Top One to One Questions for Better Management in 2025

Effective one to one meetings depend on asking the right questions. When you rely on generic prompts like "how's it going," you get surface-level answers. This approach misses opportunities to find challenges, recognize achievements, or align on development goals. A productive one to one is not a status update. It is a dedicated space for dialogue that builds trust and improves performance.

Using specific, purposeful one to one questions transforms these check-ins. They become strategic conversations that directly support your team members' growth and wellbeing. This guide offers a bank of questions for different situations, from routine check-ins and performance discussions to career development and remote work challenges. You will learn to move beyond routine conversations and build a more transparent, supportive, and effective relationship with each person on your team.

This article provides you with:

• A categorized list of impactful questions for any scenario.
• Actionable tips for phrasing and follow-up prompts.
• Guidance on when to use each type of question.
• Short templates you can adapt for your one to one meetings.

These structured prompts help you prepare for every discussion. You will consistently cover what matters most. By improving the quality of your one to one questions, you make every meeting a valuable investment in your team's success and your effectiveness as a manager.

1. How are you feeling about your work and wellbeing?

This foundational check-in question signals that you care about your team members as people, not just as contributors. It combines professional and personal states to acknowledge the connection between them. By asking about wellbeing alongside work, you create psychological safety. This is a key component of high-performing teams, as identified in research like Google's Project Aristotle. The question gives employees permission to discuss challenges outside of immediate tasks, from workload stress to personal matters that affect their focus.

Why this question works

This prompt moves the one to one beyond a status update. It opens the door for conversations about burnout, engagement, and work-life balance. When an employee feels safe enough to share their true state, you get insight into potential roadblocks before they escalate. It is one of the most effective one to one questions for building a relationship based on trust and support.

Acknowledging an employee’s wellbeing is not an HR function; it is a leadership responsibility. This question shows you see and value them as a complete person.

How to implement this question

• When to ask: Use this question at the beginning of your one to one. This timing shows it is a priority, not an afterthought. It also sets a supportive tone for the rest of the meeting.
• Listen actively: Your first job is to listen without thinking of a solution. Let the employee speak fully. Sometimes, the act of sharing is what is most needed.
• Follow up consistently: If an employee shares a specific concern, make a note to check in on it in your next meeting. This action shows you listened and you care about the outcome.
• Maintain confidentiality: Reassure your team member that personal details shared will remain private. This is critical for building and maintaining trust.

For example, a manager who asks this question might learn that a team member is struggling with childcare issues. This knowledge allows the manager to proactively discuss flexible work arrangements, which prevents a dip in morale and productivity. It turns a potential problem into an opportunity to offer support.

2. What accomplishments are you proud of since we last met?

This strength-based question shifts the focus from problems to wins and successes. It encourages employees to reflect on their achievements, which reinforces positive behaviors and builds confidence. Inspired by strengths-based management approaches, this prompt counterbalances the tendency for one to one meetings to concentrate on gaps or areas for improvement.

By starting with a celebration of what went right, you create an optimistic and motivating tone for the conversation. It shows that you value progress and recognize effort, not just outcomes tied to major project milestones. This is one of the essential one to one questions for building a culture of recognition.

Why this question works

This prompt builds employee morale and helps them connect their daily work to a sense of purpose and achievement. It provides you with a clear view of what the employee values and what motivates them. Documenting these wins creates a positive data trail that is useful for performance reviews. It prevents recency bias and ensures a balanced assessment of contributions over time.

Focusing on what is working is as important as fixing what is broken. Success is a powerful teacher, and this question helps you and your employee learn from it.

How to implement this question

• When to ask: Ask this question right after the initial wellbeing check-in. This sequence moves the conversation from the personal to the professional on a positive note.
• Probe for details: When an employee shares a success, ask follow-up questions like, “What part of that process made you most proud?” or “What skills did you use to make that happen?” This helps them state their strengths.
• Document the wins: Keep a running list of these accomplishments in your shared one to one notes. This serves as a reference for performance reviews and promotion discussions.
• Encourage replication: Discuss how the team or individual can replicate this success. Ask, “What can we learn from this win to apply to our next project?”

