How to Run an Online Challenge: The Ultimate Guide to Building Your Audience Fast

Tired of creating content that nobody sees? Learning how to run an online challenge could be the game-changer you need.

While other creators are grinding away posting content into the void, savvy entrepreneurs are using challenges to build engaged audiences in days, not months.

And the best part? These audiences are primed and ready to buy.

Let me show you how to run an online challenge that actually works…

Why Online Challenges Are Your Secret Weapon for Growth

Let’s get real about why most audience-building strategies fail.

Posting consistently on social media? It’s a slog.

Blogging? Takes forever to gain traction.

SEO? Don’t even get me started.

Online challenges cut through all that noise.

Here’s why learning how to run an online challenge could transform your business:

• Creates Urgency – Limited timeframe drives immediate action
• Builds Community – Participants connect with you and each other
• Demonstrates Expertise – Showcases your knowledge in action
• Delivers Results – Participants see tangible progress
• Nurtures Connection – Daily interaction builds relationships fast
• Generates Social Proof – Success stories fuel future growth

According to HubSpot, interactive content generates 2x more conversions than passive content. Challenges are interactive content on steroids.

Let’s break down exactly how to run an online challenge that converts strangers into customers…

What Makes a Challenge Different from Regular Content?

A challenge isn’t just a series of posts or emails.

It’s a structured experience with a clear transformation.

Here’s what makes challenges uniquely powerful:

When you learn how to run an online challenge, you’re not just creating content.

You’re creating an experience that transforms your audience while positioning you as the expert they trust.

This trust is what makes selling your digital products at the end feel natural, not forced.

Planning Your Challenge That Actually Delivers Results

The biggest mistake people make with challenges?

Jumping in without a solid plan.

Your challenge needs strategic foundations:

Set Goals That Serve Your Business

Every successful challenge starts with clear objectives.

What do you actually want to accomplish?

Be specific about what success looks like.

Vague goals = vague results.

Identify Your PERFECT Challenge Participants

Not everyone is the right fit for your challenge.

You need participants who:

1. Have the problem your challenge helps solve
2. Are motivated to take action
3. Could benefit from your paid offerings later

Create a detailed profile of your ideal participant:

The more specific you get, the more targeted your challenge will be.

For a deeper dive into understanding audience needs, check out the demographics guide from Investopedia on defining your target market.

Structure Your Challenge for Maximum Impact

Your challenge needs a clear beginning, middle, and end.

The structure should build momentum and deliver quick wins.

Here’s a proven timeline that works:

The 5-day format works exceptionally well because it’s long enough to deliver value but short

The 5-day format works exceptionally well because it’s long enough to deliver value but short enough to maintain momentum.

For more insights on structuring learning experiences, check out my guide on how to create a workshop.

Creating Challenge Content That Keeps People Engaged

Your challenge content can make or break the experience.

Boring, theoretical content = high dropout rates.

Here’s how to create challenge content that keeps participants hooked:

Design Every Day to Deliver a Quick Win

Each day of your challenge needs to stand alone as valuable.

Structure your daily content like this:

• Clear Daily Outcome – What they’ll accomplish today
• Concise Teaching – Just enough theory to understand (10-15 min max)
• Actionable Task – Something they can complete in 30 minutes or less
• Accountability Check-In – Way to share progress and get feedback
• Preview Tomorrow – Teaser of what’s coming next to maintain momentum

Remember: Results drive engagement.

The faster participants see progress, the more likely they’ll stick with your challenge.

Use Multiple Media Types to Keep Things Fresh

Don’t just rely on one content format.

Mix it up to appeal to different learning styles:

Using multiple formats keeps your challenge fresh and engaging.

It also accommodates different learning preferences, making your challenge more inclusive.

For more ideas on creating effective learning materials, check out my guide on how to create printables as companion resources.

Promoting Your Challenge to Fill It with the Right People

Even the best-designed challenge won’t work if nobody knows about it.

Here’s how to fill your challenge with the RIGHT participants:

Leverage These Platforms for Maximum Reach

Different platforms work better for different types of challenges.

