200 One-on-One Meeting Questions Great Managers Ask in 2026
Jan 15, 2026
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11
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AI Summary by Fellow
Great one-on-one meetings don't happen by accident. The difference between a productive conversation that builds trust and a forgettable status update often comes down to one thing: the questions you ask.
The world's best managers understand that one-on-ones are their most valuable tool for coaching, developing, and retaining talent.
As Kim Scott writes in Radical Candor, these are "your must-do meetings" and "your single best opportunity to listen, really listen, to the people on your team."
But even experienced managers struggle to move beyond surface-level check-ins. That's why we've compiled 200 one-on-one meeting questions across 16 categories to help you have more meaningful conversations with your direct reports.
Losing track of what you discussed in previous one-on-ones? An AI meeting assistant can capture your conversations automatically, so you can focus on the person in front of you instead of taking notes. Start your free trial →
Why do one-on-one meetings matter for managers?
One-on-one meetings are the foundation of effective management. Research from Gallup shows that employees who meet regularly with their managers are almost three times as likely to be engaged as those who don't. These dedicated conversations create space for coaching, feedback, career development, and relationship-building that can't happen in group settings.
Andy Grove, the legendary Intel CEO who grew the company's revenue from $2,672 million to $20.8 billion, put it simply in High Output Management: "It is the principal way their business relationship is maintained. Its main purpose is mutual teaching and exchange of information."
Regular one-on-ones help you discover and address issues before they become crises, create a culture of continuous feedback, and foster the positive work relationships that drive productivity and retention.
How should you structure a one-on-one meeting?
The best one-on-one structure balances consistency with flexibility. Too rigid, and you'll stifle authentic conversation. Too loose, and you'll waste time on status updates that belong in email.
A proven framework includes time for a personal check-in, your direct report's priorities and concerns, your updates and feedback, development and growth discussion, and clear action items with owners and due dates.
The key is letting your direct report drive most of the agenda. As Julie Zhuo explains in The Making of a Manager, one-on-ones let you discuss topics that may never come up otherwise, including what motivates team members, their long-term career aspirations, and how they're generally feeling about their work.
For meeting frequency, weekly one-on-ones work well for smaller teams, while bi-weekly cadences may be more realistic for managers with larger teams. The important thing is consistency. As Yolanda Lau of FlexTeam advises, managers should aim for one-on-ones at least three out of every four weeks.
Pro tip: Instead of scrambling to remember what you discussed last time, use AI meeting notes to automatically capture key points and action items. You can even query Ask Fellow before your next one-on-one to review what commitments were made.
What are the best questions to ask in a first one-on-one?
The questions you ask when starting a new relationship set the tone for everything that follows. Focus on understanding expectations, communication preferences, and what success looks like for your new team member.
Questions to set expectations and build trust
What are your expectations for this role?
What are you most excited about?
What does success look like to you?
What are some pitfalls we should avoid?
Why did you decide to work here?
Is there anything you'd like to know about me?
What makes one-on-ones most valuable for you?
Who is the best manager you've ever had? What did you like about their approach?
How do you prefer to receive recognition, publicly or privately?
What's your preferred method of communication for different types of updates?
How can I tell when you're stressed or frustrated?
Are there manager behaviors you know don't work well for you?
What career goals should I know about so I can help you achieve them?
Any surprises since you've joined, good or bad, that I should know about?
What can I do to help you succeed in your first 90 days?
What questions help you check in on workload and wellbeing?
Regular check-ins help you stay connected to what's actually happening with your team members, not just what shows up in project trackers. These questions surface both tactical updates and emotional state.
Questions for ongoing check-ins
What's top of mind for you right now?
What did you accomplish last week that I might not know about?
What went well since we last met?
Is there anything you weren't happy about?
What did you learn recently?
What were your main priorities since our last conversation?
What will your priorities be between now and our next meeting?
How can I help remove obstacles for you?
How's your energy level these days?
Questions about life outside work
Building genuine relationships means caring about the whole person. These questions show you see your direct reports as more than their job titles.
How's life outside of work?
How's your work-life balance feeling lately?
What hobbies do you enjoy outside of work?
How was your weekend?
What are you reading or watching these days?
How are things with your family?
What's a personal goal you're working toward this year?
If you could give your younger self some advice, what would it be?
How do you discuss priorities and productivity in one-on-ones?
Understanding how your direct reports spend their time reveals opportunities for better alignment, delegation, and support. These questions help you coach without micromanaging.
