What to Cover in Your First One–on-Ones as a New Manager

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I’ve had the privilege of training hundreds of managers, and one of the scariest moments for many new leaders is their first one-on-ones with their new team members.

Whether you were hired from outside the company or promoted within, the first one-on-one meetings set the tone for your relationship with your direct reports. It’s a critical first impression.

Broadly, you have two goals in this first meeting:

  1. Get to know each other
  2. Learn more about them and their challenges

You’ll have time to dive into nitty-gritty work details later. This first meeting isn’t the time for that. For now, you need to build rapport and begin getting comfortable with each other.

Here are five tips for your first one-on-ones with your team:

1. Create as casual of an environment as possible

If you’re working in an office, consider doing your first one-on-one meeting off-campus at a nearby coffee shop or lunch joint. This will help the meeting feel more conversational and less business-y, like two friends getting together to catch up.

If you’re working remotely, establish an informal tone by telling them at the start of the call that your main goal today is just to get to know each other.

The more casual, the better because you want your direct report to feel comfortable opening up to you.

2. Start with non-work topics

Every employee wants to know that you care about them as a person — not just as a revenue-generating, metric-hitting automaton. The best way you can bond with someone is to begin with discussing non-work stuff.

Consider asking questions like the following:

  • I always like to hear about people’s lives outside of work. What are some of your favorite hobbies?
  • What’s been the best part of your week?
  • What would constitute a “perfect” day for you?
  • Where is the next place you hope to visit?

Non-work conversation can also lighten the mood and make it easier to talk about work-related topics, which you’ll dive into next.

3. Ask about their work

Feel free to linger on the non-work questions for a while because again, the main purpose of this first meeting is just to get to know each other. But eventually, you’ll slowly pivot to work-related questions.

Here are a few questions I’ve found helpful to ask in initial one-on-ones:

  • What did you do for work before joining our company?
  • I’d love to hear more about how the team has been doing. What do you think is one of the team’s biggest strengths? How about one of our biggest weaknesses?
  • What did you like most about your last manager?
  • What qualities are most important to you in a manager?
  • What’s one of your career goals?

If the prior manager is still at the company, don’t ask any direct questions about that person’s weaknesses. But if that manager left the company and your direct report seems open to sharing, you can ask a more direct question like, “What do you wish your last manager did differently?”

Your goal here is to understand what this person needs from you as a leader.

4. Ask about their challenges

Every employee generally experiences minor frustrations, inefficiencies, or roadblocks that de-motivate them and prevent them from being as successful as they could be.

Begin unpacking those things with questions like the following:

  • What do you wish was different on the team?
  • What’s one of the biggest challenges you’ve been facing lately?
  • What’s one roadblock that you wished was removed in your daily work?
  • If you could change one thing at our company, what would it be?
  • What do you wish management understood about the realities of your work?

The challenges you uncover will help you generate an initial list of improvements (both large and small) that you want to make on the team.

5. Identify some quick wins

One of the best things you can do to quickly build trust and earn respect as a new manager is to solve small problems that have been bothering the team.

Whenever I join a new team, I look for a few quick wins I can generate that will demonstrate three things to my direct reports:

  1. I’m listening to you.
  2. I understand your problems.
  3. I will work diligently to solve those problems and make your life better.

Sometimes it’s possible to identify a few quick wins in your first one-on-ones with everyone. Other times, you won’t identify these until your second or third meetings. But overall, you want to look for small annoyances that you can resolve quickly.

Here are a few examples of what “quick wins” look like:

  • If your team has complained about the bad coffee in the break room, buy a new coffee maker.
  • If team members say they don’t know their colleagues well, schedule a team activity or happy hour.
  • If your team is frustrated by your department’s slow approval process for expense reimbursements, change the policy to make it simpler and faster.

Again, these items don’t have to be big. They just have to be quick. Often, resolving small problems can have a disproportionate impact on team morale, confidence, and trust.


I know initial one-on-ones can seem scary, but I promise they’re not that bad. Just focus on getting to know the other person and learning more about them.

If you follow these tips, you’ll lead these initial meetings like a pro:

  1. Create as casual of an environment as possible
  2. Start with non-work topics
  3. Ask about their work
  4. Ask about their challenges
  5. Identify some quick wins

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