Elevate Your One-on-One Meetings: 100 Questions for Managers and Employees

One of the most effective ways to foster open and honest communication is through a regular one-on-one meeting.

These meetings allow team members to connect personally, discuss their goals, challenges, progress, and offer support and guidance. It also develops a feeling of trust, which increases employee engagement, productivity, and overall job satisfaction. The result is a stronger bond between managers and their direct reports.

According to Gallup, there is a relationship between employee engagement and productivity, meaning one-on-one meetings can lead to increased productivity.

However, another challenge arises. How do you maintain a conversation that keeps your direct reports engaged without feeling like a monologue?

With so much on your plate, developing new and relevant one-on-one meeting questions can be challenging.

We’ve compiled a list of 100 one-on-one meeting questions that will fuel your management and help you get the most out of your meetings. If you’re keen to take your one-on-one sessions to the next level, these questions can be a great place to start.

Introduction to the 100 One-on-One Meeting Questions

Get the most out of your one-on-one meetings with our list of 100 tried and true questions. Whether you’re a manager or an employee, these questions will fuel your management and help drive productivity, communication, and growth.

What Kind of One-on-One Questions Can Managers Ask Employees?

As a manager, addressing the tasks and projects your team is working on and supporting their personal and professional growth is essential. Here are some categories of questions that can help facilitate these discussions:

Questions about growth and development: These can help managers understand their team member’s career goals and how they can support them. Examples include “What are your long-term career goals, and how can I support you in achieving them?” and “What skills or areas of knowledge do you feel like you need to develop to reach your career goals?”

Questions to help improve communication: Effective communication is essential to the success of any team. These questions can help managers gauge how team members feel and identify areas for improvement. Examples include “Do you feel like you have the information you need to do your job effectively?” and “Is there anything I can do to help improve the way we communicate as a team?”

Questions about employee motivation: Understanding what drives team members is crucial to motivating and engaging them. These questions help managers understand what motivates each team member and how to use that information to improve performance. Examples include “What motivates you at work?” and “What can I do to help you stay motivated and engaged?”

Questions to address challenges, roadblocks, and concerns: One-on-one meetings are an excellent opportunity for team members to discuss any issues or concerns they may face. As a manager, listening actively and offering support and guidance as needed is essential. Examples of questions in this category include “Is there anything that’s been holding you back or causing you to stress at work?” and “What can I do to help you overcome any challenges or roadblocks you’re facing?”

Questions for getting feedback from your direct report: Regular feedback is essential for personal and professional development. These questions help managers gather constructive feedback from their team members and identify areas for improvement. Examples include “What feedback do you have for me as your manager?” and “Is there anything I can/could do differently to support your development and success?”

What Kind of One-on-One Questions Can Employees Ask Managers?

One-on-one meetings allow managers to ask questions and employees to voice their concerns, seek guidance, and learn more about the company and their career development. Here are some categories of questions that employees can ask their managers during a one-on-one meeting:

Questions about career growth and personal development: These questions can help employees better understand their career path and what they need to do to advance within the company. Examples include “What are the key skills or experiences that will help me advance within the company?” and “Is there any specific training or development that you think would benefit me?”

Questions about priorities, productivity, and strategy:  When employees understand how their role contributes to the company’s overall goals, they are more likely to be focused and productive. Examples of questions for the category include “What are the company’s top priorities right now?” and “How does my role fit into the overall strategy?”

Questions about communication and feedback: Clear communication and regular feedback are essential for personal and professional growth. These questions can help employees better understand how they’re performing and how they can improve. For example “Is there anything I can do to improve my communication with you or the team?”

Questions around company culture and motivation: Understanding the values and culture of the company can help employees feel more connected and motivated. These questions can help employees better understand what makes the company unique and what it means to be part of the team. A good example is “What is the company’s mission and vision?”

Questions around supporting your manager and managing up: One-on-one meetings allow employees to learn how to best support their manager and contribute to the team’s overall success. These questions can help employees understand how to be more effective and support their manager’s goals. For example, “How can I be more proactive in helping to achieve the team’s goals?”

Other Considerations for One-on-One Meetings

In addition to coming up with thoughtful and relevant questions, a few other considerations can help make your one-on-one meetings more effective and productive.

