Q & A Questions: 108 Questions to Ask When Starting a Conversation With Anyone

These are some pretty interesting times that we live in. On one hand, we can access more information about anybody and everybody at the tip of our fingers. Simply Google their name or stalk their LinkedIn, and you’ll be met with their life’s history. But on the other, we must ask ourselves how well we really know the people that we spend time around?  

In Dale Carnegie’s timeless classic How To Make Friends and Influence People, he emphasises the importance of developing a genuine interest in people. This can be done through asking questions, and listening and remembering their responses. Give people a chance to express themselves, and you’ll find that you’ll deepen your relationships with family, friends and colleagues.

If you are looking for even more ways to get to know your colleagues, friends or even family, try Brightful Meeting Games. You'll find the best icebreakers all in one place, completely free.

Here is a list of great conversation starters to help you learn more about people

1. What are your top three traits?

2. What’s something that makes you unique and completely different from anyone else?

3. What was your biggest failure?

4. What is the best compliment that you’ve ever received?

5. What’s something that everyone else does that you wish you didn’t?

6. How do you picture your ideal future?

7. What was your favorite subject in school?

8. How would someone else describe you?

9. If you could change one thing about yourself, what would it be?

10. What makes you the happiest?

11. What is the best advice you’ve ever received?

12. What was your biggest failure?

13. What is something that only you can do?

14. What are your top three positive traits?

15. How would your closest friends describe you?

16. What is one of the best memories you have?

17. What was the stupidest mistake you’ve ever made?

18. What was the stupidest thing you’ve ever done?

19. Why do you think you became the person that you are today?

20. What is something you do just to be different?

21. What is something you’re so good at that other people think that you’re lying?

22. If you could just have two friends, dead or alive, with whom would you want to spend time?

23. What’s one of the most amazing things you’ve seen?

24. What is something you want to be remembered for?

25. What’s something that would surprise people about you?

26. How would someone you loved describe you?

27. What’s one of the most important lessons you’ve learned from the past?

28. What was the most expensive thing you’ve ever purchased?

29. When and where were you the happiest?

30. What is something you want to do in your lifetime?

31. What’s one of the best memories you have?

32. Who has had the biggest influence on you in your life?

33. What’s one of the most amazing things you’ve seen?

34. What is the best compliment that you’ve ever received?

35. How would your boss describe you?

36. What’s something that you did that was embarrassing but taught you a lesson?

37. What is something that only you can do?

38. What are you expecting in the next ten years?

39. How would your best friend describe you?

40. What is something that you’re good at that you should be proud of?

41. Who do you admire?

42. What are your top three passions?

43. What makes you different from everyone else?

44. What is something that you’re really good at?

45. How would the people you spent the most time with describe you?

46. What is your biggest failure?

47. What is the best compliment that you’ve ever received?

48. What makes you the happiest?

49. What is something you’re so good at that other people think that you’re lying?

50. What are your top three dreams?

51. How would a stranger describe you?

52. What is one of the worst things you’ve ever seen?

53. What is something that you want to be remembered for?

54. What is the most embarrassing or funny thing that has happened to you?

55. What’s something that you want to do in the future?

56. What is the best piece of advice that you’ve ever received?

57. What are you interested in that most people haven’t heard of?

58. What is something you’re so good at that other people think that you’re lying?

59. What is something you’re really good at?

60. What is the best piece of advice you’ve ever received?

61. How would the people you’re with right now describe you?

62. What’s your biggest fear in life?

63. What was the stupidest mistake you’ve ever made?

64. What is the most amazing thing you’ve ever seen?

65. What was the biggest mistake you’ve ever made?

66. What is your “bucket list” of things that you want to achieve?

67. What was the biggest lesson you learned?

68. Who do you admire?

69. What makes you unique?

70. What is the most embarrassing or funny thing that has happened to you?

71. What’s the best way to describe you?

72. What’s the most expensive thing you’ve ever purchased?

73. What was the stupidest thing you’ve ever done?

74. What’s something you could teach me about?

75. What is something you’re so good at that other people think that you’re lying?

76. What are you most proud of when it comes to your personal life?

77. What was your first job?

78. What is something you’re proud of?

79. What’s something you’re so good at that other people think that you’re lying?

80. What was the stupidest mistake you’ve made?

81. What is your bucket list?

82. What is something that you want to learn more about?

83. What is the stupidest thing you’ve ever done?

84. What are you most proud of?

85. What was your biggest failure?

86. What was your biggest failure?

87. What’s one of your worst memories?

88. What’s something that you’re really good at that people always compliment you on?

89. What’s one of your favorite memories?

90. If your friends were writing an autobiography of you, what would they call it?

91. What’s something that you want to do in the future?

92. What is something that you’re really proud of?

93. What was your biggest failure?

94. What is something that everyone else does that you wish you didn’t?

95. If you won the lottery tomorrow, how would you change your life?

96. What’s the biggest regret of your life?

97. What do you look at to keep yourself motivated and inspired?

98. What’s one of the best memories you have?

99. What is something you’re really good at?

100. What is something that makes you unique?

101. What’s the worst thing that’s happened to you?

102. What’s something you are proud of, regardless of success or failure?

103. How would your parents describe you?

104. What is the most embarrassing or funny thing that has happened to you?

105. What’s something you’re so good at that other people think that you’re lying?

106. What is the most difficult obstacle you’ve ever overcome?

107. What was the biggest mistake you’ve ever made?

108. What is the best piece of advice you’ve received?