How to Close More Sales with a Winning Questioning Process

Blog124_QBehindtheQ.docx-1Prospects buy when they want to fix, accomplish or avoid something. Often, however, they’re unaware they have a problem, let alone a need.

That’s why learning the art of smart questioning accelerates closing more sales, as nothing else can.

Blog124_QBehindtheQ.docx-12Lots of salespeople struggle to close sales. According to CSO Insights’ 2015 Sales Compensation and Performance Management Study, only 54.6 percent of sales reps produce enough revenue to meet quota. That’s barely half

And unless you ask the right questions, you won’t uncover the right needs. Unless you ask the right questions, you won’t understand the what problems to solve, leaving you flying blind and unable to offer a useful perspective to potential buyers.

When prospects hear a product pitch, their kneejerk reaction is “I’m totally satisfied with my current situation, provider . . .”  They seem to be satisfied because they’re unaware of any problems. Besides, they’re turned off by ubiquitous product pitches.

Just because they’re unaware doesn’t mean a problem doesn’t exist.

Only three percent of people in the market are looking for your solution right now. Six to seven percent are open to a solution (they know the need is there), and a whopping 30 percent will never buy even if you gave a steep product discount.

Golden Sales Triangle

The golden triangle of sales is that three percent who are looking, added to the six to seven percent who are open, on top of the remaining 60 percent not currently in the market. We must help this group see a reason to change and buy our solution.

But we can’t do it unless we uncover the need, establish the value, and lay out the consequences of not acting now.

Business issues and pains are the underpinnings of a value-based message. When you use your sales conversations to (1) tie solutions to business problems and (2) show your differentiation, you create a captive audience that understands the importance of actively participating in their own rescue. As research has shown, we live in an era when product innovation alone cannot be the basis for corporate success.

So how do you lay the groundwork for a value-based sales conversation? With effective discovery and a systematic process of questioning. And that begins with smart meeting planning.

Most good advisors and salespeople do set up agendas, prepare the right information to discuss prospect issues, and they analyze how the product or service matches the prospect need (if they know it). You cannot imagine how even small, subtle, incremental improvements in meeting preparation can pump up closing ratios.

Know versus Need-to-Know

For any prospective opportunity, there are things you know and things you need to know to sell your solution. A solid questioning process, backed with skillful questioning separates high performers from the wannabes.

You simply can’t bring perspective to a prospect until you understand key aspects of their business and situation. In preparing for a meeting, I pull out a blank piece of paper and line out two columns: What I Know and What I Need to Know. For example:


Of course, you must be tactful about the order in which you ask these surface questions. What I want to talk about now is the questions behind the questions which make up a smart sales dialogue.

Salespeople who call on prospects with well-researched, well-prepared sales questions are likely to walk into that golden sales triangle with surprising results. So here’s four main objectives in any initial sales dialogue:

  1. To establish yourself as a credible professional and partner by being prepared and thoughtful in the sales questions you ask;

  1. To seek to understand the prospect’s current situation, which includes validating what you’ve researched or the assumptions you’ve made, and to uncover new information you need;

  1. To uncover a broader and deeper range of information from strategic objectives to what they’re  trying to fix, accomplish or avoid to how each decision maker personally feels about making a change;

  1. To seed new ideas and either influence or disrupt the prospect’s current thinking.

Smart Questioning

With these objectives firmly in mind, your next step is to develop and ask a series of questions to engage clients in conversation. The sequence of your questions is very important. Start with questions that require a yes or no response to get information confirmed and to start the flow.

  • It’s my understanding that you currently have 500 employees, is that correct?

  • I understand that you currently use XYZ claims processing system, do I have the right?

  • From what I read, it looks like last year’s revenues were around $100 million, is that correct?

Now we need to dig into the information needed to ultimately to align your solution with the prospect’s need. These questions will be open-ended to encourage the prospect to speak more.

  • Can you give me an overview of how the XYZ system works with your internal processes?

  • Has the slow cycle time caused any production issues? Can you give me some more details?

  • What impact has slow cycle time had on productivity? Who’s been impacted? What’s the effect of that?

  • If you were to make three changes to the XYZ system to improve performance, what would they be?

  • What is your time frame for getting started with a new system?

  • What does your decision-making process look like and who will be involved?

Notice the sequence; it flows in a natural way.

Whenever you bring new solutions to a prospect, you are asking them to change, which has a personal impact on him and others. To that end, people buy for their own reasons, so we want to understand how they feel.

  • How do the current users feel about making a change to a new system?

  • What is your opinion of what improvements need to be made?

  • What sensitivities do I need to be aware of?

We also need to use the meeting to give some information (not selling our solution yet). Think of questions that can give information, but also get information.

  • Have you thought about this aspect? It’s something we’ve helped other clients address with some of our solutions.

  • One of the possible alternatives is to do this, what is your opinion as a possible solution?

Blog124_QBehindtheQKey: Your Listening and Pacing Skills

As important as specific, well-conceived questions are, listening and pacing carries great weight in the sales dialogue. It’s tempting to fire off questions, one after another. If the prospect faces a barrage of questions, the conversation can seem more like an interrogation.

A side note: When you study gender communication styles, as I do, it is important to remember that men don’t care for a lot of questions; they can experience it as an intrusion. They prefer to communicate with a clear purpose and to solve a problem. So stay on point. On the other hand, women like a lot of questions, ask many themselves, and doing so fulfills one of their communication purposes, which is to share information.

Your best approach is a conversational one. Ask a question. Listen attentively for the answer. Acknowledge what the prospect says, and check your understanding of the answer. Then, ask a follow-up question. You want the discussion to be free-flowing, natural, and enjoyable, not a questionnaire to be checked off.

The most important thing to remember about sales questions is this:  Don’t wing it. The other party will quickly see through your lack of preparation and feel less valued as a client.

As a sales leader, develop a winning questioning process as one of the key skill areas for your salespeople. Perfect it and you have a competitive advantage.

If you’re truly dedicated to winning more sales opportunities, then don’t waste the prospect’s time or your own. Go into each meeting meticulously prepared to engage your prospect, and then begin the very human task of establishing a meaningful relationship. You will position yourself as a partner and value-added resource in the process. And the benefits are limitless.

See you on upside,


For more information on how to simplify the complex sale, go to Or call William L. MacDonald in San Diego at PleinAire Strategies LLC at 760.340.4277 or 213.598.4700

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