In the fast-paced world of commercial insurance, new trends and technologies seem to emerge daily. But some strategies stand the test of time—particularly when they’re rooted in deep client empathy, practical experience, and a commitment to legacy. In this post, we reflect on insights shared by Kevin Ring from the Institute of WorkComp Professionals during a recent Power Producers Podcast. Kevin joined David Carothers to honor the contributions of industry legend Preston Diamond and explore how his wisdom still applies in today’s sales landscape.
Preston Diamond’s name is synonymous with workers’ compensation excellence and sales mentorship. His decades-long dedication to helping producers grow, adapt, and think differently has impacted thousands of agencies. When Kevin Ring revealed the release of a new book compiling Preston’s weekly sales letters—affectionately referred to as “The Diamond Playbook”—it wasn’t just about selling books. It was about preserving a legacy.
The compilation honors the decades of practical, boots-on-the-ground advice that Preston delivered consistently through faxes, emails, and later, online content. These weren’t lofty theories—they were battle-tested ideas that agents could apply immediately. Publishing the book while Preston is still here to see the impact he made is a lesson in gratitude and timing. We must not wait until the funeral to celebrate those who’ve changed our professional lives.
One of Preston’s foundational philosophies was this: clients don’t buy insurance—they buy peace of mind. They want assurance that, when disaster strikes, someone will be there to help. Kevin emphasized that the traditional product-pushing approach is outdated and ineffective. Producers must understand where their clients are going, what keeps them up at night, and how insurance fits into their long-term goals.
When you focus on understanding and solving problems—not pushing policies—you earn trust and stay relevant. It’s a subtle shift, but it transforms the entire sales process. Insurance sales is no longer about the premium; it’s about the outcome the client wants.
One of the funniest—but most alarming—revelations in the podcast was that a sales letter Preston wrote in the 1990s about agency websites is still relevant today. Back then, he warned that too many websites were just digital business cards. Fast-forward 30 years, and guess what? Not much has changed.
Many agency websites still list the carriers they represent, their lines of business, and a phone number. That’s it. No expertise. No storytelling. No educational content. And certainly no optimized SEO strategy.
If your website isn’t building trust before you even speak with a prospect, you’re losing ground. It’s no longer optional—your digital presence is your resume.
A standout moment in the episode came when David Carothers shared a case study about pressure washing insurance. After identifying it as a niche opportunity, he built a dedicated content strategy around it. He optimized every blog post using Yoast SEO tools, focusing on metadata, internal linking, slug optimization, and content readability. The result? His agency ranked #1 for search terms like “pressure washing insurance Florida” and “pressure washing insurance Tampa.”
Better yet, the leads started coming in daily—without any paid advertising.
These inbound leads weren’t cold either. As co-host Kyle Houck explained, these prospects had already consumed content, understood the value, and reached out with buying intent. The “sale” was already halfway done before the first phone call.
Kevin introduced a powerful concept that many producers overlook: client share. Too many agencies chase new business at the expense of deepening existing relationships. But it’s far easier to grow within your current book than to constantly chase new clients.
Producers should inventory their existing clients’ coverage to identify missing lines of business. Are they buying personal auto elsewhere? Do they have commercial umbrellas, cyber liability, or EPLI through another broker—or not at all?
Focusing on client share improves retention, boosts revenue per client, and solidifies your role as their go-to advisor.
What does your client expect when you walk into a meeting? Do they want a polished professional in a three-piece suit—or someone who understands their world?
Kevin and David shared real-world examples of producers being fired for showing up overdressed or driving luxury cars to job sites. In industries like agriculture, construction, or logistics, clients may see a suit and tie as a disconnect from their day-to-day reality.
Authenticity wins. Being relatable doesn’t mean sacrificing professionalism—it means prioritizing human connection.
Want to build unshakable loyalty? Help your clients grow.
Kevin shared examples of agencies connecting commercial clients with personal lines clients through vendor directories, co-hosted events, or even meal introductions. A restaurant client might offer discounts to personal lines policyholders. Contractors might be featured in a “preferred vendor” magazine that goes to new clients as part of their welcome kit.
This creates exit barriers. If you’re generating business for them, why would they leave over a 5% premium savings?
Preston’s writing reminds us that practical wisdom, when consistently applied, always wins. Whether you’re building inbound strategies, refining your agency website, or becoming the trusted advisor every client wants—you don’t need to reinvent the wheel. You just need to apply timeless principles with today’s tools.
As Kevin said, this isn’t pie-in-the-sky theory. It’s practical, down-to-earth sales advice that still works. From recognizing client needs to honoring legacy, from storytelling to digital positioning, the path to growth hasn’t changed—it’s just expanded.
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