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WORST vs BEST Sales Questions to Ask

How do you make even MORE SALES? You ask even BETTER QUESTIONS.

So, I want to break down the top three absolute:

  1. WORST type of questions you can ask in roofing sales
  2. BEST roofing sales questions to ask your customers.

With this, you’re going to learn how to close even more deals more easily while making your customers wildly happy.

Welcome or welcome back, by the way. Adam Bensman here, The Roof Strategist. Everything I do here is designed to help you and your team smash your income goals and give every customer an amazing experience.

And amazing experiences are created through relationships. In fact:

  1. Relationships are rooted in two-way conversations.
  2. One of the biggest pitfalls of roofing sales training at large is that there’s so much emphasis on communicating one way. We get so focused on how we pitch, how we present, how we showcase, what we can do, and how we demonstrate our value.

With that, we often overlook asking questions.

Now, this doesn’t tie into closing questions. I’m talking about building value by understanding how to best serve our customers. And the best way to do that is through often-overlooked questions.

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Questions, Control & Dialogue in Roofing Sales

Now, I want to ask you a couple of questions.

  1. Who IS in control when a question is asked? The person asking the question is the one in control. I want to ask you another question.
  2. Who FEELS like they’re in control when a question is asked? Usually, the person answering the question feels like they’re more in control.

THAT is why it’s so beautiful to ask great questions in the sale because:

  • You get to stay in control of the dialogue.
  • Your customer feels like they’re in control.
  • This can create a deeper relationship, which means getting more yeses from homeowners.

After all, when a customer hands you that $20,000 final balance, it’s like a “Thank You” note, saying:

  • Thank you for taking the time to explain all of this to me.
  • Thank you for helping us through the process.
  • Thank you for making this so easy.
  • Thank you so much for taking the time to get, help me get to where I am today.

THAT is the ultimate gift, and that’s why I want you to think about questions as an even better way to serve your customers.

One of the easiest ways to do that is by learning to ask good questions — and by learning what the difference is between the good versus the bad questions to ask in roofing sales.

So, let’s get to the worst versus the BEST types of questions to ask your customers in roofing sales.

Worst Roofing Sales Questions #1: Complex Questions

Some of the WORST types of questions in roofing sales are complex questions. Now, complex questions go something like this:

Hey, when it comes to selecting a roofer, what’s most important to you?

How do you and your wife decide what value means to you?

Those are complex questions. I’m asking about:

  • Their decision-making process
  • What are they looking for in a contractor
  • How they define or recognize value
  • TOO MUCH at once

Now, many of us think that complex questions get complex answers —BUT it really doesn’t work that way. In fact, most of the time, the simplest questions bring out the most complex answers.

Example: If I asked a homeowner, “What are you looking for in a contractor?” they’re likely going to explain far more to me than if I asked what’s important to them when it comes to selecting a roofer. If you feed them possible answers in your question — like asking if they care about experience, reviews, or whatever else, there are good chances that they’re just going to pick one of those words you fed them. They’ll grab onto one or two things, and that’s IT.

The conversation’s OVER because we fed it to them. The same thing goes for two-part questions. If I ask what’s most important and then I follow up with a more specific question (“Is it how long they’ve been in business, their ratings online, and value?”), they’re going to skip the first question and only answer the second one.

With that, the conversation is DONE.

So, we need to remember that complex questions often lead to:

  1. Very simple answers
  2. Short answers that don’t help us advance the sale.

On the other end of the spectrum, simple questions CAN lead to very complex answers.

Example: Have you ever asked a stranger, “Hey, did you grow up here?” If they didn’t, they probably will share more of their background and life story. “No, I didn’t grow up here. I was actually born in Nashville, Tennessee. My dad was in the military, so I grew up as a military kid. I lived on four bases in three separate countries. I speak two different languages, and we bounced out all over the place.” So, one simple question can open up a very complex answer with lots of information.

So, complex questions are the worst type to ask, and simple questions are the best.

Worst Roofing Sales Questions #2: Dead-End Questions

Dead-end questions are those that do not have any follow-up to further the dialogue. I see this happen ALL the time when I do roleplay. In fact, I’ve been traveling the country doing roleplay at speaking events across the country. During these events, I will:

  • Pull an audience member onto the stage.
  • Do some live roleplay with that audience member.
  • Ask a question like, “What’s most important to you when it comes to selecting a contractor?”

The response is usually something like, “We really want someone who’s been in business for a while. We want someone who’s going to stand behind their work and provide a good value.”


