Greg Isenberg’s Content Calendar for Community Managers: 60 Days of Proven Prompts

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If you’ve ever asked yourself, “What do I post next to spark real engagement in my community?” you’re not alone. That's where Greg Isenberg’s content calendar comes in—a practical, proven system designed for community managers who want to drive connection, conversation, and loyalty. Today, I'll walk you through what makes this calendar so effective, share 60 days of prompts, and break down the strategies behind the magic. Let’s jump in.

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Greg Isenberg’s Content Calendar for Community Managers: 60 Days of Proven Prompts

Why Greg Isenberg? Understanding the Mind Behind the Calendar

First, let’s talk about why Greg Isenberg is the go-to resource for content and community playbooks. Greg’s resume speaks for itself: a serial entrepreneur, advisor to billion-dollar startups, founder of Capitaly.vc, and the mastermind behind thriving online communities. His hands-on approach and practical insights have helped shape how brands, creators, and startups nurture genuine engagement. Greg’s ideas aren’t just theories; they’ve been tested and optimized in the wild. If you want actionable advice that works, he’s your guy.

What Makes Greg Isenberg’s Content Calendar Unique?

There are hundreds of content calendars floating around, but Greg Isenberg’s approach prioritizes easy, scalable prompts and proven community psychology. It aligns content with your community’s journey while making planning stress-free. Here’s what stands out:

Actionable prompts: Designed to inspire immediate response and interaction.
Cyclical structure: You can reuse the calendar every 60 days without feeling repetitive.
Rooted in engagement strategy: Each prompt drives a specific kind of member action—sharing, learning, or bonding.

It's the difference between a built-for-you roadmap and a random content checklist.

How a 60-Day Content Calendar Transforms Community Management

Consistency is everything in community management. With a 60-day content calendar, you’ll never scramble for ideas again. It shifts you from reactive to proactive by:

Eliminating content guesswork
Saving time and brainpower every week
Strengthening member loyalty through reliable touchpoints

I’ve seen communities double their engagement simply by getting ahead on planning. For more on this, see our blog post: Consistency is Key: How to Scale Community Engagement.

60 Days of Greg Isenberg’s Proven Prompts

Let’s get tactical. Here’s a sample breakdown of Greg Isenberg’s 60-day prompt calendar approach—hands-on, ready to use, and flexible enough for any niche.

Monday: “Wins and Challenges” – What went well this week? What are you struggling with?
Tuesday: “Introduce Yourself” – New member spotlight or fun fact threads.
Wednesday: “Resource Share” – Swap tools, books, or podcasts.
Thursday: “Ask Me Anything” – You or a guest answers member-submitted questions.
Friday: “Shoutouts & Gratitude” – Recognize contributions or say thanks.
Saturday: “Weekend Challenge” – Prompt action or reflection, like ‘try X and report back.’
Sunday: “What’s Inspiring You?” – Share quotes, photos, or experiences for a lift.

Repeat with new angles or variations for a full 60 days, keeping things fresh but predictable.

Building an Engagement Strategy with Greg Isenberg’s Prompts

Prompts only matter if they fit into a wider engagement strategy. Greg’s methodology connects each prompt to member psychology:

Belonging: Personal introductions break the ice.
Accountability: Sharing wins or challenges motivates progress.
Celebration: Shoutouts create positive feedback loops.

Mix in prompts that cover all three, and you’ll hit every emotional driver your members need to stick around.

Optimizing Prompts for Different Community Platforms

Every platform has its quirks. Tailor Greg’s content prompts to where your community lives:

Slack/Discord: Use threads, emojis, and scheduled posts for continuous conversation.
Facebook Groups: Pin prompts and use polls for instant interaction.
Circle/Discourse: Combine announcements with direct tag notifications to ensure visibility.

Test what drives the fastest replies—then double down.

Incorporating User-Generated Content into the Calendar

User-generated content (UGC) supercharges engagement. Build UGC right into your calendar:

Feature member stories once a week
Host themed photo or idea contests
Let members suggest topics for future prompts

This approach not only lightens your workload but helps members take ownership, which is key to long-term retention.

Keeping Prompts Fresh and Avoiding Repetition

Even the best prompt can go stale. Here’s how I keep Greg’s calendar evergreen:

Rotate themes every two months
Solicit member feedback on prompt fatigue
Mix formats: image-based, polls, open-ended, and challenges

If you spot lagging engagement, tweak and reboot—adaptability beats perfection every time.

Tracking Engagement Metrics: What to Measure from the Calendar

You can’t improve what you don’t measure. With Greg Isenberg’s system, I focus on:

Post reply count
Unique commenter participation
Member retention after responding

Track week-over-week shifts and double down on what works. For more on metrics, see our blog post: How to Measure Community Engagement Like a Pro.

Encouraging Lurkers to Participate Using Greg’s Prompts

Lurkers make up most communities—but Greg’s prompts lower the bar to join in. Start with:

Low-stakes questions (“What would you bring to a desert island?”)
Anonymous polls
Encouraging small wins (“Thanks for your first reply!” badges)

Over time, these small nudges convert observers into contributors.

Integrating Visuals for Greater Impact

Strong visuals multiply your prompt’s reach. I incorporate:

Custom graphics for weekly themes
GIFs or memes relevant to your members
Screenshots of member highlights (with permission)

Visual prompts spark 30-50% more replies in most communities—don’t overlook them.

