In my discussions with sales leaders and executives, a question often emerges:

“How do I make sure that my sales guys are on the ball?”

To address this, I’m sharing 5 crucial deal-review questions that can maximize deal velocity and win rate.

Let’s dive in.

Q1. How did your customer arrive at their due date?

Often, you’ll notice team members smile sheepishly because the due date on their opportunity is typically their own estimate.

If you see a due date aligned with month-end or quarter-end, it’s likely just a guess.

Q2. How does your customer evaluate whether this project is a good investment?

Now, when you ask a question like that, what you’re really trying to find out is, what truly is the criteria that your customer is applying, to decide on your project?

I’ve come across very few salespeople who actually know the customer’s criteria for making a decision.

Q3. How does your customer relate your project to their CEO’s KPIs?

What you’re really testing here is, has your sales team connected the dots from your capabilities, products, or services to the customer’s measurable and monetizable business outcomes?

If your team can’t clearly connect the dots, the customer definitely will not be able to do so as well.

Q4. When your customer contact says Yes, who are three people within the company who can say No?

This question addresses stakeholder mapping and consensus management.

Has your sales team secured buy-in from all decision-makers or is their confidence based on the approval of only one individual?

This is vital to avoid delays or last-minute obstacles in the deal process.

Q5. How does your customer monetize your differentiation?

This one is my personal favorite.

If the customer isn’t monetizing your differentiation, there is no real differentiation.

Without differentiation, your offering is reduced to a commodity.

Q6. Tell me all the reasons why you’ll lose this deal.

Typically, sales reviews focus on how to win a deal.

This counterintuitive question forces your team to confront reality and identify the risks that could jeopardize the deal.

Sales is about systematically eliminating risks.

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

You’ll be amazed at the insights you can gain simply by asking the right questions.

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