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Why Salespeople Should Use Conditional Questions

This strategy helps producers collaborate with prospects by providing them insights with the goal of helping them make better, more informed decisions.
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why salespeople should use conditional questions

In the classic movie “Glengarry Glen Ross," the character Blake was the quintessential salesman who exercised high-pressure tactics to close the deal—“always be closing." In his mind his clients were marks to be played.

Selling has come a long way since then. Buyers are far more sophisticated, mostly due to the increased availability of information. As a result, high-pressure tactics often don't work and, in many cases, create buyer resistance.

Today, producers and other sellers are encouraged to work more collaboratively with prospects by providing them insights with the goal of helping them make better, more informed decisions. The more collaborative approach allows the prospect to make small but significant decisions throughout the buying journey.

These mini decisions, positioned by the producer, help advance the sales process and build alignment around future steps to be taken, ideally leading to closing the deal and an insightful and rewarding buying experience for the prospect.

Conditional language, or language that positions an outcome based on a specific set of conditions occurring, can be a powerful selling strategy. When used in a questioning format, conditional language encourages the buyer to consider alternative and sometimes contrasting outcomes. 

The opposite of conditional language is the use of statements. Statements or assertions can be risky in selling, particularly when collaboration is the goal. They can cause friction as buyers often view them as challenges rather than insights.

Consider this example:

StatementConditional StatementConditional Question
Your workers compensation audit is incorrect and you are being overcharged.
It is likely your workers compensation audit is incorrect and, as a result, could be causing you to pay more than necessary for your workers' compensation insuranceIf you were to discover your workers compensation audit was incorrect and causing you to pay more than you should, would you want to do something about it?


When confronted with statements, prospects are more likely to question the authenticity and accuracy of the assertion. The seller leaves little room for error and if they are proven wrong it is likely the buyer will dismiss future statements or claims.

Conditional language can also be used when producers want to test their buyers' readiness to close or when trying to identify hidden objections that would prevent a successful close.

Utilizing conditional test closings throughout the sales process can prevent producers from moving too quickly through the sales process and incorrectly assuming they are in alignment with the buyer.

A conditional close we developed and find most effective is called the “clear and confident question." The clear and confident question can be used midway through the sales process, typically after the buyer's pain points have been identified, but before the solutions are presented. It goes like this:

“John, it appears we've identified a number of areas that are of concern to you. Let's recap. [The producer talks through each of the areas of concern identified in the sales process.] Now, John, our next step is for me to get together with my team and develop some options for you to consider to address these risks. I'll bring these solutions back to our next meeting and we'll walk through them together, taking as much time as you need.

Because a lot of work is going to go into this next phase, and because we've both invested a lot of time together already, I want to get a read on how you're feeling today. Let's assume we come back with solutions that make sense and you are clear and confident these solutions are the right next steps to help you address the issues you said were important. Would there be any barriers to us moving forward in a business relationship?"

Once asked, it is critical that the producer listens carefully to the response to identify any challenges or obstacles shared by the prospect.

Assuming challenges are identified, such as learning there is another decision-maker or perhaps another agent has been invited in, it is critical to stop the process and gain agreements around how you will proceed.

This step should be repeated in the presentation of solutions meeting as well. It sounds a bit different, but the concept is the same.

“Well, John, we're finally at the point of the process where we can begin to share the solutions and recommendations to the challenges and risks we identified together. At the end of our last meeting, we identified several areas of concern with your existing insurance program. Today, I'm pleased to share how our agency is prepared to help you address these issues and to help you reduce your risks.

Before we jump in, I just want to be sure we are on the same page. Assuming you are clear and confident in our approach to address the risks we identified together, is there any reason we wouldn't move forward in a business relationship?"

Keep in mind this isn't about putting a lot of pressure on your prospect. It is, however, intended to make sure both parties agree on the next steps and the path forward. This approach also prevents producers from providing solutions too early, which frequently causes them to “get rolled."

The clear and confident question concept is intended to help producers remain in control of the sales process. It's not about asking the prospect to be your client. It's about discovering potential obstacles that would prevent them from moving forward with you in a business relationship.

Susan Toussaint is a practice leader at Oceanus Partners, a ReSource Pro company. Oceanus Partners is a firm dedicated to helping insurance professionals working in all lines of business insurance improve sales and client retention.

Thursday, April 1, 2021
Sales & Marketing