Ice Breakers and “Get to Know You” Questions

While the focus of one-on-one meetings should be work-related topics, starting with an ice breaker or “getting to know you” question can help create a more relaxed and comfortable atmosphere. When meeting someone for the first time or when you haven’t had a chance to get to know one another well, asking these questions can be beneficial.

Some examples of ice breaker questions include “What do you like to do in your free time?” and “What hobbies are you into when you are not at work?”

Why is it Important to Have a One-on-one Meeting Agenda?

There are several advantages to owning a one-on-one meeting agenda. They include:

• Focused discussions: Agendas keep meetings focused and prevent tangents or digressions by outlining topics in advance.
• Improved preparation: Team members can prepare for the meeting in advance, leading to more productive and meaningful discussions.
• Better use of time: By outlining the topics and questions, an agenda can help everyone to maximize their time better during the meeting.
• Helps with decision-making: By focusing on a single topic at a time, an agenda helps team members make better decisions and ensure that all points are covered.
• Clear action items: By defining each agenda item, the team can ensure that everyone clearly understands their roles and timelines.
• Increased accountability: Having a clear agenda can help both parties hold each other accountable for following through on commitments and completing tasks.

Sharing Ownership of the Agenda Between Managers and Employees

Sharing ownership of the agenda is an essential aspect of effective one-on-one meetings. While the manager should facilitate the meeting and ensure that all critical topics are covered, team members are also responsible for raising issues or concerns during discussions.

One way to ensure that both parties have a stake in the agenda is to involve team members in the planning process. This could mean asking for their input on what topics they would like to discuss or allowing them to suggest items for the agenda. This approach can foster a sense of ownership and collaboration and align the meeting’s focus on the needs and concerns of both parties.

If you’re looking for a more structured approach to one-on-one meetings, Airgram offers a range of template agendas to help you get started. These templates include:

An OKR goal-setting one-on-one meeting agenda template: This agenda assists managers and team members in setting clear goals for the meeting. This template can define specific objectives, metrics, or key results (OKRs) for a project or initiative.

 

A weekly one-on-one meeting agenda template: This tool helps managers and team members track progress, discuss issues, and set weekly goals. It can review and evaluate performance from the previous week, identify potential problems or roadblocks that may arise in the coming week, and outline redress measures.

A career development meeting agenda: Managers and team members can use this tool to discuss career development needs, set goals for job performance and professional growth, and create action plans for implementation. This template helps managers identify an employee’s strengths, weaknesses, and potential growth areas and create a plan for addressing those needs.

Peer one-on-one meeting agenda template: This agenda template is for coworkers who meet regularly to discuss projects, coordinate activities, and make decisions. The purpose is to keep coworkers updated on ongoing projects, share information and resources, and facilitate group decision-making. The template includes sections listing team sync, teamwork challenges, and feedback.

Compensation review meeting agenda template: This agenda template facilitates a discussion between an employee, their manager, and HR about compensation. The purpose of the meeting is to review the employee’s performance and determine whether they are eligible for a raise or merit increase. This meeting helps managers identify areas where the employee excelled so they can highlight them during discussions about compensation.

Other templates that Airgram offers include:

• One-on-one coaching
• Quarterly performance review meeting
• Monthly one-on-one meeting
• Bi-weekly one-on-one meeting
• Skip-level meeting agenda templates

Each template has a list of topics and questions to guide your discussions. There are also tips and best practices to make the most of the one-on-one meetings.

In general, a typical one-on-one meeting agenda might include the following:

• An ice breaker or “getting to know you” question (as mentioned above)
• A Review of the past week or month (accomplishments, challenges faced, etc.)
• A discussion of any obstacles or roadblocks that you are likely to encounter
• A discussion of priorities for the coming week or month
• Next steps and action items for both the manager and the team member

A structured agenda can help keep one-on-one meetings focused and productive. Still, it helps to be flexible and allow spontaneous conversations or unexpected issues that may come up.

