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April 10th, 2026
2 min read
You got lucky. And I mean that seriously.
If your client is asking about captives and nobody else has gotten to them yet, you still have time. But that window doesn't stay open forever. Someone is going to have that conversation with them. The only question is whether it's you or somebody else who shows up prepared.
Here's how you handle it next time. You go back to them first.
You don't wait for them to bring it up again. You reach out, and you say, " Hey, you asked me about captives at our last meeting, and I want you to know I went and did some research. I wanted to make sure I understood it before I put it in front of you." That's it. That one sentence turns a moment of weakness into a demonstration of exactly what a trusted advisor looks like.
And then here's what you say when you're in front of them. There's something I've been looking into that I think is worth a conversation. I'm not saying it's right for you. I don't know yet. But based on what you've told me about your insurance spend and your claims history, I think we should at least look at it together. Come at it with advantages and disadvantages. This is what is good about it. Here's what's not good for everybody. Let's see if it makes sense for you.
That's the whole first conversation. You're not selling anything. You're not asking for documents. You're not explaining how a captive works from top to bottom. You're just opening a door and letting your client decide if they want to walk through it.
Now here's the part that really matters. If you put this off and they come back to you having already received a captive proposal from someone else, you are going to be playing defense from the weakest possible position. Your client is going to ask you why you didn't bring this to them. And the honest answer, that you weren't ready, is the one answer that costs you the relationship.
You don't have to be the captive expert in that conversation. You just have to be the person who showed up. We'll help you with everything else. The resources, the answers and the support to back you up when the questions get hard.
But you have to start the conversation. And the best time to do that is right now, before someone else does.
It's always your client. Never ours.
Warren Cleveland launched Captive Coalition after firsthand experience as an independent agency owner revealed a major gap in the market: agents lacked access to the knowledge and resources needed to compete with large brokerages offering captive insurance solutions. Warren brings over a decade of insurance leadership—including as President of ReNu Insurance Group—and a career that spans aviation, real estate, and commercial insurance. His mission is to ensure agents stay in control, keep their best clients, and confidently lead with captives. Warren Cleveland, ACI, CIC, AAI
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