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Why people ask this
This question works because the yes-or-no split always surprises the room — someone answers in a way nobody expected, and the conversation starts from there. Work and school questions are popular because everyone has the same bad-meeting and dumb-detention archetypes — recognising them in someone else’s life is the whole point. Have You Ever questions work because they give everyone the same binary entry point — yes or no — and then let the room decide how far to go. A quick nod counts. A ten-minute story also counts. The format never forces anyone to say more than they want to, which is exactly why people do.
What do players say?
11 responses
Based on 11 answers so far, 36% of players say yes — making this less common than most people assume.
Discussion starters
- → Who in the group is most likely to have asked for a raise?
- → What's the full story — and who in the group is most surprised by your answer?
- → What is the worst meeting you have ever sat through?
- → What is the dumbest reason you have been in trouble at work or school?
- → What is the strangest job interview you have done?
Asking for a raise can reveal a lot about your confidence, ambitions, and career aspirations. It’s a moment that opens doors to honest conversations about your value at work. Curious about how others handle this nerve-wracking question? Start playing and learn more about workplace dynamics.
What This Question Really Asks
This question dives into your personal experience with asserting your worth and navigating professional growth. It challenges you to reflect on your communication skills and ambition. When you consider classic workplace questions, asking for a raise is one of the most impactful topics because it reveals your confidence and career goals.
- Have you ever taken a risk to improve your situation at work?
- Are you comfortable advocating for yourself?
- How do you handle rejection or disappointment?
- Do you know your market value and worth?
- Would you consider asking for a raise as a normal part of career growth? Explore more questions about work & school
How to Use This Question
| Setting | Tone | Best for | Tip |
|---|---|---|---|
| Friends game night | Humorous, light-hearted | Breaking the ice about career ambitions | Use playful stories about fake scenarios to lighten the mood |
| First date | Subtle, genuine | Getting to know each other's ambition levels | Frame it as a shared curiosity, not a serious request |
| Team meeting | Professional, confident | Discussing personal growth openly | Use this as a segue into broader discussions about salaries and evaluations |
| Family dinner | Casual, honest | Sharing your career progress | Keep it light — focus on your goals rather than specifics |
| Party | Relaxed, informal | Connecting over work stories | Have fun with the story before asking yourself deep questions |
When You Say "Yes"
- You are confident about your worth and contributions.
- You have been proactive in your career development.
- You value transparency and honesty in the workplace.
- You are open to feedback and negotiation.
- You see yourself as deserving of growth opportunities, maybe even considering sharing funny past experiences about work rejections.
When You Say "No"
Not everyone has asked for a raise, and that's perfectly okay. Sometimes, it reflects comfort with current conditions or uncertainty about how to approach the topic. It might also reveal a concern about rocking the boat or potential repercussions.
- You prefer to wait for formal reviews or company announcements.
- You’re unsure of how to bring up your request tactfully.
- You feel the timing isn’t right or fear conflict.
Best Follow-Up Questions
- What motivated you to decide whether or not to ask for a raise?
- How do you prepare for a conversation about compensation?
- What has been your most memorable workplace negotiation?
- Do you think asking for raises is more common now than in previous years?
- Which strategies do you recommend for confidently discussing growth with your boss? Explore other work & school questions to learn more about navigating professional environments.
Thinking about asking for a raise? Remember, practicing your scenarios makes perfect. Want to turn your work conversations into fun game nights? Try playing with friends or building a custom set at our game creator.
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