Memorialize Your Wins to Reflect on Your Success

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.

Know Why You Won

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.

Reflect on Your Success

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.

Memorialize Your Wins

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.

Producers

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The commercial insurance industry is in the middle of a quiet evolution.

While most conversations still revolve around premiums, deductibles, limits, and carrier appetite, a different category of risk transfer has been gaining traction beneath the surface—parametric insurance. It is not new, but it is finally becoming accessible, relevant, and actionable for middle market producers who are willing to think differently about risk.

In a recent episode of the Power Producers Podcast, I sat down with Brian Thompson from Descartes Underwriting to unpack what parametric insurance actually is, what it is not, and why producers who ignore it may be leaving their clients—and themselves—exposed.

This article breaks that conversation down into practical, producer-friendly language and shows how parametric insurance fits into modern middle market risk management.

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Cyber

Why Standalone Cyber Insurance Beats BOP Extensions Every Time: Protecting Clients from Modern Threats

The insurance industry is full of shortcuts. Some producers look for ways to streamline the quoting process, others avoid hard conversations with clients, and many rely on endorsements or extensions because they are “easier” than diving into the details. Nowhere is this more dangerous than in the world of cyber insurance.
Too many agents assume that a cyber endorsement on a BOP or commercial package policy is “good enough.” It isn’t. In fact, treating a BOP cyber extension as a replacement for a standalone cyber policy leaves clients dangerously exposed, puts producers at risk of losing accounts, and opens the door to costly errors and omissions (E&O) claims.
Cyber threats evolve faster than any other area of risk, and endorsements simply can’t keep up. If producers want to protect their clients and themselves, it’s time to understand why standalone cyber insurance is non-negotiable.

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Cyber Insurance Risk Management: Why MFA, MDR, and BYOD Policies Can’t Wait for a Hard Market

The cyber insurance market has softened in recent years. Requirements that were once rigid — like mandatory multi-factor authentication (MFA) or endpoint detection and response (EDR) tools — have been relaxed by many carriers. But here’s the danger: just because carriers aren’t demanding these safeguards today doesn’t mean businesses can afford to ignore them.

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