One-on-One Questions for Managers to Ask Employees

One-on-one meetings allow managers to connect with team members personally, discuss their goals and challenges, and offer support and guidance. To help you make the most of these meetings, here is a list of 50 one-on-one questions to ask your employees:

Career goals:

• What are your long-term career goals, and how can I support you in achieving them?
• What skills or areas of knowledge do you need to develop to reach your career goals?
• How do you see your role evolving within the company over the next year or two?
• What are your short-term goals?
• What are the biggest challenges you’re facing right now, and how can I help you overcome them?
• What skills or areas of knowledge do you need to develop to reach your short-term goals?

Challenges and concerns:

• Is there anything holding you back or causing stress at work?
• How can we work together to overcome any challenges or roadblocks you face?
• Is there anything you need help with regarding your workload or responsibilities?
• Is there anything you feel you’re missing out on because of your work commitments?
• How can I help you feel more supported and empowered in your role?
• What can I do to help you feel more confident in your abilities?
• Are there any changes we need to make to your work environment or schedule that would make a big difference in how things are going?
• What’s been most challenging so far this year—and why?

Feedback:

• What feedback do you have for me regarding my performance as a manager?
• Is there anything I could do differently to support your development and success?
• What do you appreciate most about working with me so far?
• What can I do better to support your growth and development within the company?
• What should we focus on in the next month?
• What would help you be more successful at work?

Personal development:

• What are your strengths, and how can we leverage them to help you succeed in your role?
• What areas could you improve in, and how can I support you in developing those skills?
• What resources do you need to succeed in your current role? What is your career vision, and how can I help you achieve it?
• What are your goals for personal development, and how can I support you in achieving them?

Work and projects:

• What are your top priorities for the coming week or month, and how can I help you achieve them?
• Are there any projects or tasks you’re particularly excited about or looking forward to?
• How do you prefer to receive feedback, and how often would you like to receive it?
• Is there anything that you need more guidance or support on?
• Is there anything you feel you’re missing out on because of your work commitments?

Time management:

• What are your top priorities for the coming week or month, and how can we help you achieve them?
• How do you like to get organized and stay on track with your work?
• Are any projects or tasks stressing you out now, and if so, why?
• What would help free up more of your time so that you could focus on other things?

Communication and collaboration:

• How do you prefer to communicate with your team and colleagues?
• What can you do to improve our communication or collaboration?
• How do you feel about the level of support and guidance you’re receiving from your team and colleagues?
• Are there any specific communication or collaboration challenges that you’re facing?
• Is there anything I can do to improve my communication with you or the team?

Company culture and values:

• What do you like most about working for this company?
• What are the company’s values, and how do they shape the way you work?
• Is there anything you want the company to do differently regarding culture or values?
• How do you feel you fit in with the company culture and values?
• What can we do to foster a more positive and supportive company culture?
• How do you feel about the level of transparency and open communication within the company?
• Is there anything you feel you’re missing out on because of the company culture or values?

Work-life balance:

• How do you feel about your work-life balance now?
• Is there anything you feel you’re missing out on because of your work commitments?
• How can I help you achieve a better work-life balance?
• How do you feel about the level of support you’re receiving from the company regarding work-life balance?
• Is there anything you would like to see the company do differently regarding work-life balance?

Asking these questions during one-on-one meetings can help managers better understand their team members, goals, and challenges and offer support and guidance as needed. By fostering open communication and collaboration, managers can create a more positive and productive work environment for their team.

One on One Questions for Employees to Ask Managers

One-on-one meetings also allow employees to ask their managers questions to discuss their goals and career development, address any challenges or concerns, and get feedback and support. Use this list of 50 questions to help you prepare for your upcoming one-on-ones with your manager:

Career development:

• What are your expectations for my career growth within the company?
• How can I take on more responsibility or advance within the company?
• Are there any specific skills or areas of knowledge that you feel I should focus on developing?
• How can we create a career development plan that aligns with my goals and the company’s needs?
• What resources or support do I need to succeed in my role?
• Are there any specific projects or responsibilities for which you feel I would be well-suited?

Company goals and strategy:

• What are the company’s long-term goals, and how does my role fit that vision?
• How do the company’s strategy and direction impact my role and responsibilities?
• How can I contribute to the company’s success and growth?
• How can I align my work with the company’s goals and priorities?
• Do you have any specific projects or responsibilities that would help me better understand my role and the company’s direction?
• What opportunities are there for me to take on more leadership or management responsibilities within the company?

