One-on-one meeting questions are an important tool for a manager, and yet they are usually dull and the same as last year. The form often has ten questions, they are asked of everyone in the same order, and the answers are familiar before they are said.
Good questions concern the particular person in the conversation, and they cannot be answered with yes or no.
This page collects 30 example questions grouped in two ways: by situation, for when you are facing the first conversation with a new team member, a quiet team member or a conversation in which nothing came of last time's agreements, and by theme, for when you want a structure for a regular one-on-one or an annual development discussion.
The questions are examples and inspiration, not a checklist. A 30-minute one-on-one fits three to five questions, an hour-long development discussion five to eight, and the best ones often emerge only during the conversation.
How a development discussion as a whole is prepared, held and taken into everyday work is described in the guide development discussion: what it is, why it matters and how to do it well.
How to recognise a good one-on-one question
Three rules are enough: openness, the person rather than the fire, and follow-up questions.
The question is open. If it can be answered with yes or no, it is a statement, not a question. "Are you happy with your work" produces "yeah, it's fine". "What is best about your work right now, and what drains the most energy" produces a conversation.
The question concerns the person. A general question produces a general answer. When the question refers to something the manager has seen themselves, the answer is concrete. "I noticed the final phase of the project took a lot out of you. What happened there?"
One question at a time, and a follow-up after it. The best follow-up is almost always the same: "How do you notice that?" or "Give me an example." The answer to that is what a one-on-one is for.
One-on-one meeting questions by situation
The same structure does not work in every conversation. Below are four situations in which the questions should be chosen differently from a regular one-on-one.
The first one-on-one with a new team member
A new team member has no past period to review. The job of the conversation is to find out what they expect and what they have already noticed.
- What has surprised you most, for better or worse, during the first months?
- What did you know about this job before starting that turned out to be wrong?
- What do you hope for or need from me over the next three months?
A quiet team member
When a team member answers briefly, the manager easily fills the space themselves. Then the questions should be made concrete and given time to be answered. Silence after a question is not a problem, it is thinking.
- What is something in your work that you do well, but few people know about?
- When did you last think that something should be done differently, but did not say it out loud? What was it?
- If someone new started in your job, what would you advise them first?
When nothing came of last time's agreements
This is the most common situation, and it is usually skipped awkwardly. It should not be skipped. It should be the first topic of the conversation.
- Last time we agreed to do this. Why has it not happened?
- What should I have done differently for it to happen?
- Do we now agree the same thing again, a smaller version, or something else entirely?
When the strategy or goals changed mid-period
When the organisation's direction changes, the one-on-one is where the change is translated into one person's work.
- What does the new direction mean in your work in practice?
- What should you do more of, less of, and not at all any more?
- Which of the skills you have now becomes more important, and which less?
One-on-one meeting questions by theme
Six themes for a regular one-on-one or an annual development discussion. Three or four themes are enough for one conversation. Always start with a check-in and end with agreements.
Check-in
- How are things? What is on your mind right now?
- What frame of mind did you come to this conversation in?
- How would you describe the past six months?
How the work is going and the past period
- What have you been proudest of during the past period?
- What is best about your work right now, and what drains the most energy?
- What keeps recurring as a problem even though it has been discussed?
Skills and direction
- What would you like to be able to do a year from now that you cannot do today?
- What can you do that this role does not currently use?
- Which direction would you like your role to develop in over the next couple of years?
Collaboration and the team
- What works in our team's collaboration, and what does not?
- In which situations are you left alone with things where you would need others?
- What is not said out loud in the team, even though it should be?
Leadership and feedback for the manager
- What would you like more of from me as a manager, and what less?
- When did you last feel you were not listened to? What happened then?
- Which decision or policy has remained unclear to you?
Wellbeing and workload
- How are you coping? What is the heaviest thing right now?
- Is your workload such that you can do your work well?
- Is there something you have wanted to talk about, but the moment has not felt right?
The last question is worth asking in every one-on-one. It can change the direction of the conversation.
Questions not to ask
Some traditional one-on-one questions do more harm than good.
- "Where do you see yourself in five years?" Few people know, and the answer is either invented or cautious. Ask about the next step instead.
- "Are you happy with your pay?" Pay deserves its own conversation. When it is on the table, nobody talks honestly about development.
- "Do you have problems with anyone?" The question invites either denial or naming names. Ask instead in which situations collaboration gets stuck.
- "What are your strengths and weaknesses?" A job interview question with a ready answer. Ask in which situations skills do not feel sufficient or where help is needed.
- "Do you have any questions?" At the end of a conversation the answer is always no. Ask what has not been talked about yet.
How to choose the questions
A 30-minute one-on-one fits three to five questions, an hour-long development discussion five to eight, when each is given time and followed by a follow-up question. A selection that works:
- One check-in question.
- If the situation is one of the four described above, its questions first.
- Two or three questions from the theme that is current for this particular person. Not from all of them.
- One question for the manager themselves, for example question 25.
- Finally question 30: is there something you have wanted to talk about.
Ready-made structures in which to place the questions can be found in three development discussion templates for managers, and the most common mistakes that even good questions fall to in common mistakes and benefits of development discussions.
Our recommendation: not a question bank or a form, but the employee's own reflection and dialogue
The questions on this page are there to support a manager's thinking. We do not recommend turning them into a form or a question bank that is gone through with everyone in the same order. That brings you back to where you started: a conversation whose answers are known in advance.
We recommend two things instead.
The employee's own reflection before the conversation. Instead of a list of questions, give the team member room to think for themselves about what they want to talk about. Three questions are enough: what has gone well, what has been difficult and what do you want to talk about. At Entteri the traditional form felt oppressive to some team members and was left unfilled. When it was replaced by the team member's own choice of topics, the conversations flowed even with the quieter ones. The experience can be read in Entteri's customer story.
Dialogue in which the topics come from the team member. When the team member raises the topics themselves, the manager's job is to ask the follow-up questions: how do you notice that, give me an example, what should be done about it. The topics are the right ones because they are their own. At Quanscient this brought topics into the conversations that would not have surfaced with a form. It is described in Quanscient's story.
Topaasia's development discussion is built on this principle. The team member picks from the cards the topics that feel important right now and explains their choices. The manager acts as the game master, listens and asks. Mia Santala from Saranen Consulting describes the difference like this:
"I was surprised to get such extensive reasoning and reflection on things. It's not always easy to articulate your own thoughts, but Topaasia makes it easier because it has a structure and a routine for moving the conversation forward."
Saranen's experience can be read in full in the customer story. Gamified development discussions, of which more than 1,310 have been played with a participant rating of 4.59 out of 5, are described in more detail on the development discussions page.
Of the thirty questions, the most important is the one this particular person is waiting to be asked. You will not find it on a list, but by listening and asking afterwards: tell me more.