Entrepreneurship can feel isolating, but sharing real stories creates powerful connections. If your community struggles to spark meaningful engagement, these experience share templates offer an easy way to encourage open, reflective conversations. Give your members the space to be authentic, learn from each other, and build lasting bonds.
Plan your content calendar and auto-post to Skool, Circle, or Mighty Networks
Experience share content taps into our fundamental need for connection and understanding. By inviting entrepreneurs to reflect on their personal journeys, you create a safe space for vulnerability, empathy, and mutual support. These posts remind members they are not alone in facing challenges, celebrating wins, or navigating uncertainty.
When people share their stories, it deepens trust and strengthens the community's fabric. Others recognize themselves in these experiences, sparking new conversations and deeper engagement. This approach not only boosts participation but also builds a culture of learning and inspiration that benefits every member.
Share a moment when you overcame a major setback in your business journey.
💡 Example: "I bounced back after my first product launch failed and learned to iterate quickly."
What inspired you to start your entrepreneurial path?
💡 Example: "I wanted more freedom in my career and to solve a real problem I faced."
Tell us about a time you felt truly proud of your business.
💡 Example: "Seeing my first repeat customer made all the hard work worth it."
What was your biggest 'aha' moment as an entrepreneur?
💡 Example: "Realizing that customer feedback is more valuable than my assumptions."
Describe a mistake you made and what it taught you.
💡 Example: "I hired too quickly and learned the importance of culture fit."
Who has been your biggest supporter in your entrepreneurial journey?
💡 Example: "My partner always encourages me, even when things get tough."
Share an unexpected lesson you learned from a customer.
💡 Example: "A customer showed me a new use for my product that I never considered."
What is the most challenging part of being an entrepreneur for you?
💡 Example: "Managing my time and setting boundaries has been the hardest part."
Tell us about the first time you made money from your business.
💡 Example: "Selling my first handmade product at a local market was so exciting."
What is one myth about entrepreneurship you have debunked through experience?
💡 Example: "I learned that working for yourself does not mean less work, just different work."
Share a tool or resource that changed how you run your business.
💡 Example: "Using a project management app helped me organize tasks much better."
What is one risk you took that paid off?
💡 Example: "Quitting my day job to focus on my business full-time led to huge growth."
Describe your favorite entrepreneurial habit or routine.
💡 Example: "I start every day by reviewing my goals and setting priorities."
What fear did you have to overcome to get started?
💡 Example: "I was afraid of failing in public, but I learned to embrace mistakes."
Share a time when another entrepreneur helped you out.
💡 Example: "A mentor introduced me to my first big client and changed everything."
Tell us about a pivot you made in your business.
💡 Example: "I switched from B2C to B2B after noticing demand from companies."
What keeps you motivated during tough times?
💡 Example: "Remembering my 'why' and talking to customers keeps me going."
Describe a moment when you almost gave up, but chose to continue.
💡 Example: "After a big client left, I nearly closed shop but found a new market."
What is your favorite way to celebrate business wins, big or small?
💡 Example: "I treat myself to a nice meal whenever I hit a milestone."
Share one lesson you wish you knew before starting out.
💡 Example: "I wish I knew the importance of building a network early on."
Tell us about a partnership or collaboration that made a difference.
💡 Example: "Teaming up with a local designer helped me reach new customers."
What personal strengths have helped you as an entrepreneur?
💡 Example: "My persistence and willingness to learn have been key."
Describe a time when you had to learn something the hard way.
💡 Example: "I trusted a handshake deal and lost money, so now I always use contracts."
What advice would you give to someone just starting out?
💡 Example: "Start small, keep learning, and do not be afraid to ask for help."
Share a moment your business positively impacted someone else.
💡 Example: "A customer told me my service helped her land her dream job."
What is one thing you wish you could do differently?
💡 Example: "I would have focused on marketing earlier in my journey."
Describe your first entrepreneurial failure and how you bounced back.
💡 Example: "My first e-commerce store flopped, but I learned and launched a new niche site."
Share a time when you had to ask for help and what happened.
💡 Example: "I reached out for advice and got connected to a helpful mentor."
What is the most surprising thing about entrepreneurship for you?
💡 Example: "I did not expect how much time I would spend on admin work."
Describe a time you took a break and how it affected your business.
💡 Example: "Taking a vacation gave me fresh perspective and new ideas."
What is one small win you had this week?
💡 Example: "I finally finished updating my website's about page."
Share a moment when you felt out of your comfort zone.
💡 Example: "Pitching to investors was nerve-wracking but rewarding."
What is one thing that keeps you up at night as an entrepreneur?
💡 Example: "Worrying about cash flow is always at the back of my mind."
Describe a business goal you set and achieved.
💡 Example: "I set out to land 10 clients in a month and I did it."
Tell us about a time you had to adapt quickly.
💡 Example: "When the pandemic hit, I pivoted to virtual workshops overnight."
What is your favorite way to recharge outside of work?
💡 Example: "I go hiking on weekends to clear my mind."
Share a business-related book or podcast that changed your mindset.
💡 Example: "Reading 'The Lean Startup' helped me embrace experimentation."
What is one thing you are working on improving right now?
💡 Example: "I am trying to get better at delegating tasks."
Describe a moment you realized entrepreneurship was right for you.
💡 Example: "After my first client thanked me for solving their problem, I felt I belonged."
Share a tradition or ritual that helps you stay focused.
💡 Example: "I start each day with a quick meditation and planning session."
What is the most valuable feedback you have ever received?
💡 Example: "A mentor once told me to stop chasing perfection and just launch."
To implement these templates, choose a prompt that resonates with your community's current mood or challenges. Post it as a discussion starter and encourage members to reply in the thread or as their own post. Rotate prompts regularly to keep conversations fresh and relevant. Recognize contributors by highlighting thoughtful responses and fostering a welcoming environment for all experience levels.
For all platforms, use these templates as text posts, discussion threads, or story prompts. On forums, pin experience share posts to keep them visible. In chat environments, use them for regular check-ins. On social media, pair with an engaging image or hashtag to increase reach.
Aim to use these templates weekly or biweekly to maintain engagement and keep conversations fresh, but adjust based on your members' activity.
Model vulnerability yourself, thank members for sharing, and create a supportive environment where all experiences are valued.
Yes, feel free to adapt the prompts to suit your community's unique focus, stage, or interests while keeping them open-ended.
Absolutely. These templates work well for breaking the ice in new groups and deepening bonds in established communities.
Try rephrasing the prompt, tagging specific members to share, or sharing your own story first to spark the conversation.
Set clear guidelines for respectful discussion and remind members they can share what they feel comfortable with. Support or privately reach out as needed.
Yes, they are also effective for in-person meetups, workshops, or mastermind groups to foster openness and connection.
Skool · Circle · Mighty Networks