Five critical questions you should ask to win the deal

Bunmi Jembola

You cannot win a good sale without critical questioning. As you may be aware, questioning is the most important part of the sale 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 vulnerability. 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 to understand how to build urgency into the sale process. I say very frequently in my trainings that the only important thing in the sale 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 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 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 very key to selling. Genuine and thoughtful questions will get the customer to talk to you and ultimately like you.


QUESTION 3: If price was not a problem will 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 it is a pointer to some other veiled fears or doubts. The answer will also help you in ascertaining 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 of your goal 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 too, people are busy with their own deliverables and they cannot be bothered with stuffs that don’t particularly add to their KPI scores. To get through the deal you will need a champion- someone who will happily do the leg work and speak for you each step all the way within the organization. Necessarily, he has to be one who is influential in the sale 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, may be not even second.


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

This one question will help you to 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 wisdom 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.


About Bunmi Jembola: I’m Nigeria’s most followed Sales Coach and Consultant on LinkedIn. I have had over a decade of sales experience spanning 4 industries while earning over N12Billion in sales value. I help sales people and entrepreneurs to accelerate their sales outcomes and replicate my kind of sales success. I help employees of corporate organizations to master their sales process through my Sales Master Class.

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