Has this happened to you? Your salesperson gives what they think is a killer pitch. They're excited. They've practiced. But the prospect's eyes glaze over, and the deal dies right there.
I see it all the time: great products dying painful deaths because salespeople start with a pitch instead of a conversation.
And I learned this lesson in the strangest of places.
Drug Dealers Taught Me More About Sales Than My First Sales Manager
After college, I moved to New York City. Every day, I walked home from the subway through a gauntlet of street hustlers.
"Hey man, want some coke?" they'd say as I passed.
When I shook my head no, they'd immediately pivot: "How about some weed?"
Another head shake.
"Rolex watch? Only fifty bucks!"
Day after day, the same failed approach. They'd start with a pitch without knowing anything about me. They had no idea what I wanted, needed, or could afford.
And day after day, I kept walking.
Sound familiar? It should, because this is exactly how most salespeople approach prospects.
The Pitch-First Model Destroys Sales
Last week, I got five LinkedIn messages that all said basically the same thing:
"I can get you 2-4 new clients every month—guaranteed! If I don't deliver, you don't pay!"
These people knew nothing about my business. They didn't know that I work with CEOs and Business Onwers, not individuals. They didn't know what makes a "good client" for me. They didn't know my values or approach.
They just pitched.
And like those drug dealers on the NYC streets, they got the same response from me—I kept walking.
My $2 Million Lesson in Discovery
Early in my sales career, I was desperate to land a big fish—a manufacturing company that could have doubled our business.
I spent weeks creating the perfect pitch deck. I rehearsed until I could recite it in my sleep. I loaded it with impressive statistics and beautiful graphics.
The big day came. I walked in confident, shook hands, and launched into my presentation.
Fifteen minutes in, the CEO stopped me cold.
"This is all very impressive," he said, "but we already have a solution for the problem you're solving. Our real issue is something else entirely."
I felt my stomach drop. I had completely wasted their time—and mine.
That day, I lost what could have been a $2 million client. Not because our solution wasn't good, but because I led with a pitch instead of discovery.
Why Discovery Must Come First
Here's what I learned: Strategic conversations build trust. Pitches destroy it.
A strategic conversation helps your client learn what they need to make a good decision. It shows them you care more about their results than your commission check.
The best salespeople spend 70% of their time on discovery and only 30% on presenting solutions. Most struggling salespeople do the exact opposite.
The $5 Million Discovery Call
I got another shot at a major client two years after my big failure.
This time, I walked in with zero slides, two high-level strategic briefs and three questions:
- Here is what we see around the corner in your industry.
- These ideas are what will let you get ahead of the curve.
- "What's working well with your current approach?"
- "What's not working that you wish was better?"
- "If we were having this conversation a year from now and you were thrilled with the changes you've made, what would be different?"
For 45 minutes, I mostly listened. I asked follow-up questions. I took notes.
When they finished sharing, I simply said: "Based on what you've told me, I think we might be able to help. May I share a few thoughts about how?"
They leaned forward. They were engaged. They wanted to hear my ideas—because those ideas were now directly tied to the problems they had just shared.
We closed that deal. It was worth $5 million over three years.
Start With Curiosity, Not Certainty
The drug dealers on the NYC streets failed because they started with certainty ("You want drugs") instead of curiosity ("What might you be looking for?").
LinkedIn spammers failed for the same reason.
The best salespeople approach every prospect with genuine curiosity. They ask powerful questions. They listen more than they talk.
Your Turn: Transform Pitches Into Conversations
This week, try this experiment with your sales team:
- Audit your current approach: What percentage of your initial prospect meetings is spent pitching versus discovery? Count the minutes.
- Flip the ratio: Challenge your team to spend at least twice as much time asking questions as they do presenting solutions.
- Create a discovery playbook: Develop 5-7 powerful questions that get to the heart of your prospect's challenges. Questions that make them think differently about their problems.
- Check with your sales manager: How are they helping your team avoid the pitch-and-chase trap? Are they modeling good discovery or reinforcing bad habits?
The street hustlers in NYC never got my business because they never took the time to discover what I actually needed. Don't let your sales team make the same mistake.
P.S. What's your most powerful discovery question? Hit reply and let me know—I'm always looking to add great questions to my toolkit!
