45 one-on-one meeting questions for employees and managers

Building a strong relationship with your team starts with meaningful conversations. These focused, regular conversations are an excellent time for team leaders to ask one-on-one meeting questions that create a strong relationship between the team members and the manager. 

By encouraging open communication and asking the right one-on-one questions, you’ll uncover valuable insights into employee performance, engagement, and team dynamics. 

Take millennials, for example. They make up a large chunk of today’s workforce, and many say that professional development opportunities play a critical role in their job satisfaction. These meetings are the perfect time to discuss growth, aspirations, and ways to help employees thrive.

One-on-one meetings also help you deliver feedback, coach employees, and build trust. The right one-on-one meeting questions can uncover valuable insights about an employee’s motivation, well-being, and goals—leaving both of you feeling heard and aligned.

How to structure a productive one-on-one meeting?

One-on-one meetings are a versatile tool for strengthening manager-employee relationships, addressing team dynamics, and aligning individual goals with organizational objectives. These conversations, driven by the right one-on-one meeting questions, go beyond day-to-day updates, creating space to discuss personal well-being, career development, and team dynamics.

By tailoring topics to the employee’s needs and priorities and asking the right questions, you can ensure that each meeting is impactful and engaging. When approached thoughtfully, these meetings not only build up performance but also build trust and mutual respect.

What is a one-on-one meeting?

A one-on-one meeting is a scheduled, dedicated conversation between a manager and their direct report. Unlike team meetings or project updates, these conversations focus entirely on the employee’s experience, performance, and needs. They provide a safe space to discuss anything from well-being and growth to relationships and goals.

Key topics to cover

Want to make your one-on-one meetings impactful? Focus on these six core areas:

1. Personal check-ins

Start by asking about the employee’s overall well-being. A simple question like, “How are you feeling this week?” can uncover personal challenges or successes that may affect their work.

2. Progress and challenges

Dive into what’s going well and where they’re feeling stuck. Ask things like, “What’s been working well in your role?” or “What’s been slowing you down?”  This gives you a chance to celebrate wins and offer support where it’s needed most.

3. Career development

Employees want to grow, and these meetings are the perfect time to discuss how career aspirations can align with increased employee productivity. Try asking, “What skills are you looking to develop?” or “Are there any projects you’d like to take on?”  It shows you’re invested in their future.

4. Feedback

Constructive and positive feedback are cornerstones of any good one-on-one. Share your observations about their performance, and don’t forget to ask for feedback about your leadership. A simple “How can I support you better?” goes a long way. 

As Alexandra Sunderland, Engineering Director at Fellow, highlights, “It’s really important to get to know your reports on a personal level, learn about them, and whatever comfort level they have with sharing their personal lives. And then also giving feedback because I think showing that you’re invested in someone’s growth by giving them helpful, well-worded feedback is a really good way to show that you have their best interests at heart and you care about them.” 

The personalized and thoughtful nature of the feedback reinforces your commitment to your employees’ growth.

5. Alignment with organizational goals

Help employees connect their work to the bigger picture by asking, “How aligned do you feel with the team’s goals?”  This cultivates a sense of purpose and can uncover valuable information.

6. Work relationships

Strong relationships lead to better collaboration. Ask questions like, “How are things going with your teammates?” or “Are there any team dynamics you’d like to discuss?”  These conversations can improve cohesion and address issues before they escalate.

How often should one-on-one meetings happen?

Regularity is key to making these meetings impactful. While the frequency may vary based on individual needs, experts recommend weekly or bi-weekly check-ins to maintain alignment and momentum. 

Richard Wanner states, “Most experts recommend holding one-on-ones weekly but acknowledge that this can be a scheduling challenge. Whatever you choose, it is important to remember that the longer you go between sessions, the less timely and less accurate the information will be, and the less likely it is that you will be able to intervene in an issue while it is still young.”​

Bi-weekly meetings strike a balance between being available for employees without overwhelming schedules. For managers with larger teams, brief informal catch-ups can supplement less frequent in-depth sessions. Organizations can cultivate trust, engagement, and productivity across their workforce by keeping one-on-one meetings structured, consistent, and open-ended.