For example, a team member might mention receiving positive customer feedback. You can then explore what specific actions led to that feedback. This analysis helps identify best practices that can be shared with the rest of the team. This amplifies the impact of an individual win.

3. What obstacles or challenges are you facing?

This direct question invites employees to bring up blockers and challenges that prevent their success. It moves the one to one from a reporting session to a collaborative problem-solving meeting. Rooted in servant leadership principles and popularized by frameworks like Radical Candor, this prompt positions you as a supportive resource dedicated to removing barriers. It helps you find systemic issues, resource gaps, or interpersonal conflicts that might otherwise go unaddressed.

Why this question works

Asking about obstacles shows that you are invested in your team member’s success and are willing to help them navigate difficulties. It builds trust by showing you are a partner in their work, not just a supervisor. By proactively seeking challenges, you can address issues when they are small and manageable. This prevents them from growing into major problems that affect deadlines, quality, or morale. This is one of the most effective one to one questions for creating a proactive and solutions-oriented culture.

Your job as a manager is to clear the path for your team. This question is your most direct tool for finding out where the path is blocked.

How to implement this question

• Ask with genuine curiosity: Your tone is critical. Ask in an open, non-judgmental way to encourage honesty. The goal is to understand, not to assign blame.
• Commit to follow-up: Take notes on the challenges discussed and create clear action items. Starting your next one to one by checking in on these items shows you are accountable.
• Empower, do not just solve: Before jumping in with a solution, ask follow-up questions like, "What have you tried so far?" or "What kind of support would be most helpful?". This empowers the employee to develop their own problem-solving skills.
• Distinguish blockers from complaints: Listen for specific, actionable issues. A legitimate blocker might be unclear requirements from another department. A vague complaint might need more probing to identify a root cause.

For example, an employee might share that they are struggling with a new software tool. This information allows you to arrange for specific training or pair them with a knowledgeable colleague. You directly resolve the obstacle and improve their capability.

4. What skills would you like to develop or improve?

This growth-oriented question shifts the conversation from current performance to future potential. It shows you are invested in your team member's long-term career progression, not just their immediate output. By opening a dialogue about professional development, you align personal aspirations with organizational goals. This creates a clear path for advancement that benefits both the employee and the company. This approach helps identify skill gaps, training needs, and mentorship opportunities.

Why this question works

This prompt transforms the one to one into a strategic career planning session. It empowers employees to take ownership of their growth and gives you the information needed to support them effectively. Discussing skill development proactively prevents stagnation and disengagement, which are common precursors to employee turnover. This is one of the most valuable one to one questions for building a development-focused culture and retaining top talent.

Investing in an employee’s skill development is a direct investment in your team’s future capabilities. This question communicates that you see their potential and want to help them realize it.

How to implement this question

• When to ask: Pose this question during quarterly or semi-annual reviews, or anytime you are discussing career paths. It links performance feedback to future growth opportunities.
• Connect to company needs: After listening to their interests, help connect their desired skills to upcoming projects or business objectives. This creates a win-win scenario.
• Create a plan: Work together to outline a specific, actionable development plan with a 90-day timeline. Identify resources like online courses, mentorship pairings, or stretch assignments.
• Provide practice opportunities: Learning is solidified through application. Assign tasks or projects that allow the employee to use their newly acquired skills in a real-world context.
• Follow up on progress: Acknowledge their efforts and discuss progress in subsequent one to ones. This reinforces the importance of their development and keeps them motivated.

For example, a team member might express an interest in learning data analysis to better understand customer behavior. As their manager, you could pair them with a senior analyst for mentorship and assign them a small-scale data project. This action provides a clear, supportive path for them to build a valuable new skill.

5. How can I better support you in your role?

This question directly invites feedback on your effectiveness as a manager and flips the script on traditional one to one meetings. Instead of asking what the employee can do for the company, you ask what you can do for the employee. This approach, rooted in servant leadership and concepts from Radical Candor, positions you as a resource and a barrier remover, not just a taskmaster. It shows humility and a commitment to your team member's success.

