Frustrated with sparking genuine engagement in your entrepreneurship community? Community challenges are a proven way to bring members together, encourage participation, and make learning fun. Use these customizable templates to launch creative, motivating challenges that get everyone involved.
Plan your content calendar and auto-post to Skool, Circle, or Mighty Networks
Community challenges tap into our natural desire for achievement, social connection, and friendly competition. When entrepreneurs are invited to participate in a shared activity, they feel part of something bigger and are more likely to contribute. Challenges also provide structure and a low-pressure way for even hesitant members to join in, lowering the barrier to engagement.
By making challenges playful and rewarding, you foster camaraderie and create memorable experiences within your community. Recognition and small rewards further boost motivation, while achievable tasks ensure that participation feels accessible to all levels of experience. This approach transforms passive members into active contributors and strengthens the sense of belonging.
Pitch your business idea in one sentence. Can you make us curious?
💡 Example: "Pitch your business idea in one sentence. Can you make us curious?"
Share your biggest entrepreneurship win from the past week!
💡 Example: "Share your biggest entrepreneurship win from the past week!"
Challenge: Find one new productivity tool and try it today. Report back with your thoughts.
💡 Example: "Challenge: Find one new productivity tool and try it today. Report back with your thoughts."
What's an entrepreneur habit you want to build this month? Share your goal below.
💡 Example: "What's an entrepreneur habit you want to build this month? Share your goal below."
30-second logo sketch challenge! Draw your business logo in 30 seconds and post a photo.
💡 Example: "30-second logo sketch challenge! Draw your business logo in 30 seconds and post a photo."
Share the best advice you ever received as an entrepreneur.
💡 Example: "Share the best advice you ever received as an entrepreneur."
Challenge: Reach out to a fellow member and swap one business tip today.
💡 Example: "Challenge: Reach out to a fellow member and swap one business tip today."
What's your favorite productivity hack? Share it for others to try.
💡 Example: "What's your favorite productivity hack? Share it for others to try."
Flash challenge: Set a 10-minute timer and brainstorm 5 new product ideas.
💡 Example: "Flash challenge: Set a 10-minute timer and brainstorm 5 new product ideas."
Post a photo of your current workspace. Any creative setups out there?
💡 Example: "Post a photo of your current workspace. Any creative setups out there?"
What's your go-to source for business inspiration? Share a link or name below.
💡 Example: "What's your go-to source for business inspiration? Share a link or name below."
Challenge: Review your homepage and find one thing to improve. What did you change?
💡 Example: "Challenge: Review your homepage and find one thing to improve. What did you change?"
If you could solve one problem for entrepreneurs, what would it be?
💡 Example: "If you could solve one problem for entrepreneurs, what would it be?"
Share a book that changed your approach to entrepreneurship.
💡 Example: "Share a book that changed your approach to entrepreneurship."
Challenge: Make one cold outreach today and share your experience.
💡 Example: "Challenge: Make one cold outreach today and share your experience."
What's your favorite tool for managing your business finances?
💡 Example: "What's your favorite tool for managing your business finances?"
24-hour challenge: Unsubscribe from 3 email lists that do not add value.
💡 Example: "24-hour challenge: Unsubscribe from 3 email lists that do not add value."
Share a mistake you made and what you learned from it.
💡 Example: "Share a mistake you made and what you learned from it."
Challenge: Set one SMART goal for your business this week and tell us what it is.
💡 Example: "Challenge: Set one SMART goal for your business this week and tell us what it is."
What is your biggest time management struggle as an entrepreneur?
💡 Example: "What is your biggest time management struggle as an entrepreneur?"
60-second sales pitch challenge: Share your elevator pitch below.
💡 Example: "60-second sales pitch challenge: Share your elevator pitch below."
What app or tool saves you the most time each day?
💡 Example: "What app or tool saves you the most time each day?"
Challenge: Write a thank you note to a customer or supporter and share your message.
💡 Example: "Challenge: Write a thank you note to a customer or supporter and share your message."
Share your favorite way to recharge after a tough business week.
💡 Example: "Share your favorite way to recharge after a tough business week."
Challenge: Find a free online resource and share how it helped your business.
💡 Example: "Challenge: Find a free online resource and share how it helped your business."
What is one thing you wish you knew before starting your business?
💡 Example: "What is one thing you wish you knew before starting your business?"
Share a screenshot of your favorite business dashboard or tool in action.
