33 Top one on one questions that are a must-ask in 2023

Kailash Ganesh
15 min read
One on one meetings

In the realm of employee engagement and productivity, a one-on-one meeting is the secret sauce that can transform your team dynamics and boost overall performance. But the catch is asking the right questions. It can make all the difference between a mundane meeting and an extraordinary one!

As the great philosopher Snoopy once said, "The difference between ordinary and extraordinary is that little extra." In our case, that "extra" comes in the form of 33 meticulously crafted one-on-one meeting questions that will turn your conversations into goldmines of insight, connection, and growth.

Imagine the look on your team members' faces when you start your next meeting with an unexpected question that sparks their enthusiasm. Picture the brainstorming sessions, the "aha" moments, and the genuine connections that will be forged through these conversations. So, let’s get started.

Remember, a successful business runs on high engagement with employees, and one on one meetings are one of the best ways to do so.

Table of contents:-

What are one-on-one meetings?

What are one-on-one meetings?

One-on-one meetings, also known as individual meetings, are dedicated conversations between a manager or team leader (based on who they direct report to) and individual team members. These meetings provide a private and focused space for discussing various topics, addressing concerns, providing feedback, and fostering a stronger working relationship.

One-on-one team meetings are typically held regularly, such as weekly, biweekly, or monthly, depending on the team's needs and the manager's preference. These meetings aim to create an open and honest communication channel between the manager and team members, where both parties can discuss work-related matters, share direct reports, and collaborate on career goals and challenges.

Key characteristics of a one-on-one meeting

Key characteristics of a one-on-one meeting

1) Privacy and confidentiality

These meetings are conducted in a private setting, allowing both the manager and individual team members to have open conversations without the fear of judgment or interruption from other employees.

2) Individual focus

The focus of a one-on-one meeting is solely on the individual team member. It's an opportunity for the manager to provide personalized attention, understand their aspirations, and address any concerns or issues they might have.

3) Two-Way street

A one-on-one meeting is not meant to be one-sided. They should encourage active participation and engagement from both the manager and the team members. Creating an environment where open dialogue and honest feedback can flourish is essential.

4) Goal Setting and progress tracking

These meetings serve as a platform for setting and reviewing goals, discussing progress, and identifying any obstacles or support needed for professional development. They help align individual goals with the broader team or organizational objectives.

5) Relationship building

A one-on-one meeting contributes to building a strong working relationship between the manager and individual team members. They allow the manager to understand the individual's strengths, weaknesses, and career aspirations, fostering trust and camaraderie.

The topics in a one-on-one meeting can vary widely depending on the team member's role, responsibilities, and current focus. Common discussion points include project updates, performance feedback, and many more which we have discussed below.

Overall, a one-on-one meeting greatly impacts leadership, engagement with employees, and overcoming team challenges. They provide a dedicated space for managers to support and empower their team members while nurturing a company culture of open communication and continuous improvement.

Top one-on-one conversation topics

Top one-on-one conversation topics

When it comes to one-on-one conversations, the topics you discuss can make all the difference in creating meaningful and engaging interactions. So, let's take a look at the top 10 conversation topics that can transform your one-on-one meeting from ordinary to extraordinary!

1) Goals and aspirations

Start by discussing your team member's short-term and long-term goals. Check-in on their aspirations and help align their objectives with the team's or organization's vision. This sets the stage for growth and personal development.

2) Progress and achievements

Celebrate successes and acknowledge your team member's accomplishments. Recognize their hard work and dedication. Discuss their current projects and the milestones they've reached, giving credit where it's due.

3) Challenges and roadblocks

Ask work-related questions to understand any obstacles your team member is facing. This could be related to specific tasks, workload management, or even personal life challenges. As a manager, you need to offer support, brainstorm solutions together, and provide guidance.

4) Skill development

You must talk to remote employees about skill-enhancement opportunities. Identify areas where your team member can grow and develop professionally and discuss additional training programs, workshops, or mentoring options that can help them expand their skill set.

5) Feedback and performance

Provide constructive feedback on employee performance, focusing on strengths and improvement areas. Use this time to offer guidance, set expectations, and ensure they have the resources needed to excel. At the same time, if you receive employee feedback, take it constructively.

6) Career development

Explore your team member's career aspirations and discuss potential growth opportunities within the organization. Share insights on different career paths and offer guidance on how they can progress in their chosen field.

7) Work and personal life balance

Show genuine interest in their well-being beyond work. Discussing work-life balance can help manager stress levels and any concerns they might have. Offer support and resources to help maintain a healthy equilibrium.

8) Personal interests and hobbies

Take a moment to connect on a personal level. Ask about your employee’s hobbies, interests, or recent experiences outside of work. This helps build rapport and shows that you value them as a whole person.

