Taking Calculated Risks (Feat: Neil Larson)

In this episode of Broken Benefits, host Lee Lewis sits down with Neil Larson, Benefits Leader at a Global 500 employer and MIT MBA, for a candid conversation about risk, responsibility, and what it truly takes to change a healthcare benefits system that isn’t working.

Drawing from his experience managing a massive, diverse health plan, Neil shares what benefits leadership looks like in the trenches — where decisions carry financial, operational, and human consequences. The discussion explores why incremental change often isn’t enough, how misaligned incentives quietly drive costs higher, and why taking calculated risks is sometimes the only path to sustainability.

Together, Lee and Neil unpack what employers often misunderstand about risk tolerance, consulting relationships, and implementation realities — and why meaningful progress requires leaders who are willing to step off the paved road, ask harder questions, and demand better alignment from their partners.

This episode is a must-listen for benefits leaders, HR professionals, and executives navigating rising healthcare costs while trying to protect both their people and their organizations.

Chapters:
0:00 - Introduction
3:38 - Big risks that paid off in Neil's career
12:54 - Getting your risky strategy approved
27:20 - "What's the job to be done?"
36:15 - Identifying crisp and clear KPI's
48:13 - What vendors and consultants don't understand
51:05 - Closing remarks