In my conversations with sales executives and leaders, they’re very curious to know if there are better ways to review deals in their pipeline. 

“What kind of questions shall I ask my team to ensure we’re proactive and effectively managing the progression of the deal?”

Today, I’m going to share with you 5 transformative deal-review questions to maximize your sales potential and win rate. 

If this resonates with you, 

Subscribe to the CXO Sales Playbook Newsletter.

Every Friday morning, I’ll email you 1 actionable tip to get your sales teams to overdeliver. (other benefits include a big bonus and company-wide recognition :). 

I advise you to pick 1-2 of your favorites and ask your sales team to see the powerful insights you can get just by asking the right questions.

Let’s get started. 

The first one is, 

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

Most often, you’ll find your team members smile sheepishly when they hear this question, because the due date on their opportunity is not the customer’s due date. 

It’s their own estimation and their hope and prayer that it’ll close by this time.

Most likely, if you see either a month end or a quarter end as the due date, you know that your team is guessing the due date.

The second one is, 

Q2. How does your customer determine whether this project is a good investment or a bad 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? 

In a lot of cases, you would get some very superficial responses.

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

The third one is, 

Q3. How does your customer describe how your project shows up on their CEO’s KPIs? 

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

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

The fourth one is, 

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

This question relates to stakeholder mapping and consensus management.

Has your sales team got the necessary buy-in from all the decision-makers? Have they covered all their bases?

This is critical to avoid any delays or last-moment hiccups in your deal progression. 

The last one is, 

Q5. How does your customer monetize your differentiation?

This one is my personal favorite.

If the customer is not monetizing it, that means there is no differentiation. Period. 

If there is no differentiation, it means there’ll only be commoditization.

Are we done? Not yet, because I’m going to throw in 1 more bonus question. (We always like to overdeliver)

It’s what the French call a lagniappe, one extra in a baker’s dozen.

If you’re only going to ask only 1 question to your team, make it this one.

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

Most often, sales reviews focus on how you could win a deal. The counterintuitive nature of this question forces your team to confront reality and identify the risks that hold your deal back. In fact, Sales is the systematic elimination of risk.  

In closing:

When you ask these hard questions with your team, make sure that you ask them softly. 

My advice is – Be hard on the issue, soft on the person.

The reason I am sharing all these questions with you is that I want each one of you to win more. 

I want each one of you to ensure that you empower your teams to win more. 

These questions are just a starting point when we start working together with our clients.

Next Step 

Subscribe to the CXO Sales Playbook Newsletter.

Every Friday morning, I’ll email you 1 actionable tip to get your sales teams to overdeliver. (other benefits include a big bonus and company-wide recognition :).