How do you introduce one-on-ones to your team?
Dongyoung Kim, CPO
When you introduce one-on-ones, answer the questions team members will have first: why they are starting, whether they are evaluations, what to talk about, and who sees the notes. Then say concretely how one-on-ones help them, and the pressure eases. You can adapt the example wording below to your team.
Four things team members wonder first
When a leader says "We're going to start one-on-ones," a few questions immediately come to team members' minds. It works better to start by answering those questions than with what the leader wants to say.
| Team member's question | How to answer |
|---|---|
| Why all of a sudden? | Explain that it is not because anyone did something wrong but to make regular time to talk with everyone. Saying you will meet the whole team on the same cadence prevents misunderstanding. |
| Am I being evaluated? | Say clearly that it is not where ratings or scores are decided. Explain that it is time to talk about everyday work and difficulties. |
| What am I supposed to talk about? | Tell them they can start with what is stuck, where they need help, or anything they are curious about. For the first few, send some example topics along with the invite. |
| Who sees the notes? | Decide in advance, in line with your organization's policy, who can see the notes, whether they are used in reviews, and whether the team member can edit them, and tell them. |
What one-on-ones give team members
Once those questions are answered, tell them how one-on-ones help them. Team members want to make time when you talk concretely about what they gain rather than why the leader needs it.
- Blockers get cleared faster. Problems that felt awkward to raise in a meeting can get the leader's help right away.
- Expectations get aligned early. Knowing what the leader considers important means less wandering on direction.
- Their work is on record. At review time they can point to what they did and how, instead of relying on memory.
- There is a place to say what they want to do. There is set time to raise what they want to learn and the roles they want to try.
Just as Harvard Business Review describes the purpose of one-on-ones as aligning on expectations and building trust (HBR, 2024), these four come down to leader and team member looking in the same direction and coming to trust each other. This article is a suggestion based on a one-on-one leader training deck from Upstream that Orblit referred to and on field experience.
Example wording
Below are a short announcement for the team channel and what to say in the first one-on-one. Adapt them to your team and your organization's evaluation policy rather than reading them as written.
Team announcement
"Starting next month, I'd like to hold a 30-minute one-on-one with each of you every two weeks. It's not because anyone has a problem; it's so I can talk regularly with everyone about what comes up at work and where you need help. It is not where ratings are decided. I'll set up times with each of you individually."
What to say in the first one-on-one
- Purpose: "This is time to work through what's blocking you and find where I can help."
- Topics: "From next time, jot down two or three lines on what you'd like to talk about the day before. If nothing comes to mind, the one thing on your mind most is enough."
- Notes: "I'll keep what we discuss in a note just the two of us see. Let's agree now on how it's used."
- Feedback: "After a few of these, please tell me whether this time is helping and what you'd change."
- 1
Purpose
Say it is time to clear blockers and find where the leader can help.
- 2
Topics
Ask for two or three lines on what to discuss the day before.
- 3
Notes
Agree together where notes are kept and how they are used.
- 4
Feedback
Ask them to say what they would change after a few meetings.
What to prepare before the first one-on-one
After introducing one-on-ones, make sure the first one runs the way you described it. If what you said and what happens differ, trust is hard to earn.
- Send the team member a form for writing topics in advance. Ben Horowitz also recommended that employees send the agenda ahead of time (a16z, 2012). A ready-made prep form is in the one-on-one doc.
- Set up the recurring event first, and focus on keeping the schedule for the first few.
- Decide first, in line with your organization's policy, who can see the notes and how they connect to reviews.
When team members find it stressful
Some team members still feel awkward about one-on-ones after your introduction. It often eases with time, but take a little extra care in the first few.
- Keep the first few to about 20 minutes. Learning that it is fine to finish early takes the pressure off.
- Share something of your own first. Hearing the leader's concern, such as "I've been worried about this schedule too," makes it easier for the team member to talk.
- Start with easy questions. Questions about facts, such as "What took the longest this week?", are easier openers than questions about feelings.
- After about three, adjust the format together. Ask, "Is this time helping? Is there anything you'd change?"
There are also things to avoid saying when you introduce them. Do not ask closed questions that end in "yes," such as "Nothing wrong, right?", imply evaluation, or promise rewards that are hard to keep. Questions team members can answer comfortably in a first one-on-one are collected by topic in the one-on-one questions list.
Frequently Asked Questions
- Q.Can I explain it to the whole team at once?
- Explain the purpose in a team announcement first, then talk it through again individually in each person's first one-on-one, because each team member worries about different things.
- Q.What if the team member says they have no topics?
- No topics is useful information too. Start with an easy question, such as how they are feeling or what weighed on them most last week. The habit of writing topics in advance builds over a few sessions.
- Q.Should team members see the one-on-one notes?
- Follow your organization's policy on sharing, but tell team members in advance. Making the purpose and ownership of the notes clear makes team members more candid. This is Orblit's suggestion.
ORBLIT
How Orblit helps
To make it easier to put this article into practice, Orblit helps in these ways.
01Team members prepare topics easily
Orblit provides an AI meeting prep that team members write themselves, and chatting with an AI chatbot organizes what they want to discuss with the leader.
02Write the notes together
A shared meeting note that leader and team member edit together makes the notes a joint asset, and permissions manage who can see them.
03Check in on how they are doing without pressure
After a one-on-one, the team member can lightly record engagement and satisfaction, and the leader can follow the change.
04Explanation and training at the start
For organizations starting one-on-ones, Education connects training, as the first step of the Orblit Momentum Program, where leaders and team members understand together why conversation matters and learn listening, feedback, and questioning skills.
Sources
- One on One · Andreessen Horowitz (Ben Horowitz) · 2012-08-30
- 5 Signs Your One-on-Ones Aren't Working · Harvard Business Review (Jen Dary) · 2024-06-03