40 One-on-one meeting questions for busy managers

Written by: Nora St-Aubin | Illustrated by: Mathieu Labrecque
Updated on: Published on: June 10, 2021 |  Reading time: 6m

One-on-one meetings with employees are a time to touch base on their workload and deliverables and check in on a personal level. They’re also the perfect moment to address any questions that your direct report has for you, or that you have for them. But it can be challenging to know what one-on-one meeting questions to ask, and what to discuss. If you’re not asking the right questions, you might not be reaping all the benefits of one-on-ones.

As a manager, you have a long to-do list and many moving parts to keep track of. You might not always have the time to craft the perfect questions for your one-on-one meetings. We get it, so we made this list, and divided the questions by subject. Use them to set discussion points in your next one-on-one meeting agenda efficiently. So you can focus on your employees’ answers, and the next steps that come from these important conversations.

40 One on one meeting questions

Questions to check in with employees

Whether it’s your first one-on-one with an employee or you’ve been doing monthly meetings for a long time, it’s always good to check in. Open up your next regular one-on-one conversation with a meeting question from the list below. These questions will help you understand what’s on your team member’s mind, so you can direct the conversation from there.

  • Can you tell me about what you’ve been working on and how it’s going?
  • What’s been on your mind in relation to work these last two weeks?
  • Can you share a recent example of a work situation in which you thrived? What were the key components that led to your success?

Did you know? Asking the right one-on-one meeting questions is a challenge for many managers, but you don’t have to face it alone. Officevibe’s one-on-one software helps you plan, track, and follow-up on every conversation in one place. Plus, dozens of recommended talking points (and many of the questions in this article) live in our Conversation Engine so you get to the topics that matter most, every time.

Plan, track, follow-up on your one-on-ones

Assess employee engagement and motivation

  • Are you excited about what you’re currently working on?
  • What motivates you to come to work?
  • How are you feeling about our upcoming projects?
  • Do you sometimes feel bored or unchallenged at work? If so, how can we make your day-to-day more motivating?

Employee performance and career development questions

  • What skills or behaviours do you demonstrate at work that are a win-win for you as well as for your team or company?
  • Do you ever have to work on more than one task at a time? If so, how could your tasks and your responsibilities be reorganized so that you avoid having to multitask?
  • In your judgement, what does our company value or expect from you with regards to your performance? Have you had the opportunity to satisfy these expectations or actualize these values in your work?
  • In your judgement, is the method for evaluating and awarding one’s job performance justified and fair?

Pro tip: have performance review meetings with new hires after their first 30 days, 60 days, and 90 days to set the tone for future performance discussions.

One-on-one questions about employee challenges

  • What elements of your work environment cause the most frequent interruptions to your productivity and how could you remedy this problem?
  • In your judgement, is your workload reasonable? If it isn’t, can you suggest solutions that we could implement together to address the problem?
  • What are the best ways for you to communicate with me when you find you lack resources whether IT, human, budgetary, material or others?
  • What are the best ways for you to communicate with me when your role and your responsibilities at work aren’t clear to you?

Ask questions about recognition preferences

  • In what context would you prefer the good work you’ve done to be underscored?
  • What kind of employee recognition would have the most positive impact on you? Do you prefer voiced appreciation of your input during team meetings, positive feedback from me in one-on-one meetings, team activities that highlight the success of a given project, or something else?
  • Do you make an effort to recognize your peers’ work and accomplishments?
  • Is there something we could do as a team to improve recognition?

Employee feedback culture and practices questions

  • How do you prefer to receive feedback?
  • Is there a piece of constructive feedback that you received recently that was particularly helpful? Why?
  • Do you feel comfortable offering your colleagues feedback on the work you collaborate on?
  • Is there anything I could give you feedback on right now, or any feedback you might have for me?

Check out our employee feedback guide for managers and find out how to give constructive feedback that helps your team.

One-on-one meeting questions about goals progress

  • Do you need to have a clearer picture of how your individual career goals allow us to attain our goals as a team or a company?
  • Do you need my help identifying which actions could help you achieve your long term goals?
  • As things stand, do you think you will be able to achieve your goal?
  • Do you think that we should work together to revise your goal, or set new ones?

Setting employee goals can be tough. In Officevibe, you can set individual goals collaboratively with employees, and connect them with your team’s collective goals. From there, you can set smaller Action Items at every one-on-one meeting, so your team members are set up for success to achieve.

Ask questions about employee work-life balance, wellness and stress

  • How are you prioritizing work-life balance?
  • Do you feel comfortable taking breaks, time off, and making use of flexible work policies?
  • Can you give me concrete examples of stressful situations you experience at work?
  • In your judgement, what’s causing the stress? Is it a sense that you lack control, a feeling that you aren’t proficient, or difficulties dealing with unpredictable or new aspects of your job?
  • Are you able to ask colleagues with more experience than yourself for help, support or input when it comes to managing stressful situations?
  • What do I do as a manager already, and need to continue to do, to support our team’s physical and mental well-being?

One-on-one questions about team climate and alignment

  • Do your colleagues know when they can interrupt you? If not, how could you communicate this to them without it undermining your ability to collaborate?
  • Are there things happening on the team that make it difficult to collaborate?
  • Do you feel that the team has sufficient resources (IT, human, budgetary, material or other) to achieve our shared team goals?
  • If there was one thing you could see our team or company accomplish, what would it be? What would help you or your team to achieve it? What do you think might get in the way?

Questions to wrap up and set next steps

  • What’s one thing you’ll put into place in the next week or two based on our conversation?
  • Is there a specific talking point we should circle back to in our next meeting?
  • Before we wrap up, can you think of anything I could do to help you out?

If agreeing to next steps is important, tracking them is even more so. Officevibe lets you assign every Action Item (to your team member or yourself!) at the end of each meeting. Then, it sends you an email on Mondays to remind you of your commitments. Action Items automatically carry over to your next one-on-one agenda in the platform, so you never lose track of what you both said you’d do.

Have a great one-on-one!

You’re a great manager, and these questions will help you have great conversations with every direct report on your team. Whether it’s discussing goals, having a difficult conversation, getting a status update, or checking in on wellbeing, you’re well-equipped to cover any talking point needed.