The journey of sales, much like a challenging puzzle, demands precision and foresight. 

Misjudge a step, and your deal could slip away. 

What if you could equip yourself with a toolkit of insightful questions to finetune your strategy and amplify your success rate?

A lot of your success comes down to how you run your sales reviews.

Today, I’ll be sharing 5 questions to ask your team, to discover the truth beneath what you’re being told. 

Choose a couple from the list below, test them with your team, and see the depth of revelations they can bring.

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

So often, the dates shared are a lofty or optimistic assessment by your sales team, it is their interpretation or their hope, without any validation from the customer.

You may even observe them fumble or deflect the question. 

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.

2. What benchmarks does the customer use to classify this investment as valuable?

What truly is the criteria that your customer is applying, to decide on your project? 

Is it an urgent priority or something that is “good to have” but not essential?

In a lot of cases, you would get some very superficial responses because salespeople rarely probe down to the heart of the problem or understand the criteria behind the decision making

3. How does your customer articulate, how your project aligns to their CEO’s objectives and KPIs?

Can your team clearly connect 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.

This question essentially gauges if your proposition aligns with your client’s strategic vision and priorities/ projects

4. Who has the power at your customer’s end to veto the deal?

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 individually aligned and collectively approved?

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

5. In what ways does the customer perceive and measure 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 we will lose this deal?

This flips the script from the usual ‘how can we win’ to a more proactive and resourceful, ‘what could possibly go wrong’. 

Recognizing potential pitfalls is the key to preemptive strategy.

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.

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If this was helpful, 

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