Focus your efforts where your ideal participants already hang out:

Pro tip: Choose 1-2 platforms and go all in, rather than spreading yourself too thin.

It’s better to dominate one channel than to be mediocre on five.

Collaborate with Others to Expand Your Reach

Want to accelerate your challenge growth?

Partner with other creators or influencers in your space.

Here are effective collaboration strategies:

• Co-host the challenge with a complementary creator
• Ask partners to promote to their audiences
• Offer affiliate commissions on any backend offer
• Feature guest experts for one day of your challenge
• Create a challenge bundle with other creators’ resources

The right partnership can instantly double or triple your reach.

Just make sure your values and audience needs align.

Create an Email Strategy That Builds Anticipation

Email is the backbone of any successful challenge.

Here’s a proven email sequence that works:

For more email marketing strategies, see my guide on how to create an email course.

Engaging Your Challenge Participants Every Single Day

Getting people to sign up is just the beginning.

The real magic happens when you actively engage participants throughout the challenge.

Here’s how to keep them excited and taking action:

Create a Community Experience That Keeps Them Coming Back

Humans are social creatures.

Make your challenge a group experience, not a solo journey:

• Dedicated Group – Create a Facebook group or community platform
• Daily Check-ins – Post specific prompts for sharing progress
• Celebration Thread – Highlight wins and breakthroughs
• Accountability Partners – Pair participants for extra support
• Group Rituals – Create shared experiences (kickoff call, completion ceremony)

The community aspect often becomes the most valuable part of your challenge.

When participants connect with each other, they’re more likely to stay engaged and complete the challenge.

Use These Engagement Boosters When Participation Dips

Every challenge has natural energy dips.

Be ready with these engagement strategies:

The most successful challenges build in these engagement boosters from the start.

Don’t wait for participation to drop before taking action.

Answer Questions and Provide Support That Creates Raving Fans

How you support participants can turn a good challenge into an unforgettable experience.

Focus on these support strategies:

• Daily Office Hours – Set times when you’ll answer questions live
• FAQ Document – Create a resource addressing common questions
• Personal Feedback – Comment on participant posts with specific guidance
• Troubleshooting Guide – Help participants overcome common obstacles
• Tech Support – Clear instructions for any platforms or tools used

Remember: Support is where you prove your expertise and build trust.

The more supported participants feel, the more likely they’ll consider your paid offerings later.

For more ideas on creating supportive learning environments, see my guide on how to create an online membership.

Analyzing Your Challenge Results to Make It Even Better

Every challenge is a learning opportunity.

Here’s how to analyze what worked and what didn’t:

Track These Key Metrics

Numbers don’t lie.

Track these metrics to measure your challenge success:

These benchmarks vary by industry, but they give you targets to aim for.

Pay special attention to where in your challenge people drop off – that’s your biggest opportunity for improvement.

Collect Feedback That Actually Helps

Participant feedback is gold for improving future challenges.

Ask these questions to get useful insights:

• What was the most valuable part of the challenge for you?
• What was your biggest obstacle during the challenge?
• What content or support would have made your experience better?
• How likely are you to recommend this challenge to others? (Scale 1-10)
• What made you say yes to joining the challenge?

Pro tip: Offer a small incentive for completing your feedback survey to increase response rates.

Make These Improvements for Your Next Challenge

Use your data and feedback to make targeted improvements:

Each challenge you run should be better than the last.

The most successful challenge creators view each iteration as a learning experience.

The Bottom Line on Running Successful Challenges

Learning how to run an online challenge isn’t just another marketing tactic.

It’s about creating a transformative experience that showcases your expertise while helping people get real results.

Remember these key principles:

• Focus on one specific outcome your participants truly want
• Create a structure that delivers quick wins and builds momentum
• Foster community to increase accountability and connection
• Provide genuine support that demonstrates your expertise
• Analyze results to continuously improve your challenge

When done right, challenges can grow your audience faster than almost any other strategy while positioning your digital products as the natural next step.

Start small with your first challenge. Focus on delivery and participant experience rather than massive numbers.

Then scale what works.

YOU GOT THIS 🙌

In your corner,
Adam