Adapting Greg Isenberg’s Calendar for Niche Communities

No two communities are the same. For niche audiences, I:

Localized prompts (language, slang, industry terms)
Special themed weeks (e.g., “Startup Fail Tales” for founders)
Collaboration with niche experts or supermembers

For practical examples in startup communities, see our blog post: Building Community in Web3: Lessons from Capitaly.vc.

Leveraging Greg Isenberg’s Prompts for Launch Campaigns

Launching something new? Stack the deck with anticipation-driven prompts:

Count-down sneak peeks (“3 days to go! Guess what’s launching?”)
Early access requests (“Want to beta test? Comment below!”)
Recap threads post-launch (“What are your first impressions?”)

Ahead-of-time planning ensures you capitalize on peak attention moments.

Automating the Content Calendar Workflow

Manual planning is a drag. Here’s how I automate Greg’s content calendar:

Use tools like Notion, Airtable, or Trello for prompt tracking
Set reminders with Buffer or Hootsuite for cross-platform posting
Calendar integrations—sync weekly themes direct to your Slack or Discord

This way, your prompts roll out steadily even when you’re busy elsewhere.

Collaborating with Your Community Using the Calendar

The best calendars are built with the community, not just for them. I recommend:

Quarterly surveys (“Which prompts were your favorite?”)
Invite members to co-host or suggest prompts
Create a rotating “member moderator” system

Shared ownership increases accountability and engagement across the board.

Managing Crisis or Low Morale with the Calendar

Every community faces tough moments. Greg’s tactical prompts help steer the ship:

Open check-ins (“How are you really doing right now?”)
Space for venting—but with clear boundaries
“What’s one positive thing?” gratitude threads

These foster trust and resilience, proving your space is more than just a content feed.

Scaling Your Community with Prompt-Driven Engagement

The right content calendar is a growth engine. As more people join:

Enable tag-based prompts (e.g., @ProductLaunchTeam)
Spin-off interest groups using strong-response prompt themes
Track which prompts attract new members, and double down

Turning prompts into rituals is what moves a group from chat room to thriving community.

Learning from Greg Isenberg’s Calendar: Real-World Examples

In one SaaS founder community I managed, “Monday Wins” threads garnered 5x more replies over eight weeks. In a remote work group, introducing a weekly “Tech Stack Show-and-Tell” prompt built a knowledge-sharing culture from scratch. The common thread? Each prompt creates a moment for members to shine, connect, or contribute.

Common Pitfalls and How to Avoid Them

Even great prompts fail if you:

Overwhelm with too many at once (keep it digestible)
Neglect follow-up (always reply and tag members in responses)
Don’t vary the format or timing

I learned these the hard way—avoid my mistakes for faster results.

Iterating Your Calendar Based on Community Feedback

After each cycle, review what hit and what missed. I suggest:

Sentiment surveys after 30 days
Open prompt suggestion threads
Spotlight top contributors who shaped the calendar

Your community will feel heard—and your content will keep evolving.

Where to Find More Inspiration: Greg Isenberg and Capitaly.vc Resources

For fresh ideas or emerging trends, tap directly into Greg’s playbooks at Capitaly.vc. They cover everything from brand building to venture capital community hacks. Watch for guest interviews, case studies, and exclusive prompts updates as the landscape shifts. For more on building a next-level brand alongside your community, read our blog post: Building a Brand That Works: Capitaly's Guide.

FAQs About Greg Isenberg’s Content Calendar for Community Managers

What is Greg Isenberg’s content calendar?
It’s a 60-day cycle of proven content prompts designed to drive engagement for online communities, based on tactics that have been tested across fast-growing groups and startups.
Can I adapt these prompts to any industry?
Absolutely—Greg’s prompts are intentionally broad but flexible so you can localize them for any niche or community.
How much time does it take to set up the calendar?
Initial setup takes 90 minutes or less for most teams. Ongoing updates can be done in under 20 minutes a week.
Do I need to use all 60 prompts?
No—the 60-day structure is cyclical, meaning you can remix or pick favorites each round while keeping things fresh.
How do I know if the prompts are working?
Track replies, new contributor stats, and member retention to spot what’s gaining traction.
What’s the best way to involve my members in prompt development?
Host feedback surveys and prompt suggestion threads every month—member-driven prompts outperform 2-to-1 in most groups.
How do I handle off-topic or negative responses?
Set clear community guidelines and reinforce positive participation through shoutouts and gentle nudges back to purpose.
Is this calendar suitable for both small and large communities?
Yes! Whether you have 25 members or 25,000, Greg’s approach scales up seamlessly.
Can I automate prompt delivery?
Definitely—use Slack schedulers, Hootsuite, or native platform tools to schedule ahead.
Where can I find more in-depth resources from Greg Isenberg?
Check out Capitaly.vc’s blog and Substack for playbooks, interviews, and case studies.

Conclusion

If you want to scale connection and create meaningful rituals in your brand’s community, Greg Isenberg’s content calendar is a field-tested toolkit you can rely on. Backed by proven psychology and practical experience, this 60-day prompt cycle will energize your community, save you time, and let your members shine.

Ready to supercharge your engagement strategy? Subscribe to Capitaly.vc Substack (https://capitaly.substack.com/) to raise capital at the speed of AI.