One-on-one meetings are among the most valuable tools for building trust, improving performance, and maintaining open communication between managers and employees. But too often, these meetings fall into a routine of status updates, missing the opportunity for deeper connection and growth.

The key to great one-on-ones? Asking the right questions. Whether you’re a manager or an employee, thoughtful questions can spark better dialogue, uncover hidden challenges, and drive meaningful outcomes.

Here’s a curated list of 100 powerful one-on-one questions—organized by category—to help make your conversations more engaging, productive, and insightful.

🔹 Performance & Goals

1. What are your current priorities?

2. Do you feel clear about your goals this quarter?

3. Where do you feel most confident right now?

4. Are there any roadblocks slowing you down?

5. What could help you be more productive?

6. How are you tracking progress on your objectives?

7. Is there any goal you think needs to be revised?

8. What’s one thing you’d like to improve this month?

9. What’s your biggest win this week?

10. Do you feel challenged enough in your role?

🔹 Career Development

11. Where do you see yourself in one year? Five?

12. Are there any skills you want to develop?

13. What projects would stretch your abilities?

14. Is there a mentor you'd like to work with?

15. Are you getting the support needed for your growth?

16. What training or resources would benefit you?

17. Do you feel like you're learning here?

18. What role would you like to grow into?

19. What motivates you to do your best work?

20. Are we helping you reach your long-term goals?

🔹 Feedback & Recognition

21. Do you feel recognized for your contributions?

22. What kind of recognition is meaningful to you?

23. Is there any recent feedback you found valuable?

24. How do you prefer to receive feedback?

25. What feedback would you give me as your manager?

26. Do you feel comfortable giving feedback to others?

27. What feedback would help you right now?

28. When was the last time you felt appreciated?

29. Is there anyone whose work you admire?

30. Have I missed any wins of yours lately?

🔹 Relationships & Team Dynamics

31. How’s your relationship with your teammates?

32. Is there anyone you find difficult to work with?

33. Who helps you do your best work?

34. What’s one thing we could do to improve team collaboration?

35. Do you feel included and respected by the team?

36. Are there any team processes that frustrate you?

37. What’s something you enjoy about our team?

38. How do you feel about our current communication style?

39. Is there anything we could do better in meetings?

40. Do you feel your voice is heard in group settings?

🔹 Wellbeing & Work-Life Balance

41. How are you feeling overall?

42. What’s been your energy level lately?

43. Are you able to disconnect from work when needed?

44. How’s your workload—too much, too little, or just right?

45. Are there any stressors outside of work you’d like me to be aware of?

46. How can I support you better right now?

47. Do you feel safe bringing up personal challenges here?

48. Is your schedule working for you?

49. What could make your day-to-day better?

50. How are you managing your work-life balance?

🔹 Alignment & Vision

51. Do you understand how your work connects to our team’s goals?

52. What questions do you have about the company’s direction?

53. Is there anything unclear about our current priorities?

54. Do you believe in the mission of the company?

55. How can leadership improve communication?

56. Are you proud of the work our team is doing?

57. What’s one thing you'd change about how we do things?

58. Do you feel part of something meaningful?

59. Are there any decisions that felt out of sync recently?

60. What would make our vision feel more actionable?

🔹 Manager-Employee Relationship

61. What could I be doing better as your manager?

62. Do you feel comfortable being honest with me?

63. How can I better support your career growth?

64. What’s one thing I should start doing?

65. What’s one thing I should stop doing?

66. Are our one-on-ones helpful for you?

67. What do you wish I understood more about your role?

68. Do you feel like I trust your decisions?

69. Is there anything I can do to build more trust?

70. How can I help you succeed?

🔹 Motivation & Engagement

71. What keeps you excited about your work?

72. When do you feel most engaged?

73. What kind of work drains your energy?

74. Is there something you're passionate about that you'd like to do more of?

75. Do you feel like your work matters?

76. What’s your favorite part of your role?

77. What’s something you’ve been meaning to try?

78. Are there any tasks you’d like to delegate?

79. How do you celebrate your own progress?

80. What would make your work more fun?

🔹 Problem Solving & Innovation

81. What’s one thing we could be doing better?

82. Are there any outdated processes you’d change?

83. What idea have you had that hasn’t been explored?

84. Are there tools or resources you’re missing?

85. Have you spotted any inefficiencies recently?

86. What would you do differently if you were in charge for a day?

87. Are there blockers that slow you down repeatedly?

88. What’s one risk you think we should take?

89. How can we simplify the way we work?

90. Is there something small we could fix that would make a big difference?

🔹 Reflection & Self-Awareness

91. What are you most proud of this quarter?

92. What’s been your biggest challenge recently?

93. How do you handle setbacks or failures?

94. What have you learned about yourself lately?

95. What’s something you want to get better at?

96. What habits help you do your best work?

97. When do you feel most confident?

98. What personal value do you try to bring to your work?

99. Who inspires you professionally?

100. What’s one thing you want to be remembered for here?

Final Thought

One-on-ones aren’t just meetings—they’re opportunities. Use these questions as a flexible guide, not a script. The goal is to foster honest, ongoing conversations that support personal growth, professional development, and team success.

Whether you're leading or listening, showing that you care through intentional questions can transform workplace relationships for the better.