Skip to content

'Trusted by roofing sales teams across the US and Canada'

Conquering FEAR That’s Capping Your Income

FEAR can really hold us back in roofing sales. FEAR can:

  • Hold us back from earning and serving as much as we can
  • Lead a lot of people to leave the industry, thinking it’s not for them (After all, let’s face it — this whole world of roofing sales is by no means the easiest joy ride of a career choice.)

When that happens, we’re forced to face ourselves, our inner demons, and our own fears in ways that we don’t in nearly any other career path. Like cubicle workers, accountants, and even folks flipping burgers, maybe they’re afraid of making a mistake. That’s it.

In roofing sales, though, you carry EVERYTHING from home with you.

That includes your childhood baggage that made you who you are and any demons you’re facing. We bring ALL this to work, and it’s NOT easy. Many folks, myself included, have faced a really challenging journey.

And maybe you’re in the middle of it right now, learning how to face and conquer those fears.

Personally, I was afraid of knocking on doors. I feared:

  • Rejection and conflict
  • Asking for the business (because I didn’t want to get rejected) and coming across as pushy.

So, instead of leaning into objections, I would shift into “nice guy” mode and get the heck out of the house (and, by the way, I covered this recently in my 3X video, so check that out if you haven’t already).

Now, those elements of fear became my income ceiling, and I knew that if I couldn’t break through that fear, it would limit my income.

And fear is something that most of us have encountered when it comes to sales. I go so far as to say ALL of us have, and not everyone will admit it. That’s what I believe.

Fear is an interesting phenomenon that lives between our heads, meaning we make it all up.

FREE “Pitch” Like a Pro Roofing Sales Training

240+ Video Library for Storm and Retail

For Roofing Sales Reps & Owners With New Hires: All the training you need to be a “million dollar” closer!


Get Instant Access
Pitch Like A Pro | Roofing Sales Training, Videos & Strategies | The Roof Strategist

A Prime Example of Fear in Roofing Sales

A gentleman emailed me last year. He’s a combat veteran who served numerous tours in some of the most dangerous places in the world, and he’s been in a tremendous number of combat situations.

So, he emails me, explaining that he never skipped a beat in combat but, in roofing sales, he’s:

  • So crippled with fear that he can’t even get out of his truck to knock on doors.
  • Driven to neighborhoods and actually turned around and went home because he was so overwhelmed by fear

This is a perfect example of how we’re all human and we create fear in our heads.

This gentleman had zero reservations about jumping into combat, and yet, he was totally overcome with fear when it came to a relatively “safe” situation of knocking on doors (and no disrespect to this gentleman).

That FEAR is what holds us back.

So, I want to share a very simple daily practice that you can begin using right now to help you conquer those fears one domino at a time, so you can:

  1. Smash your income goal
  2. Give every customer an amazing experience
  3. Build up an absolutely unshakeable sense of confidence and communicate with absolutely nothing holding you back or pulling you down.

By conquering these fears, you can become the BEST version of yourself, serving at the highest capacity possible. And that feels amazing.

So, I hope that this simple little daily practice can help you get there.

Now, before we get started, I just want to say a quick welcome or welcome back. Adam Bensman here, The Roof Strategist. Everything I do here — and on my YouTube channel, my podcast (on Apple and Spotify), and in my training center — is designed around one simple mission. And that is to help you and your team smash your income goal and give every customer an amazing experience.

So, if you like this or any of the content here, join us inside our free training center for a whole lot more. Simply text the word “FREE” to (303) 222-7133 for a link that gives you instant access to my Pitch Like a Pro roofing sales training video library, including my:

  • Roof claims crash course
  • 10 closing techniques for every situation
  • Recommended reading list
  • Signup list to secure your free copy of my book, the Roofing Sales Survival Guide, that’s coming out soon

Now, let’s dive into this topic of FEAR.

How I Encountered & Overcame FEAR in Roofing Sales: My Story

I got into roofing sales as a very thin-skinned person who is very afraid of conflict, upsetting people, and facing rejection. I just didn’t do well with it.

