A School Had a Bad Experience. Here’s What I Did About It.
- Daryl Henry
- 21 minutes ago
- 4 min read
I’m going to tell you a story I’d rather not tell—but I think it’s important. Because we made a mistake with a client, and that mistake cost them time, money, and most importantly—trust.
It wasn’t a failure in coverage. It wasn’t because we didn’t care. It was a failure in communication. And I want to walk you through exactly what happened, what I learned, and how taking full ownership—not deflecting, not explaining—was the only thing that worked.
How It Started: A Seemingly Successful Placement
This was a school account—one that had just been non-renewed by their current insurance company. They needed help fast. One of the producers on my team worked the account, pulled together options, and we got them placed with a new carrier.
We solved the big problem: property, general liability, workers comp—all buttoned up. On paper, this looked like a win.
But that’s when the real issue showed up.
The Background Check Mess
Shortly after binding coverage, the school was told they needed to revamp their background screening program and start running annual background checks on all staff and volunteers. That had never been required under the old policy.
To make matters worse, our team wasn’t totally clear on the level of checks needed. So the school assumed they had to do full FBI background checks on everyone. Every single year. That’s expensive, time-consuming, and frankly—it was a shock to them.
Now, in the end, they found a technology solution they felt good about. But it wasn’t the new process that made them frustrated.
It was the surprise. And that surprise was on us.
Strike Two: The Event and the Liquor Liability
Then came the second issue.
This school hosts an annual community event—and they serve alcohol. They pull a temporary liquor license and pour it themselves.
Here’s the problem: the new carrier required liquor liability insurance for that kind of exposure. Under the last program, they either weren’t told or weren’t charged extra. But now, they needed a separate event policy—and it cost them over $1,300.
Again, not the end of the world. He understood the reasoning after we talked about it. But when you stack this on top of the background check issue, you’ve now got a client who feels blindsided twice.
That’s when the trust started to crack.
Why I Didn’t Try to Explain It Away
Here’s the thing—both of those issues could be “explained.”
The background checks? That’s what the new carrier requires.
The liquor liability? That’s a legitimate exposure that needs to be covered.
But when a client is already frustrated, explanations just sound like excuses. And I’ve learned over the years that when you start explaining, people don’t feel heard—they feel dismissed.
So instead, I just owned it.
What I Told the Client
I picked up the phone and said:
“Look, I’m really sorry. I understand why this feels like a bad experience. We should’ve communicated better. We should’ve clarified what the background check requirements were. We should’ve asked more questions about your event. That’s on us.”
I told him, “If you feel like you need new representation, I’ll respect that. But if you’re open to working through it, here’s how I plan to make it right.”
That was it. No blame. No dodging. Just straight ownership.
What Happened Next
Once we got past the emotion and the frustration, we started problem-solving together.
For the background checks, I helped him understand what the carrier was actually looking for—not FBI-level checks, just consistency and safety. We talked about different platforms and landed on something he felt good about.
For the event, I said: “Look, the cleanest way to fix this is to hire a caterer. Let them carry the liquor liability exposure.” He agreed. Simple fix.
But here’s the key: he wouldn’t have been open to that solution if I hadn’t taken ownership first.
If I had led with “Just hire a caterer and this all goes away,” it would’ve made him feel even more dismissed. Because his real issue wasn’t the extra $1,300 or the compliance work—it was that nobody told him what to expect.
And that’s what burned him.
The Real Lesson: Surprises Kill Trust
This whole thing reminded me that in insurance—and honestly in any relationship—people don’t lose trust over the policy. They lose trust over the surprise.
They don’t want a broker who’s perfect. They want a broker who tells them what’s coming, who communicates, and who takes responsibility when things go sideways.
In this case, it didn’t matter that the background checks were a carrier rule or that the liquor liability made sense on paper.
What mattered was that he felt like he was the last to know.
If You’re a School or Nonprofit Leader Reading This
If you're reading this and you’re a school, nonprofit, or community-based organization… let me just say this:
If your broker doesn’t talk you through what’s coming, if you’re constantly getting surprised at renewal, or if things are happening in your policy that you didn’t sign up for—you deserve better.
I don’t promise perfection. But I do promise ownership.
You should never feel in the dark about your insurance. You should never be surprised by expensive endorsements, unexpected audits, or new compliance requirements no one warned you about.
If you’re in that boat, and you want to talk about how to get ahead of it—I’d be happy to have that conversation.
Wrapping This Up
I wish I could say we never make mistakes. But we do.
What I’ve learned over and over again is this:
People can forgive mistakes.
What they can’t forgive is someone who won’t own the mistake.
And in this business, that kind of trust is everything.
So if you’ve had a bad experience with your broker, or you feel like you’re constantly cleaning up messes you didn’t see coming—reach out. I’ll help you get clarity and control back in your program.
Because that’s what you actually hired us to do.
Need help with your school or nonprofit’s insurance?
Give me a call or shoot me an email. No pressure. No sales pitch. Just a conversation.
And hey—if you’ve read this far, thanks for being here. Go build something great.