In the middle market, producers don’t lose because the competition has better pricing.
They lose because the competition understands people better—their motivations, their fears, their priorities, and what makes them say yes.
On a recent episode of the Power Producers Podcast, I interviewed Don Weber, a man with one of the most fascinating professional paths I’ve ever encountered—commercial insurance producer → diamond trader → undercover intelligence asset → corporate executive coach.
And here’s the lesson: across all four worlds, the skill that determined success was the same.
This blog post breaks down the biggest lessons Don shared—lessons that can transform any producer into a true risk advisor capable of winning at the highest level of the middle market.
Dialing for Dollars: The Foundation of Persistence
Like many of us, Don began in commercial insurance with a phone book and no guidance. He learned quickly that the job wasn’t about quoting policies—it was about resilience. Producers who survive the early days develop the muscle memory of persistence that carries them far beyond the competition.
That foundation would serve him well later in life, although he had no idea just how much he would need it.
The Diamond Trade: High Trust, High Stakes
When Don entered the diamond industry, he discovered a world where:
In the diamond world, you don’t need what you’re buying. You buy because you trust the person selling it. Insurance isn’t much different. Business owners must buy it—but that doesn’t mean they must buy it from you.
Credibility sold diamonds.
Credibility sells insurance.
Intelligence Work: Seeing What Others Miss
This is where Don’s story takes a turn you’d expect from a movie script.
The diamond trade became his cover.
Multiple languages became his tools.
Hyper-observation became his lifeline.
He learned to read people in seconds: their motives, their fears, their inconsistencies. In environments where one wrong assumption could cost you your life, you develop instincts most salespeople never even consider.
And here’s the bridge:
The same observational skills that keep someone alive in hostile territory are the ones that help a producer win over a CEO, CFO, or COO in a competitive sales environment.
In intelligence work:
Sound familiar?
A CEO Is Not a CFO Is Not a COO
Most producers treat all executives the same.
That’s a losing strategy.
CEOs think in vision, growth, and direction.
CFOs think in cost, discipline, and financial impact.
COOs think in process, operations, and risk reduction.
If you deliver the same pitch to all three, you’re guaranteeing failure.
Top producers modify:
based on the role and personality of the executive.
Deep Research Is a Superpower
Don explained his approach: learn the person before you learn the business.
I take this to an extreme (and encourage my producers to do the same). For example:
When you’re able to enter a meeting and demonstrate—subtly—that you’ve taken the time to understand the executive, the company, and the culture, you separate yourself immediately.
Congruence Is Everything
In intelligence work, the best liars are the ones who believe their own lies. Their body language, tone, and face match the words coming out of their mouth.
In sales, congruence is just as powerful.
If you walk into a meeting:
the executive senses it instantly.
Elite producers practice congruence:
High-Stakes Presentation Skills
Don has coached executives from Fortune 500 companies on presentations that determine billion-dollar outcomes.
The lesson for producers?
You are always presenting.
Whether it’s:
You are being evaluated on clarity, tone, confidence, structure, and persuasion.
The best technicians lose to mediocre technicians who communicate brilliantly.
Poor Communication Kills Deals
Producers who open with:
are signaling to executives that they are transactional, not strategic.
This is why middle-market buyers treat most agents like commodities.
Want to differentiate?
Talk about:
Speak the language of leadership, not insurance.
Fraud Really Is Everywhere
From Don’s stories in intelligence work to our shared experiences in the insurance world, one truth remains:
Everyone has a price.
In our world:
Producers who don’t confront these realities lose millions in controllable premium dollars.
Insurance Is Not an Investment
Consumers think:
“I’ve paid for 20 years and never had a claim—time to get something back.”
No.
Insurance exists to protect you from the worst day of your life—not to fund your lifestyle.
A producer’s job is to reframe the conversation from entitlement to protection.
Pre-Injury Management Determines Financial Outcomes
The TV in a waiting room can cost a company $100,000.
Seriously.
If your injured worker sits in a clinic blasting plaintiff attorney commercials all day, you’ve lost the claim before it even starts.
A proactive workers comp program includes:
Risk management prevents claims.
Insurance just pays for them.
The best producers understand that distinction.
Stop Being Seen as an Insurance Agent
This is why I named my company Florida Risk Partners—not Florida Insurance Partners.
When you position yourself as a risk advisor first and an insurance agent second, everything changes:
Insurance agents quote.
Risk advisors diagnose.
One gets shopped.
The other gets trusted.
Communication Determines Your Ceiling
Don said it clearly:
“You can have the best hard skills in the world, but if you can’t communicate, your upside is limited.”
Middle-market sales is not about:
It’s about whether the executive believes:
You Are Competing for Trust, Not Premium
Executives choose the producer who:
Those are the traits that win—not spreadsheets.
Walk in knowing more about the buyer than they expect.
Selling insurance without understanding psychology is malpractice.
Quotes are a reaction.
Risk assessments are a strategy.
One size does not fit all. Ever.
If you can’t communicate the value, you don’t have any.
Fraud exists. Fear exists. Pressure exists. Prepare for them.
Executives buy clarity and protection—not policies.
From diamond trading to intelligence work to executive coaching to commercial insurance, the throughline is unmistakable:
The winners are the people who observe what others overlook.
Middle-market producers lose deals not because they’re outgunned, but because they’re out-prepared.
When you learn to profile buyers, understand motivation, communicate with precision, adapt your message, and lead with risk—not quotes—everything in your sales career changes.
Preparation creates confidence.
Confidence creates clarity.
Clarity builds trust.
Trust wins business.
Every. Single. Time.
In the middle market, producers don’t lose because the competition has better pricing.
They lose because the competition understands people better—their motivations, their fears, their priorities, and what makes them say yes.
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.
The insurance industry is entering one of the most transformative seasons in its history. For decades, our world has been shaped by carriers, underwriting cycles, prospecting methods, and the grit of producers willing to outwork their competition. But today, a new force is reshaping the landscape—and most producers, agency leaders, and industry professionals aren’t ready for it.
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.
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