Want Better 1:1s? Start With These 100 Questions

6 min read
Jul 17, 2019 11:40:34 AM

The modern workforce values coaches far greater than bosses, according to Gallup's 'State of the American Workplace'. This means that in your leadership, you should frame yourself as a part of the team, working for their success, rather than as a task manager, maximizing outputs and minimizing uniqueness. Great coaching starts with great questions. As a leader, your imperative is to show your people the unique value of their contributions to the organization, and you can’t do that unless you first know them inside and out. To help in that process, we have compiled 100 of the best questions to ask in your 1:1s to improve your effectiveness as a leader, as well as increase your team’s engagement.

Extra Reading: Wondering how to conduct an effective one on one? We’ve compiled everything you need to know.

Ice Breaker / Kickstarter

1. What’s on your mind?

2. What is your current rhythm in or out of work?

3. What motivates you to come into work each day?

4. How is life outside of work? 

5. What is one area we could do better in? What steps would you recommend to improve?

6. What are your top 3 super powers?

7. What did you want to be when you grew up? 

8. When have you had the most fun at work (and it doesn't have to be this company, it can be past roles too)?

9. If money were no object, what would you do every day? 

10. How well do you feel like you relate to you coworkers? Do you view them as friends? 

11. Pick a question to ask me about my background and / or career. 

Day-to-day Role:

12.  List three things that motivate you to do your work each day. 

13. When was the last time you got stuck and needed help at work? Who/what helped you get unstuck? 

14. What part of your job do you enjoy the most? And which part do you enjoy least? 

15. From a resources standpoint, is there anything that would help you do your job better? 

16. Have you been asked to do anything as part of your job that pushed you out of your comfort zone? 

17. List the top three things that you feel waste time during your day. 

18. If you were your own coach, what would you suggest for yourself?

19. What makes for a great day at work? 

20. How often do people ask you for help? What do they ask for and how long does it take you? 

21. List 3 things you would like to see happen everyday you come to work. 

22. What part of your job do you wish you didn't have to do? 

23. What’s not fun about working here?

24. Who do you admire in the company?

25. If you were me, what changes would you make?

26. What’s the real challenge with [the project] from your perspective?

27. What’s one thing we could change about work for you that would improve your personal life?

28. Overall, are you feeling compensated properly here?

29. What aspect of your job you would like more help or coaching?

30. What roadblocks or frustrations do you have that I could help resource you to eliminate?

Rear View Mirror:

31. What is a mistake you made recently that you learned a lot from? 

32. What’s a recent situation you wish you handled differently? What would you change?

33. What goals do you feel like you have accomplished professionally since you began work here? 

34. Are you having fun? Tell me about the most fun you have ever had while working here. 

35. Are you happy that you left your previous job for this one? 

36. What is the best compliment you have ever received at work? 

37. Tell me about the last time you felt proud of yourself for solving a problem on the job. 

38. What was one task from the last week you really enjoyed?

39. Have you helped a teammate recently? Tell me about it. 

40. What’s one thing you’ve experienced while working here that was different from what you expected?

41. In the last few weeks, who’s one team member you’ve enjoyed working with?

42. Do you feel like you’re using your strengths and talents here?

Forward Looking:

43. Are there any areas of your job that you would like additional training in? 

44. Tell me about your long term career goals. 

45. Who do you really admire? 

46. What are you doing really well that is helping you move towards your goals? 

47. What parts of the business would you like to be more involved in or learn more about? 

48. How long do you see yourself working here? 

49. What would make you leave this job for another?

50. What’s the biggest opportunity that we’re missing out on?

51. What are we not doing that we should be doing? 

52. What upcoming project are you most looking forward to?

53. What department or position would you like to learn more about?

54. Is there any cross-functional training that would help you feel equipped to do your job better?

Organizational Feedback:

55. What is one thing we aren't currently doing, but could be doing to grow the business? 

56. What are one or two things in our work that could be done more efficiently? 

57. Generally speaking, are you happy being employed here? 

58. If the need should arise, do you feel comfortable filling any roles other than your own in the office? 

59. How often do you think staff meetings are needed to keep everyone on the same page? 

60. What is one thing we could do to make the office more comfortable/enjoyable/fun (or just better) without spending much money? 

61. On a scale of 1-10 what level of loyalty do you feel to the company as a whole? 

62. Name the first two things you would do if you were put in charge for a day. 

63. In what ways could we improve communications around the office? 

64. Sometimes an organization gets focused on the tactical and day to day they forget to take time to focus on being creative and fostering innovative ideas. What can we do to be more creative and innovative? 

65. Do you enjoy office functions (parties, dinners) or would you rather be rewarded in some other way? 

66. Which is most important to you? Our mission, core values, or vision? 

67. Do you think our company is loyal to its employees? Why or why not?

68. What are your favorite parts about our culture?

69. What is one thing our organization says we are about, but in actuality are not about?

70. Do you feel like senior leadership cares about their staff?

71. Do you feel safe and comfortable working here?

Peer Feedback:

72. Tell me about one coworker that you feel does a particularly good job. 

73. Have any outgoing employees expressed specific issues or concerns with you? What were they? 

74. Without naming anyone specifically, do you know of anyone in the office that is unhappy? 

75. Who would you like to work more often with? Why?

76. Is everyone pulling their weight on the team?

77. Are you uncomfortable giving any of your peer’s constructive criticism? If so, why?

78. Do you feel you’re getting enough feedback? Why/why not?

79. Do you feel appreciated and liked by your peers?

80. Do you enjoy working on teams or alone?

Upward Feedback:

81. What is one thing that I could do to help you be more productive? 

82. What is one thing that me or the company could do support you in achieving your goals? 

83. Speaking honestly, what is one criticism you would have for me? 

84. Do you feel like you receive feedback often enough? 

85. How well received do you feel your opinions are when you offer them up? 

86. Is this job fitting in well with your life as a whole? 

87. What is the biggest challenge we will face this year?

88. Do you feel overworked, under-worked, or just the right workload?

89. What do you like about my management style? What do you dislike?

90. What have your past managers done that you’d like me to also do or not do?

Goal Setting / Development:

91. What work are you doing here that you feel is most in line with your long term goals?

92. What skills would you like to develop right now?

93. What do you think are the key skills for your role? How would you rate yourself for each of them?

94. Do you feel we’re helping you advance your career at a pace you would like? Why or why not?

95. What are your big dreams in life? Are you making progress on them?

96. If you had millions of dollars, what would you do every day?

97. Personally, what traits would you like to develop quicker? 

98. Are you overwhelmed by your lofty goals? Would you like help making smaller goals?

99. Who do you really admire? Why?

100. What do you want to do in your next job?

Our hope is that you’d bookmark this resource and continue to come back for more great questions to ask your team.

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