Five Critical Questions You Should Ask to Win Sales Deals

You cannot win a good sale without critical questioning. As you may be aware, questioning is the most important part of the sales process. More often than not, when you lose the sale, it is because you didn’t ask the right questions.

Here are a few questions that will greatly improve your chances of eventually closing the deal.

Question 1: As of today, what are your most important business priorities—things you need to quickly do to realize your next set of growth objectives?

This question is profound. It will help you achieve two things.

First, it will open up the customer to you with all vulnerabilities. Here, you are asking him about the most important things he needs to grow. Even if you cannot provide them, he will still be willing to talk. Everyone wants to share their worries. People always talk about the things that are most important to them. They talk passionately, and that’s what you need to win their confidence. That’s exactly what you need to have a great conversation.

Two, this question should help you understand how to build urgency into the sales process. I say very frequently in my trainings that the only important thing in the sales process is what is important to the customer. The only urgent thing is what he urgently needs. Nothing else can make him buy with a sense of urgency as much as what he considers urgent. Once you get the answer to the above question, you should tie your value propositions to that end.

Question 2: What is the single most important lesson you have learned in this business?

This is ALWAYS a deep-dive question, and it is the cleverest way to unveil his challenges. More often than not, in answering that question, entrepreneurs focus on their challenges. You can even add a follow-up question:

What one piece of advice will you give to someone starting out in this same field?

Now, these questions may not be related in any way to your sale. That is not a problem. In fact, it is all the better. It builds your credibility as one not just coming to “harvest” the income of the prospect but to provide value. In all honesty, that cannot happen without a deep understanding of the customer’s journey. As you may already know, people buy more from people they like. Not necessarily people who can solve the problem. The likeness factor is so key to selling. Genuine and thoughtful questions will get the customer to talk to you and ultimately like you.

QUESTION 3: If price were not a problem, would you be willing to buy from me?

This question arises at the objection stage, and it helps you to validate a price objection. As a rule, a price objection is not real until it has been raised twice. So when someone brings up a price objection, you want to be sure if it’s real or if it is a pointer to some other veiled fears or doubts. The answer will also help you determine if, indeed, you need to shift on price to close the deal.

QUESTION 4: If we convince you enough of our capacity to deliver on every one of your goals for this purchase, will you mind being our champion?

This question is particularly suited to B2B complex sales. In a complex sale, decision-making is often by consensus. Many people need to agree before the deal can proceed. Too often, people are busy with their own deliverables, and they cannot be bothered with stuff that doesn’t particularly add to their KPI scores. To get through the deal, you will need a champion- someone who will happily do the legwork and speak for you at each step, all the way within the organization. Necessarily, he has to be one who is influential in the sales process himself. Asking this particular question requires some tact, a good measure of buy-in, and some level of professional friendship. You may not be able to ask this at your first pitch, maybe not even the second.

This one question will help you avoid losing precious time. In every organization, there is serious politicking going on, sometimes as much as you have in a country’s political system. You want to be sure your sale is not frustrated on account of some ego play by individuals jostling for relevance or because of some interdepartmental scuffles. Since you often need everyone’s consensus to sell, it is wise to include every relevant person, department, or their representative from an early stage. Not doing so can negatively impact your chances. Just some guy who’s not even spoken to you before will bring up an issue of competence just because he hasn’t been carried along.

QUESTION 5: Is there anyone else who necessarily should be a part of this deal process?

This one question will help you avoid losing precious time. In every organization, there is serious politicking going on, sometimes as much as you have in a country’s political system. You want to be sure your sale is not frustrated on account of some ego play by individuals jostling for relevance or because of some interdepartmental scuffles. Since you often need everyone’s consensus to sell, it is wise to include every relevant person, department, or their representative from an early stage. Not doing so can negatively impact your chances. Just some guy who’s not even spoken to you before will bring up an issue of competence just because he hasn’t been carried along.

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