings, in fact, skip-level meetings? You may want to read this piece here on the frequency of skip-level meetings.

#3: Prepare an agenda — with input from your employee.

You’ll want to spend at least 15 minutes brainstorming thoughtful, specific questions you might want to ask. Recall that the purpose of your one-on-one meeting is to uncover potential issues and concerns, so your questions should be targeted around this. For your first one-on-one meeting with an employee, this often means asking prophylactic questions — questions that reveal what the other person’s work preference and expectations are, so you can account for them as a leader.

As an example, here’s an agenda template for your first one-on-one meeting with an employee:

Personal connection (10 min.)

  • Anything surprise you during your first week or so here?
  • What’s confusing or unclear? Anything you’d like more context on right now?

Issues (20 min.)

  • What can I make sure to do in the next 2 weeks that would help make your onboarding process even smoother?
  • How would you describe your ideal working environment? (E.g., Are you a morning person or afternoon person? Do you prefer more social interaction or solid times of working independently?
  • Do you have any work-related pet peeves? What do you think you tend to be more sensitive to than most, regarding work preferences?

Career direction (10 min.)

Next steps + takeaways (5 min.)

You’ll also want to invite your employees to write their own questions and add any topics they’d like to discuss on the agenda. This helps the one-on-one meeting feel more like a conversation, rather than a dictation.

#4: Don’t cancel the meeting. Only reschedule it if you have too.

Consistency with one-on-one meetings matter. You speak volumes about how you prioritize the other person’s time with how well you prepare and how consistently you show up for your 1-on-1 meetings with them. Move or cancel your first one-on-one meeting with an employee and it sends the message loud and clear: “Listening to you doesn’t matter that much to me.”

You’ll also want to reflect: How did that meeting go? Did the questions you ask seem to have been useful? Were you fully present and engaged during the meeting, or were you feeling rushed and your mind elsewhere? This will help you calibrate how the one-on-one meeting can be improved for next time.

Don’t sweep this first one-on-one meeting with an employee aside. It’s not a thing that’s getting in the way of the real work. Those emails and to-do lists can wait. The one-on-one meetings you have with your team are the real work. And the first one sets the tone for the rest.

💪 Ready to have your first one-on-one meeting with an employee? Be sure to check out Know Your Team to help you run it well. You’ll get hundreds of question suggestions, agenda templates, and more, to help you execute on all the suggestions I shared in this article.

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Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.