200 (Not Boring) Questions To Ask To Get To Know Someone Better Pt 2

Turning small talk into real talk.

Let’s continue with the next series of questions on getting to know someone better.


No matter how a person feels about his or her job, the fact is, pretty much everyone spends a lot of time and energy at work. To help you get to know someone better, “facilitate a conversation where you are left knowing how they feel about their career,” Hendrix says. For example:

41. What’s your favorite thing about your current job?

42. What annoys you most?

43. What’s the career highlight you’re most proud of?

44. Do you think you’ll stay at your current company awhile? Why or why not?

45. What type of role do you want to graduate to after this one?

46. Are you more of a “work to live” or a “live to work” type of person?

47. Does your job make you feel happy and fulfilled? Why or why not?

48. How would your 10-year-old self react to what you do?

49. What do you remember most about your first job?

50. Did you start working immediately after finishing school? Why or why not?

51. What’s the worst job you’ve ever had?

52. What originally got you interested in your current field of work?

53. Have you ever had a side hustle or considered having one?

54. What’s your favorite part of the workday?

55. What’s the best career decision you’ve ever made?

56. What’s the worst career decision you’ve ever made?

57. Do you consider yourself good at networking?

58. What career advice would you give to your younger self?

59. Do you believe in having a “five-year plan”?

60. How do you separate your work life from your home life?

61. When will you know you’ve “made it”?

62. Are you looking forward to retiring, or do you plan to work as long as possible?

63. Have you ever had “imposter syndrome”?

64. What do you think about workaholics?

65. What qualities do you look for in a boss?

66. Do you have a professional mentor? If not, do you want one?

67. Do you have a work best friend?

68. Are you into after-work happy hours?

69. How do you motivate yourself in your career?

70. What’s the best career advice you’ve ever heard?

71. What’s the worst career advice you’ve ever received?

72. When you started your current job, what most surprised you?

73. How do you pick yourself back up after making a mistake at work?

74. How do you deal with work stress?

75. What energizes you about your career?

76. What’s one work-related thing you want to accomplish in the next year?

77. Who has had the biggest impact on your career choice?

78. What does your family think of your career?

79. What’s the best thing you’ve learned in your current position?

80. If you could do it all over again, would you pursue the same career? Why or why not?


A great way to get to know someone on a more personal level? Learn about the people they love. “Asking questions about close relationships can lead to stories, and sharing stories leads to connection and an experience of being seen by one another,” Hendrix explains. Try:

81. How much time do you spend with your family?

82. Who do you most like spending time with and why?

83. Were you close with your family growing up?

84. How do you define your family now?

85. What traits are most important to you in your family members?

86. Who are you the closest to and why?

87. Do you want a family of your own?

88. What’s your favorite family tradition?

89. If you could change your relationship with a family member, would you? If so, with whom?

90. What was it like growing up as the youngest/oldest/only child?

91. Does your family take vacations together?

92. What’s your favorite family memory?

93. What TV family most reminds you of your own?

94. Do you ever wish you were raised differently?

95. What’s the best piece of advice a family member has given you?

96. Do you wish you had more siblings? If so, why?

97. Did you ever hide anything from or lie to your parents?

98. If you had a family business, what would it be?

99. Do you and your family have any nicknames for each other?

100. What’s your favorite way to spend time with your family?

101. How do you show your family you love them?

102. Have you ever been to a family reunion?

103. What’s the most important holiday you spend with your family and why?

104. Who in your family would you describe as a “character”?

105. How do you feel about family events?

106. What’s something your family would be surprised to learn about you?

107. Which family member do you confide in most?

108. How do you deal with arguments between family members?

109. If you have children, how do you want to raise them?

110. What’s more important: family or friends?

111. Do you have any friends you would consider family?

112. Has your family ever pressured you to act a certain way?

113. Did you ever get to meet your great-grandparents?

114. What personality traits do you share with your relatives?

115. What physical traits do you share with your relatives?

116. What stories did your family members tell you growing up?

117. How did your parents (and/or grandparents) meet?

118. What makes you proud of your family?

119. Who’s the newest member of your family?

120. What can always bring your family together?

And that’s enough for today.  80 more questions to go.   You’re probably seeing these questions in your dreams.  Oh, gave away some of tomorrow’s questions.  See you then.


Author: Dennis Hickey

There are no limits to success to those who never stop learning. Learning will nourish your personal growth. I hope you enjoy this website and visit often so you too keep learning and growing.

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