Advantages of consistent one-on-one meetings

One-on-one meetings do require effort, but it’s undoubtedly worth it. These meetings, supported by well-structured one-on-one meeting questions, can deliver transformative benefits for your team. Let’s look at why they’re such a game-changer:

1. Improved employee engagement

Did you know that 76% of employees with empathetic managers report being highly engaged at work? Regular one-on-ones are your chance to connect with employees, address concerns, and align career goals. It’s no surprise that employees who feel heard and supported are more engaged and motivated.

According to Maggie Wool from Better Up, regular one-on-one check-ins have become increasingly important, with their frequency rising significantly since the pandemic. 

These meetings are essential for maintaining strong connections, especially with remote employees, and play a key role in improving engagement and performance.

2. Higher retention rates

Employees are far more likely to stay in a role when they feel supported. Regular one-on-ones provide clarity and reassurance, which translates to greater loyalty.

3. Improved performance and productivity

When employees know how their work contributes to the company’s goals, they’re more motivated to deliver results. Regular discussions about performance and objectives create accountability and drive productivity.

4. Stronger manager-employee relationships

One-on-ones build the foundation for trust and collaboration. These meetings give employees a safe space to share concerns, offer ideas, and receive coaching. Over time, these relationships become stronger and more productive, especially when combined with regular performance reviews that provide structured opportunities for feedback and growth.

Managers who focus on building trust during one-on-ones report fewer misunderstandings and more cohesive teams.

5. Increased psychological safety

Teams with high psychological safety are 27% more likely to report increased collaboration and innovation. 

Psychological safety is the #1 factor in high-performing teams, as Amy Gallo – author of the HBR Guide to Dealing with Conflict and Getting Along –  shared. She highlighted the research of Amy Edmondson, who coined the term ‘psychological safety’, and whose research on team behavior, alongside Google’s project Aristotel, proved that teams thrive when employees feel safe to share honest feedback, admit mistakes, and propose ideas without fear of judgment.

One-on-one meetings should be part of the activities that create this safety net. They should be a private, supportive space where employees can speak freely and explore new ideas.

How to prepare for one-on-one meetings

When both managers and employees come ready to discuss meaningful topics, these sessions can actually be valuable both short and long-term. 

Here’s how you can set the stage for a productive, meaningful conversation:

1. Set a clear meeting agenda

Meetings with clear agendas are far more productive. A shared agenda keeps everyone on track and ensures you tackle what matters most. Make it a living document where you and the employee can add topics beforehand.

Use a recurring one-on-one agenda template alongside the right one-on-one meeting questions to make your meetings more efficient and impactful. Structure the agenda into sections for updates, challenges, and goals to keep conversations focused. This approach helps you cover essential topics without veering off course and creates a consistent framework that promotes productive dialogue.

You can also include recurring themes like progress updates, career growth, and well-being. 

Try asking, “What’s the most significant challenge you’re facing this week?” to kick things off.

You can also start by using the feedback you gain from regular surveys. This way,  you show employees that you truly read and value it. For example, with HeartCount’s weekly or bi-weekly pulse checks, you can gather real-time feedback on eight categories of employee engagement, including well-being. 

2. Create a comfortable environment

People open up more when they’re comfortable. Whether you’re meeting virtually or in person, the setting matters. A relaxed environment allows team members to feel at ease and promotes meaningful conversation.

• For virtual meetings: choose video calls with cameras on to make the interaction more personal. Minimise distractions and ensure a stable internet connection. For clarity, I suggest noise-cancelling headphones.
• For in-person meetings: Opt for a neutral, relaxed location like a lounge or café. Avoid overly formal spaces, like the manager’s office, which can feel intimidating. Remember, it should be more like a stay conversation than an exit interview.

For example, if you run a hybrid team, you can alternate between virtual check-ins and in-person coffee chats. This mix balances efficiency with a personal connection, making the meetings more engaging and strengthening employee motivation through meaningful interactions.

