A few years ago, I was with a founder chasing a large enterprise prospect.
Customer had a real problem—systems crashing, missed SLAs, unhappy customers.

Founder and team were doing Follow-ups.
Chasing for Demos.
Emailing Decks.

But the buyer?
Cold. Disinterested. Busy.

At one point, the founder said something that stuck with me:
“It feels like I care more about their problem than they do.”

And that’s the trap.

The Doctor is panicking. But the Patient feels fine.
That’s why there’s no urgency.
No buying energy.
No deal.

Here’s the brutal truth in enterprise sales:

You’re not selling a product.
You’re facilitating a diagnosis.

And unless the patient feels the pain,
they won’t book the surgery.

7 Signs You’re Acting Like the Overeager Doctor:

↳ You’re following up more than they’re following through.
You’re chasing meetings, not momentum.

↳ You’re leading with solutions, not symptoms.
Diagnosing before discovery = ignored prescriptions.

↳ You’re talking about your company more than their risks.
No one buys a tool. They buy the threat of not using it.

↳ You’re showing ROI before they feel the Cost of Inaction.
Logic doesn’t move hearts. Stakes do.

↳ You’re selling to a need that hasn’t been admitted yet.
Until they say, “Yes, this is a problem,” your deal is fiction.

↳ You’re playing the vendor, not the guide.
Patients don’t want pills. They want someone who’s seen the disease before.

↳ You’re stuck in ‘sales process’ mode instead of ‘buying process’ mode.
Shift from stage-gating to sense-making.

So, how do you flip the script?

Make the patient feel the pain—before you pitch the cure.

Here’s a simple tactical flow:

➡️ Start with symptoms
“Are you noticing [X] happening more often?”

➡️Surface stakes
“What happens if this continues for the next 3 quarters?”

➡️Reveal ripple effects
“How’s this affecting your team / margins / growth plans?”

➡️Co-diagnose the root cause
“Sounds like we’re dealing with [Y]. Seen this in 4 other orgs.”

➡️Offer optionality, not a pitch
“There are a few ways to handle this—want to explore?”

When they start asking questions,
when they follow up,
when they escalate the urgency…

➡️You’ve made the shift.

The patient is now ready for the surgery.

And you?

You’re not selling anymore.
You’re healing.

If your deals are stuck, maybe you’re playing the wrong role.
Be less salesperson.
Be more specialist.

Your best sales will feel like second opinions. 😍