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5,000 Interviews, One Big Learning
A 5-step empathy framework that turns silence into sales
Howie Chan
August 31, 2025
Dear Legend,
Let me ask you something…
Have you ever had a brilliant idea, one that could truly help someone, and yet, when you shared it… it landed with a thud?
They didn’t buy.
They didn’t shift.
They didn’t care.
You did the research, crafted the right words, made a rational case, you even had data to support your idea.
And still they didn’t move.
Why?
Most people think it’s a messaging problem. Or a confidence problem. Or a sales problem.
But it’s none of those. It’s something deeper and something much earlier in the process of influencing and convincing.
It’s an empathy problem. 🤯
Here’s the promise
In this issue, I’m going to give you a proven, practical framework that will help you:
Build a high-trust, high-performance team
Win more customers and keep the ones you already have
Get people to listen, lean in, and say “yes” without pushing, posturing, or persuasion tricks
The tool?
Rob Volpe’s Five Steps to Empathy, applied directly to your two most important audiences:
👭 Your team
💰 Your customers
(Who is Rob? Rob Volpe is a leading voice on empathy in leadership, author of Tell Me More About That, and the CEO of Ignite 360, a research and strategy firm that works with brands like Whole Foods, Target, PepsiCo, and LinkedIn. Through thousands of in-depth interviews and years of studying human behavior, Rob developed the Five Steps to Empathy: a practical framework used by top executives and entrepreneurs to lead, connect, and influence with power and heart.)
❤️ Heartset: Your feeling of being misunderstood is also what your audience is feeling
When you put out a proposal, an offer, or an idea and you get crickets, you probably feel really crappy. Why don’t they get it? Why am I misunderstood?
The crazy thing is, that feeling right there, that ache, is probably what your team and your customers are also feeling.
Unseen.
When people feel unseen, they shut down.
They ghost.
They underperform.
They doubt.
They churn.
They leave.
They don’t feel like they have to do anything for you.
But when someone feels seen?
Heard?
Understood?
They open.
And in that opening, influence becomes effortless.
“Empathy reduces resistance. It softens the armor.”
🧠 Mindset: From “I need to convince them” to “I need to first understand them”
This shift is incredibly important. Applying empathy accomplishes two critical things for influence.
The first is content.
When you truly understand your team and your customers, the content will become more relevant. Your solution will actually solve a real pain. Your idea will actually bring a needed change.
The second is context.
When you understand your audience. When they feel that you truly care, either through in-person non-verbal cues, or directly stating the work you’ve done to understand them, you’ve designed the conditions in which a yes is more likely (they simply like you more, this invokes the Liking principle, but more on that later.)
🧰 Skillset: The Five Steps to Empathy
Rob Volpe’s framework is more than theory, it’s been battle-tested inside Fortune 100 companies, major marketing orgs, and high-stakes leadership rooms.
Dismantle Judgment
Ask Good Questions
Actively Listen
Integrate into Understanding
Use Solution Imagination
And we’re going to apply it in two ways:
For business owners: How to get more customers (and keep them)
For team builders: How to build high-performance, loyal teams
For Business Owners
How to Win More Customers and Retain the Ones You Have
1. Dismantle Judgment
Stop assuming your customers are irrational, cheap, or flakey.
Start having the mindset of curiosity: “What fear or frustration is behind their hesitation?”
2. Ask Good Questions
Ditch the survey and get on a phone call with them. Or take them out to coffee or lunch. Ask:
“What almost made you say no?”
“What was it about the offer that felt misaligned?”
“What was going on in your life when you started looking for this?”
3. Actively Listen
Track emotions, not just answers.
Write down how they speak, not just what they say.
Use their words in your copy, emails, sales calls.
4. Integrate Into Understanding
Take feedback personally: not as offense, but as insight.
What are they trying to say… underneath what they’re saying? Write down your “so what” to ink it into your understanding, instead of just pulling quotes.
5. Use Solution Imagination
Help them co-create with you and then visualize the win.
Ask:
“What would you need so the problem goes away entirely?”
“If this solved your problem perfectly, what would life look like?”
That’s what they’re buying. Not your product. Their transformation.
And it all starts with empathy.
For team builders:
How to Build a Loyal, High-Trust, High-Performance Team
1. Dismantle Judgment
When you assume your team member is lazy or “not leadership material,” they’ll feel it.
Instead, be curious about the belief they might be carrying that’s holding them back.
2. Ask Good Questions
Replace: “Why didn’t this get done?”
With: “What got in your way and what would’ve helped?”
Better questions unlock better conversations. And better performance.
3. Actively Listen
During your next 1:1, do this:
Turn off notifications. Ask one meaningful question.
Then shut up and let them fill the space.
That’s where the gold lives.
4. Integrate Into Understanding
They’re not “difficult.” They’re guarded.
They’re not “checked out.” They’re afraid.
Rehearse their story from their point of view and when you write that down in a journal or type it up in Notion, you can better ink it into your mind.
That’s how empathy grows.
5. Use Solution Imagination
Don’t solve every problem yourself.
Ask:
“If this worked out in the best way possible, what would it look like for you?”
“If you were able to accomplish all you set out to do, what would have been the support that was critical?”
Let them see themselves as part of the win.
That’s what creates commitment.
Ready to hone your empathy superpower? How will you use it this week?
When we exercise empathy, one of the principles of influence is heavily at work.
That’s the Liking Bias.
The Liking Bias isn’t just a feeling, it’s science.
Multiple studies show we’re far more likely to comply with, trust, and follow people we like and empathy is what creates that likability.
In Cialdini’s persuasion research, people said “yes” more often to those who shared similarities.
In neuroscience studies, empathy lights up the same reward circuits as food and money.
And our brains actually feel pleasure when similar people succeed.
Bottom line? People don’t say yes because you’re right.
They say yes because they like you.
And people like you… when they feel seen by you.
The Legend Effect Podcast
In this episode, empathy expert Rob Volpe drops an emotional truth bomb: “You can’t influence anyone who feels judged by you.”
We dive deep into why most entrepreneurs fail to connect, even when they’re saying all the right things and what to do instead. Rob breaks down his Five Steps to Empathy, shares what 5,000+ interviews taught him about human behavior, he teaches the curious breath (I do it on the show!) and reveals the surprising neuroscience behind why your team isn’t speaking up… and your customers aren’t buying.
If you want more influence, loyalty, and sales — this conversation is your playbook.
Make your mark, live your legend 🤘🏽
See you next Sunday!
Howie Chan
Creator of Legend Letters
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