Travel is full of surprises — and so is real estate. Both require patience, emotional intelligence, and the ability to get what you need without creating friction.
This past weekend, I was reminded just how valuable great negotiation skills are… and surprisingly, it happened at the Hyatt Regency in Atlanta after the world’s longest two-hour flight on Frontier Airlines.
My wife and I were traveling from Chicago to watch the Indiana Hoosiers in the College Football Peach Bowl. Our flight was supposed to leave O’Hare at 5:50 a.m. and land in Atlanta by 8:00 a.m. — but as anyone who has flown Frontier knows, things rarely go as planned.
From uncomfortable seats to zero amenities, Frontier is the definition of “you get what you pay for.” After leaving the gate on time, a mechanical issue sent us back to wait for an open gate. Ninety minutes later, we finally took off — already drained before the day even started.
When we landed around 9:30 a.m., all we wanted was to get to the Hyatt, drop our bags, and take a nap. The only problem? The hotel was completely sold out and not allowing check-in until 3pm.
But what happened next is something I use daily in my real estate business — and something I teach my team.
Most People Ask. Negotiators Connect.
When people walk up to a hotel front desk, they usually say: “Hi, checking in — any chance our room is ready?” Simple. Direct. And extremely common. But as Chris Voss (former FBI negotiator and author of Never Split the Difference) teaches, negotiation isn’t about the request — it’s about the framing.
So when the associate at the Hyatt said: “Hi! How may I help you?”
I took a different approach: “Hi! We’re checking in… but I have a random question for you. Have you ever had the luxury of flying Frontier Airlines?” He laughed immediately.
That’s what Voss would call tactical empathy — showing you understand the human experience on the other side of the counter.
I followed up with: “Well… we had the full Frontier experience this morning, so if by any chance you have a room ready, we would be incredibly grateful.”
He smiled and replied: “After flying Frontier? Say no more. I’ll get you a room. You need it.” And he did.
This Works in Real Estate Every Day
Real estate is full of “asks”:
• A seller wants the best price
• A buyer wants a concession
• An appraiser wants justification
• An inspector wants context
• A listing agent wants clarity
• A landlord wants reassurance
Most agents rush to the ask — the terms, the price, the win. But the best negotiators — the ones who consistently win for their clients — start by creating connection. Chris Voss says: “Negotiation is not an act of battle; it’s a process of discovery.” In a real estate transaction, discovery happens when you make the other side feel understood. Not manipulated. Not pressured. Understood. Just like the hotel associate, people open doors (sometimes literally!) when they feel a human connection.
How This Principle Shows Up in My Real Estate Business
Whether I’m helping a buyer compete in a multiple-offer situation or a seller navigate tough market conditions, the strategy is the same:
✔ Lead with rapport: Before discussing terms, I always relate to the other agent — their workload, their seller’s situation, their timeline. People negotiate more openly when they feel respected.
✔ Tell a short, relevant story: Just like my Frontier flight anecdote, storytelling cuts tension. It makes the conversation human — not transactional.
✔ Frame the ask gently: Instead of demanding: “My client needs a price reduction,” I’ll ask: “Would you be opposed to exploring a solution based on what we uncovered in inspection?”
✔ Make the other side feel like a partner: Not an opponent. When people relax, they collaborate. When they collaborate, your clients win.
The Big Takeaway
Whether you’re asking for early check-in or negotiating a six-figure real estate deal, the formula is the same:
✔ Create connection
✔ Use empathy
✔ Add a little humor when appropriate
✔ THEN make the request
Because the truth is…
Getting what you want isn’t about pushing harder — it’s about relating better.
And If You Need a Negotiator on Your Side…
This experience reminded me why negotiation is one of the most important skills in real estate — and one of the core reasons clients hire me and my team. If you’re thinking about buying, selling, or investing and you want someone who understands both the technical and human side of negotiation… I’d love to help.
