Dear Friend,
Business owners ask thousands of questions. How do I grow? How do I hire the right people? How do I increase profits? How do I beat my competition? Those are all good questions. Important questions.
But in nearly 30 years of sitting across the table from business owners, I've noticed that almost nobody asks the one question that matters most:
"What don't I know that could destroy everything I've built?"
That question almost never gets asked. And that's exactly why it becomes so expensive.
Early in my career, I believed my job was to answer questions. A client called, I gave them a quote, I bound the policy. That was the job. Today I understand my responsibility is much bigger than that. My job is to ask the questions nobody else is asking. Because hidden risks don't announce themselves. They don't send you an email or knock on your office door. They wait — quietly, patiently — until the day they become a crisis.
Let me give you a real example.
I worked with a general contractor who had just landed the biggest contract of his career — a multi-year project worth several million dollars. He was thrilled. His team celebrated. They mobilized immediately, hired subcontractors, purchased materials, and got to work.
Nobody reviewed the contract language with his insurance broker.
Buried in that contract was an indemnification clause that fundamentally shifted liability exposure onto his company in ways his existing policy wasn't structured to handle. The contract essentially made him responsible for categories of risk that his general liability policy specifically excluded. He had signed it. His attorney had reviewed it for business terms. But nobody — not his lawyer, not his previous agent, not anyone on his team — had asked the one question that mattered: "How does this contract change our insurance exposure?"
Six months into the project, a subcontractor incident triggered a claim. And when the dust settled, that indemnification clause pointed directly at my client for liability his policy didn't cover. The contract he celebrated signing had quietly created the very gap that now threatened his business.
One conversation could have prevented it. Thirty minutes of reviewing that contract language against his coverage would have identified the gap before he ever broke ground. The fix would have been an endorsement or a policy adjustment — not cheap, but a fraction of what the uncovered exposure ultimately cost him.
That's the conversation that never happened. And it was the most expensive silence of his career.
I see versions of this constantly. Companies invest hundreds of thousands of dollars in new equipment but never update the values on their policy. Owners proudly expand into three new states but never ask whether their protection strategy expanded with them. Businesses sign contracts worth millions without anyone asking how those contracts changed their liability profile.
These aren't careless people. They're focused people — focused on building, serving customers, making payroll, growing. And while they're focused on all the right things, the unanswered questions quietly compound in the background.
The most valuable words I can say to a business owner aren't "here's your quote" or "here's your renewal." They're these:
"Let's talk about something you may not have considered."
That's where real protection begins. Not with paperwork. With perspective. Not with answers. With better questions — the kind that expose assumptions, challenge comfort, and reveal blind spots before they become breaking points.
Every business owner deserves someone in their corner who isn't afraid to ask difficult questions. Because difficult questions today prevent devastating answers tomorrow.
Protection Principle #2:
The most expensive risk in your business isn't the one you're managing. It's the one nobody thought to discuss.
Continue the Journey
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Before you lock your office tonight, ask yourself one question: What risk has nobody taken the time to discuss with me?
The answer may be the most valuable conversation you'll ever have.
Protecting what matters,
John Crist
Founder, Prestizia Insurance
Founder, The Protection Circle
Author, The Prestizia Protection Playbook
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