Funny enough, though, when I got into door-to-door roofing sales, my first sale ever was from a cold call off a commercial sign.

I shared this story in many other videos, so I’ll spare you from it here. Still, I remember the FEAR I had at the time. I vividly remember sitting in my truck, covered in sweat (I just left the gym), and seeing a “For Rent” sign.

As I picked up the phone and dialed, my hands were trembling. There I was, more afraid to make a cold call without having to see someone or be there face to face at the door. That’s just another example of how all this fear was just in my head.

So, my fears were the BIGGEST challenge for me to overcome. And all I kept thinking was, I’m just NOT cut out for this. I have to learn these skills.

Then, I started to realize that I had this talent hiding inside me; I just had to chisel away at all of this garbage and baggage that trapping that part of me.

Thought Experiment: Think of this like concept like a sculpture, with sales prowess hiding inside and not yet shown. Those different layers of fear, created by my inner demons and baggage, were blocking me and getting in my way. They had to be slowly chipped away. It’s like chipping away at the fear to reveal our true inner talent, our true confidence, and a FEARLESS salesperson. We just have to chip away at the block of fear to reveal all of that.

So, remember this analogy moving forward, especially when it comes to the two ways people approach this challenge.

Path #1 to Deal with Fear in Roofing Sales: Avoidance

With the path of avoidance, the thought process is, If it makes me afraid, I’m going to stay away from it. In roofing sales, that can specifically mean:

  • Driving into the neighborhood and leaving
  • Not cold calling
  • Not knocking on doors but, instead, doing anything else to avoid knocking on doors, like mailing letters

With avoidance, does that chip away at the block of FEAR?

No, it doesn’t. In fact, avoidance almost even strengthens our fear because avoiding things we’re scared of can reinforce that fear. We feel safe avoiding it, and for many people, it maintains or even amplifies that fear.

So, instead of conquering the fear, avoidance just makes it worse. You’re not going to chip away at the block of fear if you don’t look at it.

Path #2 to Deal with Fear in Roofing Sales: Face It Head On

What do we need to do to conquer our fear in roofing sales?

We have to:

  1. Look at it. We need to be able to confront our fear.
  2. Tackle it. We have to pick up the tools we have and start tackling our fears.

So, how do we make this a daily practice?

Avoidance does NOT work.

Instead, we have to look at our fear, pick up the tools, and intentionally tackle that fear to:

  • Chisel away those parts of us that no longer serve
  • Reveal the confident, fearless salesperson within us

To do that, we need to face those fears daily. That’s why I invite you to participate in the Daily Fear Challenge.

The Daily Fear Challenge for Roofing Sales Reps

If you choose to take up the Daily Fear Challenge, your mission is to write down your fears in roofing sales. Literally, put pen to paper and list out your fears.

Now, this is the stuff that so many people don’t talk about because, in my opinion, there’s too much ego involved in sales.

What I love about sales, though, is that:

  • It’s just a really big game of personal development, challenging us to learn how to communicate and solve problems.
  • We just get paid really well by getting better at doing that.

So, when I look at this challenge of chiseling away all those components that are keeping me trapped, I need to:

  1. Pinpoint EXACTLY what those fears are.
  2. Face those fears head-on.
  3. Tackle them one at a time.

Most Common Fears in Roofing Sales

Most of us share the same fears in roofing sales. Of course, we’re all different, and our fears can be unique at times. Still, for the most part:

  • Most of us in roofing sales have the same fears.
  • Our fears change as our skill sets develop.

Some of those fears that roofing sales reps tend to share are the fear of:

  • Public speaking: Some people get nervous, scared, or embarrassed when they have to talk in front of groups or crowds.
  • Knocking on doors: Approaching the door or even the unknown of what happens when it opens can be a source of fear for many.
  • Rejection or conflict: This can also be tied to a fear of asking for the business and coming across as too pushy.
  • Not earning enough money: With this fear, it may be more about not succeeding or hearing, “I told you so,” from family who questioned your ability to work on commission or sell roofs.

We need to identify these fears.

