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Better Meetings

97 one-on-one meeting questions for better discussions

Illustration of two people communicating

While there's no silver bullet for becoming a great manager, hosting collaborative and engaging one-on-one meetings will help get you there.

You might already be hosting regular one-on-ones as part of your role, or maybe you’re diving into them as a first-time manager.

Either way, use this list of one-on-one meeting questions to get to know your direct reports better, understand project and goal progress — and build a better, stronger team! 

Collaborative, question-based agendas for 1:1 meetings

Let’s be real: we’ve all been in a one-on-one meeting that felt like a grill session (where every little move is being questioned) OR a boring project status update conversation that could’ve been an email. 

To keep the focus on the employee, ask them to help create an agenda for the conversation. Collaborative, question-based agendas — ones that both parties contribute to and engage with — set the stage for much more productive conversations. Plus, they provide you with an opportunity to provide honest feedback, increase employee engagement, and develop new skills.

Start with a one-on-one meeting template that keeps a similar structure across each conversation, while mixing in a new section or questions depending on each employee’s progress, seniority level, and length of time at the company. 

Collaborative agenda with questions

In Vowel, you can create collaborative agendas and view them from your Upcoming tab — an easy way to add questions as you think of them!

One-on-one meeting questions by category

Use this list of one-on-one meeting questions to create a standard (but adaptable) meeting agenda for every employee conversation. 

When asking one-on-one meeting questions (whatever type they are), make sure you’re using active listening and taking note of action items, whether that’s tagging you or the employee in collaborative notes or sending an email or Slack summary after the meeting. 

Getting-to-know-you questions

Getting to know someone outside of their work helps you understand their personal life, including motivations, life goals, and interests — which can be helpful when you want to give them feedback or praise them for a job well done. 

If you’re new to working with a direct report, you’ll likely want to sprinkle in more of these questions in your first few one-on-ones until you know more about them. 

Some examples of “getting-to-know-you” questions include: 

  • Who or what inspires you in both life and work?

  • What motivates you in both life and work?

  • How do you like to receive praise/feedback? 

  • What do you enjoy doing in your free time? 

  • Are you a morning or night person? 

  • Where do you see yourself in ten years?

  • What does your ideal day off look like?

  • What’s the best advice you’ve ever received? What about given? 

  • What three words would a friend use to describe you?

While these questions might not seem important, knowing the answers can help you build rapport with team members and understand them at a more human level — which, ultimately, improves your working relationship!

Working style questions

Back in the day, employees were expected to clock in and clock out in the same way, at the same time. But that’s no longer a reality — especially in today’s dynamically changing workforce. 

Understanding each employee’s unique working style will help you not only set them up for success, it will help set you up for success (and not get frustrated). Like the first set of rapport-building questions, these are often best asked when you’re first getting to know an employee, but feel free to use them at later points, or if your working situation changes. 

A few working style questions: 

  • Why did you join this company? Why did you want this specific role?

  • Do you prefer to work the same hours every day or a more flexible schedule?

  • How do you prefer to start your work day?

  • How do you prefer to end your work day?

  • What time(s) of day are you most productive? 

  • What energizes you at work? Drains you?

  • What’s one professional skill you’re currently working on?

  • What’s one thing that’s pleasantly surprised you about working here at [company]? 

  • What’s your biggest work pet peeve?

  • What productivity tools do you use to stay organized and on top of things?

You might be pleasantly surprised by the answers to these questions — and could even learn a thing or two about yourself in the process! 

Check-in questions

The best check-in questions come from a genuine place: wanting to understand how to help each employee succeed in their unique roles. For these types of questions, really think about what each person on your team is doing and how you can help them. 

Here are some employee check-in questions: 

  • What’s changed the most since our last one-on-one conversation?

  • Have you learned anything new since our last conversation?

  • How do you feel about your overall workload?

  • Are any tasks taking longer than you expected? Shorter? 

  • What are your goals for this week? How can I or the team help you achieve them?

  • What are your biggest bottlenecks?

  • Do you need any additional resources or tools to accomplish your goals?

  • What has been taking up the majority of your time lately?

  • What new ideas have you had lately? 

...and few more ideas from this Effective 1-on-1 Agenda by Radical Candor:

  • What’s on your mind this week? 

  • How happy were you this past week? 

  • How productive were you this past week? 

While these check-in questions are mostly about work, they can be an indicator for a person's well-being. Don’t forget to ask how someone is doing outside of work or note if they seem stressed. Are there any life challenges happening? Do they need time off for anything? 

Project-specific questions

While we don’t suggest using one-on-one meetings purely for project check-ins, they can still be an important part of a productive meeting. Make sure you’re setting the stage for solutions and collaborative problem-solving instead of status updates. 

Here are some good project-specific questions: 

  • What are the biggest changes on [project] since we last talked?

