How many times in your real estate career have you been in a situation where you have an opportunity to ask a question, but simply freeze and can’t find one?

Many of us know how to ask a question. However, it’s not about the question. It’s about what has been asked that makes the question so powerful.

When you’re asking questions when meeting real estate clients and you listen with intent, the results can be amazing.

I love the following quote:

“The stupidity of people comes from having an answer for everything. The wisdom of the novel comes from having a question for everything.”

— Milan Kundera

Read it again, and again and do it one more time.

We use questions throughout our calls, networking and sales process. However, do you know what questions to ask? This is where you want to make sure you understand the who, what, why, where, when, and how that relates to what you are selling, especially if you are offering real estate.

The answers to these questions will help you set the foundation for the story you will tell in your offer. Or, they will help you identify if the fit is not right, and you should move on.

We present you the two question types:

1) The “Get To Know You” Question

You want to learn something new and gain knowledge about people, places, and things within an organization. This may be specific to operations, policy, approach, or how they are addressing the problem we solve.

2) The “Understanding” Question

In this phase, you want to confirm/understand something you think or believe. This could be something that you’ve read during some research. Or, it could also be something that you’ve heard over the course of multiple discussions with your client. You need to make sure you understand the needs, wants, and preferences of your clients.

Talk like a reporter, Think like a real estate salesperson

Who, what, why, where, when, how—these are the foundation of questions that you use to gather information, a.k.a “Learn new stuff” questions.

I like to think of asking questions using a reporter’s skill. A reporter is focused on building the story. Amazing reporters like to remove the nonsense and get straight to the facts and real stories.

Another way to view this is from the perspective of a very young child. It’s important to have a great level of curiosity. A true interest in understanding why people want to sell or buy, or how someone thinks about the market, or why something is important for the customers.

This is about them. Their story, their journey, and their wishes. You are looking for information to build out their stories.

  • Who cares?
  • Why do they care?
  • What do they care about?
  • How are they doing the thing they care about today?
  • What would they do if they did not have to worry about X?

Based on your questions and using the who, what, why, where, when, and how, you will start to build a connection and understand the preferences of a client

What we do wrong when asking questions

In the world of asking questions and getting to know your clients, you can also make some mistakes. Let’s talk about the most common ones:


Closed-ended questions are the ones where your clients can simply answer with YES or NO. You can’t always avoid this question, but when building that story for your clients you need as much information as possible.


We are all guilty of this, but it does send the wrong signal. Are you the decision-maker? Do you own the budget? When do you plan on making a decision? How are you planning on buying? How can I help you make a decision today?

These questions also have a time and a place.

However, if you put your customer through the 20 questions to validate business-fit, it’s highly likely that they think they are being pushed through your process. This is one of the top sales mistakes you can make.


Remember when a client gives you some valuable information. The answer of your client could have highlighted a problem they face that you did not anticipate, but your product can solve.

Reflective questions work well to validate information, confirm understanding, and support engaging conversations.


  • Don’t make assumptions.
  • Do ask questions when you don’t understand your clients or the term they use.
  • Don’t limit your questions on assumptions, passed deals, or trends.
  • Do use your own language. It’s important to ask questions using your own voice and style.

This is a nice little exercise. Take a piece of paper and write down 20 questions you can use for future clients. Use the two types of questions and avoid mistakes. Collect the information and see how much information you can collect. I promise it will make selling a whole lot easier.