**Fun employee survey questions** like quirky "would you rather" prompts can completely shift how engagement surveys feel. Instead of the usual dry forms, these questions bring a spark—getting employees to laugh, think, and respond more openly.
Participation is much higher with **would you rather questions** because they're fast, easy, and just plain enjoyable. When you layer on AI follow-up questions that dig into the "why," you can turn a simple choice between two options into rich insight about your team's culture and needs.
This approach works incredibly well for employee engagement surveys, making feedback more authentic and actionable. I’ll walk you through 50 ready-to-use prompts and how to set up AI-powered follow-ups and guardrails for safe, effective conversations. To get started creating your own, check out the AI survey generator from Specific.
50 would you rather questions for employee engagement surveys
Let’s dive into a bank of **would you rather questions**, grouped by work style, benefits, culture, growth, communication, and work environment. Infusing fun into surveys pays off—with **conversational formats increasing survey completion rates by 40% compared to traditional forms**. [1]
Work Style
Would you rather work from home every Monday or have Fridays off every other week?
Would you rather tackle one big project at a time or juggle several small tasks?
Would you rather have a standing desk or a comfy office chair?
Would you rather start your workday at 7 AM and finish early, or start at 10 AM and finish later?
Would you rather have quiet focus hours daily or flexible, interruption-friendly work times?
Would you rather attend fewer but longer meetings, or more but shorter check-ins?
Would you rather work independently on solo projects or collaborate on team projects?
Would you rather get instant feedback or have scheduled performance reviews?
Would you rather work four 10-hour days or five 8-hour days?
Would you rather brainstorm ideas in a group or develop them on your own before sharing?
Benefits & Perks
Would you rather receive an annual wellness stipend or an extra week of paid vacation?
Would you rather have flexible hours or a consistent, fixed schedule?
Would you rather choose your own tech gear or get a company-issued package?
Would you rather get free snacks and drinks at work or a monthly lunch voucher?
Would you rather have pet-friendly offices or subsidized public transit?
Would you rather have access to an onsite gym or childcare services?
Would you rather get an end-of-year bonus or spot recognition throughout the year?
Would you rather have extra parental leave or tuition reimbursement?
Would you rather get paid for volunteering days or get discounts for wellness apps?
Would you rather have a sabbatical after five years or more annual leave each year?
Company Culture
Would you rather attend fun team retreats or receive personal development budgets?
Would you rather be part of a diverse, global team or a close-knit local group?
Would you rather celebrate wins with team lunches or after-work socials?
Would you rather participate in friendly competitions or collaborate on volunteer days?
Would you rather have open workspaces or designated quiet zones?
Would you rather have "no emails after hours" or flexible work messaging etiquette?
Would you rather have a transparent leadership style or clear but formal communication?
Would you rather lead company traditions or help create new ones?
Would you rather have monthly recognition ceremonies or peer nomination programs?
Would you rather have themed office days or quarterly team activities?
Growth & Development
Would you rather learn from mentorship or attend formal training courses?
Would you rather rotate between departments or specialize in your current role?
Would you rather work toward a promotion or develop new skills within your current position?
Would you rather attend industry events or take online courses for development?
Would you rather have more opportunities for stretch projects or lead process improvements?
Would you rather get regular feedback or have autonomy to experiment and learn?
Would you rather set your own learning goals or have guidance from your manager?
Would you rather get certified in a new field or deepen your expertise where you are?
Would you rather attend workshops with external speakers or participate in peer-led learning?
Would you rather have career coaching or leadership shadowing programs?
Communication & Collaboration
Would you rather have video calls for collaboration or stick to chat and email?
Would you rather get constructive criticism in person or in writing?
Would you rather share updates in daily standups or weekly summaries?
Would you rather have transparent project boards or just status emails?
Would you rather brainstorm in open forums or in small groups?
Would you rather have open-door policies or book 1:1 check-ins?
Would you rather have all-hands meetings monthly or quarterly?
Would you rather share feedback anonymously or openly?
Would you rather work with teammates across time zones or with everyone on the same schedule?
Would you rather join quick impromptu chats or schedule time to connect?
Work Environment & Well-being
Would you rather work in a modern open office or in a quiet, private space?
Would you rather have natural light all day or mood lighting to set the tone?
Would you rather dress casually every day or have themed dress-up days?
Would you rather control your own office temperature or let facilities manage it?
Would you rather have plants and greenery or art and decor in the office?
Would you rather take power naps or long walks during breaks?
Would you rather have music playing (at a low volume) or a silent workspace?