  • Who or what is the bottleneck on [project]?

  • Do you have any concerns about hitting [goal]?

  • Do you have enough time to accomplish [goal/project]?

  • Where do you think I can be most helpful?

  • What hasn’t gone as you had hoped? Why?

  • What are you working on next?

  • Is there anything you’d like to take a few minutes to work through together? Or book another session for? 

Project-specific questions not only reveal task details and timelines, they can help you gauge how enthused (or not) someone is about what they’re working on. If your employee starts to respond unenthusiastically, or seems unengaged or even frustrated, asking more “why” questions can guide you to the core of their feelings so you can address them head-on. 

Collaborative notes in Vowel

Take collaborative notes while you have your one-on-one meeting to record any ideas, decisions, or follow-up items. In Vowel, a collaborative notepad is viewable at all times and anyone in the meeting can contribute to it.

Problem-solving questions 

This is where the team member and you (the manager!) can help really tackle internal hurdles together. By crafting open-ended questions, you allow space for exploration and ideation without any limits on creativity. 

  • What’s the biggest hurdle the team is facing right now? 

  • What’s your typical approach to solving problems?

  • If all limitations were removed, what are some ideas you have?

  • If you knew we couldn’t fail, what would you try?

  • What are some of the worst ideas you can think of?

  • What are two improvements you’ve made to the team over the last six months? How did these improvements solve problems either on the team or company level?

You may not need to ask these in every check-in meeting, but keep one or two of them on the list of rotating questions to ensure the employee knows you value their feedback and ideas. 

Career development questions

Asking professional development questions gives managers a glimpse of the future path for each employee — and whether they see themselves being an individual contributor or leading a team in the future. This ensures that you’re not shoving a square peg in a round hole when it comes to promoting employees at the organization. 

Here’s a list of questions to prompt career conversations: 

  • In the last [time period] at [company], what are you most proud of? Least proud of?

  • How would you like to make a bigger difference at the company?

  • What professional or career-related opportunities are you most excited about pursuing?

  • What are your most valuable talents and skills? Do you feel like your current role plays on your strengths? 

  • Are the responsibilities of your role what you expected? Why or why not?

  • What are your career goals for the next six months? Year? Five years? How can I help you achieve them?

  • If you could have any role at [company], what would it be and why?

  • How do you see this industry changing in five years? What about [insert type of role]?

  • What work habits could you improve on? 

  • What are your long-term goals?

...and a few more questions from this Career Development 1-on-1 agenda by Susan M. Heathfield: 

  • What would you like to accomplish this year? 

  • Are there any projects you’d like to implement, expand, or join? 

  • Do you think any of your current duties could benefit from additional resources or training? 

Tip: If both participants are comfortable with it, it's a great idea to record career development one-on-ones. This gives both parties a chance to revisit the meeting throughout the quarter, or before you have your next career development meeting. In Vowel, you can record a meeting with one click (and go off the record at any time).

OKR planning questions

Do you use OKRs at your current company? If you’re unsure what this acronym means, it stands for Objectives and Key Results — aka specific goals with achievable results.

Once you’ve implemented OKRs at a team or organizational level, here are the best OKR-planning questions to ask in one-on-one meetings: 

  • Are you on track to hit your [insert OKR here] this quarter? If not, what can we do to help you achieve it?

  • Are you properly resourced to achieve your key results?

  • What are the main actions/initiatives taken so far to achieve the outcomes?

  • Do you have any concerns about the strategic goals or OKRs of the team and company?

Even if you don’t use the OKR format for performance management, understanding how individuals and the team are progressing towards their individual goals helps you address issues early and course-correct as needed. 

Manager feedback questions

While we all *wish* we were perfect managers, everybody has room to improve. Creating an open dialogue with your team on how you’re doing can help you understand your blind spots and make them feel even more invested in the company and your relationship. 

And while this might feel a little scary for you, chances are it’s even scarier for the employee! Make sure you create a comfortable, open, and honest environment where the employee knows they won’t receive backlash for giving you feedback

Amanda Natividad tweet on manager feedback

A few questions to help you learn more about what’s working and not working: 

  • Do any of our processes seem inefficient to you? If so, how can we fix them?

  • Are you clear on your responsibilities, objectives, and goals? If not, how can I help fix that so you can do your best work?

  • Reflecting on the week, is there anything that could have gone better in how we worked together?

  • What are three words you’d use to describe me at work? 

  • What’s one thing you wish I’d do more of? Less of?

  • If you were in my role, what’s one thing that you would do differently?

  • In what ways can communication between executive leadership, managers, and employees be improved?

  • How would you improve our team meetings?

  • Am I giving you enough feedback?

Receiving this feedback might make you uncomfortable, but it will ultimately make you a better leader. And make sure to ask these questions regularly — growth is not a one-and-done process!

