BL&T No. 139: The Tale of Five Roofers

Agency Leadership

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is sent weekly on Mondays. In every edition, I share lessons learned in agency leadership, life, and e-commerce. This post does not include all the details shared in the newsletter sent via email. Subscribe here.


"'What they mean is that you shouldn't try to sell to a client by telling them what you would do for them if they hire you. You should just start consulting right then and there.'"

From "Getting Naked" by Patrick M. Lencioni [Book]  


Late last year, we came home from a trip to find one of our skylights had leaked (and had likely been slowly leaking for a while before that). We couldn't have been less excited to embark on a repair. I started my search by looking up certified Velux (skylight brand) installers companies via their website. The issue was that none of these companies would repair the skylight AND the damage to the drywall inside the house.

I contacted the previous owners for tips, and they referred me to a team who worked on the house while being built. In fact, this team installed the skylights. We were excited to hear they could fix the damage inside and out. We were hopeful it would be smooth sailing from there. We were wrong.

Let's call this team T&T. T&T came to see the damage and told me they'd be in touch within a week. Over a week later, I finally got an estimate, but I'd already become impatient and started looking elsewhere for a different perspective. Anxious to fix the leak, I decided to give up attempting to have the exterior and interior repaired together. I went through my voicemails and found two companies that had previously responded to Velux website outreach. We'll refer to them as Roof & Co and A+ Roofing.

Roof & Co came by and looked at the damage. After the project manager came down from our roof, he told me a piece of plywood had popped up under our shingles, and someone had repaired the other skylights with caulk. What started with replacing one skylight became replacing nine plus a good portion of the roof. They sent their estimate with a copy of their insurance, a Velux one-pager, and a link to a folder of photos of our roof. They didn't include any options beyond their recommendation.

A+ Roofing met with my wife, Dana. They didn't bring up any issues with the roof but recommended replacing at least two skylights. Their estimate included pricing for two skylights vs. replacing all of them. The PDF also included some photos of the house with captions. They were the first company to bring up potential tax savings by incorporating solar elements with replacement skylights.

As you can imagine, the repair cost was much more than planned. Unsure how to move forward, we let time pass by. I remember thinking this must be how clients feel when they decide they need a website redesign and go dark after receiving proposals.

A trip to the Philadelphia Home & Garden Show

Later in the month, Dana and I got four free tickets in the mail for the Philadelphia Home & Garden Show. We decided to go with my parents and check it out. Within 15 minutes of walking the show, a company we'll call MIGHTY Home Improvements aggressively approached us, asking about our roofing needs. Funny coincidence. Dana and my parents walked away, but I engaged. I can't remember if I had concluded that we should consider replacing our entire roof before or after this interaction, but regardless, this was when I decided to explore the option.

MIGHTY got all my information and set up an appointment for the next day. It was odd how insistent they were about Dana being in attendance. I didn't love how pushy they were, but I gave them credit for scoring an appointment with a cold lead. At the same time, I thought about the many people who likely share contact information in hopes of ending the interaction. I wondered if this was what it felt like to be a brand walking around at conferences I recently attended, like NRF and Shoptalk.

On our way leaving the show, we came across a booth with sample shingles and other roofing materials. It was fun to experience the materials firsthand. Only one guy was at the booth, so we waited for him to finish with a customer — an older gentleman who seemed to be sharing his life story.

Once we had a chance to chat with the roofing guy, he was low-key, answered all our questions, and offered to set up a free estimate if we were interested. He wasn't pushy and honestly seemed to care less about whether or not we scheduled an appointment. It was oddly refreshing. We, of course, shared our information and got a free estimate on the books. We'll call this company S+S Exteriors.

Although we were ready to explore a roof replacement, I only shared the leak issue with the two companies. I was curious to get their fair take on the leak that began this journey.

I can't remember why, but we ended up rescheduling with MIGHTY. Like past appointments, I figured they'd come by, check out the roof, speak with me for a few minutes, and be on their way. However, when I rescheduled, they insisted Dana was around again, then told us to plan for an hour-long meeting. Part of me wanted to call it off, but I was anxious to get their assessment.

