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“Because your company is only as STRONG as you are.”
Forward-thinking roofers tune in to get help building STRONG companies, sales teams, leaders, systems, marketing, relationships, culture, and financials.
Whether you own a own a roofing company, manage one, or sell roofs - subscribe to the channel for content that will help you:
1) Close even more roofing sales.
2) Adapt to new roofing industry trends and changes.
3) Take control of your roofing marketing and lead generation.
4) Improve D2D roofing sales.
5) Build the roofing company of tomorrow.
Hosted by Adam Bensman
- Started in D2D roofing sales in 2011
- Former Roofing Company COO (multi-state)
- Creator of the Roof Strategist Sales System (used nationwide for retail + storm)
- Founder of The Roofing STRONG Alliance by TAMKO™ (formerly known as the Roofing & Solar Reform Alliance)
- Author of the #1 Best-Selling Book: The Roofing Sales Survival Guide: Beat the Odds, Overcome Yourself, and Win Big
Content produced on or before 5/13/26 was previously produced by The Roof Strategist, TAMKO makes no representations or warranties regarding the content.
How do you make even more sales?
You ask even better questions.
So in this video, I wanna share with
you a breakdown of the top three
absolute worst type of questions
that you can ask in roofing sales
compared to the absolute best questions
that you can ask in roofing sales.
And in doing so, you my friend, are
gonna learn how to close even more deals
even easier, and make your customers
wildly happy, which is what we do here.
Welcome.
Welcome back, Adam Besman, and
everything I do is designed
to help you and your team.
Smash your income goal and give
every customer an amazing experience.
And amazing experiences are created
by the way, of relationships.
And relationships are founded
in two-way conversations.
And one of the biggest pitfalls of
of roofing sales training at large
is that there's so much emphasis on
communicating one way, how we pitch,
how we present, how we showcase, what
we can do, how we demonstrate our value.
But what we often overlook is
asking questions, and this doesn't.
Tie into closing questions.
I wanna talk about building
value through understanding how
we can best serve our customers.
And the best way to do that is through
questions, but often it's overlooked.
So I want to ask you a question.
Who is in control?
The person asking the question or
the person answering the question?
My guess is you got it right.
The person asking the question
is the one in control.
I want to ask you another question.
Who feels like they're more in control,
the person asking the question or the
person answering the question, and my
guess is you got that one right as well.
The person answering the question is
the one who feels like they're more in
control, which is why it's so beautiful
to ask great questions in the sale
because you get to stay in control of
the dialogue, whereas your customer feels
like they're in control, which leads to
a deeper relationship, getting more yeses
and homeowners giving you the ultimate.
Gift in the entire world, which is
saying thank you as they hand you
a deposit check or a final payment.
Have you had that happen to you?
Where a customer's giving you
that $20,000 final balance
and saying thank you so much.
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.
Who else?
Hands over such large sums
of money and says, Thank you.
That is the ultimate compliment
that you did an incredible job
and the way I look at money, it's
not, let's get more commissions.
You know?
It's not the broey like, yeah, let's go
get the commissions and buy the cool car.
I look at money as
collecting thank you notes.
I want all my customers to say
thank you so much for helping
me through this process.
Thank you so much for changing my life.
Thank you so much for taking the time
to get, help me get to where I am today.
That is the ultimate gift.
So I want you to think about
questions as an even better
way to serve your customers.
So you, my friend, can collect
even more thank you notes and
then spend those thank you notes
however you want, having fun, right?
And of course, investing in providing
opportunities for your friends and family.
But I did wanna spend a moment just
breaking down that very big disconnect
between the traditional broey sales of
material acquisition and Flaunt versus.
Really looking at how do we provide
an incredible service to our
customers where they literally thank
us while they're giving us money.
And one of the easiest ways to do that
is by learning to ask good questions.
Because you're in control.
They feel like you're, they're
in control, and you're able to
navigate the sales process to
give them exactly what they need.
But in order to get there, we need to ask.
Good questions and not the worst type.
So let's get to it.
There's three types of questions
that we're gonna break down today.
First, showcasing the worst type of
questions, and I'm gonna help you
fix it and then teach you how to s.
Ask the best type of questions
ready to get started?
Let's rock and roll first.
The worst type of questions
are complex questions.
Now, a complex question
is something like this.
Hey, when it comes to selecting a
roofer, what's most important to you?
You know how long they've been
in business, their reviews,
their accreditation and value.