3. Start with a personal check-in

Don’t dive straight into work—start with a personal touch. Begin the meeting with a question like, “How are you feeling this week?” or “How was your weekend?” It’s a simple way to build rapport and a strong relationship with your employees. 

Understanding their personal and professional context can lead to more productive conversations.

This check-in also acts as a natural transition into deeper conversations. Employees will feel more at ease and ready to discuss work-related topics, especially when approached with thoughtful, open-ended questions that encourage dialogue and trust.

4. Encourage open dialogue

These meetings aren’t for managers to talk and do project check-ins. They’re for relationship building and nurturing, so they should be a safe space for the employee to talk. Use open-ended questions and active listening to create a two-way conversation. Here are some examples:

• “Is there anything you’d like to change about how we collaborate?”
• “What’s one area where you think the team could improve?”

Active Listening Tip: Show you’re engaged by reflecting back key points. For instance, if an employee shares a challenge, respond with, “I hear that X is an obstacle. Let’s explore ways we can address that together.”

These meetings are also a great opportunity to solicit employee feedback about your leadership, team processes, or overall work environment. 

Questions like “What feedback do you have for me?” or “How can I better support you?” can build trust and uncover areas for improvement.

As Mike Abrashoff, Commander of the USS Benfold in retirement, aptly said, “It all came down to employee engagement. It all came down to recognition. It all came down to leadership, which led to every sailor feeling ownership and accountability for the results. You can ask a team to accomplish a mission, but you can’t order excellence.” 

This highlights how effective leadership, rooted in recognition and engagement, can create a space where employees feel valued and empowered to perform at their best.

5. Document and follow up

Documenting your meetings is an excellent way to build trust and accountability. Take detailed meeting notes, especially about action items, and follow up in the next session.

For example, if an employee expresses interest in developing new skills, follow up with training opportunities or resources by the next meeting. This shows you’re invested in their growth.

6. Practice empathy

Empathy isn’t just nice to have—it’s essential. Show genuine interest in understanding your employee’s perspective, especially during tough conversations.

For instance, if someone is underperforming due to personal challenges, approach the topic with care. 

Try saying, “I’ve noticed you’ve seemed a bit off lately. Is there anything outside of work that’s been affecting you, and how can I support you?”

Empathetic conversations reduce stress, build trust, and create a safe environment where employees feel valued.

Remember: Preparation doesn’t take long, but it makes a world of difference. By setting the right tone and structure, you can turn your one-on-one meetings into powerful tools for connection, growth, and success.

45 one-on-one meeting questions for employees and managers

Asking the right questions during one-on-one meetings is key to unlocking insights, building trust, and driving employee engagement. 

Below is a categorized list of impactful questions for managers and employees tailored to promote growth, improve communication, and address challenges effectively.

General check-in questions

Start your meeting on a positive note by checking in with your employee. These questions set the tone and show you genuinely care.

• How are you feeling this week?
• What’s on your mind lately?
• Is there anything outside of work that’s been affecting you?
• Are there any wins—personal or professional—you’d like to share?

General check-ins encourage openness and help you understand your employee’s state of mind.

Progress and goal-tracking questions

Focus on achievements and roadblocks to keep things on track. These questions help you identify where your support can make a difference.

• What progress have you made on your key goals since our last meeting?
• What challenges are you facing right now?
• Are there any tools or resources that could help you achieve your objectives?
• Do your current goals still feel relevant, or do they need adjustment?

Career development questions

Help your employees grow by exploring their aspirations. These questions can inspire new opportunities and show that you’re invested in their future.

• What skills would you like to develop in the next quarter?
• What projects or responsibilities are you most excited about right now?
• How do you see your role evolving over the next year?
• Are there any stretch assignments you’d like to try to challenge yourself?

87% of millennials value professional development opportunities, making growth conversations essential for job satisfaction.

Feedback-oriented questions

Feedback isn’t just about sharing your thoughts—it’s about listening to your employees, too. Create a safe space for honest, constructive feedback.

