The Conversations That Change Everything

How to unlock clarity, momentum, and wild ideas—in just one intentional exchange.

Jun 27, 2025

It started with a single question:
“What would this look like if it were easy?”

A friend asked me that on a walk.
I was venting about burnout, overcomplicating my business, tinkering with a product no one asked for. I stopped mid-step.

That one line—so casual, so non-threatening—cut through weeks of fog.

I went home, deleted three projects, simplified my offer, and made more in one month than I had in the last three.

We all have moments like that.
Moments where someone says just the right thing—and our whole direction shifts.

That’s the power of a good conversation.
It doesn’t just motivate. It moves you forward.

The Credibility Builder

I used to think strategy was the answer to everything.
I made 12-month plans. Built funnels. Wrote vision docs.

But the biggest breakthroughs in my business?
They’ve come from conversations about what’s possible.

Thank you Dr. Dorothy Martin-Neville, Mary Shakun, Gordon Melville, Machen MacDonald and David George Brooke

Dinner tables, voice notes, mastermind calls.
A single question—asked at the right moment—can realign your entire business.

One of the most powerful? It comes from Dan Sullivan.

The Dan Sullivan Question (And Why It Works)

The entire book The Dan Sullivan Question centers around one transformative line he uses with clients, partners, and teams. It’s not a sales tactic—it’s a relational tool designed to unlock deeper motivation and long-term clarity.

💬 Here’s the question:

“If we were having this conversation three years from today, and you were looking back over those three years, what has to have happened in your life — both personally and professionally — for you to feel happy with your progress?”

That’s it.

Simple on the surface. But when you ask it—and give someone space to answer—it often leads to breakthroughs.

Why it works:

It bypasses small talk and surface goals.
It invites future-focused clarity on their terms.
It builds trust instantly.
It turns casual conversations into coaching moments.

And then there are the follow-ups:

What dangers do you need to eliminate?
What opportunities do you need to capture?
What strengths do you need to maximize?

Together, these turn a question into a roadmap.

Dan’s used this in over 20,000 entrepreneurial conversations. People have literally said it changed their life.

🛠️ The Meaty Middle: Creating Your Own Transformative Conversations

Let’s get practical.
Here’s how to use this kind of questioning in your life and work:

1. Start With Possibility Prompts

Don’t go tactical too soon. Start with big, imaginative openers:

“What would this look like if it were easy?”
“What do you secretly wish was true?”
“What would make this fun again?”
“What would you do if no one could see you fail?”

These spark truth. They get you and others talking about what matters.

2. Practice the Dan Sullivan Model

Memorize the question. Use it often. And let people think.
Most people rarely get asked what they want in a meaningful way.
Be the person who asks it—and listens well.