75 One-on-One Meeting Questions (By Category)

What makes a good 1:1 question?

Good 1:1 questions are open-ended, non-judgmental, and invite the other person to think rather than just report. Avoid yes/no questions. Avoid questions the employee will interpret as evaluative ("how do you think you're doing?"). The best questions create space for something you didn't expect to hear.

1. Check-in and work updates (9 questions)

Use these to open the meeting and understand where attention is needed — not as a status report request.

What's at the top of your mind this week?
What are you most focused on right now? What's the biggest obstacle?
What do you need from me to make progress this week?
Is there anything you're stuck on that I could help unblock?
What went well last week that you want to make sure we notice?
Is there anything you're worried about that hasn't come up yet in the team?
What's taking more time than it should be? Why?
Is there anything on your plate that shouldn't be there?
What's something you accomplished last week that you're proud of?

2. Wellbeing and workload (8 questions)

Check in on energy and sustainability — not just output. Burnout signals appear here before they show up in work quality.

How are you feeling about your workload right now — stretched, balanced, or underloaded?
How's your energy been this week compared to normal?
Is there anything outside of work affecting your capacity that's useful for me to know?
What's the most draining part of your week right now?
Are there any meetings or processes that feel like wasted time to you?
How are you feeling about the team dynamics lately?
Is there anything about the way work is organized that's making things harder than necessary?
On a scale of 1–10, how energized do you feel about the work right now? What's behind that number?

3. Goals and priorities (8 questions)

Ensure alignment between the employee's daily work and the goals that matter.

Which of your goals feels most at risk right now? What would help?
If you could only work on one thing this week, what would have the most impact?
Are your current goals still the right ones, or should we revisit them?
What's one goal you have full control over, and one where you're dependent on others?
Is there anything that's getting in the way of achieving what you committed to this quarter?
Are there any goals you don't fully understand why they matter?
What would "great" look like on your most important goal this quarter?
Is there anything you're working on that doesn't connect to any of your goals?

4. Career development (10 questions)

Ask these regularly — monthly or quarterly — not just at review time. Development conversations should happen continuously.

What skill do you most want to develop in the next 6 months? What would practicing that look like?
What part of the work are you finding most engaging right now? How could we give you more of that?
What's a project or responsibility you'd like to take on that you haven't had a chance to yet?
Where do you see yourself in 2 years? What would you need to get there?
What's the gap between what you're doing today and what you want to be doing?
Who in the organization do you admire? What do they do that you'd like to develop?
What competency feels like your biggest gap for getting to the next level?
Is there a part of your development plan you feel stuck on? What's making it hard?
What type of work energizes you? What drains you?
What would you need to feel confident about your growth path here in the next year?

5. Feedback — giving and receiving (10 questions)

These questions make feedback a two-way habit. Ask the "what could I do differently?" questions every few weeks — not just when you sense a problem.

From manager to employee

Is there feedback I've given you that didn't land the way I intended? What would have been more helpful?
What's one thing you wish I would stop doing?
Are there decisions where you wish I had asked for your input first?
Is there anything I'm not noticing about your work or situation that I should be aware of?
What could I do to be a better manager to you specifically?

From employee to manager

What's something I've been doing that I should keep doing?
What's one area where you think I could grow or improve?
Is there a decision I made recently that you would have made differently? What would you have done?
What would help me get promoted / move to the next level?
Is there any feedback you've been holding back that would be useful for me to hear?

6. Team and organizational health (7 questions)

Understand team dynamics and organizational friction that may not surface in project work.

Is there any tension on the team that you think I might not be fully aware of?
Who on the team do you find easiest to work with? Hardest? What's behind that?
What's one thing the team does really well that we should protect?
What's one thing we're doing as a team that we should stop doing?
Is there anyone on the team who isn't getting the recognition they deserve?
Are there any cross-functional relationships that feel difficult or broken right now?
What's one process or decision the organization makes that frustrates you most?

7. Big-picture and retention questions (7 questions)

Ask these quarterly. These are the questions that tell you, months in advance, whether someone is thinking about leaving.

What would make this job the best job you've ever had?
Is there anything that would make you think about leaving the company? What would have to change to make staying the obvious choice?
What's something this company does well that you don't see anywhere else?
What's one thing you wish you'd known before joining?
If you could change one thing about the company, what would it be?
What's your favorite type of work? Are we using your strengths enough?
Are you proud of the work you're doing here? What would make you prouder?

8. Questions for new employees (6 questions)

Use in the first 90 days. These build trust early and surface integration problems while they're still fixable.

What's been surprising about the role so far — positively or negatively?
Is there anything about how we work that's confusing or that you wish someone had explained?
Who have you found easiest to connect with? Is there anyone you haven't had a chance to work with yet that you'd like to?
What would help you feel more effective in the next 30 days?
Is there anything about the team or the way we work that concerns you?
What are you most excited about? What are you most nervous about?

How to use these questions

Don't read from this list in the meeting. Before the meeting, pick 2–3 questions that feel most relevant given what you know about the person and their current situation. Add them to the shared agenda in advance so the other person has time to think. The goal is a conversation, not an interview.

In Harmny, both manager and employee add agenda topics before the meeting. Action items created during the session carry forward automatically to the next meeting. See 1:1 meetings.