Do you suck at asking questions?

As we know, questions are the holy grail of sales, but it’s not just about asking questions in general, it’s about asking the right questions.

You can cause yourself a lot of pain in the marketplace when you don’t know how to create a connection. And so I want to do a lesson entitled “Do you suck at asking questions?” Now, I title it that way because I want you to be introspective about how good are you at asking questions. But even if you are good at asking questions, I want you to know that you’re probably not asking the right questions. And so in this video and blog post, I want to share with you three specific examples of questions that can have a tectonic impact on how fast you create influence and how fast you create trust.

People Who Ask the Best Questions Win

One of the things that I believe is the notion of he or she who asks the best questions wins. And so the formula right now is to learn how to ask questions you’ve never asked so you can learn the things you’ve never learned so you can solve the things you have never solved. That is the formula.

And if I can do that, then I create a massive value in the one-to-one relationship. Now, you see in front of me, my book High Trust Selling, is celebrating its 20 year anniversary right now. It’s crazy that this book was written 20 years ago and it is still selling today. And I remember on a recent podcast, somebody asked me have the laws changed? And I said, absolutely not. They haven’t changed. And he goes, how could you have seen then what laws you would need to write so that today they would be the same? I said, it’s a really great question. And one of the filters I had was in writing this book and when this book was completed, if I got hit by a truck the next day, my filter was would these questions still be relevant a hundred years from now?

And if the answer was yes, then they went into the book. And so what’s really interesting about the whole question thought process is it’s the holy grail of how to create influence. It’s the holy grail of connection. It’s the holy grail of I trust you, right? In the world in which you and I live, that’s all we have to go on, is trust and connection. When we have trust and connection at the highest level possible, then we get the opportunity to serve, which is the whole customer experience piece of it. But if we don’t have the first two, we don’t get the opportunity to engage that third piece. So when we talk about do you suck at asking questions, there’s a couple things that I want to bring up. One is, are you really conscientiously aware in a meeting about how much time you speak and how much time you listen?

Conversational Productivity

One of the things that we have innovated in High Trust is a concept called conversational productivity. Conversational productivity says that at most mortgage professionals, most real estate professionals, in fact, most people in selling, spend about 80% of the time talking and about 20% of the time listening. The pros have flipped that, okay? They spend 20% of the time asking game-changing questions, and I’m going to give you the three. And then they spend 80% of their time listening. So the very first thing you need to do right here right now is to take a snapshot and ask yourself, what are you closer to? Are you closer to the group that is spending most of the time talking, which means you suck at asking questions, or do you identify with a group that spends much less time talking and a whole bunch more time asking and listening?

And if you’re doing that, then you are obviously in that population.

Focus on Emotional Questions

There’s another element of this, particularly in financial services. And that is, if you follow that formula, then you must follow this formula, which is 80% of the time when you are talking, you should be talking about emotional things, and 20% of the time economic things, the industry has that backwards. We spend a lot of time talking about the economics and not anywhere near the amount of time talking about the emotions. So when we invented the next innovation, if you will, the iteration on High Trust Selling, it was based on coming up with question categories. And these would be categories in which you could formulate a single question or two to be able to use effectively in your dialogue process.

It doesn’t matter if you’re dialoguing with an end-user, it could be a borrower, it could be a buyer, it could be a seller in real estate. It could be a wealth management client prospect, it could be interviewing, if you’re interviewing people to bring on your team, all of that applies, right? And it also applies if you’re a leader where you just want to keep momentum of relationship going, you want to keep just making sure that you’re adding value and learning where people are at. And so, even though there’s six categories, I will only demonstrate three right now.

The Three Types of Questions You Should be Asking

They happen to be the three that I personally think right now are working really, really well in the market. And one of them is a question and it is in what we call the fear category. And a fear question would sound like this. What do you fear the most right now? And then you can add like about buying a home, about financing a home, about selling a home, about anything you want around fear.

Asking Fear-Related Questions

If you have a business partner, I could say what are you afraid of right now in business? What do you fear? That’s a very intentional way to create connection because the end of the question sounds like this, what do you fear about buying your first home and how can I come alongside you and help that fear go away? Or what do you fear right now in business, and how can I help? Or as you think about the future, what are you most afraid of and how can we get that handled now so we can proceed with confidence? It’s not that I want people to go into a fear state, they’re already there. What I want to do is I want them to know that I want to help them through it, because everybody who does anything, especially when it involves large sums of money is going to have some level of fear.

So it’s not a negative thing. It’s not a bad thing. Even you have fear, I have fear, right? And so people can help us get over fear. What is it that we are afraid of, then we can begin to move forward? So that’s a question category. Second question category. So we move from fear and we go to present.

Asking Present State Questions

So there are present state questions. A present state question might sound like this, given the fact that you own a home right now, what are the things you have enjoyed the most and what are the things that have given you the most conflict or the most challenge? So that’s present day. We’re not going to be talking about the new home yet, we’re going to be talking about this home. Or if I’m a real estate agent right now as an owner of a home and this being the second home that you’ve sold, what are you concerned with and what do I need to be aware of so that we can make sure all of that is handled in this sale?

Or if I’m working with a business partner right now, if you evaluate your business, what are you most concerned with and how can I help? It’s not what I’m afraid of it’s just what am I most concerned with? It doesn’t mean I’m fearful. It just means I’ve got some concerns, right? I can use this in marital relationships. I can use this in parental relationships, a leader to a salesperson. Hey, given where your business is right now at the end of Q3, what are you most concerned with moving towards the end of the year and into next year that I can help you get set up for success? And the thing you need to hear is that these one questions can change the direction of a relationship like that.

Okay. So we have a fear question category. We have a present question category, and then we have a future question category.

Asking Future Focused Questions

Let’s say, I’m working with a home buyer. Given your vision around real estate right now, how long do you see being in this home and what would be one or two of your real estate goals for the next five to 10 years? So that’s a future question, right? And if I ask that question the right way, I’m going to get all kinds of data, right? If I’m a business leader right now, and I can go back to that same person at the end of the third quarter, I can say, now that you’ve successfully completed three quarters, and we’re heading into the fourth quarter, where do you see your business in the next two to four years? And let’s build a plan over the next 12 weeks to execute beginning January of next year. How does that sound?

So it’s always about the future. Define the perfect home for you in the next 10 years. Let’s say this is a first-time home buyer, right? Find the perfect home for you in the next 10 years. So we always put a date on it, right? So what I want to do is I want to have you understand that in this just quick video vignette, it’s just about really making sure that the questions you’re asking are not only intentional, they’re not something you’re doing. They’re actually something you desire to engage around because you do want to learn what people actually want. And here’s what I know for sure. If you talk less and you ask less, but more engaging questions, you’ll get far more things from the client prospect that you can now do to blow their mind, to add value to their life.

And if you keep this discipline up, even in a marriage, like how did we do last week? How can we improve this week? And what are some of our goals for the next 30 days? That’s a great question, right? So all I want you to do is just get really, really clear that it’s less questions, not more. It’s better questions. Okay? And its questions where you can really listen. And from listening, you’re going to get the goods.

Two Free Guides to Help You Ask Better Questions

I have two free documents for you. One is the High Trust interview. One is the Talk Less, Sell More white paper. If you have not downloaded those yet, go ahead and download those. They’ll help you as you continue to create mastery around the fine art of asking questions and listening.


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