9) Feedback on leadership

Encourage your team member to provide enough feedback on your leadership, management style, and team dynamics. This demonstrates that you're open to continuous improvement and fosters a team culture full of mutual trust and respect.

10) Future growth opportunities

Discuss potential career paths, promotions, or new projects on the horizon. Paint a vision of what the future holds and demonstrate your commitment to their professional growth.

Remember, these topics serve as a starting point, and it's important to tailor your conversations to the individual needs and interests of your team members. Engaging in thoughtful discussions on these topics will create an environment of trust, motivation, and growth that will also help in employee retention.

Why is a one-on-one meeting with employees necessary?

Why is a one-on-one meeting with employees necessary?

In the fast-paced world of modern work, where time is a precious commodity, a one-on-one meeting stands as a beacon of meaningful connection and effective leadership. These meetings go beyond mere checkboxes on a manager's agenda. They are essential for cultivating strong relationships and nurturing a company culture of growth.

By dedicating focused time to each team member, these meetings unlock a myriad of benefits. Let’s take a look at them to understand why one-to-one meetings are critical for organizations and how they contribute to engagement.

1) Building relationships

A one-on-one meeting provides a dedicated space for you to build strong, meaningful relationships with your team members. By engaging in open conversations, you establish trust, rapport, and a sense of camaraderie. This foundation of connection sets the stage for better collaboration and increased satisfaction of employees.

2) Communication and feedback

Regular one-on-one meetings facilitate clear and effective communication channels. They give you the opportunity to provide timely feedback on performance, recognize achievements, and address any concerns or issues. It's a chance to align expectations, clarify goals, and ensure everyone is on the same page.

3) Employee engagement

Engaged employees are the heart and soul of a high-performing team. A one-on-one meeting allows you to involve team members in their growth and development actively. Discussing their goals, aspirations, and challenges demonstrates that you value their input and are committed to supporting their success.

4) Individual development

These meetings are ideal for having career conversations and discussing individual development plans. By understanding each team member's strengths, weaknesses, and aspirations, you can tailor development opportunities to their specific needs. This enhances their skills and knowledge and boosts their motivation and satisfaction in their role.

5) Problem-solving and roadblocks

A one-on-one meeting offers a safe space for team members to share any roadblocks they might be facing. Whether it's a technical challenge, interpersonal conflict, or workload issue, addressing these concerns in a supportive environment allows for collaborative problem-solving. Together, you can find solutions and overcome obstacles more effectively.

6) Retention and loyalty

When employees feel heard, valued, and supported, they are more likely to stay with your organization for the long term. Regular one-on-one meetings demonstrate your commitment to their growth, well-being, and success, fostering a sense of loyalty and reducing turnover rates.

7) Alignment and accountability

A one-on-one meeting ensures alignment between individual goals and team or organizational objectives. By regularly discussing progress, you can track performance, address any deviations, and maintain accountability. This keeps everyone focused and motivated toward achieving shared goals.

8) Recognition and motivation

These personal meetings provide an opportunity to recognize and celebrate achievements. By acknowledging your team members' hard work, you boost morale and motivation. Additionally, they allow you to identify and address any factors that may be demotivating or hindering employee performance.

How should managers drive the one on one meetings?

How should managers drive the one on one meetings?

First and foremost, as a manager, it's crucial to set the tone for the meeting. Start by expressing your genuine interest in your team member's well-being and growth. You can begin with a warm greeting and a genuine inquiry about how they're doing.

For example, you might say, "Hey, Sarah! How has your week been? Anything exciting or challenging happening that you'd like to discuss?"

Next, allow your team member to share their thoughts, progress, and concerns. Actively listen and show empathy. Encourage them to open up by asking open-ended questions and giving them the space to express themselves fully. For instance, you could say, "Tell me about the project you've been working on. How do you feel it's progressing? Are there any specific challenges you've encountered?"

During the meeting, strike a balance between discussing work-related topics and exploring their personal growth and development. Remember, these conversations aren't solely about tasks and deadlines; they are about understanding your team member as a whole person.

As the manager, it's important to provide constructive feedback and guidance. Be specific and highlight both strengths and areas for improvement. Offer actionable suggestions to help them enhance their performance.

For instance, you might say, "I really appreciate your attention to detail in your recent report. Your analysis was spot-on. Moving forward, I'd love to see you explore more creative solutions to the challenges we face. I believe it would add even more value to our team's work."

Lastly, ensure that you establish clear action items and follow-ups. Summarize key points discussed during the meeting and collaboratively set goals or next steps. This helps create accountability and ensures progress.

Remember, creating an open and supportive environment where your team member feels valued and heard is key. You'll foster a culture of trust, engagement, and collaboration by driving the one-on-one meeting with a conversational approach, active listening, and a genuine interest in their growth.

