How I Negotiated Ice Cream Out of a “No Substitutions” Menu - A Lesson in Possibility

How a Dinner Plan Turned Into a Negotiation Challenge

It started as a simple idea—an intimate dinner for 10 to kick off an EOS Mastery Cohort in San Antonio. Nothing formal, just a chance to connect before the EOS Annual Quarterly Collaborative Exchange (QCE).

Then the guest list grew. And kept growing. Suddenly, we had 30 people. Then 31. Then 32.

That’s when the logistical challenges started.

The restaurant had the space, but they wanted another $500 for the second room. Non-negotiable, they said. And the food menu? Set in stone. No substitutions. No flexibility. No ice cream.

Most people would take that as the final say. Not us.

After all, limits are usually just unchallenged assumptions.

Instead of pushing back, we reframed the conversation. Rather than asking, “Can we get the second room?”—a yes-oriented question begging for rejection—we went with a Calibrated Question™:

“What would need to happen for us to use that second room effectively?”

That simple shift changed the dynamic. Instead of shutting the door, the restaurant had to think in terms of solutions. It moved them from resistance to problem-solving.

And that was just the beginning.

The Ice Cream Standoff at The Alamo: "No" Was Just the Starting Point

One of my team members, Brittany, was looking at the menu when she pointed out the fine print: No substitutions. She shrugged. That was that.

But I had other plans.

“Brittany, I want ice cream.”

“It says no substitutions, Jonathan.”

“I see that. But let’s go get some ice cream anyways.”

She rolled her eyes. “They’re going to say no.”

“Perfect. Let’s see how this plays out.”

Brittany knows the Black Swan skills, and she also knows that if you’re getting too many easy agreements, you’re not negotiating hard enough. So she reached out to the staff and started with an Accusations Audit™:

“You probably think I didn’t read the menu. 

You probably think I’m being a difficult New Yorker.”

That wasn’t an accident. The first thing people do in a negotiation is brace for conflict. A well-placed Accusations Audit™ defuses their defensiveness before it even happens.

And sure enough, instead of rejecting her, the event coordinator softened, even smiled.

“Let me check with the chef.”

Minutes later, he came back—and not only were they willing to serve ice cream—the chef would make homemade ice cream just for us. Any flavors we wanted.

Not just an agreement—a resounding, enthusiastic, heck yes.

We polled the group. “What is your favorite flavor?”

We ended up with three: one classic, one unexpected, and one that, to this day, I can’t remember, but I know was the best thing I tasted that night.

And then came my next big ask.

I didn’t want the waiter to bring the ice cream. I wanted the chef.

Not just because I wanted to thank him. I wanted to shift the dynamic. I wanted to turn this moment into an experience.

The chef was a total introvert. Not used to being in front of a crowd. And English wasn’t his first language.

So when he stepped out from the kitchen, he was visibly nervous.

“I’m so embarrassed,” he said.

We didn’t let him feel that way for long. We gave him a standing ovation. We thanked him. We made him feel like he was a part of the event.

That was the real negotiation win—not only getting the ice cream, but making it matter.

And when the ice cream hit the tables? It became the highlight of the evening.

The Hidden Lesson Behind This Negotiation Win

The Black Swan Method™ is a negotiation approach for expanding what’s possible.

It’s about moving through obstacles like they don’t exist.

It’s about making people feel seen and understood instead of pushing against them.

And it’s about playing the game at a different level—where obstacles become invitations.

Most people read “No substitutions” and stop. The great ones ask, “What needs to happen to make this work?”

You’re Negotiating Every Day—Even If You Don’t Realize It

Most people assume negotiations only happen in boardrooms, sales meetings, or hostage crises. But the reality? Every interaction where you want or need something is a negotiation.

Every time you make a request.
Every time you ask for flexibility.
Every time you shape how someone sees a situation.

If you assume no one will budge, they won’t. But if you walk in expecting solutions, they tend to show up.

And the best negotiators? They don’t push. They guide.

Here’s how you do it in any situation:

1. Use Calibrated Questions™ to reframe the conversation. Instead of asking “Can we do this?”, try “What would need to happen for this to work?” It forces the other side to think with you, rather than against you.
   
   
2. Deploy an Accusations Audit™ before objections arise. If you know someone is about to say no, take the wind out of their sails. “I know this is against policy, and I know it might seem like an unreasonable request…” Preempt their resistance, and they’ll feel more open to problem-solving.
   
   
3. Make them feel like they’re winning. The best negotiations don’t feel like negotiations. They feel like collaborations. That’s what happened with the chef—he wasn’t just making ice cream, he was part of something bigger.
   
   
4. Ask for the “ice cream” in your life. How many times do you take rejection at face value? How often do you miss an opportunity simply because you assumed the answer wouldn’t change?
   
   

The world belongs to those who see possibilities where others see limits.

What will you ask for next?