The Socratic sales move
The prospect had the smoking gun evidence in his hands.
His current service provider was failing him. The assessment provided by my client in the discovery process proved this beyond any doubt whatsoever. The situation was actually worse than the prospect feared when he started looking for alternatives.
So what did he do?
He gave his current service provider another chance.
Why do smart business owners make decisions like this—and what should you do when it happens to you as a salesperson?
The Story Behind the Stall
Every Tuesday, I coach 100+ MSP sales pros and business owners on their sales process. During our weekly "office hours," we dig into real-world deals, roadblocks, and strategy breakdowns.
This week, a rep shared a scenario that perfectly illustrates why good deals go sideways.
Her prospect was worried about compliance. It was clearly a priority—he'd already lost confidence in his current MSP's ability to manage it. So the rep offered to run a comprehensive assessment. Not just a surface-level check. A deep dive.
The results confirmed the prospect's worst fears and uncovered vulnerabilities he hadn't even considered.
The rep expected this would lead to a switch. Instead, the prospect said he'd take the assessment back to his current provider and give them one more chance.
Sound familiar?
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Let's Be Honest: It's a Bad Business Decision
Sticking with the current provider, in this case, is objectively a poor choice:
They've already violated his trust
Any sense of peace of mind is gone—now he's doing the oversight
They left him vulnerable and at risk
In a fast-moving tech landscape, he'll likely be in an even worse spot 12 months from now
But here's the thing—that's not where the real breakdown happened.
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The Salesperson's Real Mistake
The rep's biggest error wasn't the pitch or process—it was her mindset.
"I didn't want to come across as high pressure," she told us.
So she held back. She avoided the hard questions. She didn't challenge the decision—even respectfully. She didn't coach.
And that's exactly what was needed.
Sometimes, applying healthy pressure is what helps someone make the right call. That's what a good coach does.
A personal trainer pushes you to do one more rep when it's uncomfortable. A business advisor pushes you to take action when you're hesitating. And a great salesperson? They help people make better decisions—even when that means confronting the friction head-on.
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"But What If I Push Too Hard and Lose the Deal?"
Look, if you don't apply some pressure or make the right moves, you've already lost this deal anyway.
When a prospect takes your assessment back to a failing provider for "one more chance," they're choosing the comfortable path over the smart one. That rarely ends well for anyone.
But here's what most reps miss—if you handle this right, you're not just trying to save this deal. You're positioning yourself for the inevitable next conversation.
The key is reading the room and calibrating your pressure appropriately. You're not attacking their decision—you're respectfully challenging their thinking. There's a difference.
Think of it like the personal trainer analogy. Some friction often represents growth. The question isn't whether to push—it's how to push in a way that helps rather than hurts.
Done right, six months from now when they're back in the market (and they will be), they'll remember not just that you diagnosed the problem, but that you respectfully coached and advised them. And you were right.
That puts you first in line.
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The Socratic Move
So how do you apply the right kind of pressure?
Ask questions that help the prospect arrive at the conclusion on their own. It's the Socratic approach to sales—use thoughtful, respectful questions to coach better decision-making.
Here are a few examples:
"Do you really want to be the one responsible for overseeing IT strategy and compliance going forward?"
"What gives you confidence this time will be different than last time?"
"At the pace tech is changing, what makes you think you won't be in an even riskier position six months from now?"
You're not making them wrong. You're helping them see what's right—for the business.
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