Most sales leaders focus on how to win the deal. But the exceptional ones?

They focus on why they might lose it.

That mindset shift is what separates good from great.

In my experience coaching sales teams at companies like Microsoft, SAP, and Workday, I’ve observed that the best leaders have a unique ability to uncover hidden risks and opportunities that others miss – simply by asking the right questions.

Today, I’m sharing 3 powerful questions that can transform your pipeline of opportunities into actual revenue – especially for deals you want to win this quarter.

Let’s dive in.

Question 1: How did your customer arrive at their due date?

Watch your team’s reactions carefully.

You’ll often see sheepish smiles because the timeline isn’t actually the customer’s – it’s your team’s hopeful estimate.

If that date coincides with month-end or quarter-end, it’s likely just an educated guess.

This simple question helps you separate wishful thinking from reality, giving you a more accurate forecast.

Question 2: How does your customer relate this project to their CEO’s KPIs?

What you’re really testing here is whether your team has connected the dots from your capabilities to measurable, monetizable business outcomes.

Because if your team can’t connect these dots, your customer definitely won’t be able to.

When we engage with Fortune 500 executives, this question often reveals that sales teams are focused on features and functions rather than business impact.

Question 3: Tell me all the reasons why you’ll lose this deal?

This is my personal favorite.

Most reviews focus on how to win. The counterintuitive nature of this question forces your team to confront reality and identify the risks holding your deal back.

Remember – Sales is the systematic elimination of risk.

When you ask these questions, do so gently. Be tough on the issue, but gentle with the person.

These 3 questions help you make the invisible visible.

Try them in your next sales review and watch what happens.

Remember, your customer’s risks are your opportunity in disguise. Spot them early—and you’ll become the partner they trust to solve them.

What’s your go-to sales review question—the one that changes everything when it’s asked?

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If this was helpful,

1.Subscribe to the CxO Sales Playbook

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2.Take Our Deal Review Quiz

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3.Review Our Clients & Case Studies

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