Communication and feedback:

• How do you prefer to communicate with me, and how often would you like to check in?
• Is there anything you feel I need to improve or develop further in my role?
• How can I better communicate my goals, progress, and needs with you and the rest of the team?
• What feedback do you have for me as an employee?
• How can I ask for help or guidance more effectively when needed?
• What is the best time to reach out for feedback?
• What are your expectations for my performance and development, and how can I better meet those expectations?
• What are our company’s biggest challenges, and how can I help solve them?

Support and resources:

• What resources or support do I need to succeed in my role?
• How can I best support you, the company, and my colleagues?
• How can we improve our communication?
• What do you need from me to feel confident that I am performing well in this role?
• What is the best way to ask for more resources or support?
• How could I better communicate my goals, progress, and needs with you and the rest of the team?

Work and projects:

• How do you see my role evolving within the company over the next year or two?
• What projects or tasks would you want me to work on?
• How can I better align my work with the company’s goals and priorities?
• How do you prefer to receive updates and progress reports from me?
• How can I improve my performance or productivity in my role?

Company culture and values:

• What are the company’s values, and how do they shape the way you work?
• How does the company measure success, and what is my role in achieving that success?
• What’s your vision for the company over the next year or two?
• How do you like to work, and how can I better support you and the rest of my team?
• What are some best practices for productively giving feedback?
• If I’m ever struggling with something at work or need advice on handling a situation, is there someone else who would be more appropriate for me to talk to first?
• What values are vital for me to embody for us to be successful?
• How do you define success?
• What should I do to be a good teammate and an effective leader at this company?
• What are some of the most important things I need to know about working here?

Time Management:

• How do you prioritize your tasks?
• Do you use any time management software?
• Do you have any tips for managing my time more effectively?
• What are your favorite tools for managing meetings and meetings in general?
• What is the most important thing for me to know about your work ethic?

Conflict Resolution:

• What are your expectations for how team members should handle conflicts or disputes?
• How can I better communicate and resolve conflicts with my colleagues and team members?
• How can I better support and collaborate with my colleagues and team members to prevent disputes from arising?
• How can I improve my conflict-resolution skills?

By asking these questions in a one-on-one meeting, you can better understand your manager’s expectations and goals and get valuable feedback and support for your career development.

The Ultimate 1:1 Meeting Template

One-on-one meetings are an excellent way for managers and their immediate reports to keep in touch, share updates about work progress, and set goals.

Having a script (or template) on hand can help keep conversations on track, reduce stress, and ensure that both parties get what they need from the meeting.

The following is an example of what a one-on-one meeting template could look like:

The OKR Goal-Setting One-on-One Meeting Agenda from Airgram

This template helps managers and employees set clear, measurable goals and work together to achieve them. It includes several sections:

• Analysis of the previous quarter: This is where the manager reviews and reflects on the last quarter’s performance and identifies any lessons learned. This can include discussing what went well, what didn’t go as planned, and what to do differently.
• Objectives for this quarter: In this section, managers and employees can set SMART (specific, measurable, achievable, relevant, time-bound) goals for the coming quarter. These goals should be aligned with the company’s overall objectives and accompanied by critical actions and milestones to help track progress.
• Open discussion: This section allows for a collaborative and open-ended conversation between the manager and the employee. They can discuss how to achieve the goals set in the previous section, the resources needed, and any potential barriers or challenges that may arise. They can also set timelines, deadlines, and budgets to help achieve the goals.
• Next steps: In this final section, the manager and employee can review the action steps agreed upon in the open discussion and identify any next steps or follow-up actions to take. This can include setting up additional meetings or check-ins to track progress and provide support as needed.

The OKR goal-setting one-on-one meeting agenda template helps managers and employees set clear and achievable goals as they work towards common objectives. This can help drive productivity, engagement, and overall business success.

Conclusion

One-on-one meetings can be a powerful tool for managers and employees to build strong relationships, increase productivity, and drive business success. You can make the most of these meetings by using a clear agenda, asking targeted one-on-one questions, and fostering open communication, collaboration, and growth.

Use these 100 one-on-one meeting questions and templates outlined to create a structured and meaningful one-on-one meeting experience that drives actual results.