🏡 The Leak, the Ladder, and the Illusion of Trust

🧠 What a roof leak taught me about fiduciary duty, asymmetric relationships, and why micro-communities matter more than ever

During the two days of non-stop rain in Toronto at the end of May, my better half and I were awakened in the middle of the night by water dripping from the ceiling—right in the middle of our bedroom.

After installing the necessary bucket and towels, we reached out to our roofer and general contractor, who had worked on our roof (and redone it) not once but twice in the past five years. I don’t think anyone ever expects a leak, but with a new roof and new windows, this was definitely not on our radar.

Obviously, when morning came—after pretty much a sleepless night—I called our insurance company to get organized. In the meantime, our roofer called to let us know he would be there a few hours later. I was unfazed. Not my first leak, not their first leak—a pain in the butt, but in the grand scheme of things, a non-problem. Of course, I had to cancel my meetings to accommodate the visits and calls, but still—no biggie.

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As expected, the roofer came toward the end of the morning to check things out. First thing he asked for was a ladder to get on the roof. Well, I don’t know about you, but I don’t have a ladder. I’m not in the habit of climbing onto my roof—I’m sure it’s a lovely vantage point, but that’s what rooftop patios are for. And with that, the shitshow began: where can we get a ladder? And not just any ladder—a ladder of a specific height.

Okay, so now I’m calling a friend on my street who—Murphy’s Law—happens to be in NYC on business. Thankfully, she answers and thinks she has the right type of ladder. Then I have to reach out to her husband, which I promptly do after she shares his number. Thankfully, he answers—yes, he’s home, yes, he has the ladder.

So here I am, climbing into the roofer’s truck—clearly not expecting passengers—while it’s still pouring rain. We make it to the end of my street and, after some back and forth, leave with the lighter ladder with fewer features (it doesn’t wash the dishes). Back to my house. Naturally, some Uber is parked across the edge of my driveway, which hadn't been an issue earlier when the roofer just parked in front of my neighbor’s garage. Thankfully, the driver saw that I looked partially disheveled and clearly on the verge of a nervous breakdown and promptly vacated the spot. This didn’t stop the roofer from blocking my other neighbor’s driveway—because why not?

Finally, we make it to the top level. Still pouring rain. He gets on the roof. I’m lighting a candle, expecting to see him fall through one of my skylights any second.

Eventually, he comes back. Diagnosis? Uncertain. Could be a pipe. Of course, it started leaking during torrential rain—it must be a pipe! Oh wait, there’s no pipe in that room. Could be the neighbor’s skylight. He shows me pictures of how badly the neighbor’s skylight was installed. But based on its location—even if there is a problem—I really don’t see how we’d be affected. Not the top candidate. Could be one of our fans—maybe getting warmer. But based on the photo, there’s no water accumulation around the fans, and the water seems to accumulate in a spot above… hmm. Seems like a clue that the issue is actually right there. Then: could be our fireplace exhaust. And then—ta-da—a picture of the exhaust, not only rusty but corroded, with a massive hole in it.

I’ll spare you the many back-and-forths related to the leak, but—as always—every experience is an opportunity for reflection.

First: who on freaking earth shows up to inspect a roof without a suitable ladder?

Second: the roofer and his team had been on this roof many times over the past five years and never thought to mention that the fireplace exhaust was damaged? That didn’t seem like valuable information to share?

Third: I assume roof leaks are pretty standard for a roofer. So how did this become a game of "spot the 7 differences"? I’d think there are obvious ways to test where a leak is coming from. Put some dye in the high-suspicion areas and see what color shows up in the bedroom, for example. I haven’t ChatGPT’d it, but I’m pretty sure there’s a structured decision tree to track a leak—probably 10 ways to do it efficiently. Which brings me to my fourth point…

Every possible reason—even the most random—was thrown out except the most obvious one: the brand new, still-under-warranty roof is leaking.

⁉️So What Do We Learn?

That fiduciary duty should be extended to any relationship based on asymmetric information and expertise.

What is fiduciary duty, exactly? TY Google for the following definition:

“A fiduciary duty is a legal and ethical obligation of a person (the fiduciary) to act in the best interest of another person or entity (the beneficiary). It involves a relationship of trust and confidence, where the fiduciary is entrusted with powers and responsibilities for the benefit of the beneficiary. Fiduciary duties are often implied in certain relationships, such as between a lawyer and client, a director and a corporation, or an agent and a principal. The most common fiduciary relationships involve legal or financial professionals who agree to act on behalf of their clients.”

“Generally, a roofer does not have a fiduciary duty to their client. Fiduciary duties are a high standard of care, requiring a party to act in the best interests of another.”

So expecting a party to act in the best interest of another is not a basic requirement in most commercial relationships—excluding law and finance (more or less). Ironically, I’m better equipped to pressure-test my lawyer or financial advisor than I am my roofer or car mechanic.

Why the double standard? I doubt the average person knows more about construction or mechanics than they do about finance or law. Shouldn’t we assume we’re all vulnerable when it comes to specialist knowledge?

In the very straightforward context of this leak, fiduciary duty would have meant: 1) the roofer shows up with a ladder, 2) he tells us years ago that the exhaust is damaged, and 3) he takes responsibility that the brand-new roof he installed might be leaking. But he’s not obligated to do any of that. His only obligation was to install the roof—properly or not seems to be up to his discretion. Maybe offering him a coffee helps? Not even sure anymore.

In an ideal world, we wouldn’t need fiduciary protections. We’d all be ethical, and all would be well. But we don’t live in that world. In this one, integrity is seen as boring, nitpicky, and business-unfriendly.

Which is why trust matters even more. And micro-social recommendations. Can you trust a Kardashian to point you to the best product for you? Probably not. But your friend? Probably yes. That’s why the rise of micro-social networks, niche communities, and micro-influencers is one of the most significant trends shaping the digital and social landscape today.

Since we can only hope that the other side of a commercial relationship will act in our best interest—at a time when everything seems to be monetized and monetizable—having trustworthy people around us is key. Of course, that brings its own challenge: loyalty, nepotism, incompetence—“Yes, he sucks, but I trust him.” But that’s a topic for another time.

So what did we learn?

In any relationship, keep an eye on:

• Who has a conflict of interest?

• Who has integrity?

• And never underestimate the power of a second, unbiased opinion. 😉

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.