How Humor and Curiosity Can Help You Build Real Relationships (and Get Callbacks!)
Jun 23, 2025
In a world flooded with marketing noise, missed emails, and ghosted follow-ups, Ray Engan brings a refreshing and hilarious solution to the table: humor, curiosity, and a little bit of human connection. In his conversation with James Marland on the Scaling Therapy Practice podcast, Ray shares a down-to-earth and laugh-out-loud look at how to genuinely connect with others, even total strangers.
Let’s explore Ray’s biggest lessons, hilarious analogies, and the secret to getting people to call you back.
From Comedy Clubs to Corporate America
Ray Engan didn’t start as a corporate communication expert. His story begins on stage, doing stand-up comedy and writing for late-night television. “I had to walk into Rock Springs, Wyoming, with a bunch of bikers playing pool... and I had five minutes to talk them out of playing pool and watch my show,” he shared. Talk about learning how to win people over!
After years in comedy, Ray transitioned to sales and later to leadership training. Everywhere he went, sales skyrocketed, not because of aggressive tactics, but because of his unique way of connecting with people.
The Real Problem: Nobody Calls You Back
“People build rapport, but they’re missing connection,” Ray said. “We lost five years of people skills.” Post-pandemic communication habits have shifted, and Ray believes the ability to genuinely connect is more important than ever.
His mission? Help entrepreneurs, speakers, and coaches get back to building real human relationships.
What You’re Doing Wrong (Probably)
Ray’s top mistake people make when trying to connect?
“Stop asking questions when you first meet someone. You don’t have the right to ask yet.”
Wait, what? Isn’t asking questions how you build rapport? Not exactly. According to Ray, friends make statements, not questions. Statements feel more natural and less intrusive. For example:
Instead of: “Hi, what do you do?”
Try: “That’s a cool background photo, looks like you love hiking.”
Statements invite conversation, while questions can feel like an interrogation.
Curiosity is King
Curiosity is one of the main drivers in Ray’s framework for authentic connection. “It’s what gets your emails opened, your posts read, and your phone calls answered,” he explains.
Three powerful elements to spark a connection?
- Curiosity
- Relevance
- Specificity
And one more bonus? Humor. “Humor is instant likability, trust, and rapport—all rolled into one,” Ray said. People remember how you make them feel, and laughter breaks down walls fast.
Humor Isn’t Just for Comedians
You don’t have to be Robin Williams to use humor effectively. “You can show a funny cat video and still be the most memorable speaker in the room,” Ray joked. It's not about being the funniest—it's about bringing levity, being relatable, and easing tension.
Fun fact: In most workplaces, the funniest person is often perceived as the best worker. Whether that’s fair or not, it's a real psychological phenomenon that savvy communicators can use to their advantage.
The Power of a 7-Word Email
If you want one actionable takeaway that could earn you thousands in income this month, here it is:
“James, it’s been too long. Let’s catch up.
Ray”
That’s it. No long intros. No hard pitches. Just a simple message of reconnection.
Ray ran a holiday challenge encouraging participants to send this kind of short message. Many reported thousands of dollars in new business—one even made $15,000 in December alone, the slowest sales month of the year.
Pro tip: Use curiosity-based subject lines like:
- “Saw your doppelganger today”
- “Remember me?”
- “Funny story about our last meeting”
Connection Before Conversion
Trying to make a sale too early is a huge mistake. As Ray put it: “The faster you ask for money, the less of it you get.”
Before someone buys from you, they need trust. Build that trust, and they’ll buy more—and stay longer. But push the sale too soon, and they’ll walk away.
Ray compares it to dating. “Marketing is like flirting. Sales is like dating. And a proposal? That’s your long-term commitment.” You wouldn't ask someone to marry you on the first date—don’t do it in business either.
Introducing: The Lean In Factor
Ray’s new program, The Lean In Factor, teaches entrepreneurs, speakers, and coaches how to build what he calls “the familiarity of friendship.” Whether you’re introverted or extroverted, this system helps you:
- Own the room at networking events
- Get more callbacks
- Build authentic, no-pressure sales relationships.
One of his favorite opening lines? “I’m looking for a hero… and I hope it’s you.”
Memorable. Bold. Conversation-worthy.
Final Thought: Selling Is Helping
James summed it up perfectly: “Your ideal client is looking for your solution… Selling is awesome when you’re solving real problems.”
Ray’s approach is a beautiful mix of confidence, empathy, humor, and real-world communication tips that anyone can use today.
Resources
- Ray Engan’s Website: humorspeaks.com
- LinkedIn: Ray Engan on LinkedIn
- Weekly Livestream: Roadblock Removal for Speakers and Coaches, Wednesdays at 2 PM EST
- Leadership Through Laughter: leadershipthroughlaughter.com
- Ray on Facebook
- Listen to the show STP 121
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