A team offsite

A team lead opening an offsite with colleagues who report to her and see each other every day at work. There is a power difference and they all go back to work on Monday.

99 questions
  1. When did you last run to catch something, and did you catch it?
  2. When did you last argue out loud with a machine?
  3. When did you last hold a door open far too long?
  4. When did you last arrive far too early, and how did you kill time?
  5. When did you last speak first to someone in a lift?
  6. When did you last raise your hand before you were sure?
  7. When did you last teach somebody a shortcut, and did it work?
  8. When did you last take a shortcut that took longer?
  9. When did you last stay up past midnight finishing something?
  10. What advice do you hand out that you have never once taken?
  11. What are you good at that you would rather nobody found out?
  12. What do you always say yes to and always regret by Friday?
  13. What did a teacher tell you off for that you still do?
  14. What cannot you stand in others that you do every single day?
  15. What do you say you will do at the weekend and never do?
  16. What could you teach me to do properly in the next ten minutes?
  17. What do you know how to fix that most people would throw away?
  18. How exactly do you make your coffee or tea in the morning?
  19. What's a shortcut you worked out yourself that nobody taught you?
  20. What smell do you notice that nobody else in the room does?
  21. What's the hardest thing you can do with your hands?
  22. What's the right way to end a phone call?
  23. How do you decide which queue to join at the supermarket?
  24. What could you draw from memory better than anyone here?
  25. What does everyone do wrong that you know the right way to do?
  26. Do I seem like someone who sings in the car? Why or why not?
  27. Guess what the person on your left eats for breakfast, and why.
  28. Do I seem like someone who keeps every receipt? Why or why not?
  29. Guess which of us was the loudest child, and why.
  30. Guess who here would carry a spider outside. Why them?
  31. Guess how the person on your right spends a free Sunday morning, and why.
  32. Guess what I would order in a restaurant I've never been to. Why?
  33. Do I seem like someone who reads the comments? Why or why not?
  34. Guess who here has a collection nobody knows about. Why them?
  35. When did you last read the manual before pressing the button?
  36. When did you last fix something at home with the wrong tool?
  37. When did you last cook a dish from memory, and who taught you?
  38. When did you last mute yourself to laugh at something off-camera?
  39. When did you last get lost without a phone to save you?
  40. When did you last kill a houseplant?
  41. When did you last teach someone to do something with their hands?
  42. When did you last apologise to a machine?
  43. When did you last build something with your hands that still exists?
  44. When did you last leave a party early, and what did you say?
  45. When did you last get a haircut you had to live with?
  46. When did you last send a message to the wrong chat window?
  47. When did you last abandon a book halfway, and at which page?
  48. When did you last stop to watch a stranger do their job well?
  49. When did you last see your name spelled wrong on something official?
  50. What kitchen rule do you break every single time you cook?
  51. What did work teach you that your friends now complain about?
  52. What hobby do you own all the equipment for and never do?
  53. What do you eat constantly and would never serve to a guest?
  54. What invitation do you always accept and dread by the day itself?
  55. What did you teach yourself wrong and still use anyway?
  56. What part of your work do you enjoy that others find boring?
  57. What do you leave until the last minute and still get right?
  58. What cable are you keeping for a device you no longer own?
  59. What did every other child find easy that you found impossible?
  60. What do you refuse to automate, and how long does it take?
  61. What lives in your bag that you have never once needed?
  62. What will you finish this year that you said that about last year?
  63. What did you hate at first and now defend to other people?
  64. What kind of message do you rewrite five times before sending?
  65. What have you never read that everyone assumes you have?
  66. What tradition do you complain about and would miss if it stopped?
  67. What small detail do you fix that nobody else ever notices?
  68. What do you refuse to lend, and who ruined it for everyone?
  69. What did you assume on your first day that turned out wrong?
  70. What can you fix that most people pay someone else to fix?
  71. What could you teach us to do properly in ten minutes?
  72. What's the right way to load a dishwasher, and who taught you?
  73. What's the best way to spend three hours in your hometown?
  74. What's in your fridge right now that you could turn into dinner?
  75. What do you make that people always ask you to bring?
  76. What do you spot on a walk that nobody with you sees?
  77. What do you know well enough to shout at the television about?
  78. What's a skill from an old job you never get to use here?
  79. What did you spend an entire weekend learning and never use again?
  80. What's a stain or a mess you know exactly how to get out?
  81. What have you repaired at home using nothing but a video?
  82. What's the first thing beginners get wrong at something you do well?
  83. What can you do with your hands that you learned by watching someone?
  84. What software do you know so well that watching others use it hurts?
  85. What's within arm's reach right now that you'd hate to lose?
  86. What's a word your family uses that nobody else would understand?
  87. Do I seem like someone who makes the bed every morning? Why?
  88. Guess what I do first when I get home, and why you think so.
  89. Guess what the person on your left does on a Saturday morning, and why.
  90. Guess which of us could talk their way out of a parking ticket. Why?
  91. Guess who here still owns a toy from childhood, and why them?
  92. Guess my first job, and what makes you say that.
  93. Guess what I would bring to a potluck, and why you expect that.
  94. Do I seem like someone who talks to strangers on trains? Why?
  95. Guess what I wanted to be at ten years old, and why.
  96. Guess who here would reach the karaoke microphone first, and why them?
  97. Do I seem like someone who keeps a houseplant alive? Why or why not?
  98. Guess how I spend a free evening, and what makes you think that.
  99. Guess what's in my bag that nobody would expect, and why.