The silent deal killer

I lost the deal last week.

And not in a dramatic, fireworks-ending kind of way.
Not with a “we’ve decided to go another direction” or a pricing battle I fought to the bitter end.

It was a quiet death.
One that came after months of good vibes, strong engagement, buying signals that felt as obvious as a billboard.

Then…

Silence.

No email.
No explanation.
Just the sound of my own thoughts bouncing around like a racquetball.

Here’s what played on repeat in my head:

• Did I say something wrong in the last call?

• Should I have pushed harder after the demo?

• Maybe I didn’t follow up fast enough? Or too fast?

• Was my proposal too long? Too short? Too… something?

I was stuck in a spiral of “me.”

What I said. What I didn’t say. What I should’ve said.

It’s a familiar loop, and I’ve noticed it tends to show up right when a deal slips away.
It’s exhausting. And honestly, it’s probably not the most helpful place to sit.

It was during a walk, you know, one of those “get out of your head” walks, when something shifted.

I realized I hadn’t really been thinking about the buyer at all.

Not like, really thinking about them.

I wasn’t asking:

• What was it like to be them?

• What were they scared of?

• What pressure were they under?

• What happened if they made the wrong decision?

And beyond that…

• What did their last buying experience feel like?

• How many internal approvals did they need?

• How many of those people were quietly hoping the project didn’t go through?

I’d been so focused on my process, my pitch, my follow-up, my sequence, that I’d forgotten something pretty important:

They weren’t just trying to buy something.
They were trying not to screw up.

That’s what I’ve been sitting with.

And the more I think about it, the more I wonder if the real job of a buyer isn't to simply make a purchase, but to not make a mistake.

Not a career defining one. Not a political one. Not a budget blowing one.

It's possible that they don’t fear committing to a product.
They fear committing to the wrong one.

And maybe the moments that cause deals to stall or vanish aren’t about us being unclear…

…but about them feeling uncertain.

And the fastest path to certainty? Maybe it’s not some clever new pitch or shiny new asset.

Maybe it’s just to do nothing. 

So I’ve been asking myself something new:

“What would it look like to use AI not to pitch better, but to help buyers feel more certain?”

Like… could I use AI to study the emotional and tactical journey of past buyers?

Could I surface:

• What problems they came in trying to solve?

• How they were solving them before?

• Why their previous approach failed?

• What questions they were carrying into the first call?

• What fears bubbled up before the yes?

• What internal pushback they faced?

• What they wish they’d seen earlier?

• etc…

And then, instead of pitching, could I offer that?

A glimpse into how others like them made the decision.

What they asked.
What they worried about.
What helped.
How exactly they made the case.

Would that help someone feel a little less alone in their process?

A little more sure?

I’m still experimenting. Still turning over rocks. Still trying to find the best way to bring this to life.

But it’s already changed the way I think about selling.

If you've read this far, maybe you’ve felt it too.

That moment when a sure thing deal fades. When your follow up sits unopened. When your calendar feels a little too empty.

If so, maybe don’t ask what more you could say.

Maybe ask:

What’s one thing I can do to remove uncertainty for this buyer?

Even if they never ask for it.
Even if they don’t know how to name it.
Even if it seems small.

Because it’s possible that every ounce of uncertainty you lift,
makes space for something else to show up.

Like confidence.
Or clarity.
Or trust.

And that, more than anything else, might be the gift the prospect needs to gets the deal done.

If you enjoyed this check out one experiment I started last week. Includes a step by step guide to test yourself.

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