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5 Questions to Truly Connect With Your Sales Prospects These powerful questions will allow you to navigate the conversation while ensuring your prospects share information that will help you formulate a sales approach.

By Rod Santomassimo Edited by Anna Wahrman

Opinions expressed by Entrepreneur contributors are their own.

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It has long been stated that the one who asks the questions controls the conversations. While this is common sense, for many salespeople it can feel like this nugget of knowledge goes out the window when they get in front of a prospect. Their tongue either gets tied or it goes beyond the threshold of conversation and becomes a one-directional diatribe.

Asking questions, especially the right questions, cannot only provide you with clarity and a deeper understanding of the prospect's needs but, when articulated correctly, can expose their deepest desires. When you master the art of questioning, you are able to convey a solution to your future client that will make you the obvious choice to work with.

There are five powerful questions that will allow you to navigate the conversation while ensuring your prospect shares information that will help you formulate an approach that they will be attracted to. When holding a conversation with your prospect, either on the phone, meeting or webcast, timing is critical, and the wrong delivery can quickly negate you from consideration. But as important as these questions are, they mean nothing unless you listen. And as Dr. Mark Goulston wrote in his fantastic book Just Listen, you don't want to simply listen to your prospect's answers but listen for the details that will give you a better understanding of their situation. These answers will ultimately define your solution.

Related: Why Empathy Wins and Selling Doesn't

1. The origin question

This open-ended question allows your prospect to talk about their favorite subject: themselves. The core of the question is to determine their original objectives, whether they be personal or professional. For example, if you are a real estate broker, you would ask, "Would you mind sharing with me how or why you acquired this property?" A web designer might ask, "Could you tell me what your vision for your company was when you first started and what is it now?"

The origin question is beautiful in so many ways. It shows you are truly interested, you have empathy, that you care about the prospect's objectives and that you can help them get to the next step in their journey. Now, this is not a question you should start out with. Like the rest of these questions, it is a deep question, and you need to make sure you have broken the ice with the prospect before asking this.

2. The lesson question

Though everyone's world has been turned upside down over the past year due to the pandemic, we are continually hearing of people and companies that are adapting. You need to understand how your prospects have adapted so you can determine not only what they are looking for but what they are looking to avoid. If asked correctly, the lesson question will provide you with insightful information. For example, assume you are selling business insurance to a business owner. "What were some of the key lessons you learned about your business during the initial stages of the pandemic, and how do you believe your business will change going forward?" Another way of asking the lesson question is, "If you could change anything…"

Certainly, this can generate an emotional response, depending on the business you are calling on. Now change the scenario to a personal insurance line, such as life or health, and you can imagine the deep impact this question may have. Thus, use your questioning carefully. While prospect questions are meant to provide you with information so you can deliver a customized solution, they are not meant to compound any personal grief or despair.

Related: Why Ending Your Price in An Odd Number Will Increase Your Sales

3. The insomnia question

Prospecting questioning is generally tied to fact-finding and discovery of both challenges and opportunities. While your prospect may desire more money, a nicer car, a bigger apartment, a more satisfying job and so forth, these are opportunities. These are something we look forward to. The insomnia question focuses on the pain. And while pain is a key emotional driver to decision-making, too much pain will deflect from your objectives.

As a rule of thumb, the insomnia question should be asked only if you know the prospect, or perhaps during a follow-up to your initial call. The question is simple: "What keeps you up at night?" Now, it is critical that you can dissect the answer. For example, let's assume you are an accountant and your prospect tells you she is consumed with her ability to consistently make her targeted margins. While the obvious answer is that there is a cash flow issue, this implies there are possibly operational issues. It could also be personnel issues. Or it could very well be a personal issue. Perhaps the owner is concerned about her status among her peers, partners or stockholders. There is so much more than the initial response, but this allows you to step even further into the role of a solution architect with your prospective client and meet them where they are.

4. The success question

Years ago, before I started my company, my former boss would always ask me and my fellow management team members a simple yet highly impactful question. If we couldn't answer it, we couldn't pursue the idea. The question is: "What does success look like?" We've all learned to have our research done, facts checked and support handy in all management meetings. This same question will also help you set expectations and clarify the destination your prospect is seeking in order to help you develop a customized solution to show your prospect you are the obvious choice.

Understand you may need to follow up this question with more clarifying questions. For example, that same boss once asked me to take a big producer to dinner as he had heard she was thinking of leaving. As dessert arrived, I asked her, "What does success look like for you to remain with us?" She looked at me and said, "Rod, it's simple. I want what I want." Needless to say, we didn't retain her. If she couldn't define her expectations, we couldn't help her in achieving her goals.

Related: Why Your Sales Emails Aren't Working, and What to Do About It

5. The triple question

As the name suggests, this is a three-step question, and it is specifically positioned for past prospects and/or inactive clients. I first heard of this question from my friend David Newman, author of Do It! Speaking. I found it so simple that I shared it with our clients, and they continue to tell me how much business they have derived from it.

The first step is reconnection. "What's new?" What's new with you since we last spoke, last met or last interacted. Again, like all these questions, this allows your prospect to talk, share and update you on the pains and opportunities that have occurred since you last connected. It is appropriate for you to share what's new with you, how you have grown and the transactions you have completed (to display your enhanced value). Of course, if you personally know each other, what's new with your mutual families is open for discussion.

The second step is the look to the future. "What's next?" What's next for your business, what's the next step in your growth, what's the next service line you are going to offer or the next location you are going to open, what's the next hire you desperately need? "What's next?" allows your prospect to share their needs, their objectives, and yes, their next vision of success.

The final step is you asking for the business. As should be the final step in most prospecting conversations. "How can I help?" How can I help with that new service line, how can I help with the next location or finding your new hire? How can I help?

Each of these five questions is deep and will help you connect on a deeper level with potential clients — both those you've already spent some time getting to know and those you'd love to work with again. The key is for you to get your prospect to share, and when your prospect speaks, listen for the information you need to develop a solution that will sweep them off their feet. If you've conducted a prospecting call, meeting or Zoom session correctly, in the end, the prospect should feel that you understand them, that you are different, and that you are the best option to get them where they want to grow.

Rod Santomassimo is a business and sales coach, three-time best-selling author, patented inventor and serial entrepreneur. He's the founder of Massimo.Coach.

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