100 Questions

Work Most Likely To Questions: Fun, Realistic Scenarios for Colleagues

Kick off your team game night with relatable, workplace-themed Most Likely To questions. These prompts spark candid laughs and friendly debates as colleagues reveal their quirks, routines, and little workday mysteries. Perfect for breaking the ice during onboarding, team building, or after-work gatherings.

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All 100 Questions

1

Who is most likely to...

text their own calendar over meeting etiquette

2

Who is most likely to...

forget to mute their mic during a video call

3

Who is most likely to...

become the go-to person for IT support for the team

4

Who is most likely to...

send a casual Slack message during a serious deadline

5

Who is most likely to...

cancel a meeting at the last minute to protest a policy

6

Who is most likely to...

become the resident spreadsheet wizard

7

Who is most likely to...

forget to save a document right before a crash

8

Who is most likely to...

text a coworker about lunch plans mid-standup

9

Who is most likely to...

become the master of the agenda and never miss a point

10

Who is most likely to...

forget to clock out and stay late accidentally

11

Who is most likely to...

text their manager with a typo-filled update

12

Who is most likely to...

become the team cheerleader during tough projects

13

Who is most likely to...

forget a client call after a calendar invite changes

14

Who is most likely to...

text their boss to ask for flexible hours

15

Who is most likely to...

become the coffee savant who brews the best office coffee

16

Who is most likely to...

forget to attach the file in an important email

17

Who is most likely to...

text a colleague to cover a shift at the last minute

18

Who is most likely to...

become the most reliable reviewer for drafts

19

Who is most likely to...

forget their badge at the door and improvises

20

Who is most likely to...

text a mentor for feedback right after a presentation

21

Who is most likely to...

become the person who remembers everyone’s birthday

22

Who is most likely to...

forget to log a billable hour before the deadline

23

Who is most likely to...

text the best practice for onboarding a new hire

24

Who is most likely to...

become the go-to for conflict resolution in the team

25

Who is most likely to...

forget to update the project status in the spreadsheet

26

Who is most likely to...

text a colleague about a quick win during a crisis

27

Who is most likely to...

become the master of the inbox with perfect prioritization

28

Who is most likely to...

forget to respond to an urgent email thread

29

Who is most likely to...

text a colleague to celebrate a win after the meeting

30

Who is most likely to...

become the calm voice during a high-pressure kickoff

31

Who is most likely to...

forget to set the status on a task board

32

Who is most likely to...

text their supervisor with a polished update every Friday

33

Who is most likely to...

become the expert on company policies during audits

34

Who is most likely to...

forget to back up their laptop before a trip

35

Who is most likely to...

text a coworker to brainstorm ideas late at night

36

Who is most likely to...

become the mentor for new hires in the first week

37

Who is most likely to...

forget to log out of the shared computer

38

Who is most likely to...

text their team a concise summary after a long call

39

Who is most likely to...

become the champion of cross-team collaboration

40

Who is most likely to...

forget to mention a risk in the weekly update

41

Who is most likely to...

text a colleague to double-check a budget

42

Who is most likely to...

become the master of writing crisp meeting minutes

43

Who is most likely to...

forget to bring the projector remote to a presentation

44

Who is most likely to...

text a teammate to celebrate a milestone

45

Who is most likely to...

become the keeper of the team’s knowledge base

46

Who is most likely to...

forget to file a required compliance form

47

Who is most likely to...

text their manager with a constructive suggestion

48

Who is most likely to...

become the most punctual person in the department

49

Who is most likely to...

forget to update contact lists after a promotion

50

Who is most likely to...

text a coworker to cover an urgent task

51

Who is most likely to...

become the wizard of calendar invites and room bookings

52

Who is most likely to...

forget to save a draft before a network outage

53

Who is most likely to...

text their colleague to defend a dubious deadline

54

Who is most likely to...

become the person who can de-stress a tense standup

55

Who is most likely to...

forget to check in with a remote teammate

56

Who is most likely to...

text a vendor with a courteous, firm tone

57

Who is most likely to...

become the habits role model for new staff

58

Who is most likely to...

forget to fill out an expense report

59

Who is most likely to...

text their group to test a new software feature

60

Who is most likely to...

become the go-to person for presentation design

61

Who is most likely to...

forget to update the team about a policy change

62

Who is most likely to...

text a colleague to propose a quick retro after a project

63

Who is most likely to...

become the liaison for cross-functional projects

64

Who is most likely to...

forget to share the final version of a document

65

Who is most likely to...

text a teammate to celebrate a successful rollout

66

Who is most likely to...

become the most reliable person for last-minute tasks

67

Who is most likely to...

forget to confirm a meeting room booking

68

Who is most likely to...

text their manager to request a resource increase

69

Who is most likely to...

become the guardian of project deadlines

70

Who is most likely to...

forget to sync with the product team

71

Who is most likely to...

text a coworker to align on a risky decision

72

Who is most likely to...

become the champion of work-life balance in the team

73

Who is most likely to...

forget to notify the team about a change in plans

74

Who is most likely to...

text a junior colleague to explain a complex process

75

Who is most likely to...

become the master of creating clear, actionable briefs

76

Who is most likely to...

forget to sign off on a critical document

77

Who is most likely to...

text their supervisor to request a one-on-one feedback

78

Who is most likely to...

become the resident data detective during audits

79

Who is most likely to...

forget to notify the client of a delay

80

Who is most likely to...

text a teammate to keep morale high during tough quarters

81

Who is most likely to...

become the keeper of the sprint backlog

82

Who is most likely to...

forget to update the project backlog after a meeting

83

Who is most likely to...

text a colleague to pitch a sustainable workaround

84

Who is most likely to...

become the central point of contact for escalations

85

Who is most likely to...

forget to include stakeholders in a critical email

86

Who is most likely to...

text a coworker to brainstorm a post-mortem plan

87

Who is most likely to...

become the person who documents all decisions

88

Who is most likely to...

forget to unmute to answer a question

89

Who is most likely to...

text their team to celebrate a successful demo

90

Who is most likely to...

become the master of effective onboarding checklists

91

Who is most likely to...

forget to set reminder notifications for deadlines

92

Who is most likely to...

text a colleague to review a risky proposal

93

Who is most likely to...

become the advocate for transparent communication

94

Who is most likely to...

forget to file a quarterly report

95

Who is most likely to...

text their manager with a gratitude note for support

96

Who is most likely to...

become the steward of the project roadmap

97

Who is most likely to...

forget to log off after a long day

98

Who is most likely to...

text a teammate to propose a cross-training session

99

Who is most likely to...

become the go-to for contract terms clarification

100

Who is most likely to...

forget to update the risk register after a new issue

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Why This Theme Works

Work settings are a goldmine for relatable behaviors, inside jokes, and everyday mishaps. Everyone has a distinct work style, from meeting-minute memory to late-afternoon energy crashes, which makes for lively conversations and light competition. These questions encourage teammates to share anecdotes, highlight strengths, and celebrate quirks in a respectful, fun way.

Best Occasions

Ideal for team socials, offsite retreats, or casual Friday gatherings. Works well with small to medium groups (6–20 people) where voices can be heard and everyone can participate. Integrate into icebreaker rounds, or mix into a longer game with quick-fire prompts during coffee breaks, lunch-and-learn sessions, or after-work mixers.

These work-themed Most Likely To questions are a sure-fire way to spark honest laughter and meaningful conversations among colleagues. Use them to break the ice, celebrate strengths, and build team camaraderie. Give them a try at your next meeting or social—you might discover someone you didn’t know well who shares a surprising and relatable habit.

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