• What feedback do you have for me?
• How can I support you better as a manager?
• What have I done recently that’s helped—or hindered—you?
• Is there anything about our team’s processes you’d like to improve?

Feedback questions build trust and promote continuous improvement on both sides.

Well-being and work-life balance questions

Want to show your employees you truly care? Ask about their mental and physical well-being. These conversations can prevent burnout and promote a healthier work-life balance.

• How are you managing your workload?
• Do you feel like you have a good balance between work and personal life?
• Have you taken enough breaks or PTO recently?
• Is there anything causing you stress that we could address together?

Relationship-building questions

Strong teams are built on strong relationships. These questions focus on team dynamics and interpersonal collaboration.

• How are things going with your team members?
• Are there any conflicts or concerns within the team you’d like to address?
• Who on the team do you enjoy collaborating with the most, and why?
• Do you feel like others recognize your contributions, and what can we do to strengthen employee recognition within the team?

Vision and alignment questions

Help your employees connect their work to the company’s big picture. When employees see how their efforts contribute to organizational goals, they feel more engaged and motivated.

• Do you feel connected to the company’s vision?
• Is there anything unclear about our current direction or priorities?
• What excites you most about our organizational goals?
• How do you see your role contributing to the company’s success?

According to McKinsey, 70% of employees say their work defines their sense of purpose, which directly drives their performance and productivity.​

Problem-solving and innovation questions

Encourage employees to share their ideas and address persistent challenges. These questions empower them to take ownership and drive innovation.

• What’s one thing you’d change about your role or the company?
• Do you have any ideas for improving our processes or workflows?
• Are there any outdated practices we should reconsider?
• What’s the biggest opportunity you see for our team right now?

Innovative questions help employees feel valued and give them a platform to make a difference.

Tailored questions for specific employee groups

Customizing your approach for different employee groups ensures inclusivity and relevance:

For new hires:

• What’s been the most helpful part of your onboarding process?
• Do you feel like you have the resources to succeed?
• What’s one thing that surprised you about working here?
• How can I support you as you adjust to your new responsibilities?

For employees seeking growth opportunities:

• Are there additional responsibilities you’d like to take on?
• What leadership skills would you like to develop?
• Do your current projects align with your career aspirations?

For long-term employees:

• What keeps you motivated in your role after all these years?
• Are there any legacy processes you think could use a fresh perspective?
• Do you feel like your contributions have been recognized and valued?

For remote workers:

• How do you feel about the frequency and quality of team communication?
• Are there any challenges in your work-from-home setup we can address?
• Do you feel connected to our company culture despite working remotely?

When you need feedback from specific employee groups but are short on time, you can use custom surveys. For example, HeartCount’s custom survey feature lets you easily send surveys to targeted individuals or teams within the company. 

Making the most of these questions

Want to maximize the impact of your one-on-ones? Here’s how:

• Choose the right mix: Tailor questions to the employee’s current priorities and needs.
• Listen actively: Don’t rush. Give employees space to elaborate and truly feel heard.
• Follow up: Document their answers and revisit them in future meetings. This shows you’re serious about taking action.

Building stronger teams with one-on-ones

Regular one-on-one meetings are more than just routine check-ins; they are a cornerstone of effective leadership and employee development. By encouraging open communication and addressing topics ranging from personal well-being to career growth, these meetings help managers build trust and create meaningful connections with their teams. The right questions empower employees to share their ideas, overcome challenges, and align with organizational goals, driving both individual and company success.

As seen in numerous studies, organizations that prioritize structured one-on-ones experience better engagement, higher employee retention, and improved productivity. Whether you’re focusing on feedback, progress, or innovation, these conversations provide a platform for transformative growth and collaboration.

Ready to make your one-on-one meetings more impactful? HeartCount offers tools to streamline communication and uncover actionable insights during these critical conversations.

Take a product tour today and discover how HeartCount can help you enhance your one-on-one meetings, boost engagement, and build a thriving workplace culture.