For professional trivia hosts, thinking up questions to ask others comes naturally – live trivia companies in New York City and elsewhere are in the question writing business, after all. But for managers and business owners like you with budgets to meet, sales targets to hit and strategic objectives to fulfill, taking the time to craft the perfect questions to learn more about your staff is likely a luxury that you simply cannot afford.

As such, here’s a nice, big list of 100 non-threatening, office-friendly questions you can ask your employees, which will go a long way beyond “how are you” to show that you truly care about them not just as workers, but as people (they also double as some revealing interview questions…!):

  1. 1.     How are your children/parents?
  2. 2.     Where did you and your husband take your honeymoon?
  3. 3.     What’s your favorite type of cuisine?
  4. 4.     Do you have a favorite movie genre?
  5. 5.     What was the most exotic vacation you’ve been on?
  6. 6.     What kind of music do you listen to?
  7. 7.     Do you prefer Windows or Mac? Why?
  8. 8.     What is your dream car?
  9. 9.     What was the most incredible exotic place you’ve ever traveled to?
  10. 10.   What’s your biggest pet peeve?
  11. 11.   Do you have any pets?
  12. 12.   If you could paint this office any color you wanted to, what would it be?
  13. 13.   Are you a plant person?
  14. 14.   Which of your 5 senses is the strongest? How about weakest?
  15. 15.   Do you prefer white, dark or milk chocolate?
  16. 16.   Do you have a favorite animal?
  17. 17.   Where would you choose to live: by the ocean, in the mountains or in the woods?
  18. 18.   What is the 1 thing in this world you are most proud of?
  19. 19.   Do you have any hobbies?
  20. 20.   What’s your favorite cartoon character? How about Muppet?
  21. 21.   What was your favorite TV show growing up?
  22. 22.   What was the last really great book you read? Why?
  23. 23.   Where were you during [fill in famous event here]?
  24. 24.   Have you ever had a letter or Op-Ed published in the newspaper?
  25. 25.   Do you volunteer anywhere?
  26. 26.   Do you know any good riddles or brain teasers?
  27. 27.   What other languages do you know?
  28. 28.   Have you ever won anything? What was it?
  29. 29.   What’s the most incredible view you’ve ever seen?
  30. 30.   Are you handy at fixing things?
  31. 31.   If you could close your eyes and be anywhere on earth when they opened, where would you be?
  32. 32.   What’s your favorite fruit/vegetable? Least favorite?
  33. 33.   If you could be on any TV game show, which one would it be?
  34. 34.   Who would you choose to be your mentor, if you had the choice?
  35. 35.   How long have you lived in this town?
  36. 36.   What’s your favorite thing to do on weekends?
  37. 37.   If you could choose 1 amenity to add to the workplace, what would it be?
  38. 38.   What’s your favorite color?
  39. 39.   What’s your favorite nursery rhyme?
  40. 40.   What was your all-time, best-ever Halloween costume?
  41. 41.   Have you ever been in a helicopter? How about a submarine?
  42. 42.   Do you remember your first time in an airplane?
  43. 43.   What’s the 1 dish you absolutely, positively will never, ever eat?
  44. 44.   Are you artistic?
  45. 45.   Have you ever sang karaoke? What’s “your” song?
  46. 46.   Who did you first see live in concert?
  47. 47.   What’s your favorite flavor Jelly Belly?
  48. 48.  If you enjoy wine, what’s your favorite region?
  49. 49.   Have you ever run a marathon? How about climb a mountain?
  50. 50.   What’s a fear you’re proud to have overcome?
  51. 51.   Have you ever had to serve on jury duty? What was it like?
  52. 52.   Have you ever had any type of facial hair? (please, for men only…)
  53. 53.   Which museum is your absolute favorite? Which are you dying to go to?
  54. 54.   Who was your most influential schoolteacher, and why?
  55. 55.   Do you have a favorite place you turn to for news?
  56. 56.   Do you maintain a blog? What do you blog about?
  57. 57.   Which sports team(s) do you root for?
  58. 58.   Who was the most influential person in your life?
  59. 59.   Do you enjoy exercise, yoga or meditation?
  60. 60.   What was (or is) your favorite video game?
  61. 61.   Who is your favorite comedian?
  62. 62.   What was the last thing you heard or saw which made you laugh out loud?
  63. 63.   Have you ever met anybody famous? Do you have any photos I could see?
  64. 64.   Do you cook? What’s your favorite recipe?
  65. 65.   Do you play a musical instrument?
  66. 66.   Can you recommend any good shows for me to see?
  67. 67.   Have you ever gone camping? What’d you think?
  68. 68.   If you had just 1 box for all of your stuff, what would you put in it?
  69. 69.   What was the longest trip you ever took?
  70. 70.   Have you ever been told you look like a celebrity? Who? Do you agree?
  71. 71.   If you could go back in time to any era, which would it be?
  72. 72.   Which superhuman power do you wish you had?
  73. 73.   What would be the title of your autobiography?
  74. 74.   Who would play you in the movie adaptation of your life?
  75. 75.   What’s your favorite myth, legend or fairy tale?
  76. 76.   What was the single-most influential event in your lifetime?
  77. 77.   Are you right or left handed?
  78. 78.  What’s 1 professional or personal skill you wish you had that you don’t?
  79. 79.   What’s the 1 movie or novel you wish there was a sequel to?
  80. 80.   Do you have a favorite board or card game?
  81. 81.   Do you know any good trivia questions?
  82. 82.   Have you ever driven/piloted anything other than a car or light truck?
  83. 83.   Have you ever had anyone throw you a surprise party?
  84. 84.   If you were doing something else besides this, what would it be?
  85. 85.   What’s the coolest experience you ever had?
  86. 86.   Do you have a favorite season?
  87. 87.   Have you ever been to a “black tie” event? What was it like?
  88. 88.   What’s your favorite guilty pleasure when it comes to candy?
  89. 89.   Can you read music?
  90. 90.   Have you ever been on the radio or TV?
  91. 91.   What’s the 1 piece of advice you would give others about life?
  92. 92.   If you could live to see 1 future event, what would it be?
  93. 93.   What’s the 1 thing you’ve waited in line the longest for?
  94. 94.   If you could start your own dream business, what would it be?
  95. 95.   What do you like on your pizza?
  96. 96.   Do you have a favorite article of clothing?
  97. 97.   Have you (or would you) ever skydive?
  98. 98.   What’s the longest book you’ve ever read?
  99. 99.   What excites you so much that it keeps you awake the night before?
  100. 100.  If you could splurge on 1 must-have item, what would it be?

Any one of these questions will invariably reveal something about your staff, allowing you to get to know them better, and to help build mutual openness and trust.

Can you think of any others?