Questions about priorities and time management
What are your top three priorities right now?
What percentage of your time goes to meetings versus deep work?
What would you like to spend more time on?
What would you like to spend less time on?
How is [specific project] going? How do you feel about it?
When do you do your best work: morning, afternoon, or evening?
How do you like to organize your day?
What are the biggest time wasters in your typical week?
How do you know when you've had a productive day?
How could I help you be more productive?
Are there tools or resources that would make your work easier?
What meeting could we eliminate or shorten?
If your team spends significant time in meetings, an AI meeting notetaker can give everyone that time back. Instead of one person frantically capturing notes, everyone stays engaged while AI handles the documentation. See how it works →
What questions measure and improve employee engagement?
Engaged employees are more productive, more innovative, and more likely to stay. These questions help you understand what drives motivation and where friction exists.
Questions about engagement and satisfaction
How does your current work compare to your expectations when you started?
Do you feel your work is appreciated?
What motivates you to come to work each day?
How often do you get to use your strengths at work?
What's your favorite part of your job?
Is there anything about your job you really don't enjoy?
What have you been happiest about this past month?
What have you been less happy about?
After [X] time at the company, how do you feel overall?
What are you most proud of accomplishing here?
What's one new thing you'd like to work on?
What could we do to make your work more enjoyable?
What projects are you working on that you wish you weren't?
Are there projects you'd really like to work on?
On a scale of 1-10, how happy are you at work?
What would it take to get you to a 10?
How do you surface challenges and roadblocks?
Your direct reports often know about problems before you do. Creating psychological safety around discussing challenges helps you address issues early, before they become crises.
Questions about obstacles and concerns
When have you felt stressed or overwhelmed recently? How can I help prevent that?
Are there any obstacles preventing you from doing your best work?
Is anything slowing you down or blocking you right now?
Is there an aspect of your job that needs more support or coaching?
What challenges have you faced recently? How can we work through them together?
Is any part of your job unclear or confusing?
What's the one thing that would make the biggest difference in your ability to succeed?
Are there decisions you're waiting on that are holding you back?
What questions help you become a better manager?
The best managers actively seek feedback on their own performance. These questions take courage to ask, but the insights they generate are invaluable for your growth.
Questions to receive feedback and improve
What's something I should consider changing about my leadership approach?
Would you like more or less direction from me?
What would you do differently if you were in my position?
What could I do to invest more in your growth?
What's one thing you think I don't want to hear but should?
If you were me, what would you change about how our team operates?
Do you feel I represent the team well to the rest of the company?
Do you feel I acknowledge your positive contributions?
What's your favorite thing I do as a manager?
What could I do to help us work better together?
What feedback do you have for me, both positive and constructive?
What do you like about my management style?
Can you think of something I've done recently that you disagreed with?
Is there something I'm doing that I could delegate to someone else?
How do you give and receive feedback effectively in one-on-ones?
Feedback flows both ways in effective one-on-ones. These questions help you understand how your direct reports prefer to receive feedback and create opportunities for growth conversations.
Questions about feedback preferences
Do I give you enough feedback?
Do you prefer written feedback you can digest, or are you comfortable with verbal feedback?
What's the best feedback you've received in the last 90 days?
What's one area you think you could improve?
What's one thing you think you should do more of?
What's one thing you could start doing to get better results?
What's one thing you could stop doing?
Is there a project or skill where you'd like more feedback?
Is there an aspect of your job where you'd like more coaching?
What type of feedback is most valuable to you?
What type of feedback are you missing?
At your last performance review, we discussed [X]. How's that going?
What questions support growth and development?
Career development conversations signal that you're invested in your team member's future. These questions help you understand aspirations and create paths to achieve them.
Questions about learning and growth
Do you feel challenged at work? Are you learning new things?
What would you like to accomplish by the end of the year?
What would you like to learn more about?
What skills would you like to develop?
What have you learned or improved recently?
What can I do to help you be more successful?
Is there someone in the company you'd like to learn from?
If you could have any mentor, who would it be and why?
Are there skills that would be useful for you to develop soon?
Are there conferences, workshops, or training you'd like to attend?
If you could take a course in anything, what would it be?
What habits would you like to develop?
What habits would you like to break?
Questions about career goals and aspirations
What do you love most about your work?
Do you feel you're advancing in your career?
Do you see yourself as an individual contributor or moving into management?
What do you want the peak of your career to look like?
What are three long-term professional goals that matter to you?
What work are you doing here that's most aligned with your long-term goals?
