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How My Ego Almost Cost $3,600

What a leaky roof taught me about my ego.

Two construction companies offered proposals to replace the roof. One was $3,600 more than the other.

Which would you choose?

Company 1 – Mid-sized business $13,500

A phone call revealed the company had administrative staff ready to schedule appointments. A week later, their estimator arrived to measure the job. He related potential concerns about the work and the estimate accuracy because he didn't bring a ladder to inspect the damage. Nevertheless, they delivered on their promise of a proposal within three days.

Company 2 – Small business $9,900

The earnest local roofer arrived the day after I called for a site review. After climbing to view the wind damage, he offered an immediate temporary repair. When he heard I already had one proposal, he asked me to give him a fair opportunity to do the work, which I thought was unusual. It seemed like pleading. He suggested submitting an insurance claim, delivered the promised proposal on time, and then sent a contract.

The contract was a template proposal sold by a law firm, and the italicized text that instructed the user what to edit and insert into the form was still on the document. In addition, there were other errors, including inconsistent capitalization and even blank areas without the required customized insertions.

photo of a pen and a paper with a signature
When is a contract not a contract?

I favor working with small businesses, yet I was bothered by the mistakes on the contract. There were even invoices from other jobs erroneously included in the proposal folder.

The choice was between the scattered local small business offer and a more expensive option from the larger company that appeared more professional. My clients often ask for my help with conundrums like this, but this one was mine.

A third estimate was another week away, and storm-tossed shingles meant the roof might be leaking, despite the temporary repair.

I needed to choose quickly.

My bias tilted me to assume, “Once the contractor understands why the contract errors are making me hesitate, he’ll fix them. We’ll both be happy.”

I wanted him to look good, not only to inspire my confidence in his significantly less expensive work, but also because my focus is helping people be their best. Unfortunately, I forgot (ignored?). I wasn’t with one of the curious and self-reflective people I usually interact with. My ego got the better of me.

My ego got the better of me, and it didn’t go well.

I called to tell him I preferred his services for several reasons, including his offer to patch the roof on the spot to prevent further damage. However, I was concerned about the numerous errors in his contract. Those mistakes and the inclusion of paperwork from other jobs left me anxious about his attention to detail.

He defensively said he would remove the contract template instructions if I insisted, but he didn’t think it was important.

As the Queen of Typos, I know proofreading on a screen is even harder than on paper. I thought he might appreciate learning the trick of highlighting areas of a form template that need customization. It has helped me avoid the same errors.

“I know on-screen proofing for forms can be a problem, so I’m letting you know an easy way to be sure they’re right. I want an accurate contract I can sign, and I want you to look good as a small business owner.”

There was a long moment of silence.

“I do look good,” he stated.

Ow, my unsolicited advice backfired. I felt as arrogant as he sounded.

Inhaling, I said, “OK. Please bring an to updated copy to sign.”

When he brought the contract for signatures, he was less brusque, and we didn’t mention any more about our somewhat tense phone conversation.

Yes, there were still some errors in it. I chose to ignore them based on his quick temporary repair that prevented more damage, his knowledge and caveats of roofing procedures, interesting stories of current and past projects, and good online reviews. Despite the sloppy contract, I still wanted the less expensive option from a small local company.

two people installing a roof
Roofing craftspeople

In the end, the roof was replaced by his hardworking team on a cold winter day, it looks great, and I learned a valuable reminder to ask if someone wants my advice—at a $3,600 savings.


No one is perfect, and some of the most valuable life lessons come from unexpected places. We're wise to notice and learn from them. Sometimes it takes a team and a lot of humility.

Expand your team with a trusted coach who has learned, and continues learning, from personal and client experiences.

Not sure where to start?

Leslie Robison
Let's talk.


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