Podcast Episode

Hard Conversations That Make Your Team Better

The Heart of Entrepreneurship·Dave Kashen and Jesse Pujji·14 October 2026·38 min

About this episode

Telling someone a hard truth only helps if they can actually hear it. In this second half of a two-part conversation on feedback, Dave Kashen and Jesse Pujji move from caring personally to challenging directly, and dig into how to say hard things in a way that lands. Dave opens with a framework he calls speaking inarguably, drawn from the Conscious Leadership Group, Nonviolent Communication, and Stanford's "Touchy Feely" class. The biggest trap in giving feedback is stating your stories about someone as if they were facts, and Dave shares a split-brain study showing how confidently the mind invents explanations that turn out to be wrong. He breaks down the four things nobody can argue with (facts, thoughts, feelings, and wants), and Jesse shares how swapping the word "should" for "want" changed the conversations he had at home and at work. From there, they get practical about making feedback a normal part of how a team works. Dave walks through the Conscious Leadership Group's sentence stems, a simple four-part feedback script, and feedforward framing. Jesse shares the zero-to-10 rating habit his team uses after sales calls and the hot seat exercise that opened up feedback in every direction across his leadership team. The conversation closes on the conversations leaders avoid most: letting people know where they stand. Drawing on the quarterly ratings system from The Great CEO Within, Dave explains how to tell someone they're below the bar without blame, why he believes a leader's responsibility is to believe in the greatness of their people, and why learning to feel the fear and speak up anyway is one of the most important ways a leader grows.