Keeping your entrepreneurship community engaged year-round can be challenging, especially as members' attention shifts with the seasons. Seasonal post templates help you spark timely and inclusive conversations, making your community feel fresh and relevant. Use these ready-made prompts to connect members and celebrate what's happening now.
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Seasonal posts tap into the shared experiences and moods that come with different times of year. By referencing holidays, weather changes, or seasonal business trends, you make your community feel timely and alive. This builds a sense of belonging and keeps members coming back to see what's new.
Entrepreneurs often work in isolation and appreciate opportunities to reflect on how seasons impact their work or mindset. Inviting members to share seasonal stories and traditions also opens up a space for diverse voices, fostering connection and empathy across backgrounds.
As the seasons change, how does your business adapt? Share one seasonal shift you make.
💡 Example: "As the seasons change, how does your business adapt? Share one seasonal shift you make."
What is a favorite holiday tradition you have that inspires your entrepreneurial journey?
💡 Example: "What is a favorite holiday tradition you have that inspires your entrepreneurial journey?"
Do you set new goals at the start of each season? What is one goal you have for this season?
💡 Example: "Do you set new goals at the start of each season? What is one goal you have for this season?"
How do holidays impact your workflow or sales cycle?
💡 Example: "How do holidays impact your workflow or sales cycle?"
Share a photo or story of your workspace decorated for the current season.
💡 Example: "Share a photo or story of your workspace decorated for the current season."
What seasonal events or trends do you look forward to in your industry?
💡 Example: "What seasonal events or trends do you look forward to in your industry?"
As a new quarter begins, what is your biggest focus?
💡 Example: "As a new quarter begins, what is your biggest focus?"
What is the most unexpected way a holiday has affected your business?
💡 Example: "What is the most unexpected way a holiday has affected your business?"
Do you take time off during holidays? How do you prepare your business?
💡 Example: "Do you take time off during holidays? How do you prepare your business?"
What is your favorite seasonal productivity tip?
💡 Example: "What is your favorite seasonal productivity tip?"
How do you keep your team motivated during slower seasons?
💡 Example: "How do you keep your team motivated during slower seasons?"
Are there seasonal community events or markets you love to join as an entrepreneur?
💡 Example: "Are there seasonal community events or markets you love to join as an entrepreneur?"
Share a lesson you learned from past holiday sales or promotions.
💡 Example: "Share a lesson you learned from past holiday sales or promotions."
What local or cultural holidays do you celebrate while running your business?
💡 Example: "What local or cultural holidays do you celebrate while running your business?"
How do you thank your clients or customers during the holiday season?
💡 Example: "How do you thank your clients or customers during the holiday season?"
Do you have a favorite season for launching new products? Why?
💡 Example: "Do you have a favorite season for launching new products? Why?"
What is one thing you love about working through this season?
💡 Example: "What is one thing you love about working through this season?"
Does your business have any seasonal offers or services?
💡 Example: "Does your business have any seasonal offers or services?"
Share a seasonal challenge you are facing and how you are overcoming it.
💡 Example: "Share a seasonal challenge you are facing and how you are overcoming it."
How does the weather influence your work routine or customer behavior?
💡 Example: "How does the weather influence your work routine or customer behavior?"
What is one seasonal tradition that helps you recharge as an entrepreneur?
💡 Example: "What is one seasonal tradition that helps you recharge as an entrepreneur?"
Do you change your marketing approach as holidays approach? How?
💡 Example: "Do you change your marketing approach as holidays approach? How?"
What is your favorite way to celebrate milestones during the holiday season?
💡 Example: "What is your favorite way to celebrate milestones during the holiday season?"
How do you keep your business inclusive during global holidays?
💡 Example: "How do you keep your business inclusive during global holidays?"
Share a favorite seasonal quote that motivates you.
💡 Example: "Share a favorite seasonal quote that motivates you."
What is one way your business gives back to the community during holidays?
💡 Example: "What is one way your business gives back to the community during holidays?"
Do you notice changes in customer engagement during certain seasons?
