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How Do I Bring Captives Up Without Sounding Pushy?

April 9th, 2026

1 min read

By Warren Cleveland

Hero Image How Do I Bring Captives Up Without Sounding Pushy?
How Do I Bring Captives Up Without Sounding Pushy?
2:22

I Want to Bring This Up But I Don't Want My Client Thinking I'm Just Pushing Something New on Them.

The only reason your client would think you're pushing captives is if you came in selling it like a silver bullet. Like there's nothing wrong with it. Like they should definitely do this. That's the version of this conversation that feels like a pitch. And that's on you, not the topic.

Here's the thing. Captives aren't for everyone. And if you walk in saying that from the start, the whole dynamic changes. You're not a salesperson with something to move. You're an advisor with something worth looking at.

So don't lead with the answer. Lead with the question.

There's a strategy 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 how you manage risk, I think we should at least explore it together.

That's it. That's the whole first conversation. You haven't asked for documents. You haven't explained how a captive works. You haven't committed to anything. You've just opened a door and let your client decide if they want to walk through it.

Come at it with curiosity, not conviction. Here's what's good about it, here's what's not for everybody, let's see if it makes sense for you. That's a completely different conversation from the one you need to have; here's why it's going to change everything.

Business owners aren't offended when their trusted advisor brings them a new idea. They're offended when their trusted advisor shows up unprepared, oversells something they don't fully understand, or wastes their time. None of those things have to happen here.

You don't need to be the captive expert in the room. You just need to be the person who started the conversation with enough confidence that your client takes it seriously. We'll give you the resources to back it up. We'll help you prepare for the questions they'll ask. And if it turns out captives aren't the right fit for this client right now, that's okay too. You still showed up as the advisor who was thinking about their business when nobody asked you to.

That's what keeps good client relationships from becoming vulnerable ones.

We'll help you with everything else.

It's always your client. Never ours.

Warren Cleveland

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