Philip Guarino speaks with executive coach Jon Passaro about how leaders navigate pressure, self-doubt, and growth. They explore how reflection and coaching help high performers make better decisions and lead more effectively.

From mobile phone insurance and broadband installation to the transformation of leading real-estate marketplace SeLoger within the Aviv Group, the conversation explores how leadership culture, incentives, and technology can be realigned around customers — and how doing so improves business performance. Throughout the discussion, Caroline shows that making customer love an organizing principle starts on Day 1.

In this episode, Denise Silber welcomes Professor Daniel Elfenbein, Harvard alum and entrepreneurship researcher at Olin Business School. Together, they explore the delicate balance entrepreneurs must strike between confidence and overconfidence, commitment and detachment, and the hard truth of knowing when to pivot—or when to quit.