“I call it the Win-Win Inquisition. Not because I’m interrogating you, but because I’m relentlessly curious about your business. There’s a difference.”
Every time I say that, I watch people pause. Sometimes they smile. Occasionally they laugh. But they always lean in, and that’s exactly the point. Let me explain.
Where This Started
I sold my first product at around 10 years old, and I didn’t know it was a sales lesson at the time.
Some family friends took me to a Kansas University football game, and by halftime my buddy and I were bored out of our minds. So, we asked his parents if we could run through the stadium collecting the plastic cups people had already used and left behind. They said yes. Once we hauled our treasure back to his house, we asked his mom if we could run them through the dishwasher. She said yes. (To this day I’m still amazed she said yes.)
Only then did the actual selling start. We went through the neighborhood with a stack of clean cups, and we didn’t sell them one price fits all. Small cups went for a nickel, mediums for a dime, larges for a quarter. And we didn’t knock on just any door. We looked for the houses with the flags out front, the neighbors who actually had some connection to the teams printed on the cups. Those were the sales that closed.
Looking back, that afternoon had three separate asks inside it, not one. Convincing the parents to let two kids loose in a stadium full of strangers’ trash. Convincing a mom to hand over her dishwasher for a project she had every reason to say no to. And only after that, the cups themselves, priced and pitched based on who was actually going to want them.
I didn’t have language for any of it then. But that’s the Win-Win Inquisition in miniature: earn the trust before you ask for anything bigger and know who you’re actually talking to before you make the pitch. I just didn’t give it a name until decades later.
The Name Is Intentional
When most people hear “inquisition,” they think pressure. Interrogation. Someone across the table trying to extract something from them. And honestly? That’s not far from how a lot of sales conversations actually feel.
But that’s not what I built.
The Win-Win Inquisition is rooted in something far simpler, and far more powerful: genuine curiosity. The kind that says I want to understand your world before I say a single word about mine. The kind that treats every client conversation as an education, not a transaction.
I’ve spent over 35 years in enterprise technology sales. And the single most important lesson I’ve learned isn’t about closing techniques or objection handling. It’s this:
Sales is nothing more than an educational process.
You educate me on your challenges. I educate you on what’s possible. And somewhere in that exchange, if we’re both being sincere and earnest, we figure out whether there’s a path forward together.
That’s the inquisition. And when it works, everybody wins.
A friend of mine once told me that makes me a “Connector,” borrowing Malcolm Gladwell’s term from The Tipping Point for the rare people who seem to know everyone and can’t help introducing them to each other. I never set out to be one. I just kept asking questions long after most people would’ve stopped.
That’s the name, and that’s the philosophy behind it. Turns out “inquisition” was never the scary part. Now for the fun part: watching it actually survive contact with a real client, with real money and real risk on the table, and no script to hide behind.
That’s Part 2.