Imagine we're 10 years in the future and the company has grown exponentially. What role do you see yourself in?
Have any of your goals changed since we last discussed this?
How do you help employees develop new ideas?
Sometimes the best thing a manager can do is ask the right question to spark creativity. These prompts help your direct reports think through ideas and gain confidence in their problem-solving abilities.
Questions to spark innovation
Are there any new ideas you'd like to discuss?
What options are you considering?
What do you need to develop that idea further?
What could be your first step?
Can you explain that idea in a different way? I want to make sure I understand.
What does your ideal outcome look like?
What's making it hard to reach that outcome?
What do you think is the best course of action?
What's the worst-case scenario you're worried about?
On a scale of 1-10, what's the likelihood of this succeeding? What would make it a 10?
What questions improve team dynamics and culture?
Strong team dynamics don't happen by accident. These questions help you understand interpersonal relationships, identify friction points, and build a more collaborative culture.
Questions about team relationships
How do you find working with the team?
Do you think we're headed in the right direction as a team?
How do you find working with [specific colleague]?
Have you helped other team members recently?
Have you received help from anyone on the team?
Do you feel comfortable giving constructive feedback to your peers?
Are there people on the team you think could work together more effectively?
What could we do to improve team dynamics?
Are there aspects of our team culture you'd like to change?
How do you feel about how we communicate about our work?
What team-building activity would you suggest?
Do you think our team activities are inclusive? How could we improve?
What's something we should start doing as a team?
Is there a difficult conversation our team needs to have that we're avoiding?
Do you think we work well together as a team? What would make us more effective?
Who works really well together on the team?
How is [new team member] doing?
How have you been getting along with other teams in our department?
What questions help you understand company perception?
Your direct reports have unique perspectives on how the organization functions. These questions surface insights about company culture, strategy, and opportunities for improvement.
Questions about the broader organization
How do you feel about the priorities of teams you depend on?
What are other teams working on that seems unimportant or counterproductive?
What are other teams not doing that you wish they would?
Have you talked to those teams directly about your concerns?
Do you think our team is well recognized in the company?
What would you change about our product?
What's the biggest problem in our organization?
What's the #1 opportunity for our company?
What's the biggest risk for our company?
What's your favorite part about working here?
If you were CEO, what would you change today?
What do you love about our company culture?
What aspects of company culture would you change?
How can we make our company more inclusive and diverse?
What's the most inefficient process in the business?
What should we be doing as a company that we're not?
If something would make people want to leave, what would it be?
What area of the company would you like to learn more about?
Have you been disappointed by any company decisions this year?
Do you think we've communicated our company values clearly?
What's one thing we could do to improve internal communication?
When have you felt proudest to be part of this company?
How do you improve the quality of your meetings?
Meta-conversations about your one-on-ones help you continuously improve their value. Don't be afraid to ask whether your time together is working.
Questions about your one-on-ones
Are our one-on-ones a good use of your time?
Are there meetings you feel you should be part of but aren't?
What are our most useful meetings?
Do you feel like you have too many or too few meetings?
How could we make our team meetings more productive?
Should any of our recurring meetings be shorter?
Should we stop running any meetings altogether?
What went well in [specific meeting]?
Is there a status update meeting we could replace with async communication?
What could have gone better in [specific meeting]?
What's the most valuable part of [specific meeting]?
What's the least valuable part of [specific meeting]?
Pro tip: If you're having trouble remembering what was discussed in previous one-on-ones, you're not alone. Ask Fellow lets you query your meeting history with natural questions like "What commitments did Sarah make last month?" or "What concerns has the team raised about the product launch?" Try it free →
What questions should you ask remote employees?
Remote work creates unique challenges around communication, inclusion, and belonging. These questions help you stay connected with distributed team members.
Questions for remote team members
What would help us improve daily communication?
Do you feel the company supports remote staff effectively? How could we do better?
Do you feel included in our decision-making processes?
How do you manage distractions during the day?
Do you feel connected to the team despite the distance?
What tools or processes would make remote collaboration easier?
Are there in-person opportunities you wish you had access to?
What questions should you ask at the end of every one-on-one?
The final moments of a one-on-one often surface the most important topics. As Bilal Aijaz, CEO of Polly, explains using the "doorknob analogy," patients often ask doctors their most difficult questions as they're reaching for the doorknob to leave.
Closing questions
Is there anything else on your mind that we didn't cover?
What are the key takeaways from our conversation today?
What action items do you have? What are mine?
