Challenge funnels: What they are and how to build one

Your webinar converted 2.3% last month.
That's not a you problem. That's a structure problem.

Single-touch engagement… whether it's a webinar, an ebook, or a white paper…

… asks for all the attention at once.

You deliver value, then pivot to the pitch. Often the relationship is shallow because the time invested is shallow.

And this isn’t to say webinars don’t work. I’ve got a client spending $250k/mth driving traffic to a webinar right now that is crushing.

But I am saying that challenge funnels work differently.

They spread engagement across 5-7 days. Each day is a micro-commitment. Each micro-commitment increases psychological investment.

And often by day 5, participants have built enough momentum that your offer feels like the natural next step.

The conversion difference is measurable: 15-25% of challenge completers buy, compared to 1-3% of webinar attendees.

Why challenges convert better: The psychology

When someone shows up for 10 minutes a day over a week, they're making a different kind of commitment than sitting through a 60-minute webinar.

The mechanism is simple:

Each day they participate, they're telling themselves, "I'm the kind of person who finishes things." This triggers Cialdini's commitment and consistency principle… people experience psychological pressure to behave consistently with their previous actions.

By day 3, they've already invested time and effort. The sunk cost fallacy kicks in. They've come this far. They want to see it through.

By day 5, they've experienced real results. Not just information. They experience actual transformation. That's what webinars can't deliver. You can't transform someone in 60 minutes. But you can over 5-7 days of implementation.

The architecture: How to build this

Here's the framework. I'll walk you through the why, then the how.

Pre-challenge sequence (3-5 emails):

Your goal is building anticipation and securing the initial commitment. That first registration is a micro-commitment. The emails leading up to day 1 reinforce that decision and increase the likelihood they'll show up.

Email 1 (immediately after signup): Celebrate their decision. Make them feel smart for joining. Include a small preparation task. Save the sender email, add to calendar, join the community, etc. Each small action builds commitment.

Email 2 (2 days before start): Build anticipation. Tease the methodology. Share a success story from a previous participant. The goal is social proof + curiosity.

Email 3 (1 day before start): Urgency and final preparation. "We start tomorrow" messaging. Technical details. One more community invitation. Set expectations for timing and format.

Daily challenge emails:

This is where most people overcomplicate things. Each email follows the same structure. Consistency matters more than creativity here.

Start every email the same way: Celebrate yesterday's completion. This creates social proof and reinforces the commitment pattern.

Then: Today's transformation focus. Be specific. "Today you'll build your first automated follow-up sequence" is better than "Today we're covering email automation."

Next: The 5-10 minute action step. Keep it achievable. The goal is completion, not perfection. Every completed day strengthens the psychological investment.

Include a community element: "Share your result in the group and tag someone who's crushing it." Peer accountability increases completion rates by 34%. Or have them reply to each day’s email so you know they did the thing.

End with tomorrow's preview: Open loop. Create curiosity. "Tomorrow we're covering the one email most people get wrong—the one that makes or breaks conversion."

Post-challenge conversion sequence (7-10 emails):

Email 1 sends immediately after day 7. Massive celebration. They finished something most people quit. That's meaningful. Make them feel it. Include a soft offer.

Emails 2-3 are social proof amplification. Other people's results. Case studies. Success stories from previous challenge graduates. You're building belief that the transformation is real and sustainable. This heavy sales.

Emails 4-5 introduce the logical next step. Not a hard pitch. Just: "Here's what people typically do after completing the challenge." You're showing them the path, not pushing them down it. This is aggressive selling.

Emails 6-7 handle objections and add urgency. This is where scarcity matters. Things like limited spots for implementation, special pricing for challenge participants, bonuses that expire, etc. The urgency is real because the offer is genuinely limited.

The content structure: What actually works

Your challenge needs to deliver a specific, achievable transformation. Not information. Transformation.

Days 1-2: Early wins

Give them a result they can see or feel in the first 24 hours. This proves the methodology works. It also activates the sunk cost fallacy immediately. They've invested time and gotten results. They're bought in.

Example for email marketing: Day 1 isn't "Understanding email deliverability." It's "Write and send your first re-engagement email today." They see opens and clicks within hours. That's proof.

Days 3-4: Progressive complexity

Now you can go deeper. They trust you. They've seen results. They're ready for more sophisticated concepts.

This is where you demonstrate expertise. The webinar can't go this deep because it's trying to cover everything in an hour. Your challenge has the time to build properly.

Days 5-7: Integration + bridge to offer

Show them how the pieces fit together. They've learned 5-7 discrete skills or concepts. Now you show them the system—how these pieces work together.

Then you reveal: The system they've been experiencing is a simplified version of your paid offer. They've seen it work. They know it delivers results. The paid version is the complete implementation.

This isn't manipulation. It's showing them what's possible and offering them the full version.

Often I tell clients I have 2 rules for daily action items.

Rule #1: The action cannot take longer than 10 minutes. Anything longer than that and it seems too complicated.

Rule #2: Tie each action to a daily habit or routine your subscribers already have. For example - I helped a brand do a movement challenge and we had people do 20 squats while brushing their teeth.

The idea is that everyone has little routines they do every single day and if you can tie your challenge to those routines - it increases the odds of them doing the daily action and completing the challenge. (And increases the odds of them buying after the challenge.)

What you actually need to build this

Don't overthink the tech stack.

You need:

• Email platform (whatever you're using now probably works)

• Landing page (your existing builder is fine)

That's it. The psychology matters more than the tools.

Optional but valuable:

• SMS reminders (increases daily participation by 15-20%)

• Behavioral tracking for lead scoring

• Progress dashboards

• Video hosting

• Community platform.

But start simple. The first challenge will be messy regardless of how fancy your tech is. Better to learn the system with simple tools than get bogged down in implementation.

I like proving the challenge concept via just email first. And once we prove the challenge works, we’ll run it again, but this time with additional education provided via video.

The implementation reality

Your first challenge won't be perfect.

You'll underestimate content creation time. Your email timing will need adjustment. Participation will drop on day 3 (it always does—that's when people get busy).

But here's what matters: Each challenge gets better. You refine the content. You optimize the timing. You improve the transitions.

The second challenge converts better than the first. The third converts better than the second.

When challenges make sense (and when they don't)

Build a challenge if:

• You can articulate a specific transformation achievable in 5-7 days

• Your methodology is worth teaching (it creates IP and competitive positioning)

• Your average deal size justifies the content investment

• You want positioning beyond "faster/cheaper/better"

Skip challenges if:

• You're selling low-consideration commodity products

• Your business model requires high volume, low-touch sales

• You have no system to nurture leads who don't immediately convert

Most B2B service businesses, consultants, and SaaS companies should be running challenges. It's one of the few lead generation systems that gets better with time instead of degrading.

Next steps

Have questions about challenges? Or want an outside perspective? Reply with your offer, audience, and website, and I’ll record a video of 3 potential challenges you could run to attract more of your ideal clients to you and convert them with a challenge.

Tyler