How to Participate in the Daily Fear Challenge

So, to start overcoming fear in roofing sales, take up the Daily Fear Challenge, and here’s how you do it:

  1. Write down your fears.
  2. Choose one of your fears and challenge yourself to face that fear every single day.

Now, let’s go through some examples to face some different fears.

Roofing Sales Fear #1: Knocking on doors.

If you’re afraid of knocking on doors, bring some humor into it. Challenge yourself to:

  • Knock on that door.
  • Have a goofy smile when they answer the door.
  • Say, “Hey, I’m in the neighborhood today collecting high fives for smiles.”
  • Reach forward and see if someone’s willing to give you a high five.

Now, will that fail and backfire? You bet.

Will it work a bunch of times? Of course.

Do people smile when they give you a high five? Yes — many folks can’t help but smile. When they do, they’re disarmed.

So, there’s a fun way to challenge yourself to overcome those fears. I even had one member of our Pitch Pro Movement challenge their team to do the chicken dance the minute that homeowners answer the door.

Why? Because if that doesn’t scare you, I don’t know what does.

So, the challenge is to collect a high five every single day.

Roofing Sales Fear #2: Being Pushy

Another common fear is being too pushy. This was something I had to face because I was afraid of cold calling.

So, if you share this fear, here’s your challenge — when you see a “For Rent” sign or “For Sale” sign at a commercial property:

  1. Pick up the phone.
  2. Dial the number and make the call.


You’re NOT going to get better at doing things by avoiding them. You HAVE to force yourself each and every day to do them.

Roofing Sales Fear #3: Being Pushy

I recently did a video on this (my 3X video), talking about being persistent and not pushy.

So, each and every day you hear an objection, you can overcome it three times by asking a “how” or a “what” question.

When you go on this journey, pinpointing exactly what you are afraid of, you’re going to:

  1. Look at it right in the face.
  2. Grab that chisel.
  3. Slowly, with each dial of that cold call, chip away at the block.

When you lean into those objections each and every day to conquer your fear of being pushy:

  • You build up this momentum.
  • Before you know it, you’ll reveal a NEW version of yourself that you didn’t recognize.

If you saw me about 10 ½ years ago, you would not even recognize me.

I had the same energy and enthusiasm, but the confidence was not there — and:

  • My speaking cadence and communication skills were nowhere near as refined.
  • I didn’t have the thick skin that I developed through dealing with conflict.

Looking back at who I once was, I barely even recognize the Adam of a decade and a half ago.

Now, I wish the same journey for you because, truthfully, that’s what I love about the roofing sales industry. I don’t care about roofs.

What I love is it is the ultimate life challenge to chip away at that block of fear and reveal the BEST version of you.

Bonus Tip: Use Meditation to Improve Your Focus

If you have a hard time focusing — maybe you have ADHD or the idea of sitting still and focusing is daunting (it was for me, and I knew that focusing was key to increasing my income) — start meditating.

Personally, I hate sitting still for a long time. It makes me anxious. So, I meditate every single morning.

I do this because it forces me to sit still and be silent.

When I began meditating, even 2 or 3 minutes of meditation felt like an eternity. But soon, it felt nice, and I was onto 5 and 10 minutes. Then, I was up to 20 to 25 minutes.

And I just learned to develop this calm mind by facing my fears and sitting with myself.

So, in summary, your mission is to:

  1. Identify that which you are afraid of.
  2. Find that thing that you’re afraid of and give yourself a daily challenge to FACE THAT FEAR EACH AND EVERY DAY, so you can chip away at that block to reveal your confidence.

I hope this helps inspire you to tackle one fear each and every day by gamifying it and having FUN.

Want More Roofing Sales? Or Training For Your Team?

We’ve helped thousands of sales reps overcome the same sales challenges you’re probably facing. Like not getting enough leads, getting stuck on objections, or not closing sales in the house.

Learn how we can help you:

  • Get trained up in a lightning-fast 9.5 hours
  • Self-generate more leads
  • Become a confident closer

Pick a time for your 1-on-1 demo.

Or use the links below to get instant access, 100% Risk-Free! Backed by our 30-Day ‘NO BS’ Money Back Guarantee.

For your sales team?

Individual sales rep?

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