7 Things to consider while conducting a one-on-one meeting

Things to consider while conducting a one-on-one meeting

In the realm of effective leadership and fostering strong relationships with your team members, a one-on-one meeting holds a special place. These dedicated conversations provide a unique opportunity to connect on a personal level, address concerns, and foster growth.

However, conducting a successful one-on-one meeting goes beyond simply scheduling a time slot on your calendar. It requires careful consideration of several essential factors to ensure that the meeting is productive, impactful, and conducive to building trust and engagement.

So, let's explore seven crucial things to keep in mind when conducting your next weekly one on ones.

1) Prepare with purpose

Before the meeting, take the time to prepare a meeting agenda that outlines the right talking points you want to discuss. Be clear on the objectives you want to achieve during the meeting. This ensures that the conversation stays focused and productive.

2) Create a safe and comfortable environment

Set the stage for an open and honest conversation by creating a safe and comfortable environment. Ensure privacy, minimize distractions, and encourage open dialogue by actively listening, showing empathy, and being non-judgmental.

3) Active listening and empathy

Practice active listening during the meeting. Give your full attention to the team member, maintain eye contact, and show genuine interest in what they have to say. Demonstrate empathy by understanding their perspective and validating their feelings or concerns.

4) Encourage two-way communication

Remember that a one-on-one meeting is not meant to be a one-sided lecture. Encourage your team member to actively participate and engage in productive conversation throughout. Ask open-ended questions, invite their input, and give them space to share their thoughts, ideas, and concerns.

5) Provide constructive feedback

A one-on-one meeting offers a valuable opportunity to provide feedback on performance and development. Be specific, provide examples, and offer constructive suggestions for improvement. Balance positive feedback with areas where growth is needed to foster continuous learning and development.

6) Set actionable goals and follow-up

As the meeting progresses, collaboratively set actionable goals or next steps. Ensure that these goals are specific, measurable, attainable, relevant, and time-bound (SMART). Discuss how progress will be tracked and establish a follow-up plan for future meetings to monitor and support their efforts.

7) Maintain confidentiality and trust

Build and maintain trust by assuring confidentiality within the one-on-one meeting. Respect the privacy of the discussions and avoid sharing sensitive information without proper consent. This creates a safe space for team members to share their thoughts, concerns, and aspirations.

Common mistakes in conducting one-on-one meetings

Common mistakes in conducting one-on-one meetings

To ensure your one-on-one meeting is fruitful and impactful, it's important to be aware of and clear of these pitfalls. Here, we'll explore ten summarized points on common mistakes made during one-on-one meetings.

  1. Lack of preparation: Failing to prepare an agenda or not reviewing relevant information beforehand can lead to unfocused and unproductive meetings.
  2. Dominating the conversation: Talking too much and not allowing the employee to share their thoughts can hinder open communication and hinder engagement.
  3. Neglecting active listening: Failing to actively listen and show genuine interest can make employees feel unheard and undervalued.
  4. Overlooking personal development: Focusing solely on work-related topics and neglecting discussions on personal growth and aspirations can limit engagement.
  5. Avoiding difficult conversations: Shying away from addressing performance issues or providing constructive feedback can hinder employee development and progress.
  6. Lack of follow-up: Failing to follow up on action items or commitments made during the meeting can create a sense of disengagement and undermine accountability.
  7. Inconsistent frequency: Irregular or sporadic one-on-one meetings can diminish their impact and hinder the establishment of a consistent feedback loop.
  8. Overlooking recognition: Neglecting to acknowledge and recognize employee achievements and contributions can demotivate and decrease morale.
  9. Micromanaging: Using a one-on-one meeting as an opportunity to micromanage and excessively control can create a negative atmosphere and impede employee autonomy.
  10. Not seeking employee input: Neglecting to ask for employee input on their own development, goals, and challenges can miss out on valuable insights and hinder engagement with employees.

33 Best one on one questions to ask your employees

To make the most of these conversations, asking the right questions that encourage meaningful dialogue and provide valuable insights is important. So, we have compiled a list of 33 best one-on-one questions divided into various categories, each designed to address different aspects of employee engagement, growth, collaboration, motivation, and more.

Click to copy survey questions   content_copy

Questions to set expectations and to know each other

In order to establish a solid foundation and create a positive working relationship we have compiled three questions that will help you set expectations, understand your employees' goals, and foster mutual understanding from the start.

  1. What are your short-term and long-term career goals?
  2. How do you prefer to receive feedback and recognition?
  3. What can I do as your manager to support your success?

Questions about employee growth

Supporting your employees' growth and development is essential for their job satisfaction and long-term success. The following queries will allow you to delve into their aspirations, identify areas for growth, and align their professional goals with the organization's objectives.

