Frustrated with sparking lively discussions in your entrepreneurship community? Would You Rather questions are a playful, engaging way to get members thinking outside the box and sharing their views. Transform routine conversations with these ready-to-use templates that inspire creativity and connection.
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Would You Rather questions are a proven method to invite participation from members of all engagement levels. By framing two intriguing scenarios, you lower the barrier to entry since members only need to choose between options. This simplicity encourages even the quietest members to chime in.
These questions also tap into the entrepreneurial spirit by prompting imaginative thinking and creative problem-solving. They enable members to explore hypotheticals, share unique perspectives, and reflect on their own values and priorities. When members explain their reasoning, they reveal insights about their approach to business, risk, and innovation, fostering deeper connections within the community.
Would you rather launch a startup with unlimited funding but no team, or a world-class team but limited funds?
💡 Example: "I would pick the world-class team, because great people can make magic happen even with fewer resources!"
Would you rather pitch to your dream investor or land your dream client?
💡 Example: "Dream client for me, because revenue is king!"
Would you rather have your product go viral overnight or grow steadily for five years?
💡 Example: "Steady growth. Virality is exciting but can be hard to sustain long-term."
Would you rather work 80 hours a week on your passion or 20 hours on something profitable but boring?
💡 Example: "I'd choose passion projects. Life is too short to be bored!"
Would you rather fail fast and learn or succeed slowly with no major setbacks?
💡 Example: "Fail fast! Every misstep is a lesson."
Would you rather build a niche product for a small loyal audience or a mass-market product with fierce competition?
💡 Example: "I love the idea of a loyal audience, so niche product for me."
Would you rather bootstrap your business or take on investors from day one?
💡 Example: "Bootstrapping feels safer to me, at least in the beginning."
Would you rather have a viral marketing campaign or a steady stream of word-of-mouth referrals?
💡 Example: "Word-of-mouth is the best form of marketing!"
Would you rather launch your product early and iterate or wait until it's perfect?
💡 Example: "Launch early! Feedback is gold."
Would you rather have a mentor with industry experience or one with a huge network?
💡 Example: "Industry experience is more valuable to me."
Would you rather work from a bustling co-working space or from the comfort of your home office?
💡 Example: "Home office all the way!"
Would you rather sell a company for a big one-time payout or keep it for ongoing income?
💡 Example: "Ongoing income is more appealing to me."
Would you rather spend your budget on R&D or on marketing?
💡 Example: "R&D is where the magic happens!"
Would you rather be the face of your brand or stay behind the scenes?
💡 Example: "I prefer being behind the scenes."
Would you rather build a product you love or one you know will sell?
💡 Example: "If it doesn't sell, the love doesn't pay the bills!"
Would you rather get free publicity in a major magazine or a paid ad on your favorite platform?
💡 Example: "Free publicity is always a win!"
Would you rather grow your audience locally or go global from the start?
💡 Example: "Local first, then global."
Would you rather create a new market or disrupt an existing one?
💡 Example: "Disruption is exciting but risky!"
Would you rather have a flexible remote team or everyone in one office?
💡 Example: "Remote teams give you access to more talent."
Would you rather win a prestigious entrepreneurship award or double your current revenue?
💡 Example: "Revenue is more useful for me right now."
Would you rather work on one big idea or juggle multiple smaller projects?
💡 Example: "I like focusing on one big idea."
Would you rather launch a physical product or a digital service?
💡 Example: "Digital service, less overhead!"
Would you rather have a business partner who is creative or one who is super organized?
💡 Example: "Organization helps keep things moving."
Would you rather get real-time feedback from users or see your product featured on TV?
💡 Example: "User feedback is more actionable for me."
Would you rather take a sabbatical to travel or use that time to build a side project?
💡 Example: "Travel! Inspiration comes from new places."
Would you rather have a huge following on one platform or a small but engaged audience on several?
💡 Example: "I prefer engaged audiences across platforms."
Would you rather hire for culture fit or for skills?
💡 Example: "Culture fit, you can always teach skills."
Would you rather have a product with lots of features or one that's super simple?
💡 Example: "Simple always wins with me."
Would you rather attend a startup conference or a skills workshop?
💡 Example: "Workshops are more hands-on."
Would you rather be known for innovation or for customer service?
💡 Example: "Customer service is my top priority."
Would you rather spend your time networking or refining your product?
💡 Example: "Refining my product is more satisfying."
Would you rather never run out of ideas or have unlimited time to execute?
💡 Example: "Unlimited time would be a dream."
Would you rather be an early adopter or wait and learn from others' mistakes?
💡 Example: "I prefer to learn from others first."
Would you rather have a business that's famous but barely profitable, or unknown but highly profitable?
💡 Example: "Profit wins over fame every time."
Would you rather launch your business in a city you love or the best market for your product?
💡 Example: "Best market gives you the best chance to succeed."
Would you rather automate most tasks or have a team handle them manually?
💡 Example: "Automation saves so much time."
Would you rather get daily feedback from your customers or from your team?
💡 Example: "Customer feedback is what matters most."
Would you rather work on something that changes the world or something that makes you rich?
💡 Example: "Changing the world is my dream."
Would you rather invest in a promising founder or a proven idea?
💡 Example: "Founders make all the difference."
Would you rather build a SaaS business or an ecommerce brand?
💡 Example: "SaaS is more scalable."
Would you rather compete with giants or carve your own niche?
💡 Example: "Niche markets are less crowded."
Post these Would You Rather templates regularly to spark conversation, especially during slow periods or when welcoming new members. Rotate question styles to keep things fresh and appeal to different personalities. Always encourage members to share not just their choice, but also why they picked it, to deepen the discussion. Pin a new question weekly, use them as icebreakers in events, or include them in your newsletters for cross-platform engagement.
Would You Rather templates work across all platforms. For forums and groups, use polls or comment threads. On chat platforms, pin the question for visibility. For social media, use interactive features like stories or polls and follow up with a summary of the best responses to highlight community voices.
To engage your entrepreneurship community, frame 'Would You Rather' questions around real startup decision points, such as 'Would you rather bootstrap your business and retain full ownership, or raise venture capital and scale faster but dilute equity?' This sparks relevant discussion and allows members to share personal experiences or seek advice on funding strategies.
Absolutely. Entrepreneurs frequently face the challenge of pivoting versus staying the course. Craft prompts like 'Would you rather pivot your business model in response to market feedback or stick to your original vision despite early obstacles?' This resonates with founders who have faced tough strategic choices and encourages sharing of insights on adaptability.
Try prompts like 'Would you rather launch your startup with a co-founder who complements your skills, or go solo for complete control?' Such questions directly address founder dynamics, which is a frequent topic in entrepreneurship circles and can lead to rich discussions on collaboration, equity splits, and decision-making.
Pose scenarios such as 'Would you rather launch quickly with an MVP and gather user feedback, or spend more time perfecting your product before going to market?' This encourages entrepreneurs to discuss lean startup principles, risk tolerance, and approaches to validating ideas.
Definitely! Consider questions like 'Would you rather rapidly scale your startup and chase aggressive growth goals, or focus on sustainable, steady expansion even if it takes longer?' This gives members a chance to weigh in on their risk appetite and growth philosophies, key themes in entrepreneurship.
Create prompts like 'Would you rather work 80-hour weeks for 2 years to achieve rapid traction, or aim for a balanced lifestyle with slower but steady business growth?' This acknowledges the mental health challenges entrepreneurs face and invites candid conversations about hustle culture versus sustainability.
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