30 Great Questions To Ask In One On One Meeting

One-on-one meetings are a crucial tool for managers to connect with their team members, understand their challenges, and provide support. A well-prepared meeting agenda is essential in ensuring these meetings are productive and focused. These meetings offer a unique opportunity to foster open communication, build trust, and drive employee engagement.

To make the most of a one-on-one conversation, it’s essential to ask the right questions that encourage meaningful dialogue and insight. This article explores 30 powerful questions that can transform your one-on-ones into productive, insightful conversations.

Section 1: Understanding Employee Well-being, Engagement, and Priorities

1. How are you feeling this week? This simple yet powerful question opens the door for employees to share their overall state of mind. It acknowledges that their feelings matter and can impact their work. By asking this, managers show empathy and create a space for honest dialogue about any personal or professional challenges the direct report might be facing.
2. What’s your top priority right now? Understanding an employee’s current focus helps managers align their expectations and provide necessary resources. It also offers insight into how the employee prioritizes tasks and manages their workload. This question can lead to discussions about project timelines, resource allocation, or potential roadblocks.
3. What challenges are you facing in your role? By directly asking about challenges, managers invite employees to voice concerns they might otherwise keep to themselves. This question can uncover issues ranging from technical difficulties to interpersonal conflicts, allowing managers to offer support or intervention where needed.
4. Is there anything blocking you from being productive? Productivity blockers can be diverse – from inefficient processes to lack of information or tools. Identifying these obstacles allows managers to take action, removing barriers and enabling employees to perform at their best.
5. What accomplishment are you most proud of since our last meeting? Celebrating successes, no matter how small, boosts morale and motivation. This question allows employees to reflect on their achievements and feel recognized for their hard work. It also gives managers insight into what the employee values and considers important in their role.

Section 2: Goal Setting, Career Aspirations, and Career Development

1. Do you feel you’re making progress on your goals? Why or why not? This question encourages employees to reflect on their performance and progress. It can reveal whether goals are realistic, if additional support is needed, or if goals need to be adjusted. It also opens up a conversation about potential obstacles or changes in priorities. One-on-one questions like this are crucial for understanding an employee's progress and challenges, fostering engaging conversations, and strengthening team alignment.
2. What skills would you like to develop further? Understanding an employee’s aspirations for skill development helps managers provide appropriate learning opportunities. This question shows that the company is invested in the employee’s growth and can lead to discussions about training programs, mentorship, or new project assignments.
3. How can I better support you in your role? By asking this directly, managers invite feedback on their own performance and show a willingness to adapt their management style. This question can uncover needs for resources, guidance, or changes in communication that can significantly improve the employee’s work experience.
4. Is there anyone in the company you’d like to collaborate with more? This question can reveal networking desires, interest in cross-departmental projects, or aspirations for mentorship. It helps managers understand the employee’s broader professional interests and can lead to valuable connections within the organization.
5. What aspects of your job do you find most energizing? Understanding what motivates and excites an employee can help managers assign tasks and projects that play to their strengths and interests. This insight is valuable for increasing job satisfaction and engagement.

Section 3: Team Dynamics and Workload

1. Are there any projects you’d like to be more involved in during our one on one conversations? This question uncovers an employee’s interests beyond their current responsibilities. It can lead to discussions about career growth, skill development, or ways to incorporate more engaging work into their role.
2. How’s your workload - too much, too little, or about right? Regular check-ins about workload help prevent burnout and ensure employees are appropriately challenged. This question can reveal issues with time management, the need for task redistribution, or opportunities to take on more responsibilities.
3. What’s one thing we could change about our team processes to improve efficiency? Employees often have valuable insights into process improvements. This question empowers them to contribute to team effectiveness and shows that their opinions on workflow matter.
4. Do you have any concerns about our team or company direction? Inviting feedback on larger organizational issues during one on one conversations demonstrates trust and inclusion. It can surface valuable perspectives that management might not otherwise hear and helps employees feel more connected to the company’s overall mission.
5. What’s one thing I could do differently as a manager to better support you? This question shows humility and a willingness to improve as a leader. It gives employees a chance to provide constructive feedback and helps managers tailor their approach to individual team members.

Section 4: Communication and Feedback

1. How do you prefer to receive feedback? Understanding an employee’s preferred feedback style can greatly improve the effectiveness of performance discussions. Some may prefer written feedback, while others value immediate verbal input. One-on-one meeting questions are crucial in improving communication and feedback, ensuring that both parties are on the same page and fostering a more productive dialogue.
2. What motivates you to come to work each day? This question delves into the employee’s core drivers and can help managers align tasks and recognition with what truly matters to the individual.
3. Are there any decisions you’ve been hesitant to make on your own? Identifying areas where employees feel unsure can reveal opportunities for coaching or clearer guidelines. It also encourages a discussion about empowerment and decision-making authority.
4. How would you describe our team culture? What would you change? This question invites honest reflection on team dynamics and can uncover areas for improvement in collaboration, communication, or work environment.
5. What are your long-term career goals? How can I help you work towards them? Understanding an employee’s career aspirations allows managers to provide relevant growth opportunities and show investment in the employee’s future, which can increase retention and engagement.

Section 5: Learning and Growth

1. Is there anything you’re working on that you’re not sure is a priority? This question helps align individual work with team and company priorities. It can reveal miscommunications about task importance or opportunities to refocus efforts. Employee one-on-one questions are crucial for managers to understand their direct reports' daily challenges and obstacles, creating a safe space for open communication.
2. What have you learned recently that you’re excited about? Encouraging employees to share new knowledge fosters a culture of continuous learning. It can also reveal areas of emerging interest or expertise within the team.
3. How’s your work-life balance? Any concerns there? Regularly checking in on work-life balance shows that the company values employee well-being. It can help identify and address potential burnout before it becomes a serious issue.
4. What’s one thing we could do to improve team communication? This question engages employees in problem-solving around team dynamics and can lead to valuable suggestions for enhancing collaboration and information flow.
5. Are there any skills or strengths you have that you feel are underutilized? Uncovering hidden talents or underused skills can lead to more fulfilling work assignments and improved team performance. It shows that the manager is interested in leveraging the full potential of each team member.

Section 6: Challenges and Problem-Solving

1. What was the biggest challenge you faced last week? How did you overcome it? This question encourages reflection on problem-solving strategies and resilience. Having talking points prepared for these discussions can ensure that both managers and employees are ready to address specific issues effectively. It allows managers to offer support or guidance on handling similar situations in the future.
2. Is there anything coming up that you’d like more guidance on? Proactively identifying areas where an employee needs support can prevent future issues and demonstrates a commitment to their success.
3. What’s one thing you wish you had more time for at work? Understanding where employees would like to focus more of their energy can reveal opportunities for task redistribution or process improvements to free up time for high-value activities.
4. How do you feel about the amount of feedback you’re receiving? Would you like more or less? This question helps managers calibrate their feedback approach to each employee’s preferences and needs, ensuring that communication is effective and appreciated.
5. What’s one thing we should start, stop, or continue doing as a team? This final question encourages employees to think critically about team practices and suggest improvements. It empowers them to contribute to team development and shows that their opinions on team dynamics are valued.

By incorporating these questions into your one-on-one meetings, you can create a rich dialogue that addresses various aspects of an employee’s work life, from daily tasks to long-term career aspirations. These conversations build trust, improve engagement, and contribute to a more productive and satisfied workforce. Remember to adapt these questions to your specific context and the individual employee’s situation for the most meaningful discussions.