Why Holding Back Is Hurting Your Team

Every leader eventually has to tell someone a hard truth, and how it lands depends on the relationship built around it. In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji explore why candor and care work best together, and what happens to a team when fear pulls them apart. Jesse opens with his own journey with feedback: growing up in a direct household, giving feedback constantly at McKinsey, and becoming a CEO whose directness left people intimidated, until holding his tongue didn't work either. Dave grew up with very little conflict and had to grow the other way, learning to bring what he calls "fierce love." Using Kim Scott's Radical Candor framework, they unpack obnoxious aggression and ruinous empathy and trace both back to a leader reacting from threat or protecting themselves. From there, Dave explains the emotional bank account and the withhold, withdraw, project cycle from conscious leadership, showing how unspoken feedback quietly erodes connection over time. The conversation then turns practical, covering growth conversations, asking permission before giving feedback, Marshall Goldsmith's feedforward, and the "If You Really Knew Me" exercise that shifted the energy on Jesse's new team.