In the second episode of Lessons in Failure, Will Hold, MBA, CRM, CISR (CEO & President) and Mitch Dunford (CMO) sit down with Denise Perlman, CIC, CEO of Middle Market for North America at Aon, to explore how setbacks, self-doubt, and hard-earned lessons have shaped her leadership journey. Denise traces her path through the insurance industry, from her early days at Markel to leadership roles at Marsh and ultimately Aon, while emphasizing that her success is not defined by titles, but by the moments that didn’t go as planned and what they taught her along the way.

Denise reflects candidly on a pivotal failure where she launched a national initiative with goals that were unrealistic and misaligned with her team. Without fully listening to regional leaders or understanding past context, the effort created friction and missed expectations. That experience forced her to confront the impact of ego and assumptions in leadership, ultimately reshaping her approach to prioritize listening, collaboration, and cultural alignment. She describes the emotional weight of that failure, feeling frustrated and disappointed—but credits it as a defining moment that made her a better, more intentional leader.

Throughout the conversation, Denise challenges the stereotype of the always-on, hyper-confident executive. Instead, she emphasizes the importance of balance, family, and authenticity, sharing openly about her life outside of work and the grounding support of her “Team Pearlman.” She also acknowledges her own struggles, like overextending to help everyone, wrestling with defensiveness, and managing self-doubt, while highlighting how awareness of these tendencies has helped her grow.

Listen to the full episode to hear Denise’s candid stories and discover how failure can become one of the most powerful tools for growth, leadership, and staying true to yourself.