How to run your first one-on-one meeting


The first meeting is the cornerstone for your one-on-one meetings. It sets the tone and expectations for future conversations. You’ll spare yourself from many hassles if you’ve set it up correctly.

As this is your first meeting, you usually need more time than the typical one-on-one meetings. We recommend you reserve at least an hour for this meeting. So that you don’t feel rushed to go through each topic, and you can use the time to cover topics suggested by the employee.

If you’ve not read our guide on “How to conduct one-on-one meeting”. We recommend you to read it first, it covers how to send an invitation email, and what to do in the meeting. In this guide, we will focus on the important topics to cover in your first meeting.

Prepare the agenda

The purpose of the first meeting is to show employees the “Why” and the “How” of having one-on-one meetings. You’ll need to explain to them your intention of having one-on-one meetings, and how they can benefit from it.

It is also a good time to set the correct expectation about future meetings, such as the employees are the ones that come up with the agenda. This is important because it is very unproductive for you to prepare for all meetings. Plus, the meetings are to support the employees, and they know exactly what support they need from you.

Here are the topics that you can cover in the first meeting:

  • Share why you schedule the meetings
  • Setting the ground rules
  • Get to know them personally

Share why you schedule the meetings (~10 mins)

You might have already explained in the email the reasons to have the meetings. But it is always good to tell them in person and check if they’ve any concerns or questions about the meetings.

To recap, here are some reasons for employees to have one-on-one meetings:

  • A touchpoint to keep each other in the loop for important information.
  • A private space for questions, issues, and challenges.
  • A platform to give continuous feedback and guidance on performance and career development.

You can then check with them if they have a question or anything to discuss with you. Some questions you can ask related to this topic.

  • What do you think about the frequency and timing of the meetings?
  • What’s confusing or unclear?
  • Any concern with having one-on-one meetings?

Set the ground rules (~10 mins)

Everyone has a different preference and understanding in how they do their one-on-one. Without communicating your expectations, things can run wild pretty fast. Using yourself as an example, you can start sharing what they can expect from you, what you expect from them, and asking what works best for them.

Here are some basic expectations for you. You can ask them to hold you accountable for these items. Doing so will help you to foster mutual trust and accountability.

  • On-time and consistently attend the meetings.
  • Review the topics and action items before the meeting.
  • Attentive and practice active listening.
  • Open to exchanging feedback

These are what you’re expecting from them:

  • Send you the topics before the meeting.
  • Open to issues and challenges.
  • On-time for the meeting.

Some questions you can ask related to this topic:

  • Did you have one-on-one before? What works best for you? What doesn’t?
  • What will make one-on-one valuable to you?
  • What has your past manager done that you would also like me to continue? What do you not like?

Get to know them personally (~ 35 mins)

A good relationship with your employees is the key to build trust and engagement. There is no point in doing one-on-one if the employee doesn’t speak up. As a manager, you have to develop personal relationships. But it doesn’t mean you have to share about the private part of your life. It is more about understanding who they are, why they work, what drives them. It is about seeing them as human beings, and for them to see you the same too.

The more you understand them, the more effective your leadership will be. Everybody has different strengths, weaknesses, and working styles. When you start paying attention and adjust to it, you will start seeing people appreciate you and engage in their work.

You’ll be spending most of your first one-on-one meeting on this topic. Here are some questions for you to learn more about them. As you will not have the time to ask all the questions, do pick the ones that are useful to you.

Personal connection

  • How are you doing? How’s work? How about life outside work?
  • What were you doing before this job?
  • How long have you been here?
  • What do you like to do in your free time? What are your hobbies?
  • What do you like to do outside of work? What are your hobbies?
  • Do you have a bucket list? What are they?


  • What are your current goals or projects?
  • How clearly does success look like for you?
  • Do you have issues or challenges in your work? What are they?
  • What aspect of your work do you need more help?
  • How do you feel about your team?

Work habits

  • What kind of management style works best for you? (More freedom, more guidance, etc.)
  • How does a productive day look like for you?
  • What part of your workflow do you find the best? What are do you want to improve?
  • When you have a problem, who do you ask for help?
  • As a manager, how can I best support you?

Career & motivation

  • What motivated you to work? What demotivate you?
  • Which part of your job do you enjoy the most? How about the least?
  • Career-wise, what are your long-term goals?
  • Do you feel like you’re making progress on your long-term goal here? Why or why not?
  • Where do you see yourself in 3 or 5 years? What’s your plan?
  • What are the skills you’ve wanted to learn more?


  • What aspect of your work do you need more feedback?
  • How do you prefer to receive feedback? (As it happens or during the one-on-one)
  • In what way do you prefer to receive feedback? (Email, message, in person, etc.)
  • When is not a good time for you to receive feedback? How do I know that you’re grumpy?

Conclude the meeting (~5 mins)

When it is time to end, thank them for attending the meeting. Hopefully, you’ve gained a few insights on where they need you the most and how to structure future one-on-one meetings better.

If you’ve written down any action item in your note, remember to check with them again to confirm that you both are aligned. You’ll also want to reiterate that they will be preparing the agenda for future one-on-one meetings.

Now that you’ve successfully set the cornerstone for your future meetings, you’ll have an easier time starting from now. And remember, the key to successful one-on-ones is consistency. The result of the meetings will compound over time. Sooner or later, you’ll start reaping the fruits of one-on-one meetings.

© 2021