Now, the next question’s plugged in — and the homeowner feels like they’re getting blasted by questions, without proper follow-up. That can feel like a machine gun of questions or an interrogation even.

Instead, we need to:

  1. Pump the brakes.
  2. Be patient.
  3. Take the time to ask essential follow-up questions.

These follow-up questions can include the following (with the same answers from homeowners after):

  1. When you talked about providing good value, can you share with me what good value means to you? They may respond with something like, “Well, good value means we feel like we got a fair price.”
  2. How will you determine what seems fair to you? Maybe they say that fair means everything will get done on the roof properly for a price that’s not the bottom of the barrel or super marked up.
  3. How will you choose which roofing company is best for you? They could answer, “We’re going to get a few estimates and compare them.”
  4. What will you be looking for in each estimate? Bottom dollar cost could be the answer here, but they may have other responses too.
  5. What is the single most important thing when you’re selecting a contractor? Again, answers can vary here, but whatever they say can give you more information to advance the conversation and the deal.

Many roofing sales reps will ask a question or two, but if the question hits a dead end, the conversation is over.

So, these dead-end questions are another type of worst questions to ask in roofing sales. Instead, it’s better to:

  • Ask follow-up questions. These are often how, what, when, and why questions.
  • Try to extract even more information, going deeper and inviting the homeowner to share openly.
  • Follow up with “What else?” or “Tell me a little more” to get more details and keep the conversation going.

Worst Roofing Sales Questions #3: Yes-or-No Questions

The third type of question that is the WORST to ask in roofing sales is the yes-or-no question. That’s because:

  • These are close-ended questions.
  • Yes-or-no questions don’t further the discovery or the discussion.

In roofing sales, the more information we have, the easier it is to:

  • Pick and choose from all the benefits that we can offer.
  • Guide homeowners through the process.
  • Sell to homeowners at a specific “stage,” meaning the stage at which they are in the process (There are four stages of the claims process, including no claim filed, partial payment, denial, and check in hand; in retail, there are four reasons people buy new roofs, including roof age, active problems, cosmetic upgrades, and life events).

So, the more we know about which stage they’re in — and the details of that stage — the easier it can be to sell specifically to that homeowner. That’s often overlooked.

That’s why yes-or-no questions are among the worst to ask in roofing sales.

Keep in mind, however, that you may still need to use yes-or-no questions to keep the homeowner engaged and to keep the conversation going. Specifically, you may ask tie-down questions, like:

  • Do you understand?
  • Does all this make sense?
  • Do you have any questions for me so far?

Still, when we need information or want our homeowners to feel like they’re in control:

  • We do not want to ask yes-or-no questions.
  • We want to ask questions that lead to a longer response.
  • Open-ended questions will typically serve us better than closed-ended questions.
  • There are five questions to ask — when, where, why, what, and how.

Again, don’t forget about point number one above — keep your questions simple. And be careful with the “why” questions. Here’s why.

Example: If I asked, “Why are you wearing that hat?” suddenly, you’re on the defense. Those questions can come across as accusatory, judge-y, and maybe even somewhat aggressive. They can also be intrusive and catch people off guard. So, I advise using “why” questions really sparingly. If you do ask a “why” question, make sure to be really mindful of what you’re asking, so you don’t end up insulting someone. We don’t want people to feel that way.

Recap: Worst versus Best Questions in Roofing Sales

Summing this all up, the three worst types of questions to ask in roofing sales are:

  1. Complex questions: Don’t overload questions or homeowners with information. Keep your questions short and simple. Focus your questions on one topic at a time.
  2. Dead-end questions: If you’re asking dead-end questions, you didn’t go deeper, and you won’t get the real answer. The best fix here is to ask follow-up questions. These tend to start with when, where, why, what, and how. Also, remember to use “why” and “who” sparingly. Finally, use statements like, “What else?” or “Anything else” or “Anything more?” If you do, it’ll help draw out even more information. Often, that information reveals the truth more than the first answer they gave you.
  3. Yes-or-no (or close-ended) questions: Instead, we want to ask open-ended questions, Again, we want to focus on those questions that start with who, what, when, where, why, and how. Again, use “why” with caution.

I hope this helps you ask even deeper questions to:

  1. Develop even deeper relationships.
  2. Win more business.
  3. Collect more “Thank You” notes.

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Thanks for joining me, and I look forward to sharing more with you in the next blog.