Employee feedback questions

One of the biggest parts of your job as a manager is growing employees and helping them be successful in their roles. When providing employee feedback, make sure that you’re being sincere, honest, direct, and empathetic. 

Some questions that can lead to feedback: 

  • Do you feel like you’re succeeding in your current role? If not, how so?

  • How do you feel about the problems you’re facing in your current role?

  • How would you rank your [insert skill to improve]? Why?

  • What’s stopping you from leveling up at [company]?

  • What role are you looking to grow into? 

  • How are you measuring your own success and progress at [company]?

  • What do you think you’re focusing on too much? Not enough?

  • How would you rate your overall success in this role over the last [time period]?

  • In what areas do you think you could improve?

These open-ended questions prompt the employee to open up about how they’re feeling in their role, while providing the opportunity for you to provide constructive feedback in response to their answers.

Job satisfaction questions 

Everyone wants to feel fulfilled at work. And in today’s competitive workforce, if an employee isn’t satisfied with their job, chances are they’ll quit and move on to another company that appreciates them more. 

Get to know how your team members are feeling by integrating some of these questions into your one-on-ones every month or two:

  • How do you feel about your current work/life balance?

  • Do you enjoy [company’s] workplace culture? What would you improve?

  • Do you feel connected to your coworkers? How can we improve this?

  • Do you feel respected by your team members and leadership?

  • How transparent do you feel we are as a company, especially as leadership?

  • Do you feel the workload is evenly distributed across the team?

  • How would you rate your overall job satisfaction on a scale of 1-10? Why?

  • Do you feel rewarded in your current role? 

  • Is your work challenging enough for you?

  • What would make you leave [company]?

  • How do you like your work environment?

You’ll notice a lot of “feel” questions above — that’s because job satisfaction isn’t a mathematical calculation!

Close-the-meeting questions

It’s important to end one-on-one meetings on a high note that makes your team members feel motivated and ready to tackle the rest of the week! Try to close every meeting with a couple of these questions: 

  • What are the next steps coming out of this conversation?

  • Do you need anything from other team members?

  • How are you feeling overall? 

  • Do you have any important life events coming up?

  • What can I help you with between now and the next time we meet?

  • Is there anything we didn’t cover that you’d like to discuss in our next conversation?

Remember to end the meeting on a positive note and do your part to ensure you’re not a blocker on their next steps and action items.

Reflect on your own performance and ensure that you helped to build trust, assist the employee in career growth, and provide constructive feedback. Send out any notes and schedule the next meeting in a timely follow up (if it’s not already a recurring meeting).

Action items captured in a Vowel meeting

In Vowel, you can easily tag team members in action items, which they can view from their dashboard. Integrations coming soon!

Sample one-on-one meeting agendas

Based on the questions above, a sample one-on-one meeting agenda with a new employee might look like this:

  • What motivates you in both life and work?

  • How do you like to receive praise/feedback?

  • How do you like to start your work day?

  • What energizes you at work? Drains you?

  • What professional or career-related opportunities are you most excited about pursuing?

  • Are you clear on your responsibilities, objectives, and goals? If not, how can I help fix that?

  • What are the next steps coming out of this conversation?

A sample one-on-one agenda for another employee (someone who's working on a big project, say) could look like this:

  • How do you feel about your overall workload?

  • What are the biggest changes on [project] since the last time we talked?

  • Do you have enough time to accomplish [goal/project]?

  • Reflecting on the week, is there anything that could have gone better in how we worked together?

  • What do you think you’re focusing on too much? Not enough?

  • What can I help you with between now and the next time we meet?

  • Is there anything we didn’t cover that you’d like to discuss in next week's conversation?

Start having better one-on-one meetings

Most managers we’ve talked to like to have either weekly or bi-weekly 30-45-minute meetings with each team member they manage, alongside quarterly performance reviews. The key benefits of these meetings include: 

  • Building rapport with each employee

  • Understanding roadblocks and how to remove them

  • Growing employees based on their strengths 

  • Developing high-performing teams

A regular 1:1 cadence keeps managers and direct reports on top of important projects and ensures each employee is getting dedicated time to get and give feedback. This positive impact is even more important in the times of remote work and remote teams.

Planning regular one-one-one meetings doesn’t have to be a time-sucking, energy-draining task. Use the above list of one-on-one meeting questions as a jumping-off point to create a standard (but adaptable) meeting agenda for every employee conversation.

And to become a better manager, make sure you’re preparing for each one-on-one by reviewing the agenda for each individual conversation (and what was covered the week before) AND anticipating what you might be asked and how your employee is doing. 

P.S. Looking for software to help you plan, host, and act on one-on-one meetings? Learn more about how Vowel can help you have better virtual one-on-ones or sign up and try it!