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The Four Rules of Ultimate Sales Questions

You have to create dissatisfaction to sell.

People often make decisions based on emotions and then apply logic as they attempt to support their decision. This might seem counterintuitive, but it’s more pronounced with the affluent; the bigger the decision, the larger the emotional role. Whether it’s leasing a car and justifying it by explaining the safety features, or buying a 24-foot fishing boat with a slip at the marina to “teach the grandkids to fish.”

With ultimate sales questions, the idea is to ask a question that causes another person to feel uncomfortable as it hits an emotional nerve and triggers a negative internal response. Mastery of this process is what allows rainmakers to position themselves as trustworthy professionals in social settings, oftentimes even scheduling business appointments, without anyone realizing what happened.

A simple truism regarding our world of intangibles explains this: you have to create dissatisfaction in order to sell. Making another person feel uncomfortable or planting seeds of doubt pushes their dissatisfaction “on” button. When done skillfully, it’s magical because it positions you as being helpful and trustworthy. At the same time, it stirs up the dissatisfaction that can enable you to sell your services.

These four rules will help you master the skill.

1. The question should follow a personal story. For instance, most affluent prospects, if asked directly, will tell you they trust their advisor. But, if you relate a personal story about how you did or didn’t conduct a background check on your housekeeper or handyman and then follow up by asking if they did background checks, you’re now in conversation mode. Regardless of the response, you’re positioned to ask a follow-up question regarding background checks on the professionals they use. At this point, 99 percent of the time you’re going to get a blank stare. Now you’re ready to position yourself as that trusted professional and give them a quick overview on how to conduct these background checks.

2. The question must relate to your story. In the example above, the personal story about a background check led to a similar question that set the stage for a question about background checks on professionals—all of which, when done conversationally, comes across as both natural and helpful, which are positive emotions.

Essentially, you’ve triggered an emotional reaction—negative towards the status quo, but positive towards you.

3. The question must be asked in a conversational manner. This is a skill rainmakers take time to master. They are excellent conversationalists, which means they ask good questions and are good listeners. Although this skill might appear obvious, it’s not as common as you might think among financial advisors.

Why? Because financial advisors have been trained to talk, to showcase how smart they are by talking. Asking one of these ultimate sales questions is a delicate maneuver, and it can’t come across as condescending. That’s a major turn-off.

4. Do your homework. Practice, practice, practice. Take care in crafting your personal stories; they must be short and to the point. As stated above. you must be able to tell each story and ask ultimate sales questions in a conversational manner.

Your homework should also include developing more than one story, as you’ll want to be prepared for more than one situation, complete with a question designed to stir things up. For instance:

  • Have you conducted a PC audit of your homes and boats? (for those with multiple homes and fancy toys).
  • Have you ever had anyone audit the fees associated with your portfolio?
  • Have you had your portfolio adjusted recently?  

There’s no limit to these questions, but each needs a personal story, whether it’s about you, a family member, a friend, a colleague, or a client. Stories communicate on an emotional level. From there, your mission is to conversationally ask the appropriate ultimate sales question.

Matt Oechsli is author of Building a Successful 21st Century Financial Practice: Attracting, Servicing and Retaining Affluent

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