💡 Example: "Do you notice changes in customer engagement during certain seasons?"
How do you balance work and family during festive periods?
💡 Example: "How do you balance work and family during festive periods?"
What is your go-to seasonal treat or beverage during long work days?
💡 Example: "What is your go-to seasonal treat or beverage during long work days?"
Share a seasonal marketing idea that worked well for your business.
💡 Example: "Share a seasonal marketing idea that worked well for your business."
Do you update your brand visuals for the season? Show us if you do.
💡 Example: "Do you update your brand visuals for the season? Show us if you do."
What is your biggest learning from last year’s holiday season?
💡 Example: "What is your biggest learning from last year’s holiday season?"
How do you keep your energy up when days get shorter or colder?
💡 Example: "How do you keep your energy up when days get shorter or colder?"
Do you send seasonal greetings to your network? What do you say?
💡 Example: "Do you send seasonal greetings to your network? What do you say?"
What seasonal books or podcasts inspire your entrepreneurial mindset?
💡 Example: "What seasonal books or podcasts inspire your entrepreneurial mindset?"
How do you handle end-of-year reviews or reflections in your business?
💡 Example: "How do you handle end-of-year reviews or reflections in your business?"
Share a seasonal tip for keeping customers engaged during slow months.
💡 Example: "Share a seasonal tip for keeping customers engaged during slow months."
Does your business take part in any seasonal giving or charity initiatives?
💡 Example: "Does your business take part in any seasonal giving or charity initiatives?"
What is your favorite way to unwind after a busy holiday season?
💡 Example: "What is your favorite way to unwind after a busy holiday season?"
How do you celebrate small wins with your team during busy periods?
💡 Example: "How do you celebrate small wins with your team during busy periods?"
Share a seasonal ritual or habit that helps your business thrive.
💡 Example: "Share a seasonal ritual or habit that helps your business thrive."
Pick a template that matches the current season or an upcoming holiday and post it as a discussion starter. Encourage responses by tagging a few active members or sharing your own answer first. Rotate seasonal posts regularly to keep your community content fresh and give everyone a chance to participate. Adapt language as needed to fit your community's unique culture and values.
For all platforms, use clear and concise language in your seasonal posts. Pair your prompt with a relevant image or emoji to catch attention in feeds. Pin or highlight the post for greater visibility, and encourage replies by personally responding to early commenters. Adjust the posting time based on your community's most active hours.
Craft prompts that tap into critical moments for entrepreneurs, such as asking members to share their year-end financial review strategies during tax season, or hosting a 'Pitch Deck Polish' challenge before common investor demo days. Aligning content with these cycles can drive timely discussions and support members as they navigate funding opportunities.
For pre-launch startups, focus on prompts about ideation, market research, and building MVPs during times like 'New Year, New Venture.' For scale-ups, use seasonal prompts around annual planning, team expansion during graduation season, or prepping for Q4 sales pushes, allowing each group to discuss stage-relevant challenges.
Create prompts that encourage members to share their preparations for major milestones, such as end-of-quarter retrospectives, Black Friday marketing plans, or tax-time bookkeeping workflows. This sparks peer learning and helps entrepreneurs benchmark best practices for critical business events.
Use timely prompts that invite members to discuss adaptations in response to broader market changes, such as asking how they're adjusting revenue streams during economic downturns or what post-crisis pivots succeeded. This keeps discussions grounded in real entrepreneurial challenges and showcases resilience.
Post prompts that encourage members to analyze and forecast consumer trends, like sharing lessons from last year’s holiday campaigns or strategies to combat the summer sales dip. Invite members to reflect on data-driven decisions and peer-tested tactics for navigating these seasonal fluctuations.
Yes, use quarterly or new-year themed prompts to have members set, share, and revisit business goals, then follow up with check-in prompts at strategic intervals. For example, start Q1 with 'Share your one big Q1 goal,' and mid-quarter, prompt a status update or obstacle-sharing session. This cultivates accountability and peer support tailored to the entrepreneurial journey.
Skool · Circle · Mighty Networks