💡 Example: "Share a screenshot of your favorite business dashboard or tool in action."
Challenge: Try a new marketing tactic this week and share your results.
💡 Example: "Challenge: Try a new marketing tactic this week and share your results."
What's the most creative way you have solved a business challenge?
💡 Example: "What's the most creative way you have solved a business challenge?"
Host a virtual coffee chat with another member this week. Who is in?
💡 Example: "Host a virtual coffee chat with another member this week. Who is in?"
Share a recent customer testimonial or win you are proud of.
💡 Example: "Share a recent customer testimonial or win you are proud of."
Challenge: Set a daily routine for the next 3 days and track your progress.
💡 Example: "Challenge: Set a daily routine for the next 3 days and track your progress."
What is your favorite way to celebrate a business milestone?
💡 Example: "What is your favorite way to celebrate a business milestone?"
Challenge: Share one thing you will delegate this week to free up your time.
💡 Example: "Challenge: Share one thing you will delegate this week to free up your time."
What podcast episode has inspired your entrepreneurial journey recently?
💡 Example: "What podcast episode has inspired your entrepreneurial journey recently?"
Share a photo of your first business card or logo for a throwback challenge.
💡 Example: "Share a photo of your first business card or logo for a throwback challenge."
Challenge: Spend 15 minutes on competitor research and share one insight.
💡 Example: "Challenge: Spend 15 minutes on competitor research and share one insight."
If you had to pivot your business today, what new direction would you choose?
💡 Example: "If you had to pivot your business today, what new direction would you choose?"
Challenge: Share your favorite business meme or joke for some midweek fun.
💡 Example: "Challenge: Share your favorite business meme or joke for some midweek fun."
What is one thing you automate to save time in your business?
💡 Example: "What is one thing you automate to save time in your business?"
Start by picking a challenge template that aligns with your community's interests or current topics. Announce the challenge with clear, simple rules and set a specific timeframe for participation. Encourage members to share their progress or results, and consider highlighting top contributors or creative entries. Use polls, threads, or dedicated spaces to gather responses, and follow up with recognition or small rewards to celebrate involvement. Rotate challenges regularly to keep engagement fresh and consistent.
For all platforms, use pinned posts or announcements to promote the challenge and make participation easy to find. Use hashtags or threads to organize responses. Encourage multimedia submissions where possible, such as screenshots or short videos, to increase visibility and engagement. Adjust the challenge format to suit platform norms (e.g., polls for Facebook, Stories for Instagram, threads for Slack or Discord).
You can create weekly challenges that prompt members to share real examples of how they've applied concepts like MVP development, customer discovery interviews, or rapid prototyping. For instance, invite founders to post their MVP progress or challenge them to conduct and share insights from five customer interviews. This not only boosts engagement but also facilitates peer learning around core lean startup practices.
Organize challenges where members upload their pitch decks or key slides, and the community votes or provides feedback on clarity, storytelling, and market sizing. You can theme each challenge around specific slides (e.g., problem, solution, or traction) to help founders iterate and learn from each other's approaches. Be sure to set clear guidelines around confidentiality and constructive feedback.
Design challenges that address specific hurdles, such as 'Share your top obstacle in raising pre-seed capital' or 'Describe your biggest bottleneck in scaling operations.' Encourage members to crowdsource solutions or share their own strategies and mistakes. This targeted approach ensures discussions remain relevant and actionable for entrepreneurs navigating these stages.
Create a challenge where members document and share their customer validation process, such as running a landing page test, conducting A/B experiments, or gathering testimonials. You could gamify this by rewarding detailed breakdowns of what worked—and what didn’t—when engaging early adopters. This supports a culture of evidence-based iteration in your community.
Launch challenges that pair up solo founders with team-based startups for activities like joint problem-solving, feedback swaps, or mock co-founder interviews. For example, a 'Pitch Each Other’s Startup' challenge can help founders practice storytelling and strengthen inter-founder networking, which is crucial in the entrepreneurship ecosystem.
Encourage transparency by running 'Pivot Stories' or 'Fail Forward' challenges, where founders share what prompted a major business pivot, lessons learned, and metrics before and after the change. Use structured templates prompting specifics like market signals, customer feedback, or resource allocation adjustments. Highlighting these real-life scenarios helps normalize failure as a learning tool, which is highly relevant in entrepreneurship circles.
Skool · Circle · Mighty Networks