Modern life is very busy, and it’s easy to find distractions from those more meaningful questions that float into our minds (usually while we lay awake in bed!). But that doesn’t mean we don’t all have our own thoughts, ideas and philosophies. We tend to conceal these thoughts and feelings, thinking that they’re too personal to share and that nobody would be interested in hearing them.

An effective way to get to break through superficial conversations and get to know someone else on a much deeper level is by asking personal questions that bring to surface these deeper ponderings. The next time you are unwinding with a colleague or a close friend, try asking them a personal question and see if they’re willing to share. You may find that by giving them an outlet to talk about themselves, they may find it therapeutic. If you pay attention and listen, you’ll also learn more about them, boosting your relationship with them to a deeper level.

Sometimes it takes a bit of icebreaking to get to more personal questions. If you sense the mood is a bit too stiff, then play a round of Brightful Meeting Games first. It will be sure to loosen everyone up and prime them for more meaningful relationship building.

Here’s a list of 92 Insightful Personal Questions to Ask

1. Why are you passionate about what you do?

2. Where do you see yourself in 5 years’ time?

3. What do you think makes a good leader?

4. Do you think money is important?

5. What makes you the happiest?

6. What is the most surprising fact you’ve learnt about yourself?

7. What are you afraid of?

8. What is your personal philosophy in life?

9. What do you think your role is in this world?

10. What do you believe is true about human nature?

11. When it comes to your work life, how much is due to your hard work and how much to the environment?

12. Who is your hero?

13. How do you spend your time?

14. What do you wish you had asked your parents before they passed away?

15. What is the best and worst advice you have received?

16. What does it mean to you to make a difference in the world?

17. Do you think that education is important?

18. Where is the best place in the world you’ve ever been to?

19. What are you most proud of?

20. Where is there room for improvement in your life?

21. What do you think is the most beautiful thing you’ve ever seen or experienced?

22. How do you balance your personal and professional life?

23. What do you think makes a great leader?

24. What are you most thankful for?

25. What is the biggest decision you’ve had to make?

26. What has impacted you the most?

27. Does listening to music affect you, and how?

28. What does your daily routine look like?

29. What was the worst phase in your life?

30. What do you believe is most important for happiness in life?

31. How do you spend your weekend?

32. What is your favourite movie or book series?

33. What were the best experiences and events that happened to you in the last 12 months?

34. What are you most passionate about?

35. What do you do when life gets hard?

36. What do you do to combat negative thoughts in your life?

37. What do you want to be known for after you die?

38. What makes you different from others?

39. How does it feel to be your age?

40. How would you define success?

41. What is the difference between ordinary and extraordinary?

42. How would you describe your personality?

43. What do you hope to accomplish in the future?

44. How is your relationship with your parents?

45. What is the first thing you think of when you wake up?

46. Do you like being able to communicate with others through social media?

47. What is your favourite book?

48. What motivates you in life?

49. Who is your role model?

50. How does your family feel about your work?

51. How do you feel about your relationships?

52. What are you most grateful for in your life?

53. What is the most important lesson you learnt in life?

54. How do you balance work and leisure?

55. Do you hold any convictions that you are willing to die for?

56. What is the biggest regret you have in your life?

57. Where is your favourite place to relax?

58. What inspires you?

59. How would your friends describe you?

60. What are you afraid of?

61. Is money important to you?

62. What do you do to de-stress?

63. What is a quality you admire in others?

64. Would you relocate to a place where you don’t have any family or friends?

65. How do you make decisions?

66. What is your greatest achievement?

67. How do you feel about your relationships with your family?

68. Where are you currently in your life?

69. Do you think that technology is improving lives?

70. What’s your favourite quote?

71. Who do you look up to?

72. What do you do in order to keep your friends and family close?

73. How do you react to your own mistakes?

74. What are your ambitions in life?

75. What was the best phase in your life?

76. What is your favorite quote and why?

77. Who has influenced you the most?

78. What is the hardest thing you’ve ever done?

79. Who inspires you?

80. What do you like doing in your free time?

81. How do you react to change in your life?

82. What is the biggest obstacle/challenge you are facing right now?

83. How do you live a productive life?

84. What qualities do you think are important in a family?

85. How important is your family to you?

86. What book and movie spoke to you, and in what way?

87. What do you think of your generation?

88. What will people say about you at your funeral?

89. What is one thing you want to let go of this year?

90. What was the last place you went to?

91. What do you think is the purpose of life?

92. If you were going to have an operation, what would your operation be about?