Episode 375: A Simple Strategy for Winning Customer Engagement & Long-Term Retention

The Secret to Winning Customers and Keeping Them (It’s Simpler Than You Think)

What if I told you that the key to increasing customer engagement and keeping customers for the long haul isn’t making sure they know about all the amazing content, features, bells and whistles etc. of the amazing solution you are so excited to have created for them?

So many business owners, coaches, and consultants pour their heart into creating incredible offers, only to watch potential customers not buy, disengage, drop off, or fail to get results. It’s frustrating.

But here’s the truth: Customer acquisition and retention starts with understanding what your ideal customer actually cares about.

And most businesses get this part wrong.

Today, I’m breaking down a simple strategy that ensures your customers stay engaged, committed, and excited to stick with you long-term.

The Mistake That’s Costing You Engagement & Loyalty

Imagine you walk into a store looking for the perfect running shoes.

Before you even tell the salesperson what you need, they launch into an excited explanation:

“These shoes are made with the latest shock-absorbing technology! They have triple-layered mesh, an ergonomic sole, and 24-hour moisture-wicking comfort. Plus, we just got them in six new colors!”

Cool, right?

Except… you didn’t ask for any of that.

What you really wanted was:
A shoe that prevents knee pain
Something comfortable for long-distance running
A way to improve your speed and endurance

If they had started with your needs first, you’d be much more likely to stay engaged in the conversation.

The same mistake happens in business every day.

Entrepreneurs get so excited about their offer that they lead with features, details, and logistics before ever explaining why their customer should care.

That’s why people tune out. That’s why engagement drops.

Fixing this is simple: Shift your approach from what you want to tell them to what they need to hear first. 

How to Structure Your Messaging for Maximum Engagement

The best way to win customer engagement and increase retention is to follow a simple framework: “WIIFM”, or “what’s in it for me”. This is the question your potential clients are asking themselves, and should be the focus of your offer. It’s a subtle shift in refocusing your mindset and messaging from all the amazing things you want to share about your offer, to clearly communicating why and how your solution is the one that will solve their problem.

Start with “WHY” (The Problem & Transformation They Want)

Your audience isn’t looking for more information—they’re looking for a solution to their specific challenge.

Lead with the problem they’re trying to solve and the result they want.

Example:
Instead of saying: “This program includes 12 modules, group coaching calls, and an exclusive workbook.”

Say this: “If you’re struggling to scale your business without maxing out your time, this is the fastest way to transition to a scalable model while keeping your customers engaged.”

Key Question to Ask Yourself:

• Why does my audience need this?
• What change do they want to see in their life/business?

Move to “WHEN” (The Timeline for Their Results)

Once they’re interested in the transformation, they need to know:

How long will this take?
When can I expect to see results?

Example:
“In just 90 days, you’ll have a clear, scalable system that lets you serve more clients without adding more hours to your week.”

This makes the experience feel real and achievable for them.

Key Question to Ask Yourself:

• How quickly can they start seeing progress?
• What’s the journey from start to finish?

Explain “HOW” (The Structure, Process, or Pathway)

Only after they understand the why and the when are they ready to hear about how it works.

Example:
“You’ll follow a simple step-by-step framework designed to give you clarity, action, and feedback at every stage.”

Notice how this isn’t just listing features—it’s positioning them as tools to make success easier.

Key Question to Ask Yourself:

• How does my offer remove frustration, overwhelm, or confusion for them?
• What structure makes this a simple and engaging process?

End with “WHAT” (Features, Bonuses, Logistics, & Pricing)

Only now do the details come into play.

The features, course modules, bonuses, community access, tools, and other elements are supporting details, not the main selling point.

By this point, your customer is already invested because they see the value before they hear about the logistics.

Key Question to Ask Yourself:

• How does each feature directly help them get their desired outcome?

“WIIFM” in Action

Let’s apply this to a real-world scenario:

What most people do:
“Our 12-week coaching program includes weekly live calls, video training, worksheets, and a private community.”

What actually works:
“If you feel stuck in a cycle of trading time for money and want to scale your business without burnout, this program will show you exactly how to build a system that works for you. In just 12 weeks, you’ll have a clear pathway to increasing revenue without increasing your workload. We’ve designed a simple, step-by-step process with live coaching, personalized feedback, and a supportive community to keep you on track.”

See the difference?

By leading with transformation, anchoring it to a realistic timeline, and then introducing the method, you create an engaging and retention-focused message.

The Big Takeaway: Focus on Your Customer’s Experience

At the end of the day, the most engaging offers, programs, and businesses don’t just provide information, they guide customers through a transformation.

When you reframe your messaging using this strategy, you:
Instantly capture your potential customer’s attention
Increase customer commitment & follow-through
Reduce drop-offs & disengagement
Build long-term retention & customer loyalty

Try it today. The next time you talk about your offer, start with their why, and watch how quickly engagement changes.

Take Action Now

Want to learn how to apply this to your business? Check out The Learn Academy Mentorship to see how we help business owners create scalable and engaging online programs