Would you rather have a dog-friendly office or a tech-free quiet room?
Would you rather eat lunch together with your team or have solo recharge time?
Would you rather have a playful workspace or a minimalist one?
These prompts blend fun, creativity, and deep relevance. Surveys that let people share their real preferences—while feeling safe and heard—tend to get more honest, actionable data. And since over 90% of organizations use engagement surveys to track their culture, having smart, engaging questions is more crucial than ever. [1]
Configuring AI follow-ups and guardrails
**Conversational surveys** don’t stop at the binary choice. As soon as someone picks an option, AI can immediately follow up with “why.” This probes for the real drivers—like why your team prefers video calls or autonomy in learning.
To set this up, configure the follow-up behavior so the AI always asks for reasoning. This is where you really start turning preferences into actionable insights. But it's important to set guardrails—a “do-not-ask list”—to keep follow-up questions respectful and safe. Here’s an example:
Do not ask any questions about an employee's salary, personal medical history, or family situation. Avoid questions that could be perceived as invasive or outside workplace relevance.
This ensures the conversation stays professional and comfortable. Guardrails like these are essential for sensitive survey topics—protecting privacy and compliance while still enabling deep AI-powered discovery.
You can further customize follow-up phrasing or fine-tune AI safety in the AI survey editor. For example, if you want to approach a topic gently after “Would you rather have a dog-friendly office or a tech-free quiet room?”, you could adjust the follow-up to:
Could you share what helps you feel most relaxed and productive at work, without mentioning any specific health conditions or private details?
That way, employees get a conversational, adaptive experience—never a hard form. These follow-ups make it a true **conversational survey** that adapts naturally, leading to the 40% higher completion rates seen with this approach. [1]
Using the AI Survey Editor for safe and engaging phrasing
The AI survey editor makes it effortless to refine your questions and follow-ups, all in plain language. You can chat with the editor to tweak tone, content, or structure—making your survey sound as casual, upbeat, or professional as you want.
I like to tailor questions to match how our company talks—sometimes playful, others more businesslike. Here’s how you can rephrase any question for inclusivity or tone:
Rephrase this question to be more casual and welcoming: "Would you rather get feedback instantly or have formal reviews every quarter?"
Once the AI rewords, you might get: "Would you rather get feedback on the spot, or talk about your progress every few months in a cozy review?"
If you want to make a question more inclusive, just ask the editor:
Make this question inclusive to different work arrangements: "Would you rather eat lunch together with your team or have solo recharge time?"
It might become: "When it’s time for a break, do you prefer catching up with colleagues (in person or virtually), or having some solo downtime?"
You can adjust every question’s voice to match employee expectations. Test several versions within the tool to see which ones get the most engagement or best suit your culture. That’s one of the biggest advantages—rapid experimentation and tone-fitting, all in one spot. If you’re managing surveys where safety and comfort are top priorities, you’ll appreciate how easily this editor lets you test, preview, and change phrasing on the fly.
Analyzing would you rather responses with AI
After collecting responses, Specific’s AI-powered analytics shine. I use the AI survey response analysis to surface patterns in team preferences quickly. For example, the AI can pinpoint clusters—like half the marketing team loving video meetings, while engineering prefers written updates.
You can segment by department, role, location, or tenure—so you know whether flexible hours matter more to new hires or long-timers. The AI can also flag outlier opinions or evolving trends. Here are a few analysis prompts that reveal deep insight into employee engagement:
List the most common reasons employees prefer flexible schedules over set hours.
Compare preference clusters for team collaboration (video, chat, in person) across departments.
Identify segments of employees who feel most energized by office perks, and describe what features matter most to them.
What are the primary motivators for employees choosing professional development benefits over other perks?
Are there any significant differences in work style preferences between remote and onsite employees?
When I dig into survey responses this way, the actionable insights leap off the page. Preference clusters become clear. Outliers point to potential engagement risks or big creative ideas. And because I can filter, compare, and segment in seconds, acting on feedback is actually realistic—not just a pipe dream. For surveying at scale, these insights are gold, considering that companies prioritizing feedback see nearly 15% lower turnover. [1]
Start building your employee engagement survey
Combining fun, conversational **would you rather questions** with smart AI follow-ups unlocks employee voices and drives better engagement. This approach boosts participation, quality, and actionable feedback compared to rigid forms.
Ready to engage your team? Create your own survey in minutes—Specific configures the AI behind the scenes, so you can focus on picking the perfect questions and follow-up style for your culture.
Customize everything you need—from question tone to follow-up depth—and start turning simple choices into powerful, real insights that move your team forward.