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Work Would You Rather Questions

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💼 Work deck

Work Would You Rather Questions

Four days for eighty percent, or five for full pay. A great boss and boring work, or a terrible boss and work you love. Never another meeting, or never another email.

Safe for a team away-day, and considerably more revealing than the icebreaker it looks like.

Questions in this deck

The full list.

  1. 1

    work four days for 80% pay or five days for full pay?

  2. 2

    have a great boss and boring work or a terrible boss and work you love?

  3. 3

    never attend another meeting or never write another email?

  4. 4

    be promoted past your ability or be stuck below it?

  5. 5

    work from home forever or work from an office forever?

  6. 6

    be paid more than you deserve and know it or less than you deserve and be respected?

  7. 7

    have a job with no deadlines or one with no meetings?

  8. 8

    know your colleagues' salaries or have them know yours?

  9. 9

    retire at 45 with just enough or at 65 with plenty?

  10. 10

    be indispensable and exhausted or replaceable and rested?

  11. 11

    have a manager who challenges you or one who protects you?

  12. 12

    do work that's seen or work that matters?

  13. 13

    be the expert nobody promotes or the generalist who runs things?

  14. 14

    start at eight and finish at four or ten and six?

  15. 15

    get feedback weekly or once a year and honestly?

  16. 16

    have a short commute and a small desk or a long one and a window?

  17. 17

    take a pay cut for calm or a raise for chaos?

  18. 18

    be known for one big project or for being reliable?

  19. 19

    leave on good terms and miss it or leave relieved?

  20. 20

    train someone who replaces you or never teach and stay stuck?

  21. 21

    have a job you can leave at the door or one that follows you home and fascinates you?

  22. 22

    be trusted completely and left alone or be supported closely and checked often?

  23. 23

    have a title without the money or the money without the title?

  24. 24

    work with people you like or work on problems you love?

  25. 25

    hire your own team or inherit a brilliant one?

  26. 26

    be the newest person in a great team or the most experienced in an average one?

  27. 27

    have a two-hour lunch every day or finish two hours early?

  28. 28

    do one thing exceptionally or five things competently?

  29. 29

    be told the truth about your performance or be left comfortable?

  30. 30

    have an unlimited holiday policy nobody uses or twenty-five days everyone takes?

  31. 31

    get a bonus you can't predict or a salary you can?

  32. 32

    have a mentor or have a protege?

  33. 33

    be famous inside your industry or be paid well and unknown?

  34. 34

    work nights alone or mornings in a crowd?

  35. 35

    have a job with obvious progress or one where the impact arrives years later?

  36. 36

    be made redundant with a year's pay or stay in a role going nowhere?

  37. 37

    have a manager who never praises you or one who praises everything equally?

  38. 38

    choose your hours or choose your projects?

  39. 39

    write the strategy or deliver the work?

  40. 40

    change career at forty or stay and always wonder?

  41. 41

    have every meeting stand up and last ten minutes or have half as many and let them run?

  42. 42

    be the person who says the hard thing or the person everyone finds easy?

  43. 43

    do repetitive work with good people or varied work alone?

  44. 44

    have a big office far away or a shared desk five minutes from home?

  45. 45

    be paid for hours or be paid for results?

  46. 46

    get a pay rise you didn't ask for or ask and get double?

  47. 47

    work for a small company that might fail or a large one where you might disappear?

  48. 48

    have your ideas used without credit or have credit for ideas you didn't shape?

  49. 49

    be the youngest in the room or the oldest and still learning?

  50. 50

    have three months off unpaid or three extra days a month forever?

  51. 51

    report to a committee or report to one difficult person who decides fast?

  52. 52

    be given impossible deadlines and freedom or reasonable ones and constant oversight?

  53. 53

    have colleagues who become friends or colleagues who stay professional and reliable?

  54. 54

    do work that helps strangers or work that pays for your family's comfort?

  55. 55

    be passed over once and told exactly why or be promoted and never know if you earned it?

  56. 56

    take a job for the learning or take one for the security?

  57. 57

    have a commute you can read on or no commute and no transition?

  58. 58

    run a team of twenty or be brilliant on your own?

  59. 59

    be interviewed by someone tough or be hired on a recommendation and doubted?

  60. 60

    be irreplaceable in a small place or one of many in a famous one?

  61. 61

    have your work reviewed publicly or never have it looked at?

  62. 62

    have a quiet job and a loud life or a demanding job and quiet evenings?

  63. 63

    know exactly what you'll be doing in five years or have no idea and be excited?

  64. 64

    get an apology from a manager or get a better manager?

  65. 65

    be part of something growing fast and chaotic or something stable and slow?

  66. 66

    have training paid for or have time to use it?

  67. 67

    be the one who fixes things or the one who prevents them?

  68. 68

    sit near a window with noise or in a corner with silence?

  69. 69

    do a job your parents understand or one you can explain in five minutes and love?

  70. 70

    have a contract you can end tomorrow or one that protects you for three years?

  71. 71

    be praised in front of everyone or thanked privately and meaningfully?

  72. 72

    take the difficult project and maybe fail or the safe one and definitely succeed?

  73. 73

    work for a brilliant person who is hard work or a decent person who is average?

  74. 74

    have clear rules or have complete discretion?

  75. 75

    be asked your opinion constantly or be left to work in peace?

  76. 76

    have four bosses who agree or one who changes their mind?

  77. 77

    do a job you're good at or one you're still learning?

  78. 78

    have your salary published or have everyone's published including yours?

  79. 79

    finish everything by Friday or never quite finish and always be interested?

  80. 80

    be given a budget or be given a team?

  81. 81

    have the same job for twenty years or five different ones and no pension?

  82. 82

    be the expert people call or the manager people report to?

  83. 83

    travel for work often or never leave the same building?

  84. 84

    have honest colleagues who argue or polite ones who agree and do nothing?

  85. 85

    job share and halve your pay or work full time and rarely see your evenings?

  86. 86

    start your own thing and struggle or join something good and settle?

  87. 87

    have appraisal by numbers or by someone's opinion?

  88. 88

    be in the room when decisions are made or have the decisions explained well afterwards?

  89. 89

    be underpaid and learning fast or well paid and coasting?

  90. 90

    have a difficult first year and an easy decade or an easy start and a hard ending?

  91. 91

    get feedback that stings and helps or encouragement that changes nothing?

  92. 92

    leave a job at the right moment or stay and see it through?

  93. 93

    have a job title nobody understands or a plain one that undersells you?

  94. 94

    be responsible for money or responsible for people?

  95. 95

    have a week of deep work a month or short focused days every day?

  96. 96

    work somewhere with a strong culture you must match or somewhere indifferent where you can be yourself?

  97. 97

    be known for fixing a crisis or for a year where nothing went wrong?

  98. 98

    have a career with one long climb or three fresh starts?

  99. 99

    retire and be busy or retire and be genuinely idle?

  100. 100

    be remembered by your team or be remembered by the industry?

Questions people ask

Can I use this as a team icebreaker?

Yes — the four-day question alone will fill fifteen minutes.

Is anything here about salary?

One question asks whether you'd rather know your colleagues' salaries or have them know yours. It divides rooms.

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