Why this question works

This prompt empowers your team member to voice their needs directly. This creates a culture of psychological safety and open dialogue. It helps you identify blind spots in your management style and find specific, actionable ways to improve team performance and satisfaction. An employee who feels supported is more likely to be engaged, motivated, and loyal. This is one of the most powerful one to one questions for building a partnership based on mutual respect and shared goals.

Your job as a manager is to clear the path for your team. This question is the most direct way to find out what roadblocks need to be removed.

How to implement this question

• Ask with genuine curiosity: Your tone and body language must signal that you are open to any answer, even critical feedback. Avoid any hint of defensiveness.
• Commit to action: When an employee shares a need, commit to a specific action. For example, if they ask for more autonomy, define a project where they can take the lead.
• Follow through and report back: In your next one to one, provide an update on the actions you took based on their feedback. This closes the loop and builds immense trust.
• Be patient: If your team is not used to this question, they may not have an immediate answer. Ask it regularly to show it is a sincere and ongoing offer of support. Mastering this type of dialogue is a key part of clear communication.

For instance, an employee might respond by saying they need more protection from interruptions to do deep work. As a manager, you could then help them block "focus time" on their calendar and communicate these boundaries to the rest of the team. This small adjustment can lead to a large increase in their productivity and job satisfaction.

6. How do you see your role contributing to our team and company goals?

This purpose-alignment question connects an employee's daily work to the bigger picture. It prompts them to state the link between their specific responsibilities and the broader organizational mission. Inspired by frameworks like Simon Sinek's 'Start with Why', this question shifts the focus from what an employee does to why their work matters. Answering it successfully reinforces their sense of purpose and improves motivation.

Why this question works

This prompt is one of the most effective one to one questions for increasing employee engagement and clarifying priorities. When team members see how their efforts push the company forward, their job satisfaction and commitment grow. It also serves as a diagnostic tool for you as a manager. If an employee struggles to connect their tasks to team goals, it signals a potential misalignment that you can address before it affects performance.

An employee without a clear sense of purpose is an employee at risk of disengagement. Connecting their role to the mission turns a job into a meaningful contribution.

How to implement this question

• Set the stage: Before asking, ensure you have clearly communicated the team and company goals, such as the current OKRs. The employee needs the right context to make the connection.
• Encourage self-discovery: Phrase the question to encourage them to draw the conclusion themselves. Avoid telling them how they contribute. This ownership builds a stronger connection.
• Clarify and correct: If you notice a gap in their understanding, gently guide the conversation to clarify the link. Use specific examples of how their past work directly affected a key metric or project outcome.
• Revisit quarterly: Company goals evolve. Make this a regular check-in, especially at the start of a new quarter, to ensure alignment stays strong as priorities shift.

For example, a manager asks this question and learns that a junior data analyst sees their job as "running reports". The manager can then explain how those specific reports directly inform the C-suite's strategic decisions on market expansion. This transforms the employee's perception of their work from a mundane task to a critical function.

7. What feedback do you have for me or our team?

This question transforms the one to one from a top-down review into a two-way conversation. By explicitly asking for feedback about yourself and the team, you model vulnerability and a commitment to continuous improvement. It actively builds psychological safety, a concept popularized by Amy Edmondson's research. It shows that all perspectives are valued and that it is safe to offer constructive input, regardless of hierarchy. This prompt can find insights into team processes, communication bottlenecks, or your own leadership blind spots.

Why this question works

Inviting upward feedback is one of the fastest ways to build trust and strengthen your team’s culture. It shows you are open to growth and respect your team member's observations. This question empowers employees. It gives them a direct channel to influence their work environment and your management style. When you act on the feedback you receive, you create a positive loop where team members feel heard and are more likely to share valuable insights in the future.

A manager who cannot receive feedback cannot be expected to give it effectively. Asking for input shows that feedback is a tool for everyone's growth, not just for direct reports.

