How To Ask Great Questions And Close More Deals

Have you ever wished that your prospects would just open up and tell you exactly how to get them to buy from you? I’m sure you have.

If only it were that easy.

In the last post, we discussed the importance of introducing your company and positioning yourself with your prospects. Now, we’re going to take a look at some of the best ways to understand your prospects.

If you have ever felt like you were having trouble understanding your prospects, it might be because you didn’t spend enough time in this part of the sales process. It’s a common mistake in entrepreneurial selling. After introducing your company and establishing your position, you now need to focus on getting to know the person you are talking to.

This is the part where you begin to understand where your prospect is, where they want to be, and what’s keeping them from getting there. Now is the time to figure out how your offering can make their lives easier.

Discovering the needs of your prospects is the most important part of the sales process. Without it, you have no idea how you can benefit your prospect and you’re basically shooting in the dark when it’s time to present your offering.

Many entrepreneurs find it difficult to figure out who their prospects are and what they really need. It’s a common problem.

The concepts I teach in this article are going to help you avoid many of the mistakes people make when they are trying to understand who their prospects are. You can thank me later.

In order to help make this easier to understand, we’re going to take a look at Leonard The Landscaper. Yes, I know, it’s a cheesy name. Throughout the course of this article, we will follow Larry as he attempts to gain a better understanding of his prospective clients. It’ll be fun! I promise!


Some Ground Rules

Before we get started, there’s a few important things you need to remember as you go through this process. These are some rules that you MUST follow in order to make sure you’re handling this section correctly.

Here they are:

  • No rushing. You have to take your time with this part of the process. This is where the “meat” of the conversation will happen.
  • No talking. You prospect should be doing most of the talking. Ideally, the only time you should talk during this section is if you’re asking a question, or validating something the prospect says.
  • No pitching. Seriously. No pitching. Don’t do it. You will have time for that later. If you start pitching without taking the time to get to know the prospect, you won’t know what solution to provide. If you’re not genuinely interested in your prospect, they won’t be as likely to buy from you.

Qualify The Prospect

One of the problems Larry is having is pursuing prospects that aren’t a good fit for his business. He finds someone who seems to need landscaping services, but always ends up getting rejected in the end.

For some reason, he’s having trouble discerning which prospects are truly interested and which ones aren’t. He hears a lot of the following objections:

  • “I can’t afford your services.”
  • “I don’t think I need the work done right now, but maybe later in the year.”
  • “I think it sounds good, but my husband/wife doesn’t want to do it.”
  • “My lawn is bad, but it’s not THAT bad.”

The problem is that he finds himself wasting a lot of time on prospects who aren’t really serious about having a landscaper. The time he’s wasting could be better spent with prospects who actually need and want his services.

So what’s the solution?

The solution is simple. Larry needs to qualify his prospects before going deeper into his sales process. If you qualify your prospect first, you will get a better idea of how much time you should spend with her.

When qualifying your prospect, there’s a few things you need to find out:

  • Can they afford your offering?
  • Do they have a sense of urgency?
  • How much pain is their problem causing them?
  • Are they the one that will make the ultimate decision?

The answers to these questions will help you shape the rest of your approach. You can adjust your approach based on the answers you get.

Here’s an example:

If Larry finds out that a particular prospect needs his services, but they need their spouse in order to make the decision, he can set up a time to speak with them both. This would make a lot more sense than going through his entire sales process when the person can’t actually pull the trigger right at that moment.

You may not always be able to get all of the answers you need in order to fully qualify each prospect. The idea is to get a sense of how likely the prospect is to buy from you. This is a skill that you can develop over time.


Find Out About Their Current State

One of the reasons Larry is having trouble getting new business is because his pitch seems to be falling on deaf ears. His prospects don’t seem to understand why they should use his services.

It’s because he doesn’t really understand what his prospects’ needs are. He has no idea what they are hoping to achieve by hiring a landscaper. Because of this, he’s basically pitching a generic, one-size-fits-all solution.

Since he doesn’t have a good understanding of what his prospects want, he’s not able to address their pain points. Fortunately, this isn’t a hard problem to solve.  

After qualifying your prospects, you need to get to know them on a deeper level. This requires you to ask good questions and listen carefully.

The first thing you need to do is find out about your prospect’s current situation. What are things like right now for your prospect? Are they happy with it? If not, what do they want to change?

Larry should start out by asking them what they’re currently doing as far as landscaping goes. Are they already dealing with a company? How do they feel about the quality of their yard? Does it need a major overhaul? Or just some basic maintenance?

The better Larry understands this, the more effective he will be when it comes time to make his proposal.


Find Out Where They Want To Be

When you have a good understanding of where your prospect is presently, you need to find out where they want to be. It’s a matter of figuring out what their ultimate goals are.

Here’s some questions you want to answer:

  • What is your prospect trying to accomplish?
  • Why do they want to accomplish it?
  • What, if anything have they done to accomplish this? How is it working?

These questions help you gain a better understanding of what your customer wants and needs. In Larry’s case, he needs to understand more about what his prospects want their yards to look like.

What do his prospects use their backyard for? Entertaining? Relaxing? Family time? What’s wrong with their yards right now?


What’s Keeping Them From Getting There?

Now that you know what things are like for your prospect in the presently, and you have found out how they want things to be, you have to figure out what’s keeping them from getting what they want.

Ultimately, this is what you want to know about. The obstacles that prevent your prospect from getting what they want is the problem you need to solve.

It’s all about discovering your prospect’s pain points. This is extremely important. If you don’t find out what your prospect’s problem is, you won’t be able to provide a solution.

In Larry’s case he needs to find out why his prospect isn’t happy with her yard. What’s keeping her from being able to get her yard to look the way she wants it to look?

Maybe the company she’s currently using isn’t doing a good job. Perhaps she can’t afford most landscaping services. Or maybe she needs help figuring out what type of look her yard should have.

Whatever it is, Larry needs to figure it out. This information will help Larry address his prospect’s pain points more accurately, which will increase the chances that he will get the business.

I can’ emphasize the importance of this enough. As an entrepreneur, your objective shouldn’t be to sell your products or services. Your objective should be to solve your prospect’s problems. You can’t solve problems if you don’t know what they are. It’s this mindset that will help you close more deals and grow your business.


Open-Ended vs Close-Ended Questions

The key to getting the best answers from your prospects lies in your ability to ask good questions. The information you get from your prospect depends largely on what you ask them.

There are two types of questions you can ask: open-ended and close-ended.

  • Close ended: These are questions that can be answered with a simple “yes” or “no” answer.
  • Open ended: These questions cannot be answered with a “yes” or “no.”

If you want to get the best information possible, you should rely primarily on open-ended questions. I’m not saying you should never use close-ended questions; there are times when they can serve a purpose. I’m saying that open-ended questions are much more effective when you’re getting to know your prospects.

Open-ended questions will invite deeper answers from your prospects. They encourage your prospect to talk more.

This actually has benefits beyond finding out more about your prospect. The more your prospect talks, the more rapport you will build with them. This gets them to trust you more, which will make it easier to close the deal.



If you don’t get anything else from this article, get this: your prospect needs to do as much talking as possible. Entrepreneurial selling involves getting to know your prospects.

As I said before, it’s not time to pitch or to interject your opinion. You want to encourage them to talk as much as you can.

The more your prospect talks, the better. When you feel you have enough information, then you can move on to the next section: the presentation.

Leave A Response

* Denotes Required Field