Top 150 Questions for Your One-on-Ones

Apr 10

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Don’t let the conversation end! We’ve curated a list of questions to help you discover important details from your report during a one-on-one. Without further ado, here’s the list:

Ice breakers

What are some accomplishments you’re most proud of outside of work?
What are your current priorities?
What are a few pet-peeves of yours?
What are a few things you would like to accomplish within the next few years?
If money and time were not an issue, what would you learn? Who would you become?
What is one piece of advice you would tell yourself if you could go back in time?
What skills do you wish you had learned earlier in life?
What values/beliefs do you live by?
What are you passionate about?
What are your hobbies?
How are you doing?
How was your week?
Do you have any observations you would like to share?
Is there anything we missed that you’d like to talk about next time?
What’s going on in your life right now?
How are things at home?
How do you feel about your work-life balance?
Is there anything you would like me to know about you?
How do you like to spend their free time?
Who is an important figure in your life?
Who do you admire most? Why?
What do you dream about?
What’s been on your mind?
Is there anything preventing you from being completely focused?

Work habits

25. What helps you optimize your day?

26. What factors drive you to be more or less productive?

27. At what times throughout the day do you feel the most productive?

28. What is your preferred method of communication?

29. How do you learn best?

30. What’s your schedule like?

31. Do you prefer ambiguity with room for your own interpretation or clear instructions?

32. How much autonomy do you want/have to make decisions?

33. If you could request anything to make your job easier, what would it be?

34. How do you keep yourself motivated?

35. What do you do to destress?

Current role & expectations

36. What are the highs and lows of working in your current role?

37. How well do you think your time is being used?

38. Are there any expectations of this role you feel you might not be able to meet? Why?

39. Last time we talked about __(insert topic)___, how did that go?

40. What did you work on last week?

41. What have you learned?

42. What questions do you have about your responsibilities?

43. How excited are you about what you’re working on?

44. How excited are you about your role?

45. How do you think this role can help you reach your goals?

46. What do you hope to gain out of this role?

47. Are you proud of your role/what you’re working on?

48. If you could work on anything, what would it be? Why?

49. How important do you feel your role is to the team’s success?

50. What projects would you like to work on?

51. What’s the split of your time today between X/Y/Z? What would you like to spend more/less time on?

52. In regards to increasing responsibilities, what does your timeline look like for this role?

53. What is the most challenging aspect of your role?

54. Do you find yourself being challenged enough?

55. How do you think your skills can be best utilized?

56. What does your ideal position look like?

Accomplishments & praise

57. What are some things you’ve done since you joined that you're the most proud about?

58. How often do you feel appreciated for your accomplishments?

59. Who do you think has contributed to your success the most?

60. What can I, or we as a team, do better to give recognition to those who deserve it?

61. What have you been recognized for recently? Within the past month?

62. Who do you think contributes most to the team? Why?

63. What kind of recognition makes you feel the most appreciated?

Challenges

64. What bottlenecks are you currently experiencing?

65. What roadblocks have you run into?

66. How do you get over hurdles?

67. What do you find is a big time waster?

68. What causes you the most stress out of your responsibilities?

69. How often do you find yourself getting stuck or frustrated with work?

70. Can you identify any major blocks or bottlenecks that frustrate you?

71. Do you have any concerns you think I should know about?

72. What can I, or the team, do to help you when facing challenges?

73. How have you been adjusting to __(insert situation/change)__?

74. How did the ___(project, goal, game, etc.)___ turn out?

Improvement & development

75. What would you like to improve next quarter?

76. What new skills would you like to develop?

77. What do you value most out of a career?

78. What are your current strengths and weaknesses?

79. What is the next step you see in your career?

80. What would you like to learn more about?

81. What would you like to be better at / in which areas would you like to grow?

82. In the next month, what would you like to do differently from last month?

83. Tell me about something new you have learned.

84. What tasks do you most and least enjoy?

85. What would you like further training or clarification on?

86. What are your long-term and short-term career goals?

87. What would you like further training on?

88. What resources are you in need of?

89. What areas of the industry are you interested in?

90. Is there anyone you would like me to help connect you with?

91. How do you feel about your goals for this quarter?

92. What would you like to achieve by the end of the year?

93. What can we do to achieve your goals?

94. Is there a specific role, whether within the company or outside of the company, you aspire to be in?

95. What is the big picture?

96. Why did you decide to get into [their field] as a career?

Team Dynamics

97. How is the team doing?

98. What have your interactions with your teammates been like?

99. What do you think about the team dynamics?

100. Do you have any difficulties working with anyone?

101. Do you feel you get enough support from your teammates?

102. What are the team’s strengths and weaknesses?

103. Is there anything you think we should consider changing? Why?

104. How can we improve how we operate as a team?

105. What do you think we can do to improve relationships between team members?

106. What do you think we could do better collaboratively as a team?

107. If you were the manager, what would you continue doing and what would you do differently?

108. Who do you admire the most on the team? Why?

109. What is one quality you wish you had from each teammate?

110. When there’s a disagreement with a teammate, how do you move forward?

111. What does your ideal team look like?

112. Who do you think is the most dependable teammate? Why?

113. How do you feel about how work is distributed within the team?

114. What is the team lacking?

Manager support

115. Do I offer you the right support for you to excel?

116. How could I be a better manager for you?

117. From what I’m currently doing as a manager, what works and doesn’t work for you?

118. What do you want me to stop doing?

119. What can I do to help you in your career goals?

120. What can I do to help motivate you?

121. If you were me, what would you do differently?

122. Is there anything I could do to invest more in your growth?

123. Do you think I give you enough autonomy?

124. What can I help you with before our next meeting?

125. Would you like more or less feedback?

126. What are some things past managers have done that you admire?

127. Would you like me to check-in more?

128. Am I providing enough guidance?

129. How are my communication skills?

130. What do you think I can do to improve my relationship with the team?

131. Do I set clear expectations?

132. Am I giving you clear direction?

133. What can I do to help you do your best?

134. Are you satisfied with the leadership style here?

135. What are the best parts of working with me? The difficult aspects?

Organization & culture

136. What’s the biggest problem of our organization?

137. After __X__ number of months/years at _company__, how do you feel overall?

138. How do you feel about the company so far?

139. What do you think of the team/company culture?

140. What has been pleasantly surprising to you about the workplace?

141. What made you want to work at this company?

142. Does the company live up to your expectations prior to starting?

143. Do you believe top managements’ visions align with one another?

144. Do you believe the entire organization is on the same page?

145. Do you believe our actions, what we’re working on, align with the company’s mission?

146. How happy do you think employees are?

147. How do you feel about the current direction or strategy of our company?

148. Do you believe our company follows what we preach when it comes to culture?

149. What do you wish our company would start doing?

150. What do you think the company can improve on?

151. Do you believe the company will be successful with current management?

152. What questions do you have about the company?