How to implement this question

• When to ask: Pose this question toward the end of the meeting, after you have built rapport and discussed other key topics. This placement gives the employee time to feel comfortable before sharing potentially sensitive feedback.
• Listen without defense: Your immediate reaction sets the tone for all future feedback. Listen to understand, not to rebut. Avoid explaining or justifying your actions in the moment. Thank them for their courage and honesty.
• Ask clarifying questions: To fully grasp the input, ask for specific examples. For instance, if they say you are "too hands-off," you might ask, "Can you share a recent project where you felt you needed more of my input?"
• Follow up on the input: After the meeting, reflect on the feedback. In your next one to one, report back on any actions you have taken or explain your decision if you chose not to implement the suggestion. For specific methods on structuring feedback, you can learn more about the SBI model.

8. What are your career aspirations, and where do you see yourself in the future?

This forward-looking question moves your conversation from daily tasks to long-term professional ambitions. It shows you are invested in your employee's future, not just their current output. Understanding a team member's career goals helps you identify potential retention risks, spot high-potential talent with leadership aspirations, and create personalized development plans that align their goals with company opportunities.

Why this question works

This prompt is crucial for career pathing and succession planning. It helps you understand what motivates your team members. This allows you to connect them with projects, mentors, or training that supports their growth. When employees see a clear future for themselves within the organization, their engagement and loyalty increase. It transforms your role from a task manager to a career coach.

An employee without a vision for their future is a retention risk. A manager who helps shape that vision builds a foundation for long-term commitment.

How to implement this question

• When to ask: Use this question quarterly or bi-annually during a dedicated development-focused one to one. Asking too frequently can feel repetitive. Asking only during annual reviews is too late to make an impact.
• Frame it correctly: Present the question as a way to support them. For example, "I want to make sure your work here is helping you get where you want to go in your career. What does that future look like for you?"
• Ask meaningful follow-ups: Dig deeper with questions like, "What skills or experiences do you think you need to get there?" or "What kind of projects would help you build those capabilities?"
• Co-create a plan: Work with the employee to outline actionable steps. Identify internal opportunities, stretch assignments, or mentorship connections that align with their stated aspirations. You can find resources for building these plans by learning more about career development strategies on PeakPerf.co.

For example, if an employee expresses an ambition to become a director, you can create a leadership development plan. If another team member wants to transition to a new function, you can help them explore a realistic path to get there within the company. This turns abstract aspirations into a tangible roadmap.

9. Is there anything preventing you from doing your best work?

This diagnostic question moves beyond task-level issues to find hidden obstacles that hinder performance. It is a tool for identifying environmental friction, resource gaps, or process inefficiencies. By asking this, you shift your role from a task manager to a barrier remover. This signals your commitment to enabling your team member's success. This approach, inspired by frameworks like The Coaching Habit, empowers employees to highlight blockers they might otherwise hesitate to bring up.

Why this question works

This prompt is one of the most effective one to one questions for finding systemic problems. It invites the employee to think broadly about what is holding them back. This can reveal non-obvious issues like unclear stakeholder requirements, inadequate tools, or interpersonal friction. It gives you a clear, actionable list of problems to solve, directly affecting your team member’s productivity and engagement. It shows that you are invested in their ability to perform at a high level.

Your job as a manager is to clear the path for your team. This question directly asks them to show you where the biggest roadblocks are.

How to implement this question

• When to ask: Use this question during the problem-solving or planning portion of your one to one, after you have discussed progress and priorities. It frames the conversation around future success.
• Probe for specifics: If an employee gives a vague answer, ask follow-up questions like, “What does that look like in practice?” or “What would be most helpful to you right now?”
• Take clear notes: Document the specific barriers mentioned. This creates a record you can reference and shows the employee you are taking their concerns seriously.
• Commit and follow up: Identify one or two blockers you can help remove before the next meeting. Report back on your progress to build momentum and trust.

For example, a team member might reveal that slow software approval processes are delaying their project. As a manager, you can then investigate the procurement process or provide temporary access to a necessary tool. This direct action solves a tangible problem and proves you are an effective advocate for your team.