  1. What new skills or knowledge would you like to develop further in your role?
  2. Are there any specific training or professional development opportunities you're interested in?
  3. How can we align your personal growth goals with the needs of the team/organization?

Questions about employee collaboration

Collaboration is a cornerstone of high-performing teams. Here are some questions you need to ask to understand how to enhance teamwork, encourage cross-functional collaboration, and leverage the unique strengths of your employees for collective success.

  1. Are there any projects or cross-functional collaborations you'd like to be involved in?
  2. How can we enhance communication and collaboration with other teams and within the team?
  3. Do you have any ideas for improving teamwork or streamlining processes?

Questions about work environment

Creating a positive and conducive work environment fosters productivity and improves employee satisfaction and well-being. Employee feedback can be really valuable in building a great work culture.

  1. Is there anything about the work environment that could be improved to enhance your productivity or well-being?
  2. What resources or tools do you feel would benefit your work?
  3. How can we create a more inclusive and supportive work environment for everyone?

Questions about employee motivation

Employee motivation directly impacts their performance and engagement. The following questions will provide valuable insights into what drives and energizes your employees, helping you tailor incentives, recognition, and opportunities for growth that align with their motivational factors.

  1. What aspects of your job do you find most fulfilling and energizing?
  2. How can we ensure that you feel challenged and engaged in your work?
  3. Do you have any suggestions for enhancing employee motivation and morale?

Questions about work-life balance

Maintaining a healthy work-life balance is vital for employee well-being and overall satisfaction. Here are the right questions to ask your employees about the same.

  1. How are you managing your personal life and work balance currently?
  2. Are there any adjustments or accommodations that would better support your work balance?
  3. Do you have any suggestions for promoting a healthy work and personal life balance within the team?

Questions to understand challenges and roadblocks for productivity

Overcoming productivity obstacles requires understanding the challenges your employees face. Uncover roadblocks, address resource gaps, and provide support with these three probing questions.

  1. Are there any obstacles or personal challenges you're facing that are hindering your productivity?
  2. How can we improve workflows or remove any barriers that affect your efficiency?
  3. Are there any areas where you require additional resources or support to enhance your productivity?

Questions to gauge employee satisfaction

Employee satisfaction is a key driver of engagement and retention. So, its important to assess satisfaction levels, identify areas for improvement, and enhance overall job satisfaction

  1. On a scale of 1 to 10, how satisfied are you with your current role and responsibilities?
  2. What aspects of your job or the workplace contribute most to your satisfaction?
  3. Are there areas where you feel your satisfaction could be improved?

Questions about manager effectiveness

Great managers empower their teams. So, you must seek employee feedback via tools like CultureMonkey to uncover areas for growth and refine your leadership approach. Here are 3 questions you might ask.

  1. How can I better support you in achieving your goals?
  2. Do you have any feedback or suggestions for how I can improve as a manager?
  3. Are there any specific expectations or guidance you would like from me?

Questions about team dynamics

Strong team dynamics contribute to a thriving work environment. With these questions, you can explore team strengths, challenges, and strategies for improvement.

  1. How would you describe the current dynamics within our team?
  2. Are there areas where you think team collaboration or communication could be improved?
  3. Do you have any ideas for team-building activities or initiatives?

Questions about hybrid work

Navigating the challenges of hybrid work is essential. Understand your employees' experiences, address concerns, and foster a connection with them.

  1. How are you adapting to the challenges and benefits of remote or hybrid work?
  2. Are there any tools or processes that could improve collaboration and communication in a hybrid work setting?
  3. How can we maintain a sense of connection and engagement among team members working remotely or in different locations?


1) Why are one-on-one questions important in employee management?

One-on-one questions play a crucial role in employee management as they facilitate open communication, build trust, and deepen the manager-employee relationship. By asking thoughtful questions, managers can gain insights into employee needs, aspirations, and challenges, fostering a supportive environment for growth, feedback, and collaboration.

2) What types of questions should be asked during a one-on-one meeting?

The questions asked during a one-on-one meeting should cover a range of topics, including growth opportunities, challenges, feedback, career goals, and collaboration. The goal is to address professional and personal aspects contributing to employee engagement, satisfaction, and success.

3) How often should managers ask one-on-one meeting questions to their employees?

The frequency of one-on-one questions may vary depending on factors such as team size, workload, and employee needs. However, a general guideline is to conduct them regularly, such as monthly or bi-weekly, to maintain consistent communication and provide a dedicated space for dialogue, feedback, and support.

Kailash Ganesh

Kailash Ganesh

Kailash is a Product Marketer with 5+ years of experience. He loves story-telling in the simplest way possible and he is an avid reader, movie buff, and likes to travel new places to meet new people.