How do you and your wife
decide what value means to you?
So that's a complex question
where I'm asking about their
decision making process.
What are they looking for in a contractor?
And then I'm feeding them answers
about like, oh, maybe you can answer
in this way about their reviews,
how long they've been in business.
Or is value important?
And a complex question is trying
to tackle too much at once.
And the interesting thing, as many of
us think that complex questions are
gonna get complex answers, like, oh,
if I just like go at it all these ways,
I'm gonna get all this information out.
But it really doesn't work that way.
In fact, sometimes the simplest of
questions leads to the most complex
answers, and I would go so far as to
say that happens most of the time.
I'll give you an example.
If I said to a homeowner, what are
you looking for in a contractor?
They're likely going to explain
far more to me than if I say, Hey
are, when it comes to selecting a
roofer, what's important to you?
You know, the value, uh, how long
they've been in business, their reviews.
They're usually just gonna
pick one of those words that
you fed them and say, reviews.
It's gonna be their longevity, right?
Or they're gonna grab one
or two things and that's it.
And the conversation's
over cuz we fed it to them.
Or if I bolted on, you
know, what's most important?
Is it how long they've been in business,
their ratings online and value?
How is that?
Then they're gonna like skip the first
question and only answer the second part.
Like, well, value's really
important, does a lot of money.
And then the conversation's done.
So we need to remember that complex
questions lead to very simple
answers and often short answers
that don't help us advance the sale.
But on the other end of the
spectrum, simple questions can
lead to very complex answers.
And I wanna give you an example
out outside the roofing space.
And this may in fact even
contradict my third point, so
pay attention to see how it does.
But it's a great example.
Have you ever asked a stranger,
Hey, did you grow up here?
I.
Many people who didn't grow up in that
area will tell you their whole life story.
No.
You know what?
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 fact, of those four, I was
in three separate countries.
I speak two different languages and
we bounced out all over the place.
And you get the whole thing
from one simple question,
which was, are you from here?
Okay, this is a perfect example of how
a very simple question can oftentimes
lead to a very complex answer.
Now this is conversation that is
different than our sales conversation.
And again, that question
contradicts number three.
So I want you to see if you can
guess what that contradiction is
as we progress through the video.
Alright?
Complex is the worst, simple is the best.
Make sense?
Let's continue.
Number two, the worst type of questions
is actually this, not asking follow up
questions, not furthering the dialogue.
I see this happen all the time
when I do role play, and in fact,
I've been traveling the country
doing role play and speaking at
events in in, in groups of people.
And we'll bring up an, an audience
member to do some role play, and we
will ask a question of something like,
and what's most important to you when
it comes to selecting a contractor?
And the homeowner may respond with
something like, you know, we really
want someone who's been in business
for a while who's gonna stand behind
our, our work, their work and,
you know, provide a good value.
And then, boom, the next
question's plugged in.
And the homeowner feels like
they're sitting there to a question.
Machine, gun, ch, ch, ch, ch, ch, ch.
Just blasting questions away,
uh, without a proper follow up.
So instead what we need to do is pump
the brakes and be patient and take the
time and ask the necessary follow-up
questions like, when you talked about
providing a good value, can you share with
me what does a good value mean to you?
And then they explain, Hey,
well a good value is where we
feel like we got a fair price.
And then I can ask, and how
will you and your wife determine
what seems fair to you?
You know, that's a really good question
and they may not even be able to answer.
Well, fair would be knowing everything
that's gonna get done on the roof,
where we know that it might not be
the highest estimate, it might not
be the lowest, but it, it's like
the right amount that gets the job
done where you can stand behind it.
And then now I've uncovered some things.
Or another question.
How will you and your wife choose
which roofing company is best for you?
Well, you know, we're
gonna get a few estimates.
Great.
In what is your decision
criteria look like?
You know, well, we're gonna be comparing
them here and here, and what will
you be looking for in each estimate?
And then they're gonna answer.
And how will you decide which
one gets your final vote?
They answer.
And what is the single most
important thing to you?
When it comes to selecting a contractor,
these are the follow-up questions.
So what many salespeople do is they
may get decent in asking a question,
but then the question hits a dead end
and then the conversation is over.
So those are the worst questions, is the
ones that you start, but you never finish.
So instead, the best questions are
the follow-up questions to extract
even more information, to go deeper
and to provide an environment
for that homeowner to openly and.