10. What do you need from me to be successful in achieving your goals?

This question shifts the conversation from problem identification to collaborative solutions. It is a direct way to transfer accountability. It makes clear that you, as the manager, are a resource for your team member's success. It moves beyond abstract support and prompts the employee to state specific, concrete needs, whether they are resources, decisions, or political capital. This positions the one to one as a practical working session, not a review.

Why this question works

This prompt clarifies your role and creates a clear action plan for you as a manager. It eliminates guesswork about what support is most valuable and ensures you are focused on removing real obstacles. By asking what your employee needs from you, you show commitment and build a partnership focused on achieving shared objectives. It is one of the most effective one to one questions for turning goals into completed projects because it assigns clear, immediate actions to the manager.

When you ask what an employee needs, you are not offering help. You are committing to a specific action that enables their success.

How to implement this question

• When to ask: Pose this question toward the end of the meeting, after goals and progress have been discussed. This allows the employee to combine the conversation and identify the most critical support they need.
• Document your commitments: Write down exactly what you agree to provide. This creates a record of your deliverables and reinforces your accountability.
• Set clear timelines: For any action you commit to, define a timeline. For example, "I will get you an answer on the budget request by the end of tomorrow."
• Follow through consistently: Your reliability is critical. Fulfilling your commitments is the most tangible way to build trust and show you are invested in their success.

For example, a team member might say they need an introduction to a key stakeholder in another department to move a project forward. As their manager, you can facilitate that meeting, directly removing a blocker. This transforms a potential delay into a moment of progress and strengthens your working relationship.

One-on-One Questions: 10-Point Comparison

Turning Questions into Action and Growth

You now have a bank of one to one questions designed to open meaningful dialogue with your team members. This list is more than a simple script. It is a toolkit for building trust, finding challenges, and encouraging professional growth. The real power of these conversations is not in asking the questions, but in what you do with the answers.

Active listening, genuine curiosity, and consistent follow-through are what separate a routine check-in from a transformational meeting. Each question you ask, from "How are you feeling?" to "What are your career aspirations?", opens a door to understanding an individual’s motivations, blockers, and ambitions. Your role is to step through that door, listen intently, and collaborate on a path forward.

From Conversation to Commitment

The most effective one to one meetings produce clear, actionable outcomes. Without a system for tracking these commitments, valuable insights are lost, and trust erodes. A team member who shares a challenge or a goal expects you to remember and follow up. Failing to do so sends a message that their input is not valued.

To prevent this, adopt a structured approach to every conversation.

• Document Key Takeaways: Note the most important points, decisions, and action items discussed.
• Note Your Commitments: Clearly record what you promised to do, whether it is providing a resource, removing a blocker, or finding an answer.
• Set Reminders: Use your calendar or a task manager to schedule follow-ups on both your commitments and your direct report’s action items.

This discipline ensures accountability and shows your investment in each person’s success. It transforms your one to one from a status update into a reliable system for progress and support.

Tailoring Your Approach for Maximum Impact

The one to one questions in this guide are a starting point. Your next step is to adapt them to fit each individual and situation. A new hire will benefit from questions focused on onboarding and role clarity. A senior team member might need more strategic conversations about career development and leadership opportunities.

Consider these factors when preparing for your next meeting:

• Individual Personality: Is this person direct and data-driven, or do they prefer a more personal, narrative style of communication?
• Current Performance: Is the focus on celebrating recent wins, addressing a performance gap, or setting new goals?
• Team Dynamics: Are there team-wide issues that need to be explored from an individual perspective?

By tailoring your questions, you show you see and appreciate each team member as an individual. This personalized approach is fundamental to building strong, resilient, and high-performing teams. Mastering the art of the one to one meeting is a core leadership skill. It is the most consistent and effective way to build psychological safety, drive engagement, and connect individual work to broader company objectives. Your commitment to these conversations is a direct investment in your people and your organization's future.

Ready to transform your one to one meetings from simple check-ins into growth conversations? PeakPerf provides structured templates, guided prompts, and integrated follow-up tracking to ensure every conversation is productive and actionable. Streamline your preparation and focus on what matters most, your people, by exploring PeakPerf today.