They Keep Bringing More People

Nate: So one of my SE Managers flagged something last quarter that I thought was interesting. She had an SE doing four, sometimes FIVE demos for a single deal. Same product, same use case... just more people in the room every time.

Ava: Like expanding the buying center? Different stakeholders wanting to see different things?

Nate: That's what everyone assumed at first. But when she dug into it... it wasn't that. The first demo just didn't land. The prospect walked out not understanding what the product actually does for THEM. So what did they do? They didn't say "that was a bad demo." They grabbed a colleague and booked another one. Like— maybe this person can figure out what they're talking about.

Ava: Oh... so the PROSPECT is doing damage control. They need to show progress internally, so they keep the process moving, but they're basically outsourcing comprehension to the next person in the room.

Nate: Exactly. And from our side, it looks like momentum. More stakeholders, more demos, the deal must be progressing. But it's not. It's spinning.

Ava: Welcome to Leading PreSales. I'm Ava.

Nate: And I'm Nate. Every episode, one idea, five minutes. Today— how to tell whether your deal is actually progressing or just spinning in circles.

Ava: Okay so this is interesting because on the surface, more demos looks like a GOOD sign. You're getting deeper into the organization. But what you're describing is... the opposite of that.

Nate: It is. And it doesn't feel wrong while it's happening. The AE is happy because there's activity. The SE is happy because they're presenting again. But nobody's asking... did the LAST session actually move the decision forward?

Ava: So what was happening in those demos? Same playbook every time?

Nate: Pretty much. Very feature-centric. Technically impressive. But the SE was showing what the product CAN do rather than connecting it to what the customer NEEDS it to do. And every question— even casual ones— got a five-minute deep dive into the software.

Ava: The show-and-tell trap. Someone asks a simple question and instead of "yes, we handle that"... you get a walkthrough of three screens.

Nate: Right. And the SE wasn't doing anything malicious. They were proud of the product. But the customer's sitting there watching features they didn't ask about, and after thirty minutes they've lost the thread of why they're even evaluating this thing.

Ava: And then the next demo gets scheduled, new people show up, and the SE runs... the same approach?

Nate: With minor variations. Maybe they start at a different module. But the disconnect between what the SE is showing and what the customer is trying to DECIDE— that doesn't change. It's like repeating a sentence louder instead of saying it differently. And the sales cycle just... stretches.

Ava: Okay, so how did your SE Manager actually catch this? Because like you said, from the outside it looks like a healthy deal.

Nate: She started tracking something simple. After every demo, she asked the SE one question— "what decision is the customer closer to making after today's session?" Not what did you SHOW. What DECISION did you advance?

Ava: That's a sharp question. Because if the answer is "well, they saw the reporting module"... that's not a decision.

Nate: Exactly. And when the SE couldn't answer that question clearly after demo three, she knew the deal was spinning. So she stepped in and coached a different approach for the next session. Less product, more conversation. Start with "last time we spoke, you mentioned X was your biggest challenge. Can we talk about where you are with that?"

Ava: So instead of picking up where the demo LEFT off, you pick up where the customer's PROBLEM left off.

Nate: Yes. And this is the bit that changed things. The SE went into the next meeting— no screen share. Just fifteen minutes of conversation. What's changed since last time? Who else is involved in the decision? What's still unclear?

Ava: And?

Nate: Two concerns surfaced that had never come up in any of the previous demos. Because nobody had ASKED. The SE addressed both with about ten minutes of targeted walkthrough. Ten minutes. After four previous sessions of forty-five minutes each.

Ava: That math is painful. And it gets at something bigger... we treat demos as performances when they should be conversations. The SE's job isn't to present. It's to help the customer make a decision.

Nate: And the signal is right there in front of you. If new faces keep appearing and the questions aren't getting more specific— if demo three sounds like demo one— your SE isn't building understanding. They're repeating information.

Ava: So the move here is pretty clear. After every demo, ask yourself— or ask your SE— what decision is the customer closer to making? And if you can't answer that...

Nate: Then the next session shouldn't be another demo. It should be a conversation.

Nate: I'm Nate.

Ava: And I'm Ava. See you next episode!