Share even more.
And one really way to do that,
really simple way to do that
is just to say, what else?
How will you and your wife decide
what seems like a fair value to you?
Explain, explain, explain.
And what else?
Explain, explain, explain, and what else?
And they'll explain a little more.
And then you say, Anything else?
No, that's it.
Great.
Now we've done it.
So that is what we need to do is to dig
deeper by using follow up questions.
So again, the worst questions are the
ones that start and then dead end.
The best questions are the ones
that go deeper and ask follow
ups with how, what, when, why.
All right.
And we need to remember to also
use things like, what else?
Tell me a little bit more
to extract more information.
All right.
Now this brings me to the worst
question type, which is number
three, and I told you I contradicted
this in the very beginning.
Can you guess what it is now?
The worst questions in sales, in my
opinion, are yes or no questions.
These are closed-ended questions, which
I might use, for example, like this.
If I'm selling water purification,
knock on the door, Hey, uh, do you guys
enjoy drinking clean, purified water?
Yes, duh.
Right?
I don't want to use yes or no questions
because they don't further the discovery.
They don't further the discussion.
And as a salesperson, the more
information that I have, the easier it
is for me to pick and choose from all
the benefits that we can offer, how we
help homeowners through the process.
I can say, alright,
now I can plug this in.
Example, there's those four stages of the
claims process I talk about, no claim,
partial payment, denial, check in hand.
In retail, there's the four
stages, excuse me, four reasons
people replace their roof age.
It's at the end of its life,
an active leak or a problem, a
cosmetic upgrade, or a life event
like putting a house on the market.
So the more I know about which stage
they're in, in the details of that
stage, the easier it is for me to
sell specific to that homeowner,
and that's often overlooked.
So yes or no questions.
They have their place, right?
Like I said, are you from here?
And it can lead to a, a further
answer rather than yes or no, or maybe
a tie down question or commitment
questions, or do you understand?
Does all this make sense?
Those are times where yes or no questions
can be applied and they can be applied.
Effectively.
However, when we need information
or we want our homeowners to feel
like they're in control when we need
to learn more about them, we do not
want to ask yes or no questions.
We wanna ask questions that lead to a
longer response, and those are open ended
questions that typically begin with.
Who, what, when, where, why, and how.
Those are the six questions to ask.
When, where, why, what and how.
And again, reverting back to tip
number one, keep them simple.
But I do want to caution you really
gently about one of those six words.
What is it?
It's the word why?
Because if I said to you, let's
say you're wearing a hat right now.
For example, if I said, why
are you wearing that hat?
All of a sudden you're put on the
defensive and you're like, why?
Cuz I, cuz I like it.
And oftentimes the word why can be really
intrusive and it can almost be accusatory
and put people on the defensive.
So my best advice, I throw
that word why out the window,
and I use it really sparingly.
And I'm always really conscious that if I
do ask a why question, I don't wanna make
people feel like they're being insulted.
For example, why did you
choose that insurance company?
That basically says you're a dummy.
Why do you choose them?
Right?
We don't want people to feel that way.
So there you have it, the
three worst types of questions.
In summary number one, complex questions.
Instead, keep them short, keep them
simple and hit 'em one topic at a time.
Worst question number two is the
question that starts in dead ends
because you didn't go deeper,
you didn't get the real answer.
The fix is the best type
of questions, which are.
Follow up questions.
Again, when, where, why, what and how.
And use why sparingly or even who.
And then finally, you remember to
use the statement like, what else?
Anything else, anything more.
And it'll help draw more information out.
And often it's way deeper towards the
truth than the first answer they gave you.
And the third worst type of question
are yes or no questions, often
called closed-ended questions.
Instead, we want to ask.
Open-ended questions who, what,
when, where, why, and how.
And remember, use why sparingly.
Now I hope that this video helps you ask
even deeper questions to develop even
deeper relationships, win more business
and collect more thank you notes.
Hey, thanks for joining me on
this video today, just cuz our
time here is about to wrap up.
Doesn't mean you are in my time, has to.
So if you like this video and
you want more, jump into my free
training center or right here.
And if you wanna get really good at
asking questions, you might wanna
take a look at my sales training and
sales system and there's a link below.
Or you can text demo D e m O to 3 0 3.
2 2 2 71 33 and I got a playlist for you.
I think you're really gonna love.
So if you wanna hang with me
here, jump into this one and
I'll see you in the next video.