Whether you’re a manager or employee, it’s super normal if you feel a bit nervous before a one-on-one meeting. However, a little preparation can go a long way, and having good one-on-one meeting questions in hand can help you make the most of the discussion.

Let’s get started.

Why are one-on-one meetings important?

The primary purpose of one-on-one meetings is to foster open communication and build trust. As a space for giving constructive feedback, solving problems and aligning goals, these meetings offer several opportunities for both managers and employees.

Great one-on-one meetings:

• Create a safe space for employees to share their thoughts, concerns and ideas without fear of judgment.
• Offer a structured platform for discussing performance expectations.
• Allow employees and managers to raise concerns early on, which can prevent problems from escalating.
• Provide an opportunity to discuss career aspirations and create a development plan.
• Help managers make better-informed decisions, which can contribute to the success of the company or organization.

Meanwhile, good one-on-one meeting questions can significantly improve the effectiveness of these discussions by ensuring all relevant topics are covered and both parties are satisfied.

One-on-One Meeting Questions for Managers

As a manager, you can warm up the conversation with check-in questions, and then delve deep into employee development and performance management. Additionally, asking the employee’s ideas on team dynamics and company culture will help you gain meaningful insights.

Check-in

Starting the one-on-one meeting with one of the following check-in questions can make the employee feel comfortable. They will set a positive tone, paving the way for an open, relaxed dialogue.

• How are you feeling overall?
• Is there anything specific you’d like to discuss today?
• How are you managing your work-life balance?
• Are there any new ideas or initiatives you’d like to discuss?
• What’s been a recent small win or positive moment for you?
• Is there anything that’s been particularly motivating or demotivating for you lately?
• Are there any recent changes or updates you’re struggling to adapt to?
• What’s something you’re looking forward to in the near future?
• What’s a personal project or goal you’re working on outside of work?
• Is there a recent event or experience that you found particularly interesting?

Employee Development

An employee’s career development starts with a strong foundation of support from their managers. The following one-on-one meeting questions can help the employee reflect on their current role and discover pathways for advancement.

• What are your long-term career goals?
• Do you feel your current role aligns with your career goals? If not, how can we adjust?
• Do you feel you have opportunities for advancement within the company?
• Are there any training programs or courses you’re interested in pursuing?
• Are there any specific roles or positions in the company that interest you?
• Are there any mentors or role models in the company you’d like to work with?
• What kind of feedback would be most helpful to you right now?
• What types of feedback have you found most valuable in the past?
• How can I better support your career growth and development?
• Do you feel you have enough autonomy in your role, or would you like more?

Performance Management

Performance management questions aim to facilitate a comprehensive review of an employee’s recent achievements and challenges. Utilize them to evaluate their current performance level and set actionable objectives for the future.

• How do you feel about your performance in your current role?
• What specific achievements are you most proud of in the past quarter/year?
• What are the biggest challenges in your role recently?
• How do you prioritize your tasks and responsibilities to meet your objectives?
• How do you manage stress related to your responsibilities?
• How do you handle setbacks and failures?
• Are there any tools that can help you work more efficiently?
• Are there any recurring tasks or processes that could be automated?
• What are your thoughts on the current performance review process, and how could it be improved?
• How do you stay updated on industry trends that could impact your role?

Team Dynamics

These one-on-one meeting questions are designed to assess the current state of teamwork and collaboration. By discussing these topics, managers can build a more harmonious team culture.

• How do you feel about the current team dynamics?
• What do you think are the team’s strengths and weaknesses?
• Do you feel like your voice is heard and valued on the team?
• Do you feel that the team has a clear understanding of its goals and objectives?
• Are there any team processes or meetings that could be improved?
• Do you think the team’s workload is distributed fairly?
• How does the team handle conflicts or disagreements?
• What changes would you suggest to enhance team cohesion and productivity?
• Are there any team members you feel you could learn from or collaborate with more closely?
• How can we create a more inclusive and diverse team environment?

Company Culture and Environment

For managers, it is crucial to understand how the company culture and physical environment are shaping employee performance. Asking these one-on-one meeting questions can lead to valuable insights for progress.

• How well do you think the company’s values are reflected in day-to-day operations?
• Are there any aspects of the company culture that you find particularly positive or negative?
• Do you feel the company supports a healthy work-life balance?
• How does the company handle disagreements or conflicts among employees?
• Are there any traditions within the company that you particularly enjoy or think could be improved?
• What are the changes or improvements you would suggest for the physical workspace? 
• Do you feel the office layout supports productivity and collaboration?
• What challenges have you faced with remote working, and how can the company address them?
• How well does the company handle change and adapt to new challenges within its culture?
• How does the company support employees in staying updated with technological trends and developments relevant to their roles?

One-on-One Meeting Questions for Employees

For employees, best one-on-one meeting questions focus on gaining clarity about expectations, so try to receive feedback and address problems. You can also ask questions on your career development and team dynamics as well as the company’s future to get the overall picture.

Feedback and Recognition

Constructive feedback and recognition are the backbone of professional growth. Here are some key one-on-one meeting questions to gain a deeper understanding of your role.

• How would you assess my performance on recent projects?
• Can you provide me specific examples of what I did well on or what could be improved on recent projects?
• Which skills do you think I should develop further to enhance my performance?
• How effective is my communication with the team and other departments?
• How do you view my approach to problem-solving and taking initiative?
• How would you rate my ability to handle pressure and meet deadlines?
• What specific actions can I take to enhance my leadership skills?
• In what ways can I contribute more to the team’s success?
• How well do I align with the company’s values and culture?
• How do you think my work is contributing to the success of the company?

