7 Reasons for Roofing Sales Discouragement

By Mike Coday •  Updated: 03/29/21 •  8 min read

Feeling Discouraged?

The 7 Reasons for Discouragement have remained consistent and true since the day I started in roofing sales back in 1995.

If you’re feeling discouraged as a sales person, or the people you manage are discouraged, read through these steps.

As you read through the list, I’ll try to bring out certain points that will help you identify the problem specific to that step.

By the end of this article, you’ll realize what you need to change before it’s too late for you to turn things around. Sounds good, doesn’t it?

1. Discouragement comes when something you anticipated happening does not happen (e.g. Rejected Claim, Lost Sale, Poor Prospecting Results, etc.)

Just yesterday I was talking with a roofing sales guy at Whataburger about his latest discouragements. I really like the guy. He’s a natural sales person with a proven prior track record in car sales.

He’s likeable and can be very persuasive… when he’s fully engaged… which hasn’t been very often.

When he’s not engaged, he can be negative, contrary, and full of lame excuses.

I don’t directly manage him, but I’ve counseled his sales manager to spend his time elsewhere on more than one occasion for those very reasons. I’m surprised the guy has hung in there this long, but I dig that about him.

While I finished my #7 with cheese and fried onions, fries, root beer, and fried lemon pie, I listened as he told his latest story of desperation…

Recently, he had a roof going up.

While the crew was busy working, he decided to go visit with the neighbors and offer them a free roof inspection (something I highly recommend). It didn’t take long for him to find a few people open to a free inspection.

He did his inspections on the spot (something I don’t recommend) and showed pictures of the damage to the homeowners. He even sat down with one family and listened to their long, boring stories of when they lived in Brazil.

Two of his inspections showed enough damage for the homeowner to convince themselves to call in a claim… including the folks from Brazil. Both had an adjuster visit within a week.

One qualified for a full roof replacement and the other an repair.

Everything sounds okay up to this point, right?

2. Discouragement grows when your pipeline isn’t full. Realizing that the one or two things you were counting on aren’t going to happen is discouraging.

The homeowner that qualified for a new roof suddenly went rogue. They signed a contract with a different roofing company. Discouraging? Yes. We expect more from those Brazilians!

The other claim, the repair job, didn’t want to do all of the work.

They started haggling on the repair price, requested a ridiculously low price, and ended the conversation by asking the salesman to just email over an estimate. More discouragement, right?

More discouraging was the fact that our salesman only had those two prospects in his entire pipeline. Just two! He was counting on getting at least one of the two and ended up losing both.

Without a pipeline full of prospects, that dark cloud of discouragement lowered down on him and knocked his air out. Bummer, huh?

3. Your pipeline isn’t full because you aren’t working enough to fill it.

While it was great that he went knocking for a few hours one day while his roof was going up, he hadn’t been out prospecting in a long time before then.

It only took a few hours for our salesman to do several free inspections.

What happened to the rest of the hours in his week? We all have other things happening in our life that we have to take care of, but a few hours of work every once in awhile usually won’t be enough.

Imagine how many free inspections he could get if he was out prospecting for several hours a night, several nights a week.

Working 3-4 nights a week for 2-3 hours each night 3-4 weeks a month while sprinkling in a Saturday morning here and there would greatly improve his odds of making money.

Waiting for a prospect to come find you is like waiting for an criminal to turn himself in to the police.

It happens, but the reason you remember it is because it only happens once in a blue moon.

You’ll go broke waiting for them to find you!

4. You aren’t working enough to get your pipeline full because what you’re doing is not working.

This wasn’t the first time he’s had two deals fall through on the same day. A few months ago (the last time he was really working), he had two roofs denied on the same day.

At least this time, his roofs got bought before he lost them.

That’s progress!

I’m sure he’d tell you the reason he hadn’t been out hustling the last few months is because what he’s doing isn’t working.

Actually, he had a lot of things working…

If you can do what he can do, you’re almost there. Don’t give up now!

5. What you’re doing isn’t working because you’re not learning. This is usually because you aren’t getting on-going sales training.

It isn’t always sales training, but usually that’s the reason.

However, it could also be because you’re stupid, pig-headed, negative, contrary, arrogant, or lazy.

In his case, as it is in most cases, it was a lack of learning and on-going sales training.

I’m happy to say that recently he’s been proactive about spending time with his sales manager. Instead of his sales manager having to call and encourage him to get trained, he’s been calling his sales manager and asking to ride along, pick his brain, and learn how he closes deals.

6. You aren’t getting training because it doesn’t make anybody money to spend time training you… or it doesn’t make them money fast enough to justify the time investment.

Let me just say this right now, “You need training!”

You don’t just need training. You need good training. Experienced training.

You need to learn from somebody who knows exactly what to do step-by-step to get you from “Hello!” all the way to picking up the last check from the homeowner.

Fortunately for our guy, his sales manager believes in him. His sales manager is a good trainer with the experience to get him into the money.

Remember, a teacher can’t help you get to where they’ve never been. That doesn’t stop them from trying, but don’t make that mistake.

Like I said earlier, I’ve encouraged the sales manager more than once to spend his time training somebody else, but he’s refused to let this guy go. I know for a fact that he could’ve made more money working by himself without the distraction… or at least spend more time with his family.

The sales manager has been getting a very low return for all the time he’s invested. Most sales managers and roofing companies aren’t that patient… even when they know they’ll make money from your sales. They’ll give up on you because you are slowing them down and they have bills to pay too.

Find somebody successful, hang out with them until they can’t stand you anymore, and learn to do everything they do.

7. You either give up and go back to a more reliable paycheck or you push through until you make it.

If you’re going to give up, do it now.

Just get it over with and find another job. Don’t wait another second.

You can’t afford to plunge yourself any further in debt.

Roofing sales isn’t really a job if you aren’t making money… and you won’t make any money if you aren’t working.

Quit using roofing as an excuse to waste your life. Go get a real job.

Nobody will think any less of you if you quit. Some people can do it and some people teach can’t. It was a good experience. You tried. Move on.

But if you’re going to push through until you make it, find somebody right now who can train you.

You’ll need good training if you’re going to escape the discouragement trap.


P.S. Obviously, if you’re going to get good, proven sales training, but you’re not going to take action on what you’ve learned, it probably means you’re probably either stupid, pig-headed, negative, contrary, arrogant, or lazy, right?

P.P.S. Go ahead and subscribe to the 101 Sales Tips newsletter now.

Mike Coday

Mike started selling roofs in '95 while working as a youth pastor at a small church in North Texas. A decade later he transitioned to speaking at industry conferences and training outside sales teams. Today, he works exclusively as the premier consultant to roofing company owners who are driven for growth.