EXPERIMENT #003:

TRAP QUESTIONS

I saw it the same way everyone else did. A short LinkedIn video from a sales guru.

Confident tone.
Clean framing.
A little smug.
Optimistic sales guy energy.

The technique had a name. They called them “trap questions.” The claim was that you could lower a prospect’s guard just long enough to make them question the gaps in what they already had.

We disagreed, but we ran the experiment anyway.

The premise was straightforward.

You open cold.
The prospect listens for a few seconds.
Then the reflex.

“We already have something like this.”

“We’re not looking right now.”

Instead of overcoming the objection, you agree with it.

You apologize.
You flatter them.
You lower the temperature.

Of course you already have something in place.
Most teams your size do.
You are probably pretty well set up.

Then you ask a question that quietly removes things from the table.

So I am assuming the things you care most about are already covered.
That nothing important is missing.
That the tradeoffs you accepted are not painful enough to revisit.
That whatever friction exists is manageable for now.

Each one maps directly to a differentiator your product has.
The idea is that one of them lands.
The prospect corrects you.
And in correcting you, they reopen the conversation.

The responses clustered quickly.

Bucket one.
They agreed.

“No, those things matter to us. That is actually why we chose what we are using.”

Conversation over.

Bucket two.
They acknowledged the value, then parked it.

“Yeah, those are good points. It is just not painful enough right now to make a change.”

Also over.

Bucket three.
The soft exit.

“Those are interesting. Let me talk with the team and get back to you.”

They did not.

A few weeks later, we started hearing it.
Sometimes directly.
Sometimes a follow-up reply we did not expect.

“Yeah, we actually went with someone else.”

Other times, we saw it the usual way.

A LinkedIn post about a new platform they were excited about.
A quiet announcement.
A tagged recommendation in the comments.

In almost every case, it was not because of better questions or better framing.

They were introduced.
Recommended by someone they trusted.
Pulled in through their network.

That is when it clicked.
These were not deals we lost.
They were hail marys someone else threw.

Assessment:
Good in theory. Very 1990s. This is psychological warfare dressed up as nuance.
A relic from an era when sales was trained to corner, pressure, and reframe until someone cracked.

It does not create curiosity.
It creates tension.
And tension is exactly why sales has the reputation it does.

Recommendation:
Not recommended. Trap questions do not make you clever. They make you sound like a sales guy trying not to sound like a sales guy.

Most buyers do not want to be maneuvered.
They want to feel safe, informed, and in control.

This technique does the opposite.
It reinforces the stereotype.
It confirms the suspicion.
And when the deal actually moves, it still is not because of the question.

It is because someone vouched for you. Someone trusted you. Someone opened a door you could not.

Everything else is theater.