101 One-On-One Meeting Questions for Bosses and Employees

Whether you’re an employee attending a one-on-one meeting or a leader hosting a one-on-one meeting, everyone wants to make that time spent as worthwhile and productive as possible. For that to be possible, you need to ask thoughtful and intentional questions that provoke conversation, strengthen your working relationship, build trust and credibility, and prompt feedback.

To help you get started, below you will find a list of 101 one-on-one meeting questions that employees can ask their bosses and leaders can ask their employees. It’s quite an extensive list, so the goal is not to cover as many questions as possible in one meeting. Instead, select a handful of questions before every one-on-one meeting you host or attend. The quality of the questions and conversations matters, not quantity.

Table of Contents

• Questions for Leaders to Ask Employees in One-On-One Meetings
• Questions for Employees to Ask Their Boss in One-On-One Meetings

61 One-On-One Meeting Questions for Leaders to Ask Employees

As a leader, you’re the host of the one-on-one meeting, which means it’s your responsibility to ensure the meeting is a good use of your time and your employee’s time away from their work. Therefore, your questions should be aimed at getting you the information and insight you need from your direct reports. It’s also a prime opportunity to ask questions about a person’s well-being, work-life balance, workload, professional goals, performance, and development goals/needs.

• How are you? How has life, in and outside of work, been for you since we last talked?
• Are you looking forward to anything right now, professionally or personally?
• What word would you use to describe your current state of mind?
• What’s taking up most of your headspace right now, even if it’s not work-related?
• What would be the best use of our time today?
• What are your current priorities?
• What will be your main priorities between now and the next time we meet?
• Where could you use my help/support?
• Is there anything you need my feedback or approval on immediately?
• What has been taking up most of your time since we last met?
• How do you feel about your current workload and capacity?
• How are you tracking against your deadlines?
• What is your biggest concern right now, workwise?
• Are you facing any obstacles that you could use my help removing?
• Are you anticipating any obstacles or problems that I should be aware of?
• What did you do this week that made you feel proud or accomplished?
• Have you achieved any “wins” or milestones since we last met?
• Would you say you’re feeling stressed or burned out right now? If so, what can I do to help alleviate that?
• What are some of your telltale signs when you get stressed or burned out?
• Is there anything about your job that keeps you up at night?
• Can you disconnect from work at the end of the day? If not, what is preventing you?
• Do you have everything you need from me to proceed as planned?
• Are you uncertain about any directions I have given you? If so, what can I clarify?
• Do you have any feedback for me?
• Are you getting the feedback and coaching you need from me?
• When I need to provide you with feedback, how would you like me to do so?
• Is there anything I could do more of or better that would put you at ease?
• Do you know what is required of you in your role? If not, what can I clarify?
• Do you have any ideas about how we can work together better?
• Do you feel empowered to do your best work? Why do you think that is?
• Do you have the tools/resources you need? If not, what exactly would you need?
• What is your favorite part about your current role?
• What’s one thing about your current role that, if we changed, would improve your overall well-being and sense of work-life balance?
• Is there a part of your job you enjoy that you haven’t had time to do lately?
• Does your current role make you feel challenged? Is that a positive thing? If not, what would make you feel more challenged?
• Are there any projects, committees, or teams in which you would like to participate or be more involved?
• Are there any areas of your job that you’d appreciate more or less direction from me?
• What do you think you need most from me to be successful in your role?
• Do you have any strengths, skills, or talents that feel underutilized in your role?
• How comfortable do you feel asking either myself or the team for help?
• Do you feel aligned with our [team/company] mission?
• Is the vision for our team and our contribution to the organization clear?
• Do you feel you’re on the same page with the [team/department/company]?
• Is there anything you think we should do that we aren’t currently doing?
• What about your work inspires/engages/motivates you?
• As of right now, what is your biggest source of motivation?
• Is there something or someone who has inspired you lately?
• Who do you look up to for motivation or mentorship?
• Have you encountered a situation recently that you wish you had handled better? If so, what would you do differently?
• What do you think you learned from the situation/experience/mistake?
• How do you feel about your progress on your [monthly/quarterly/yearly] goals?
• Are there any goals that we need to revise or update?
• How can I support you in meeting your [monthly/quarterly/yearly] goals?
• Are you currently working to achieve any specific career goals?
• Does your current role align with your career aspirations?
• Where do you see yourself in the next five years?
• How can I support you in achieving your professional goals?
• Is there a skill you think would be beneficial to learn or develop?
• Is there anything you have wanted to learn but haven’t had time to?
• Do you have any development goals you’re working towards that you’d like me to know about so I can support you?
• Is there a training program, event, or conference that would support your professional development?

40 One-On-One Meeting Questions for Employees to Ask Their Boss

One-on-one meetings are two-way conversations between employees and their bosses. While your boss will come prepared with questions for you, take the opportunity to ask some of your own and solicit feedback, offer support, seek clarification, and request guidance. Being prepared and taking this opportunity to ask thoughtful questions will help you stand out from the crowd, as it shows initiative, engagement, and drive. To give you an idea of what kind of questions we are referring to, here is a list of example one-on-one meeting questions for employees to ask their bosses.

• What word would you use to describe your current state of mind?
• What’s taking up most of your headspace right now, even if it’s not work-related?
• Did you have any work and non-work wins/highlights since we last met?
• What can I do to help you between now and the next time we meet?
• Is there anything I could do for you that would make your life easier?
• Is there anything you’ve been meaning to do but haven’t had the time that I can take care of for you?
• Do you have any feedback for me?
• Does anyone on our team need extra support? Can I help them in any way?
• I’m feeling overwhelmed by [insert concern here]. Could you [insert ask here]?
• Would you say I have my priorities in the right order? If not, how would you change it?
• Do you think our priorities are aligned right now?
• Is there a part of my job that you would appreciate more visibility into?
• Would you like to receive status updates on this task/project?
• How do you like to receive status updates?
• Is there something I could be doing differently?
• Is there anything you would like me to prioritize or spend more time on?
• Is there anything you would like me to spend less time on?
• If you were in my shoes, how would you handle this situation?
• What do you think success looks like in my role?
• Am I meeting the expectations you have of someone in my role?
• Can you describe what your performance expectations are of me?
• If I need your feedback or approval, what’s the best way to ask you for it?
• Is there anything else I can prepare for these meetings that would be valuable to you?
• Do you have any ideas about how we can work together better?
• Who do you look up to for motivation or mentorship?
• I’m interested in taking on additional responsibility in the future. What do you think I need to work on to get there?
• Is there a skill I could learn/hone that would make me better at my job?
• One of my professional/development goals is to [insert goal here]. Can you think of any ways you can help me achieve that?
• What are the learning opportunities available to me?
• Are there any development opportunities you recommend I investigate/take advantage of?
• I believe I could learn a lot by joining [project/committee/team]. Would that be possible?
• Who on our team can I learn something new from?
• This is where I see myself in [time frame]; how do you see me getting there?
• Looking to the future, what are you most excited and concerned about?
• What are senior leadership’s top priorities right now?
• Are you satisfied with our team’s progress toward our shared goals?
• Is our team operating at our full potential? If not, what’s standing in our way?
• Is there anything we could do better as a [team/department/company]?
• What else could I do to help the [team/department/company] succeed?
• Are there any opportunities we’re missing out on as a [team/department/company]?