Is there anything you need from me before our next meeting?
How are you feeling about everything we discussed?
What should we make sure to follow up on next time?
Is there anything you wanted to bring up but didn't get a chance to?
What was the most useful part of our conversation today?
Do you feel clear on next steps and priorities?
Is there anyone else you think I should connect with about what we discussed?
On a scale of 1-10, how productive was this one-on-one?
Did we spend our time on the right topics today?
Is there something weighing on you that you'd rather discuss next time when you've had more time to think?
What's one thing you're taking away from this conversation?
How can I best support you between now and our next meeting?
Is there anything I committed to previously that I haven't delivered on?
Is there anything that might come up this week that I should know about?
Five tips for asking better one-on-one questions
Having a list of questions is just the starting point. How you ask matters as much as what you ask.
Be specific over generic. "How's the project going?" invites vague answers. "What's the biggest obstacle you're facing on the customer dashboard redesign?" gets you actionable information.
Ask open-ended questions. Yes-or-no questions shut down conversation. Questions starting with "what," "how," or "tell me about" invite reflection and detail.
Give time to think. Don't fill silence immediately. Some of the best insights come after a pause. Let your direct report process the question.
Follow up on what matters. When someone shares something important, dig deeper. "Tell me more about that" shows you're genuinely listening.
Track what you discuss. The best one-on-ones build on previous conversations. Use an AI meeting assistant to automatically capture key points so you can reference past discussions without relying on memory. Teams at Shopify, HubSpot, Vidyard, and Motive use Fellow to make every conversation searchable and actionable.
Turn one-on-one conversations into organizational intelligence
The questions in this guide can transform your one-on-ones from routine check-ins into high-impact coaching conversations. But the insights from those conversations are only valuable if you can act on them.
Every one-on-one contains commitments, concerns, and context that shouldn't disappear when the meeting ends. Fellow captures your conversations across Zoom, Google Meet, Teams, and even in-person meetings, then makes them searchable across your entire organization.
Instead of scrambling to remember what you discussed last month, query your meeting history: "What career goals has Jordan mentioned?" or "What blockers has the team raised about the Q3 launch?" Fellow's enterprise-grade security (SOC 2 Type II certified, HIPAA compliant, no training on your data) means your sensitive conversations stay private and protected.
Your one-on-ones already contain the insights you need. Fellow helps you find them.
Frequently asked questions
What are the best questions to ask in a one-on-one meeting?
The best one-on-one questions are open-ended, specific to the individual, and build on previous conversations. Start with questions about priorities and wellbeing ("What's top of mind for you?" "How's your energy level?"), then move into development and feedback topics. The most effective managers customize their questions based on the team member's role, tenure, and current challenges rather than using a generic script.
How often should managers have one-on-one meetings?
Most management experts recommend weekly one-on-ones for smaller teams and bi-weekly for managers with larger teams. The key is consistency. According to research and experienced managers like Yolanda Lau of FlexTeam, aim for one-on-ones at least three out of every four weeks. Missing occasional meetings is fine, but the pattern of regular connection drives engagement and trust.
How do you structure a one-on-one meeting agenda?
An effective one-on-one structure includes a brief personal check-in, time for your direct report's priorities and concerns (they should drive most of the agenda), your updates and feedback, career development discussion, and clear action items with owners. Avoid turning one-on-ones into status updates. Those belong in project tools or async communication. Use this dedicated time for coaching, feedback, and relationship-building.
How do you make one-on-ones more productive?
Prepare in advance by reviewing notes from previous meetings, come with specific questions rather than generic prompts, and let your direct report own most of the agenda. Use an AI meeting assistant to capture key points automatically so both parties can stay fully present. After each meeting, ensure action items have clear owners and due dates. Following up on commitments builds trust and accountability.
What should you not discuss in a one-on-one?
Avoid using one-on-ones for detailed status updates that could be communicated asynchronously. Don't ambush employees with negative feedback they haven't had time to process. Avoid comparing team members to each other or sharing confidential information about their colleagues. One-on-ones should feel like a safe space for honest conversation, not a performance review or gossip session.
How do you ask for feedback from your direct reports?
Create psychological safety by being specific about what feedback you want ("What could I do differently to support you better?"), responding non-defensively when you receive it, and acting on the input you get. Start with lower-stakes questions ("What's your favorite thing I do as a manager?") before asking harder ones ("What's one thing you think I don't want to hear but should?"). Thank them for honest feedback, even when it's uncomfortable.
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