Problem Addressing

For employees, one-on-one meetings are a chance to share the problems they’re facing and ask for guidance on how to overcome them. The following questions can provide a framework for articulating challenges and receiving support.

• Can you help me prioritize the challenges I’m currently facing in my role?
• Are there any best practices or industry standards I should consider when tackling these challenges?
• What resources or support are available to help me address [challenge]?
• What should be my immediate next steps to address [challenge]?
• Can you provide specific examples of how similar challenges were resolved in the past?
• What’s the expected timeline for resolving these issues, and how should I manage expectations?
• Can you suggest any tools or technologies that might help me resolve these issues?
• How can I effectively communicate the challenges I’m facing to my team or other stakeholders?
• How can we adjust my goals or objectives to better align with solving these issues?
• How can I ensure that the solutions I implement are sustainable in the long term?

Career Development

A good manager is a great source of inspiration. These one-on-one meeting questions on career growth can help you learn a lot from them and develop a clear strategy for achieving your goals.

• How can I better align my current role with my long-term career aspirations?
• Can you help me identify any gaps in my current skill set?
• What opportunities exist for me to take on additional responsibilities and projects?
• What steps can I take to become a strong candidate for future leadership roles in the company?
• How can I effectively seek and incorporate feedback to enhance my performance?
• What additional training or certifications would be beneficial for my career development?
• How can I stay updated on industry trends and changes that might impact my career?
• How can I build stronger relationships with key stakeholders and decision makers?
• What are examples of successful career paths for people in my role?
• How can I better balance my work and personal life to achieve long-term success?

Team Success

How well you work with your team members can make or break your overall experience. Use these questions to foster a more innovative, productive, and respectful team environment.

• What feedback do you have on the team’s performance?
• How can we improve our communication channels and processes?
• How can we better align our team goals with the company’s objectives?
• How can we encourage more innovative ideas and solutions from the team?
• How can we improve cross-functional collaboration with other teams or departments?
• How can we balance individual work with collaborative tasks to balance productivity?
• What opportunities are there for professional development for the team as a whole?
• How can we improve our ability to adapt to changing business needs and priorities?
• How can we improve our team’s performance on [specific task or project]?
• How can we better leverage each team member’s unique skills on [specific project]?

Company’s Future

Understanding the company’s vision and how it plans to navigate the future is essential for your own career development goals. By asking these one-on-one meeting questions, you can explore company initiatives on technology, sustainability, mental health, and more.

• How do you perceive our position relative to our competitors?
• How is the company investing in research and development to stay ahead of the competition?
• What technologies or innovations are we investing in or considering?
• What are the biggest challenges facing our industry, and how is the company positioning itself to overcome them?
• Are there any new markets or product lines we’re exploring?
• What is our company’s approach to sustainability and corporate social responsibility?
• How are global economic developments likely to impact our industry and company?
• How do you see our company culture evolving in the next few years?
• What are the company’s plans for investing in employee wellbeing and work-life balance?
• How is the company leveraging artificial intelligence and machine learning to drive growth?

Frequently Asked Questions

What is another name for a one-on-one meeting?

“One-on-one session”, “individual meeting” and “individual check-in” are all alternative names to one-on-one meetings. Skip-level meetings can also be considered as one-on-one meetings as they involve direct discussion between an employee and a higher-level manager.

What should a one-on-one meeting include?

For managers, a one-on-one meeting with an employee should include a structured agenda, open-ended questions, and constructive feedback. The meeting agenda can involve a brief check-in, feedback on previous and current work, short-term and long-term goals, and resource needs. Don’t forget that a successful one-on-one meeting also requires a comfortable and professional meeting space, whether in-person or virtual.

How can I prepare for a one-on-one meeting?

If you’re an employee, you can prepare one-on-one meeting questions to ask your manager, and review both your recent work and company updates for a fruitful discussion. Meanwhile, managers can gather relevant data on the employee’s progress and outline discussion points beforehand.

How do you greet a manager in a meeting?

When greeting a manager in a meeting, a formal greeting such as “Good morning, [Manager’s Name]” or “Hello, [Manager’s Name], thank you for taking the time to meet with me” is always appropriate. In more relaxed settings, a more casual “Hi [Manager’s Name], how are you today?” can be suitable. Whichever style you choose, always be sure to make eye contact, adopt a respectful tone, and stay positive.

What are good questions to ask your manager’s manager?

Some of the best questions to ask your manager’s manager are “What kind of feedback do you receive from other departments about my work?” and “What opportunities for growth and development do you see for me in the company?” You can also ask about their vision for your team’s growth, as well as how the company is adapting to industry changes and challenges. Finally, asking about their leadership experiences can provide valuable guidance for your own career path.

How do you document a one-on-one meeting?

For accurate documentation, you can record the meeting and then convert speech to text with an AI-powered software like Maestra. This will not only save you a lot of time, but also make the meeting content accessible and searchable. That way, you can easily review and list the essential talking points, action items, and next steps.

Summary

This blog listed 100 powerful one-on-one meeting questions, 50 for managers and 50 for employees, that can lead to meaningful conversations and effective solutions. It also emphasized the importance of one-on-one meetings and how they contribute to both leadership development and employee engagement.

By embracing these practices, you can create a more constructive one-on-one meeting environment, cultivating open dialogue, mutual respect, and continuous improvement.