My question for you today is: what do you do to memorialize your victories so that you can go back and reflect on them later to remind yourself why you won? I have a very specific thing that I do, and I’m going to share that with you today.
If you’ve been following me for any length of time, you know that I am a huge believer in learning from winning. We talk so much about failing forward, and I understand. There are no losses, just lessons and all of the other stuff that highly motivational speakers will speak to you about. But there’s something to be said about learning from your wins just the same. If you don’t know why you won and how you can replicate that again, then chances are it was just luck.
I have a very, very proven process that I use to learn when I win. My approach isn’t anything overly extravagant or sexy, but it’s functional. See, I keep a copy of every agent of record letter I’ve ever gotten in my entire career. I keep them in a three-ring binder, and when I hit a little bit of a dry patch or maybe to remind myself that I’ve won some really good accounts, I’ll sit down. I’ll flip through it. I’ll look at the company name. I’ll look at the name of the person who signed the agent of record letter, and then I’ll remind myself of the process. Of the buyer’s journey that I took that person through. Of the education that I gave them. The wedges that I drove, and ultimately, how I went about asking for the order.
But there’s one other thing you have to do that I wasn’t doing early in my career. I think that you need to memorialize your wins in a three-ring binder of agent of record letters, or you could even do deck pages of account if you want to calculate insurance premiums as your benchmark. It doesn’t matter. But the other thing that you have to do is ask, why? Why did I win? Why did you decide to hire me? What did I represent to you at the point of sale that led you to trust me more than your current agent? What did I say at the point-of-sale that convinced you and pushed you over the edge? What intrigued you specifically about the value proposition that we represented that led you to believe that we have something that you’re not currently getting? You have to ask these questions because you may have said one thing different in a meeting that you’d never said before, and that’s what led you to get that account.
Memorialize your wins. Go back and reflect on them. Ensure that you’re regularly going back to remind yourself of each of those victories because it will breed further success as you push forward in your career. If you can make time, once a quarter, to sit down and reflect on what you’ve accomplished, you’re going to replicate your success and absolutely kill it in commercial insurance.
Influence is one of the most powerful tools we have in business, leadership, and personal life. Used well, it inspires people, builds trust, and creates ethical results. Used poorly, it can slide into manipulation and self-interest.
Reinvention is one of the most powerful themes in the insurance industry. Some of the best commercial producers in the country did not grow up wanting to sell insurance. They did not study risk management in college. They did not come from an agency family. They found this industry after they tried something else. They found it after life pushed them toward a career where performance, autonomy, and mindset determine the outcome.
The most successful producers in the middle market did not get there because they quoted faster, smiled bigger, or knew how to talk longer. They got there because they learned how to differentiate themselves so clearly that prospects had no choice but to see them as trusted advisors. They learned to operate like businesspeople first and insurance technicians second. They learned how to tie operational mechanics to insurance outcomes. They learned how to control their time, their pipeline, and their future.
In commercial insurance, the most dangerous threats to your book of business aren’t always visible on the loss runs. One of the most overlooked vulnerabilities for middle market producers is ignoring the personal lines needs of their business owner and executive clients.
The commercial insurance industry is one of the few professions where someone can enter with no experience, no connections, and no background in risk management and still build a long, lucrative career. But success is never automatic. It requires hunger, humility, curiosity, and the willingness to keep showing up even when the process feels overwhelming. That is why the story of Pam Seidler has already started making waves among new and aspiring commercial producers.
In an industry where tradition often outweighs innovation, artificial intelligence and automation are slowly but steadily reshaping how independent insurance agencies operate. The push toward smarter, more efficient workflows is no longer a matter of if—but when. While many agencies are still evaluating how AI fits into their operations, early adopters are already reaping the benefits of streamlined submissions, faster processing, and actionable data insights.
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