S+S Exteriors

We were disappointed to learn the S+S Exteriors guy from the show wasn't coming for the appointment. In the past, we've had prospective Barrel clients share concerns when stakeholders change throughout upfront conversations. These days, we make sure there's a thread between all conversations so clients never feel this way. Although S+S gave me a heads-up, I felt like a prospective client, worried I wouldn't get the right help.

When the owner showed up for the appointment, my concerns subsided. He introduced himself and then went up to the roof. About 20 minutes later, he came down, and we sat together in the kitchen. He looked at me (as if to gauge my response to what he was about to say) and reluctantly asked who worked on the roof previously. Well, he thought I did — that's how poorly the roof had been installed and maintained. I officially wrote off T&T.

We spoke for about an hour. The owner walked through 40-some photos he took on his phone, explaining every issue in detail. It hurt a bit to talk pricing, but he was honest and even suggested waiting to see if costs come down before working on the roof. He also brought up the solar skylight tax credit, and we brainstormed how it could save us money. It was clear there were multiple ways to go about this roof replacement, and he was willing to work with us to figure out the right solution.

At the end of our chat, we talked about his business and life outside of work. Funny enough, we were dealing with similar business challenges and are in a similar life stage.

This guy had me sold, and he hadn't sold me anything. Pricing was still top of mind but became almost secondary to having someone like this help us. He was passionate, knowledgeable, and collaborative. He left me with a folder that included everything from reference customers, shingle samples, a brochure, and other business insurance and certification documents.

At the time, I was reading Getting Naked by Patrick M. Lencioni about the power of consulting during the new business process. It was like this guy was following the playbook. I left my conversation with S+S inspired to level up the experience for our prospective clients and bring the same energy to our new business discussions. Oh, and to get our roof in better shape!

MIGHTY Home Improvements

A few days later, a MIGHTY salesperson came by for our appointment. It was around 5 pm and starting to get dark when he arrived. He spent the first 10 minutes or so talking about random stuff. The more he went on, the more concerned I got about him going on our roof without light. I figured he was used to this, but deep down inside, I hoped we didn't hear a sudden thump.

When he got done, he came inside for his presentation. Yes, that's right — a full-on iPad presentation with props. He started with a walkthrough of MIGHTY's background, including its nationwide coverage and brand ethos. I appreciated the attempt to build trust, but after 15 minutes, I was ready to hear what he thought of our roof. My mind wandered to past proposal calls with prospective clients where we were running through the slides about Barrel. MIGHTY's approach was a great reminder to touch on the right points but keep it speedy — the client wants to hear how you think you can help them!

Like Mary Poppins, he took out a bag of roofing materials and began walking through the process of installing a roof. By this point, Dana had left the table. While I found this part of the presentation fascinating and rigorously took notes, I was still waiting to hear about our roof. After the installation demo, he started talking about MIGHTY's approach to roofing. By this point, I was actually confused trying to understand "normal" roofing practices vs. theirs.

This whole presentation lasted nearly one and a half hours. When I tried to move the conversation along, the salesperson acknowledged me but kept going. We eventually started talking about our roof. He had nothing to share except how they would replace it and went on to talk about their exclusive partnerships, quality, and warranty. He still did not point out one issue he saw with our roof, so I started to pry. In doing so, I learned they couldn't replace a few of our skylights because they only carried one type. I told him this issue was a deal-breaker for us, but he continued.

He finally shared pricing. My eyes widened at the hefty price tag before he could go on to share their "sign now" pricing approach. If we signed right then and there, they'd cut the price by several thousand dollars. I told him I appreciated the sentiment, but we couldn't make this sort of decision immediately. Not to mention — we wanted the correct skylights. I was also still waiting on a quote from S+S Exteriors.

After a bit of back and forth, the salesperson said he would bring his stuff to his truck and make a call about the skylights. Upon his return, he let us know he could offer further discounts and was now presenting a deeper discount, over 10%. But we had to sign today. I initially appreciated the idea of "sign now" pricing, but this was getting out of control. I started questioning the price altogether. I let him know we weren't interested.

I came back inside, and Dana could not believe what just transpired. On the bright side, I felt like I got a masterclass in roofing. Beyond that, it was almost 8 pm, and we hadn't eaten dinner yet. Dana joked that the salesperson probably thought he was staying to eat.

