How Curious Leadership and Operational Audits Drive Middle Market Business Growth

The difference between thriving and merely surviving often boils down to one core attribute: curiosity. But curiosity alone isn’t enough. When paired with operational audits, strong leadership, and a growth mindset, it becomes a powerful tool for transformation—especially in the middle market. In this post, we explore how curious leadership and deep operational insights can revolutionize how insurance producers approach sales, consult with clients, and build long-term partnerships rooted in value.

This blog features insights from Jon Bassford, Founder & CEO of Lateral Solutions and author of The Curious Leader.

Why Traditional Insurance Sales Falls Short

The commercial insurance industry is fundamentally flawed in one significant way: the worse a company performs, the more premium they pay—and ironically, the more commission their agent earns. This misalignment creates a sales-first culture that prioritizes transactions over transformation. Many agents still operate as product pushers rather than strategic consultants.

But that model doesn’t hold up in the middle market, where businesses face complex, multifaceted risks. Producers who listen to the Power Producers Podcast understand this well. These are professionals committed to reducing the total cost of risk (TCOR) by uncovering operational inefficiencies, offering solutions, and telling a better underwriting story.

As David Carothers noted in the episode, “We’re not advocates of selling people the most amount of insurance they’re willing to pay for. We want clients to take a healthy amount of risk—but make it educated and quantifiable.” That’s where operational audits come in.

The Role of Operational Audits in Business Strategy

What if the key to driving down insurance costs had nothing to do with the insurance policy itself? According to Jon Bassford, founder of Think Lateral Solutions and author of The Curious Leader, most operational breakdowns are unrelated to the product or service a company offers. Instead, they stem from poor internal processes.

Jon shared a striking example from the automotive industry: Fisker Automotive, a company that famously went bankrupt, was shipping $80,000 vehicles without accepting payment first. That wasn’t a sales failure—it was an operations failure.

Through organizational assessments, Jon and his team examine decision-making processes, capacity for change, and operational maturity. The result is a 12-month growth plan that identifies what’s working, what’s not, and what needs to be fixed—before it’s too late.

For insurance producers, this type of audit offers a new front door into a prospect’s world. Rather than quoting a renewal, producers can start the conversation by addressing gaps in operations that may be costing the client far more than just insurance premiums. It’s a differentiator, a wedge, and a relationship builder.

Curiosity as a Strategic Advantage in Leadership

At the heart of Jon’s philosophy is a single belief: curiosity is a superpower. It’s the ability to challenge the status quo and ask why something is done a certain way—even if it’s “always been done that way.”

In his book The Curious Leader, Jon outlines how adopting a curious mindset can shift leaders from being reactive to proactive. He emphasizes the importance of asking hard questions and being willing to sit with uncomfortable answers.

“Curiosity is the willingness to ask the hard questions and challenge the status quo,” he said. This attitude allows leaders to rethink entrenched processes and uncover hidden inefficiencies that stifle growth.

For producers in the insurance industry, curiosity isn’t just a personality trait—it’s a sales strategy. By approaching each prospect with a genuine desire to understand their business, producers can better identify risk exposures, operational weaknesses, and ultimately offer more relevant solutions.

Creating a Curious Culture Through Psychological Safety

While curiosity starts at the top, creating a curious culture requires more than one person. It demands an environment of psychological safety, where team members feel safe to speak up, challenge ideas, and make suggestions without fear of retaliation.

Google famously ran a study to discover what made its teams successful. The number one factor? Psychological safety. When employees are encouraged to question processes and offer solutions, innovation thrives. When they’re afraid of speaking up, mediocrity takes root.

David Carothers shared how he uses “Stop, Start, Continue” exercises to gain anonymous feedback from team members and clients. This tool helps organizations uncover operational pain points that leadership may not see. And because the feedback is anonymous, it’s honest. He’s even used it to reduce claims by identifying over-scheduling and cutting corners in HVAC installations—insights that wouldn’t have come from a standard client intake form.

When producers create a similar environment with their clients—by asking meaningful questions and creating space for honest answers—they become more than insurance salespeople. They become trusted advisors.

The Hidden Cost of Micromanagement in Leadership

One of the most common pitfalls Jon sees in his consulting practice is the belief among business owners that they need to touch everything. Whether it’s fear of letting go or a lack of trust in their team, this mindset creates bottlenecks and leads to burnout.

“You are literally building a C-team,” Jon explains. “There are things you’re an A-player at and things you’re an F-player at. If you try to do everything, you’re going to average out at a C.”

This tendency is especially common in founder-led businesses and startups, where the owner has worn every hat at some point. But as businesses grow, the refusal to delegate creates inefficiencies, kills morale, and ultimately prevents scale.

For commercial insurance producers, this insight is gold. If you walk into a business and hear a leader say, “Everything goes through me,” you’ve found an opportunity. That company is likely struggling with decision fatigue, slow processes, and avoidable losses. A strategic producer can offer both risk management solutions and operational consulting resources to move the business forward.

Common Operational Pitfalls Holding Back Business Growth

Jon outlined several consistent issues he sees across industries and organizational types:

Leadership burnout – CEOs working 80-hour weeks because they’re involved in every decision.
Lack of clarity – Teams that don’t know what’s working and what’s broken.
Growth without infrastructure – Businesses that want to scale but are operating with processes suited for a smaller size.
Outsourcing the wrong tasks – Leaders who delegate what they’re already good at instead of what they lack expertise in.

For producers, listening for these issues during prospect meetings provides an entry point for a risk conversation that goes beyond insurance. If a business owner says they’re buried in admin work, struggling to scale, or unsure why profitability is flatlining—there’s a wedge to be driven.

From Assessment to Action: Structuring Engagements That Scale

Jon’s engagements typically start with a full operational assessment. He then delivers a 12-month growth plan that can either be executed internally or with his consulting support. The goal? Identify gaps, fix bottlenecks, and implement processes that scale.

Insurance producers can mirror this approach. By performing a baseline risk assessment or compliance audit, you can demonstrate a deeper understanding of a client’s business before ever discussing coverage. And when you educate them on risk—not just insurance—you earn the right to discuss premium.

As David puts it, “Sell the problem you solve—not the policy.”

Key Takeaways for Producers in the Middle Market

For commercial insurance professionals working with mid-sized businesses, the lessons from this conversation are clear:

Lead with curiosity, not coverage.
Approach each opportunity as a consultant, not a closer.
Use operational audits as a way to uncover risk.
Create a culture of psychological safety within your own agency—and advocate for it with clients.
Never stop asking questions. The right one might unlock the deal.

Resources to Cultivate Curious Leadership

Jon Bassford offers several free resources to help leaders and consultants explore their curiosity and assess their organizations:

Download the first chapter of The Curious Leader by texting CHAPTER to 33777.
Take the Organizational Identity Assessment by texting IDENTITY to 33777.
Evaluate your adaptability to change by texting ADAPT to 33777.

Curiosity may not be listed as a line item on a quote form, but in today’s competitive landscape, it’s one of the most valuable tools a producer can have. The most successful producers aren’t just good talkers—they’re relentless problem solvers who lead with questions, deliver insight, and make their clients better along the way. That’s what drives growth. That’s what wins middle market business.

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