The Most Common Discovery Mistakes in Mid-Market Sales

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I show a clip from Friends in my sales training sessions.

Ross and Rachel just fired their male nanny. His name is Sandy. He’s warm, present, great with the baby. Ross hates him. Always has. He just can’t explain why.

Sandy takes the news graciously. Says he had plenty of other offers. He chose them because he liked them. Ross is already relieved. Then Sandy asks one question.

“If you don’t mind telling me, what was your problem with me? Maybe it’s something I can work on.”

Ross brushes it off. Says it’s nothing Sandy did. It’s his issue. Sandy leans in. Quiet. “What is it?”

Four questions later, Ross is talking about his father. About growing up and never feeling like enough. About playing with dinosaurs in his room while his dad wanted him outside. He’s in tears in front of a man he just fired.

Sandy didn’t push. He just kept asking. And he waited.

What Ross Didn’t Know He Was Doing

I pause the clip there and ask the group what they noticed.

First answers are usually about Sandy’s tone. His patience. The fact that he had nothing to lose. All true. But that’s not the part I want them to see.

What Sandy did is what almost nobody does on a sales call.

He stayed in the question long enough to find out what was really going on.

Ross said “it’s my issue.” Most people accept that. They nod, wrap up, move on. They get the surface answer and call it a conversation. Sandy said “what is it?” and waited. Ross gave a little more. Sandy came back again. Four exchanges later, Ross was somewhere he hadn’t planned on going.

That’s not a technique. 

That’s what it looks like when someone genuinely wants to know.

The Door They Walk Past

I was working with a rep who sold leadership training. He was calling on HR managers. He’d ask about their challenges, get the standard answers, communication issues, manager development, the usual, and pivot straight to his solution.

We got on a call together. An HR manager mentioned friction across her management team. My rep started moving toward his pitch. I stopped him.

We asked her to say more. Then more after that. Turns out two of her senior managers were in open conflict and it was affecting an entire department. She’d been managing the fallout for six months. It was bleeding into her own performance review. She hadn’t told anyone outside the company.

That’s a compelling reason. The first answer wasn’t.

He’d been getting doors open and walking right past them.

One More Question

Most reps have been told to ask open-ended questions. That’s a fine starting point. It’s just incomplete.

Asking an open-ended question gets you in the door. What you do after the first answer is where the real work is.

The questions that move things aren’t complicated. Tell me more about that. What do you mean? How long has that been going on? What happens if it doesn’t get fixed?

None of those require a script. What they require is the patience to listen to the answer before deciding where to go next. And the willingness to come back when someone gives you a non-answer.

Ross said “it’s my issue.” Sandy said “what is it?”

That’s the whole move. Most people don’t make it because they’re already thinking about what they’re going to say next, or they decide the prospect wasn’t going to open up anyway so why push.

Sandy had just been fired. No leverage, no agenda, nothing to protect. So he just asked.


The reps who close the most deals aren’t the ones with the slickest pitches. They’re the ones who find out things other reps never find out. They ask one more question. They let the silence sit. They don’t take the first answer as the real one.

If you want to build a sales team with that kind of instinct, grab a free copy of The Four Pillars of Your Sales Engine. 

Click here to get it. 

Adam

Adam Boyd