We’ve never had more tools, data, or technology at our fingertips—yet many leaders feel more stretched than ever.

In this milestone one-year anniversary episode of PoolSide, we unpack a question facing public entity risk pools everywhere: Are we actually becoming more productive—or just busier?

In Episode #10, host Michelle Bechamps is joined by Ann Gergen, Executive Director of AGRiP, to explore the real forces reshaping productivity in pooling today, including:

• How AI and pooled intelligence are changing expertise, judgment, and decision-making
• The impact of shifting demographics and career longevity on innovation and advancement
• Why knowledge loss from board and staff turnover quietly erodes productivity
• How cognitive and organizational bias slows progress—even in data-rich environments

This isn’t a conversation about chasing efficiency or adopting the next shiny tool. It’s about designing productivity—intentionally, strategically, and human-centered.

The leaders who thrive won’t be the fastest movers. They’ll be the ones asking better questions, building smarter systems, and creating space for thinking—not just doing.

As 2026 approaches, leadership looks different from just a few years ago. Gen Z is now stepping into management, Millennials are running teams, and Gen X and Boomers are guiding organizations through transitions shaped by hybrid work, fast-moving tech, and bigger questions about meaning and motivation.

In this episode of PoolSide, we’re joined by Kim Lear, founder of Inlay Insights, to talk about what actually works when leading across generations—plus practical ways to communicate better, build trust faster, and get the best from multi-generational teams (without the stereotypes).

In this episode, Michelle sits down with Jack Ryan, Attorney & Co-Director at the Legal and Liability Risk Management Institute (LLRMI) — one of the nation’s leading voices in law enforcement risk management and liability — to talk about how agencies can lead with accountability and stay ahead of emerging legal trends.

We discuss:

• The most common litigation trends facing law enforcement agencies today

• How agencies can rebuild public trust and social capital after years of scrutiny

• What it really means to “take care of your own house” — and how to stay proactive before problems become lawsuits

• Practical steps for chiefs, sheriffs, and risk managers to strengthen policy, training, and documentation

In this episode, Michelle sits down with Jack Ryan, Attorney & Co-Director at the Legal and Liability Risk Management Institute (LLRMI) — one of the nation’s leading voices in law enforcement risk management and liability — to talk about how agencies can lead with accountability and stay ahead of emerging legal trends.

We discuss:

• The most common litigation trends facing law enforcement agencies today

• How departments can rebuild public trust and social capital after years of scrutiny

• What it really means to “take care of your own house” — and how to stay proactive before problems become lawsuits

• Practical steps for chiefs, sheriffs, and risk managers to strengthen policy, training, and documentation

As cyber threats grow more complex, public entities face mounting pressure to safeguard systems, data, and community trust. In this episode of PoolSide, we explore how risk pools are adapting—not just by offering cyber coverage, but by actively partnering with members to strengthen defenses. From evolving claims trends and coverage strategies to the frontlines of cyber hygiene, we discuss how shared responsibility, education, and proactive support are shaping the future of public sector cyber resilience.

With the passing of July 1 renewals, the insurance landscape continues to shift. In this PoolSide episode, we explore the mid-year state of the market—from CAT-exposed property to increasingly complex cyber threats, and from liability pressures to shifting underwriting behavior, we ask: how are risk leaders navigating renewals in 2025?

Tune in for an insightful conversation with our guests Doug Wozniak, SVP, Public Entity Group and Justin Swarbrick, SVP, Public Entity Group at Alliant.  We discuss pricing trends, underwriting behavior, and what to expect as we head toward January 1, 2026. Whether you’re brokering deals, managing risk, or guiding strategy, this episode delivers a clear-eyed look at what’s shaping insurance today.

How do you make critical decisions when failure isn’t an option—and time is running out? In this episode of PoolSide, we sit down with Jim Wetherbee, the only American astronaut to have commanded five missions in space, and is the only person to have landed the Space Shuttle five times. He is also the author of Controlling Risk—In a Dangerous World. Drawing on decades of experience in high-risk environments—from the cockpit of a Navy jet to the edge of Earth’s atmosphere—Jim shares his powerful framework for Operational Excellence and explains some of the Ten Adverse Characteristics that are commonly in place in organizations just prior to experiencing a major disaster or several minor accidents.

Whether you lead a loss control team, are executive director of a pool, or are looking for ways to train your members in accident prevention, this conversation will reshape how can help any organization operate safer, smarter, and more effectively.

Michelle and Chris McKenna, Founder/CEO and Actuary of Three Lions LLC, explore the ‘Moneyball Moment’ risk pools can have with the holistic integration of capital modeling studies into their business.

Learn how capital modeling is now designed to go beyond just solvency testing to reshaping risk management and informing more robust strategic decisions for pools.

Join host Michelle Bechamps as she interviews Ken Giffin, a strategic advisor to Bechamps & Associates in pool strategic planning and brand strategy. Together, they delve into the art of storytelling in communications and brand messaging, discussing how to make public entity pooling more engaging and effective for next generation leadership. They share practical branding examples and the importance of crafting relatable, memorable stories. Tune in for expert advice on creating a new and powerful pooling narrative that resonates with both longtime members and newer audiences.

Financial pressures are mounting—social inflation, nuclear verdicts, and rising business costs are putting some pools in a tough spot. Many haven't seen net position declines like this in years. So, how do you secure long-term financial stability?

In this episode, Dan Smereck with Strategic Asset Alliance and I dive into the biggest influences on net position and what tools pools are using in their creative strategies—navigating regulatory investment constraints, captive formation, and liquidity management to name few—to strengthen their financial position for the future.