One-on-One Meeting Questions
Good one-on-one meeting questions are open, and they’re about the other person’s work and whatever is getting in its way. The employee’s own topics come first, and your questions come after. Pick two or three for each meeting. Don’t work through a list.
The questions below are grouped by situation, from a new hire’s first month to the moment you wonder whether someone is unhappy. Each group is in a block you can copy. Paste the few you need into your shared one-on-one meeting template, under your own topics.
How to use these questions
Their agenda goes first. The direct report adds their topics to the shared document before the meeting. Start there, even when your own topics feel more urgent. Your questions fill the time after their list, or open up a topic of yours.
Use two or three questions, not ten. A one-on-one runs 25 to 45 minutes, which is room for a few real answers. Ten questions in a row feels like a survey.
Keep one shared running document. Use the same document every time, with the newest meeting at the top. Start each meeting by checking what both of you committed to last time. Your own commitments matter most. If you said you’d find something out, report back.
Write down what you agree. Each agreed step gets one owner and a date. “I’ll look into it” doesn’t count as an action item. “Maya books 30 minutes on IT access by Oct 23” does. If those commitments need to land in a wider tracker, the meeting action items template has the columns.
Keep private notes separate. The shared document should never surprise the other person. Notes about performance concerns or anything personal they told you go somewhere else. Follow your organization’s HR policy on what you keep and where.
Don’t turn it into a status update. If an answer could have gone in a team channel, it probably should have. Status belongs in the team meeting, and how to run a meeting covers that one. Use the one-on-one for things that are hard to say in a group.
For a light opener, “How’s your week going?” is usually enough. If you want warm-up questions for a group meeting instead, see check-in questions for meetings.
Your first one-on-ones with a new hire
In the first month, meet weekly. You’re learning how this person works, and they’re learning how you work. Ask about the job, the setup and how they like to communicate.
What has surprised you most since you started?
What did you expect to have set up by now that still isn't?
Which parts of the job feel clear, and which still feel fuzzy?
Who have you met that you'll work with most? Who haven't you met yet?
What would a good first month look like to you?
How do you like to get feedback: in the moment, in writing, or saved for these meetings?
When you get stuck on something, who do you ask?
What did your last workplace do well that we should think about trying here?
Which part of your onboarding felt like a waste of time?
What's the best way for me to reach you when something comes up?
What would you like these one-on-ones to cover?Your first one-on-one with someone you just started managing
If you’ve inherited a team, people already have habits, projects and expectations. Some may have been promised things by their last manager. Spend the first meeting listening.
What should I know about how this team works that isn't written down?
What did your previous manager do that you'd like me to keep doing?
What would you like me to do differently?
What are you working on now, and which part matters most to you?
Has anyone promised you something I should know about, like training, a project or a change in role?
Where do you think the team loses the most time?
What do you want to be known for on this team?
What, if anything, worries you about a change in manager?
How often would you like to meet, and for how long?
Is there a decision you've been waiting on that I could help move?Don’t confirm promises you can’t keep yet. Write them down, find out, and report back by a date you name.
Regular weekly or biweekly one-on-ones
Once things are steady, most one-on-ones are about priorities, blockers and workload. Let them talk first. Then pick from these.
What's on your mind this week?
What's the most important thing you're working on right now?
What's slowing you down?
Are you waiting on a decision from me or anyone else?
What's on your plate that shouldn't be?
How manageable is your workload right now? What would you drop first?
What went better than you expected since we last talked?
What's coming up in the next two weeks that you're unsure about?
Where would a second opinion help?
Who do you need to work with more closely but find hard to reach?
What did the last project teach you that we should repeat?
What could I do before our next one-on-one to make your week easier?“What’s slowing you down?” is the one to come back to. It often surfaces a blocker that is yours to fix.
Feedback both ways
Asking for feedback on yourself works better when the question is specific. “Any feedback for me?” usually gets “No, all good.” Ask about one behavior or one recent moment.
What's one thing I could do differently that would help you most?
Is there anything I do in team meetings that makes your job harder?
When have I given you too little context on a task?
How useful are these one-on-ones for you? What would make them better?
What did I say I'd do that I haven't done yet?
Was there a recent decision of mine that didn't make sense to you?When you’re giving feedback, open with a specific moment, then ask for their view before you decide what it means.
Can I share something I noticed in Thursday's client call?
How do you think the presentation went? What would you change?
Here's what I saw in the review meeting. How did it look from your side?
What would help you handle that differently next time?
What would you need from me to make that change?Thank people for feedback on you, and act on one piece of it where they can see.
Career and growth
The template’s Growth section suggests once a month, and that’s often enough. Ask about direction, then agree on one next step you can help with.
What kind of work gives you energy? What drains you?
Where would you like to be in two years? It's fine not to know yet.
Which skill would make the biggest difference to your work right now?
Is there a project coming up that you'd like to be part of?
Who here does work you'd like to learn from?
What would you like to do more of next quarter, and less of?
What would you like to be trusted with that you aren't yet?
What training or course would be worth your time this year?
How can I help other people see the work you're doing?
What would a good next step here look like for you?Career advice from someone outside the reporting line is useful too. A mentor meeting is a better place for that than your one-on-one.
Before or after a performance conversation
These conversations need more care. Stick to facts: specific pieces of work, with dates. Don’t promise a raise, a promotion or a review outcome that isn’t yours to decide. Formal performance processes, such as written warnings, improvement plans and pay decisions, follow your organization’s HR policy. Check it before the meeting.
Before the conversation:
How do you think the last few months have gone?