What started as an appointment with an "expert" company turned out to be a commitment we hadn't signed up for with someone only interested in selling us a new roof, not helping us solve our problem.

In the weeks that followed...

Right before I met with S+S, I followed up with Roof & Co and A+ Roofing to see if they could share a new quote for our entire roof. One sent a proposal a few days later without coming back out. The other came back a couple of weeks later before sending a proposal. Both didn't accurately capture the accurate number of skylights. Neither asked to walk it through on a call, but both sent follow-up emails.

Somewhere along the line, we had another minor leak. I knew not to panic because S+S had shown me areas where a future leak might happen; this spot was one of them.

After meeting with S+S, I pretty much decided we were going with them. As a bonus, I was happy to see their quote come in lower than expected. Their proposal also offered options with itemized pricing for specific features like the skylights. I wondered if he had anchored me high on pricing — a simple tactic we like to use when chatting with prospective clients without knowing the full scope of their needs. It's better to qualify a prospective client upfront and come in lower than get too far and lose on pricing.

In following up, I thought about the questions we typically have when chatting with prospective clients and decided to be transparent about everything. I shared who we received quotes from and what prevented us from moving forward with S+S. I also used the knowledge I gained from MIGHTY's Ted Talk and asked some follow-up questions.

Since then, I've been in touch with the S+S Exteriors owner frequently — discussing our approach, financing, and other questions. I feel bad it's taking so long, but this is a big investment, and he doesn't seem fazed. We've yet to sign any paperwork.

He and his team came out three times last week.

Once to drop off larger shingle samples and share addresses of homes they've done in our selected color options.

Once to do further investigation on the roof.

Once to grab some measurements and review gutter material samples.

These follow-up meetings further built trust with his team and surfaced issues like rotting wood and the source of the warp in our roof. (Not the same plywood issue initially shared by Roof & Co). Dana was also able to meet them and become part of the process. I felt like the Director of Ecommerce vetting the agency far enough to bring the CEO in to share their perspective.

We still don't have a contract, but S+S is now making calls (on our behalf) for issues like a noisy stove exhaust (better to fix when the roof gets replaced). At no cost, by the way, just the price of the parts.

As unpleasant as it is to take on such a major unexpected expense, we're beginning to feel some level of excitement toward the project.

By the way, MIGHTY called Dana a couple of weeks ago when I was out of town and offered lower pricing.

Why I wrote this

Thanks for coming along with me for this story. Throughout this experience, I kept thinking about what it's like to be a prospective client of Barrel. I decided to capture the story in writing because I thought spending more time with it might glean further insights.

While I talk with clients daily, it can be easy to lose sight of what it feels like on the other side of the Zoom call. As frustrating as this roofing experience has been at times, it's been fun to use it as fuel to improve our conversations with prospective clients.

Over the last several months, I've been updating and improving our new business processes — many of these changes were seeds during my experience with these roofing companies.

The story doesn't have a proper end yet, but you better bet I'll share the outcome when it's all said and done.


Here some of the takeaways on my mind from this experience:

  • Show a genuine interest in helping clients solve their unique problems and take the time to listen to their concerns and needs.
  • Manage the client's expectations before meetings so they are prepared, engaged, and able to commit the time.
  • Don't be afraid to offer up your expertise. It can feel like doing work for free, but it's a great way to build trust and create a positive impact.
  • There's merit in nice-looking sales materials and a proven process, but know the customer and their situation. A formulaic approach won't work for every lead.
  • Avoid unexplained discounts, especially when the customer didn't ask for them. Reducing the price with no rhyme or reason can make the company look desperate, the pricing look artificially inflated, or the salesperson look commission-hungry.
  • Take time to walk through the proposal with the client, especially if they're unfamiliar with the project process. It's not worth losing over a misunderstanding.
  • Cover all your bases in your proposal. Think about the questions clients are always asking as a source of inspiration.
  • Share references from the start. It shows confidence in the work and can move the process along more quickly, especially if the client contacts them early.
  • Be transparent and upfront about costs, timelines, and what factors impact both.
  • Create a consistent thread through all conversations. Never make the customer explain themselves more than once.
  • If the person leading sales has no experience on the ground, get them exposure or have them bring in the right folks to guide the client.

Thought Starter

Am I focused on selling and making a good impression or helping my client solve their problem?


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