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People think negotiation is about pushing hard, flexing status, or tossing around credentials like confetti. This story isn’t that. This is about mindset, timing, tone—and understanding that some of the best negotiations don’t feel like negotiations at all.
Let me take you back to a recent hotel stay. We were there for a conference. Three of us. Two rooms. You can do the math. That left two women in their thirties having to share a room, and frankly, that shouldn’t happen. These aren’t sorority sisters on MTV’s “Spring Break”—they’re professionals. So, naturally, the ask was simple: We need one more room.
The First Two Rejections—and Why They Were Necessary
Attempt one? We had Brittany reach out to the conference producer we knew. Crickets. Not a lack of skill on her part—the producer was slammed. They were prepping for 2,000 attendees. We weren’t top-tier in their world that weekend, so we were not getting any special favors.
Attempt two? Lauren gave the front desk a go early in the morning when she was checking in. She got a polite but firm “No.” That wasn’t on her either. Timing matters. Hotels manage inventory like airlines. At 9 a.m., their algorithm was not freeing up any inventory. They hold back 2% of rooms for emergencies—flooded bathrooms, broken ACs, whatever. The circumstances just weren't there yet.
So now we’ve got two "No"s. Most people hear two "No"s and call it quits. But here's something I stress all the time: a negotiation isn’t a single interaction—it’s a process. Sometimes it takes a week, sometimes six months. You can't give up just because the first and the second swings didn't connect.
Reframing the Ask with Tactical Empathy® and Dynamic Silence™
When I arrived, I decided I’d try it myself. Not because I thought I was more persuasive, but because I had the timing, tone, and frankly, nothing to lose.
I’m Marriott Platinum, so I walked into the “Marriott Bonvoy Elite” Line. But I didn’t use that as a hammer. Status isn’t leverage unless it’s applied with humility. I handed over my credentials and casually asked, “How impossible would it be to get an extra room tonight?”
And then I shut up.
I started counting seconds of Dynamic Silence™ . . . Dynamic Silence™ . . . Dynamic Silence™ .
That moment of pause gave the agent the space to work it out internally. No pressure. No entitlement. No pitching. Just presence. He scanned the system. I could see it in his eyes—there were rooms available. He stepped away to check with his manager.
I didn’t fill the silence, just more Dynamic Silence™.
I didn’t say, “Just so you know, I’m Platinum Elite!” I didn’t get tight or impatient. I gave him room to solve the problem and provide the implementation.
Tone Is Critical
Chris Voss always says tone is everything. He’s not exaggerating. You can’t just use a Label™ or a Calibrated Question™ and expect magic if your tone says, “I’m annoyed” or “I’m desperate.”
My tone that day was pure, relaxed Accomodator. I wasn’t emotionally attached to the outcome. In fact, in my head, I assumed I would hear “No” for a third time. That assumption freed me. I didn’t need the win to feel validated. And that emotional posture made my tone disarming—low stakes, high curiosity.
That’s why this isn’t a story about pushing for an upgrade. This is about stepping into the ask with the right energy. I walked up like any other guest—cool, casual, patient.
Negotiation Isn’t About Winning. It’s About Creating Space.
When the agent returned, he smiled.
“Mr. Smith, I have good news. We have an extra room available.”
I smiled back. “I have good news too,” and handed him a $20 dollar bill. Nothing fancy. Just a thank you. Was it a tip? A gesture? A recognition? It didn’t matter. It was gratitude without expectation. My grandfather always taught us to “spread a little sunshine” and the $20 was just a little sunshine.
Remember this: I didn’t have to fight for the room. I didn’t “win” it. I created space for the other person to solve the problem on their terms. That’s the core of Tactical Empathy®—not demanding your way, but showing up in a way that makes the other side want to help.
What This Means for You
If you want to get better at negotiating in your own life—whether it’s hotel rooms, project deadlines, or team dynamics—start here:
- Detach from the outcome. Don’t walk in needing agreement. Walk in seeking clarity.
- Use tone like a scalpel, not a sword. Calm, curious, and kind beats aggressive every time.
- Expect rejection—and embrace it. It doesn’t mean the end. Sometimes, “No” is just the first step in the real conversation.
- Master Dynamic Silence™. Most people talk through the silence because they’re nervous. Don’t. Hold the space. Let the room breathe.
Negotiation isn’t about talking people into things. It’s about showing up in a way that makes the other side feel safe enough to say yes—on their terms. When you bring patience, a clear ask, and the right tone, you create the space for better outcomes to happen. Not because you demanded them, but because you made them possible. That’s what the best negotiators do—they don’t force results. They create the conditions for them.