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Is Your Client Asking Trick Questions? Four Easy Ways to Open Up the Conversation




I’ve dedicated my life to helping people change their lives in under two minutes. From coaching clients on Shark Tank, Dragon’s Den in Canada and even Shark Tank-Australia, I’ve seen how an effective presentation can lead to a six- or seven-figure deal for my clients. From RE/MAX to Douglas Elliman, with some work on the commercial side as well, I’ve had the opportunity to help listing agents understand what it takes to pitch like a pro.

For example, take this scenario. A homeowner asks you directly:

· “So, why should we list with you?”
· “Why do you think we should move forward at this price?”
· “What’s different about your firm compared to other real estate agencies in town?”

Notice that all of these questions are a version of “tell me a little bit about yourself.” Unfortunately, this a trick question. The trick is that it sounds like an invitation to begin talking about yourself, your firm, your listings, and whatever else you may think is valuable.

But every buyer and seller always has his or her own interests at heart. The real question you’re being asked is: “Why don’t you tell me a little bit about what you do…and how it can help me?”

The best pitch—and the best conversation—always start with what your client is thinking. And clients are always thinking about themselves. We’re all wired to act in our own self-interests. If you start the conversation with what your listeners are thinking, you’ve already got their attention. If you start with the year your firm was founded, or your three other listings in Nassau County, you’ll be tuned out in a flash.

Here are four simple prompts that can help you to tap into what your clients are thinking by acknowledging what they already know. This frame of reference is the best way to introduce new information; you’ll be taking clients from a “familiar neighborhood” to a new one. Start with one of these phrases:

· “Have you ever noticed…?”
· “You know how…?”
· “Doesn’t it seem like…?”
· “I’ll never forget the time when…”

Use this to introduce something familiar, creating a context of acknowledgment. You acknowledge the client’s expertise and provide a frame of reference that’s easily recognizable. Then you follow it up with all of the details that demonstrate the value you offer. This might sound like:

“Have you ever noticed…how the traffic on this freeway is only getting worse? There’s another option that could cut your commute in half, and it’s a perfect fit for your price range.”


“You know-how…this building was just listed on the National Register of Historic Places? It’s been upgraded with solar power that’s meets all preservation guidelines, so you can have that historic home you love and the energy efficiency you want.”

Or even:

“Doesn’t it seem like…the market in Nassau County lacks long-term storage? Everyone wants to be near the city, but storage rates are sky-high. What surprised me most was when I found what’s available in Hempstead, and I think it might surprise you, too.”

If you don’t start where your clients are, your accomplishments, revenues, close-ratio, and everything else doesn’t count for much. You have to make sure things matter to the client, or it won’t matter at all. This approach is not about manipulation; it’s about connection. What’s the difference? Remembering that the client always comes first. The transaction will follow.

Use the Power of the Word ‘Because’

When I was a kid, and I would ask my parents “Why?”, their classic answer always started with “Because.” Maybe we can learn something from this simple exchange. I’m not suggesting you treat your buyers and sellers like children but remember: because is a word that’s packed with power.

Whatever you offer to your clients, offering a reason is the most compelling part of your pitch. Consider the impact of the following examples:

Example #1: “I have 22 years’ experience here on the North Shore.”

Example #2: “Because of my 22 years of experience, here’s what I’ve seen that can help you sell this property quickly.”

Do you see the difference? You work for a company of distinction, for clients who have choices. Make it easy to distinguish your unique value. Become the easiest and most logical choice by answering the question that is really at the top of your client’s mind: How can you help us?

Chris Westfall is a sought-after business consultant, communication coach, keynote speaker, and the author, co-author, or publisher of eight books. Advising hundreds of thousands of leaders from high-growth entrepreneurial enterprises, Shark Tank startups, and Fortune 100 companies, he has helped create multimillion-dollar revenue streams for businesses on four continents. He is the U.S. National Elevator Pitch Champion and the author of the new book Leadership Language: Using Authentic Communication to Drive Results (Wiley, 2018). To learn more, visit