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April 13th, 2026
2 min read
If it went badly, it probably went badly for one of three reasons. And knowing which one it was matters, because each one has a different fix.
The first is that you skipped steps. You moved too fast, made promises you couldn't back up, and the numbers didn't hold when it came time to deliver. That happens when agents work with captive managers who hand them a vague picture and tell them to run with it. No documented process. No clear steps. No way to know what was coming next. When you don't know what's coming, you can't prepare your client. And when your client gets surprised, they lose confidence in you.
The second is that your client wasn't properly brought along. They followed you into the conversation without really understanding what they were agreeing to. Business owners aren't always going to tell you they're confused. They'll just go quiet. And when you got to the part where real money was on the table, hundreds of thousands of dollars in premium and collateral, they weren't ready. Because you hadn't built the understanding that makes a decision like that feel safe.
The third is that you were working with the wrong partner, and they took the relationship from you. You did all the work, got your client to the door, and then watched someone else walk through it with them.
All three of those situations likely have the same root cause. You didn't have a documented, step-by-step sales process from the first conversation to a signed member. And you didn't have a partner who was willing to keep you in the seat the whole way through.
Here's what I would have told you before you walked in. Don't go further than the first conversation until you can show your client a written process that explains exactly what's going to happen, in what order, and what's expected from both of them and you. That document does two things. It sets expectations so nothing is a surprise. And it tells your client that you've done this before and you know where you're going.
We give every agent in our program that document. A complete sales process, step by step, from qualification through enrollment. Not a template you have to customize. Something you can hand your client on day one and say, here's how this works, here's what we're going to do together, and here's how long it's going to take.
That's the thing I wish more agents had the first time they sat down to talk about captives. Not more knowledge about how captives work. A clear map of where the road goes.
We'll help you with everything else.
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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