100+ Best "Would You Rather" Questions for Work (Funny, Safe & Deep)

Fast Icebreaker “Would You Rather” (30–60 Seconds)

These quick starters are ideal when you want energy and participation fast. They work especially well as binary poll questions that everyone can answer in one tap—then you can ask one follow-up “why?” if time allows. Load them into Poll Maker and you’re ready before the meeting even starts.

• When to use these polls: At the start of standups, kickoffs, training sessions, or anytime engagement is low and you need a fast reset.
• Best poll types for this section: Single-choice (best), multiple-choice (if you add “Depends”), and live results to spark quick discussion.
• How to act on the results: Use patterns to set team norms (e.g., meeting length, feedback format), and rotate decisions to avoid always catering to the loudest voices.

Workstyle & Collaboration Preferences

These prompts help teams choose practical defaults for communication and execution. They’re ideal as this-or-that for teams because they turn “it depends” debates into clear starting points you can refine. Run them in Poll Maker, then capture the agreed norm in your team docs.

• When to use these polls: During team chartering, process refreshes, new project kickoffs, tool changes, or after recurring friction.
• Best poll types for this section: Single-choice, ranking (to prioritize multiple workflow improvements), and “multiple choice with ‘Depends’” for nuance.
• How to act on the results: Turn the top preference into a default rule, then set a clear exception policy (what changes the default, and who decides).

Culture & Values Dilemmas (Surprisingly Deep, Still Safe)

These questions surface what people value—fairness, autonomy, recognition, learning—without turning the conversation personal. They’re strong team bonding questions because they help people understand motivations and assumptions behind decisions. Launch them in Poll Maker, then use the results as a neutral starting point for discussion.

• When to use these polls: During culture conversations, leadership offsites, engagement check-ins, post-project retrospectives, or policy reviews.
• Best poll types for this section: Single-choice for a clear lean, ranking for prioritizing competing values, and anonymous polls for more honesty.
• How to act on the results: Identify the top value trade-offs, then translate them into guidelines (what you optimize for, what you won’t sacrifice, and how to resolve conflicts).

Remote-Work Scenarios & Boundaries

Remote norms often fail quietly—until they create burnout or miscommunication. These are built for remote icebreaker games that also generate actionable agreements (camera norms, time zones, availability). Launch as anonymous or named polls in Poll Maker depending on how sensitive the topic feels.

• When to use these polls: With distributed teams, during onboarding, after a re-org, or when you notice meeting fatigue and response-time tension.
• Best poll types for this section: Single-choice for a clear default, multiple-choice when you want an “it depends” option, and anonymous mode for boundary topics.
• How to act on the results: Convert the majority preference into a written norm, then define exceptions (customer calls, workshops, crisis response) so people aren’t guessing.

Just-for-Fun Office Debates (100% Safe Topics)

Sometimes the goal is simple: laugh, connect, and move on. These are safe-for-work debate prompts that keep things inclusive (no sensitive personal topics) while still generating lively chat. They’re perfect to load into Poll Maker for a quick morale boost between heavier agenda items.

• When to use these polls: Before workshops, during team socials, at the end of town halls, or as a quick reset after intense discussions.
• Best poll types for this section: Single-choice for quick wins, multiple-choice for “all that apply” favorites, and live results for fun reveals.
• How to act on the results: Use winners to pick snacks, playlists, or celebration ideas—small follow-through builds trust that feedback is heard.

Frequently Asked Questions

These answers cover how to run Would You Rather polls at work without awkwardness, how to choose options, and how to turn results into clear team norms—whether you’re in-office, hybrid, or remote.

How do I keep “Would you rather” questions appropriate for work?

Stick to topics that won’t single out personal identities or private circumstances (health, politics, religion, finances). Keep the prompt about preferences, routines, or work processes, and add “Prefer not to say” when a question could feel personal (e.g., PTO boundaries).

How many questions should I ask in one session?

For a quick icebreaker, 1–3 questions is plenty. For workshops or team retrospectives, 5–8 questions works well if you plan a short discussion after key results. Stop early if participation drops—quality beats quantity.

Should these polls be anonymous or named?

Use named polls for light this-or-that for teams (snacks, meeting format) when accountability helps. Use anonymous polls for boundary or values topics (cameras, PTO expectations, feedback preferences) to get more honest data and reduce social pressure.

What’s the best way to write answer options for workplace WYR polls?

Keep options short (1–5 words), parallel, and mutually exclusive where possible. Avoid loaded labels (“lazy,” “micromanaged”). If reality is nuanced, add “Depends” or “Mix both” rather than creating five nearly identical options.

Are “Would You Rather” polls useful beyond icebreakers?

Yes. They’re great for clarifying defaults and revealing hidden assumptions—especially around meetings, async communication, recognition, and remote norms. Treat them as a quick diagnostic: the discussion and decisions after the vote are where the value shows up.

What poll type should I use for Would you rather questions for work?

Single-choice is usually best because it forces a clear lean and keeps the prompt true to the format. Use ranking when you have multiple potential improvements and need prioritization. Use multiple-choice when “all that apply” is genuinely appropriate (like benefits preferences).

How do I interpret a close split in results?

A close split often means you need a flexible norm: set a default (based on context) plus an explicit exception rule. For example, “Async by default, short call for blockers.” You can also segment by team/role if your tool supports it and the group is large enough.

How can I use these questions on remote calls without wasting time?

Run one poll at the start, share results immediately, and ask one targeted follow-up (“What should our default be?”). Keep it timeboxed to 2–3 minutes. This works well for remote icebreaker games that still produce a useful agreement.

What should I do if someone suggests an option I didn’t include?

Add “Something else” when you expect varied answers, then invite suggestions in a follow-up message or a second poll. If the new option is common, rerun the poll with improved choices—polls are quick to iterate.

Can I launch these polls quickly without building everything from scratch?

Yes. You can copy a prompt and options from this page and instantly load it into Poll Maker, then share the link or run it live in seconds for free.