Finding it hard to spark conversations in your entrepreneurship community? Our This or That templates make it easy to break the ice and get members talking. Use these playful prompts to inspire participation and build a more engaging space.
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This or That prompts tap into the psychology of choice, making it easy for anyone to join in with minimal effort. By offering two clear options, you lower the barrier to engagement and invite spontaneous, low-pressure participation. The quick decision-making process also creates a sense of inclusion, as every member can share their preference instantly.
For entrepreneurs, these lighthearted comparisons can reveal interesting habits, working styles, and personal quirks, helping members find common ground. This format encourages even quieter members to chime in, strengthening community bonds through repeated, playful interactions.
Early mornings or late nights - when are you most productive?
💡 Example: "Early mornings or late nights - when are you most productive? Tell us why!"
Solo founder or co-founder - which would you choose?
💡 Example: "Solo founder or co-founder - which would you choose and why?"
Coffee or tea for your brainstorming sessions?
💡 Example: "Coffee or tea for your brainstorming sessions?"
Working from home or working from a coworking space?
💡 Example: "Working from home or working from a coworking space? Share your pick!"
Bootstrapping or seeking investors - what is your style?
💡 Example: "Bootstrapping or seeking investors - what is your style and why?"
Planning everything or going with the flow?
💡 Example: "Planning everything or going with the flow? What works for you?"
Digital to-do lists or handwritten notes?
💡 Example: "Digital to-do lists or handwritten notes?"
Work in silence or with background music?
💡 Example: "Work in silence or with background music? Let us know your preference."
Face-to-face networking or online connections?
💡 Example: "Face-to-face networking or online connections? Why?"
Quick launch or perfect before release?
💡 Example: "Quick launch or perfect before release? What is your approach?"
Podcasts or books for learning new skills?
💡 Example: "Podcasts or books for learning new skills? Which do you prefer?"
Risk-taker or play-it-safe when making decisions?
💡 Example: "Risk-taker or play-it-safe when making decisions? Which one are you?"
Morning check-ins or end-of-day wrap-ups?
💡 Example: "Morning check-ins or end-of-day wrap-ups?"
Short sprints or long work sessions?
💡 Example: "Short sprints or long work sessions? What keeps you productive?"
Learning by doing or learning by reading?
💡 Example: "Learning by doing or learning by reading? Which do you prefer?"
Strict routine or flexible schedule?
💡 Example: "Strict routine or flexible schedule?"
Work solo or collaborate with a team?
💡 Example: "Work solo or collaborate with a team? Which do you enjoy more?"
Big goals or small wins to stay motivated?
💡 Example: "Big goals or small wins to stay motivated? Share your thoughts."
Email or instant messaging for team updates?
💡 Example: "Email or instant messaging for team updates?"
Pitch deck or elevator pitch - which do you prefer?
💡 Example: "Pitch deck or elevator pitch - which do you use more?"
Productivity apps or old-fashioned notebooks?
💡 Example: "Productivity apps or old-fashioned notebooks? What helps you more?"
Work from the office or work remotely from anywhere?
💡 Example: "Work from the office or work remotely from anywhere? Why?"
Launching a new product or growing an existing one?
💡 Example: "Launching a new product or growing an existing one? Which excites you more?"
Business podcasts or industry blogs?
💡 Example: "Business podcasts or industry blogs?"
Attend conferences or online webinars?
💡 Example: "Attend conferences or online webinars? What do you prefer?"
Hiring freelancers or building an in-house team?
💡 Example: "Hiring freelancers or building an in-house team? What works for you?"
Revenue growth or user growth - which is more important?
💡 Example: "Revenue growth or user growth - which is more important for your business?"
Weekly goals or monthly goals?
💡 Example: "Weekly goals or monthly goals?"
DIY marketing or hiring an agency?
💡 Example: "DIY marketing or hiring an agency? Which do you prefer?"
Big risks or steady progress?
💡 Example: "Big risks or steady progress? Which describes you?"
Quick feedback or detailed reviews?
💡 Example: "Quick feedback or detailed reviews? What helps you more?"
Hands-on leadership or delegating tasks?
💡 Example: "Hands-on leadership or delegating tasks? Which style suits you?"
Customer calls or emails for support?
💡 Example: "Customer calls or emails for support?"
Focus on one project or juggle multiple at once?
💡 Example: "Focus on one project or juggle multiple at once? What works for you?"
Celebrating wins privately or sharing with the team?
💡 Example: "Celebrating wins privately or sharing with the team? How do you celebrate?"
Learning from mistakes or learning from successes?
💡 Example: "Learning from mistakes or learning from successes? Which teaches you more?"
Focusing on product or focusing on marketing first?
💡 Example: "Focusing on product or focusing on marketing first? What is your approach?"
Daily checklists or weekly planning sessions?
💡 Example: "Daily checklists or weekly planning sessions?"
Post a This or That prompt regularly to keep your community lively. You can use them as morning icebreakers, end-of-week wind-downs, or to kick off new discussions. Encourage members to share why they chose their answer for deeper engagement. Rotate topics to ensure variety and keep things fresh. Pin popular prompts or reshare favorites to involve new members.
This or That posts work well across all platforms. Use images, polls, or story features if available, or just post the prompt as text. Adapt for platform norms: on Slack or Discord, pin the prompt for visibility; on LinkedIn or Facebook, use comments for responses; on Instagram, try Stories or Reels for added visual appeal.
To engage entrepreneurs around real-world dilemmas, create 'This or That' prompts that reflect actual startup decisions, such as 'Bootstrap your business or pitch to VCs?' or 'Scale fast with outside investment vs. grow organically?' This not only sparks debate but also surfaces shared experiences and advice relevant to your entrepreneurial community.
Absolutely! Using entrepreneurship jargon such as 'Launch an MVP vs. wait for a perfect product?' or 'Stick with your original idea vs. pivot based on market feedback?' encourages informed discussion among founders and demonstrates that your community understands the nuances of startup life.
Craft questions such as 'Focus on inbound marketing vs. outbound sales for your next quarter?' or 'Hire a content marketer vs. a sales representative first?' to encourage members to share their growth tactics, successes, and lessons learned. This fosters peer-to-peer learning tailored to entrepreneurial challenges.
Prompt discussions with questions like 'Go solo vs. seek a co-founder?' or 'Technical co-founder vs. business co-founder?' These scenarios are highly relevant for entrepreneurs and can help members weigh trade-offs, share stories, and even connect with potential collaborators.
Yes! Questions such as 'Build with no-code platforms vs. hire a developer?' or 'Use off-the-shelf SaaS vs. create proprietary software?' resonate with entrepreneurs facing resource and speed constraints, encouraging them to share practical insights and tool recommendations.
Stay updated on industry trends by following entrepreneurship news, popular podcasts, and thought leaders. Craft timely questions like 'Remote-first team vs. in-office culture?' or 'Flexible hours vs. fixed schedule for startups?' to keep discussions relevant and encourage participation from founders navigating these evolving work models.
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