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.
The commercial insurance world isn’t for the faint of heart. It’s unpredictable, chaotic, and constantly demanding producers to manage competing pressures—client needs, renewal deadlines, life events, prospecting goals, and agency responsibilities. And if you’re a middle-market producer, multiply that by ten.
In the middle market commercial insurance space, the role of the producer has never been more critical—or more misunderstood. Too many producers still view their job as selling policies instead of what it truly is: protecting the assets and livelihoods of the businesses they serve.
The middle market rewards depth, not breadth. Yet many producers still approach it like a volume game, quoting everything that moves, chasing price, and hoping activity turns into production. From the outside, it looks like hustle. From the inside of the underwriting and wholesale world, it looks like noise.
Personal lines has quietly become one of the most competitive segments in the insurance industry. Agencies that once dominated their local markets are now fighting to differentiate themselves against direct writers, digital-first carriers, and large brokers with massive content machines.
The cyber insurance market has always been unpredictable. Over the past decade, we’ve seen it move from an emerging line of coverage to one of the most volatile, swinging rapidly between soft and hard market cycles. But today, cyber has entered one of the softest markets in recent memory—and that presents a rare opportunity for both agents and clients.
For most of my 20-year career, captives felt like something reserved for the insurance elite—the jumbo accounts, the Fortune-level operations, the companies with multimillion-dollar manual premiums and entire departments dedicated to risk management. If you had asked me ten or fifteen years ago whether a $250,000 account was a legitimate captive candidate, I would’ve laughed. I thought captives were reserved for companies so complex and so large that the only rational way to insure them was to build an insurance company around their risk.
Please confirm you want to block this member.
You will no longer be able to:
Please note: This action will also remove this member from your connections and send a report to the site admin. Please allow a few minutes for this process to complete.
Responses