Which piece of work are you most proud of since we last set goals?
Where do you think you fell short of what we agreed, and what got in the way?
What did you need from me that you didn't get?
What do you want me to know before we talk about the review?After the conversation:
Which part of the review would you like to talk through again?
What do you want to work on first?
What should we check on together over the next few one-on-ones?
How would you like me to tell you whether things are on track?Write the agreed next steps in the shared document in plain language, so you both remember them the same way.
When someone may be unhappy or thinking of leaving
You might notice someone has gone quiet in meetings, stopped volunteering for new work, or sounds flat when they talk about projects they used to like. None of that proves anything. It’s a reason to ask, gently, about the work and how they feel about it.
What would make the next six months better for you?
How are you feeling about your work lately?
Which part of your job do you look forward to? Which part do you dread?
If you could change one thing about your role tomorrow, what would it be?
Is anything about the team or the workload wearing you down?
How well do you feel your work gets noticed here?
What would you like to try here that you haven't had the chance to?
What could I take off your plate that would make the biggest difference?
Is there anything I've been missing that you'd like me to know?Never ask “Are you looking for another job?” It puts the person on the spot, the only safe answer is no, and you learn nothing. If someone tells you they’re thinking of leaving, thank them for saying so. Ask what would need to change, and don’t promise what you can’t deliver.
Questions an employee can ask their manager
One-on-ones are yours too if you’re the employee. Put your topics in the shared document first, and keep a few of these in mind for when the list runs short.
What should I be focusing on that I'm not?
What's one thing I could do better on my next project?
What's coming up for the team that I should know about?
What would you need to see from me before trusting me with bigger work?
Who here should I get to know better?
Do you want problems early and rough, or once I've thought them through?
What's the biggest thing on your plate right now, and could I help with any of it?
How does my work connect to what this organization cares about most this year?If your manager’s manager holds a skip level meeting with you, many of the same questions work there.
A worked example: Sam and Maya
Fernhill Studio is a fictional design studio we use as a sample across this site. Maya Okafor, the studio lead, has a one-on-one with each person on her team.
At the Week 42 team meeting, Sam Whitlock took on action item A2: draft the onboarding checklist for the new studio coordinator, due Oct 20. The coordinator starts Nov 9. At the Oct 20 team meeting, nobody mentioned A2.
In their one-on-one the next day, Sam’s topics came first. Then Maya asked one question from the weekly list: “What’s slowing you down on the checklist?” The checklist was half done, and Sam needed Maya’s input on IT access for new hires. The blocker was hers.
Here’s an excerpt of their shared document:
ONE-ON-ONE: Sam Whitlock and Maya Okafor
Wednesday, October 21, 2026, 30 min
Follow-ups from last time
- Budget for a type design course (Maya): yes, up to $400 this quarter
- Onboarding checklist draft (Sam): half done, needs Maya's input on IT access
Sam's topics
- Harbor & Pine feedback rounds are eating into other work.
Wants a limit on rounds in future proposals.
- Would like to present Homepage v3 to the client himself, not only Priya.
Maya's topics
- Studio coordinator starts Nov 9. Checklist needs to be ready a week before.
Support needed
- 30 minutes with Maya to settle IT access for new hires.
Commitments before next time
Commitment Who By
Book 30 minutes to settle IT access Maya Oct 23
Finish onboarding checklist draft Sam Oct 30
Propose a round limit for the next proposal Sam Nov 4
Tell Priya that Sam presents v4 Maya Oct 22At the next team meeting, A2 was marked “Rescheduled: was Oct 20, now Oct 30,” with the IT access reason next to it. The old date stayed visible.
Questions to avoid
- Leading questions. “Don’t you think that deadline was fair?” tells them the answer you want. Ask “How did that deadline work for you?”
- Yes or no questions. “Is everything OK?” almost always gets “Yes.” Ask “What’s been hardest this week?”
- Questions about personal life. Don’t ask about health, pregnancy or family plans, relationships, religion, age, or other personal matters. If someone brings something up, listen, and keep it out of the shared document. If it affects their work, follow your organization’s HR policy.
- A string of whys. “Why is this late? Who approved that? Why didn’t you tell me?” sounds like an interrogation, even in a calm voice. Ask one question, then listen to the whole answer.
- “Are you looking for another job?” See above. Ask what would make the next six months better instead.
- Questions you’ve already answered. Asking for input on a decision that’s already made teaches people their input doesn’t matter. If it’s decided, say so and explain why.
FAQ
What should I ask in a one-on-one?
Start with the employee’s own topics. Then ask two or three open questions about their work: what’s slowing them down, what they’re unsure about, and what you could do before the next one-on-one to help. Add feedback or career questions when they fit, roughly once a month for growth. End by writing down what each of you agreed to do, with a date.
How often should one-on-ones be?
Weekly for new team members or during busy periods, and every two weeks once things are steady. Most run 25 to 45 minutes. Moving a one-on-one is fine. Cancelling them often tells people they aren’t a priority.
Who sets the agenda for a one-on-one?
The employee does, mostly. They add their topics to the shared document before the meeting, and those go first. The manager adds topics too, like feedback, context and changes the person should hear from you first. Keep both lists in one place, such as the one-on-one meeting template, so nothing is a surprise.
What should you not say in a one-on-one?
Avoid leading questions, yes-or-no questions, and anything about health, family plans or other personal matters. Don’t fire off a series of “why” questions, and don’t ask whether someone is job hunting. Don’t promise raises, promotions or review outcomes you can’t control. If a formal performance issue comes up, follow your organization’s HR policy.