Run to the Inevitable: High-Trust Engineering Teams | Josh Carroll

Run to the Inevitable: High-Trust Engineering Teams | Josh Carroll

From 40% Better - Engineering Leadership by Bill

February 6, 2026 · 53 min

About this episode

Josh Carroll discusses leadership, problem-solving, and creating high-trust engineering teams.

When Josh Carroll tells his engineers not to bring him their hard problems, he's actually doing the opposite—he's making sure they feel resourced enough to tackle anything. As an engineering leader with 20+ years of experience who's scaled teams at agencies, startups, and now Skylight, Josh has learned that leadership is problem-solving with people, not code. He shares why his old boss told him to "run to the inevitable"—why waiting to have hard conversations makes everything worse—and how discovering he has ADHD transformed his listening skills after painful 360 feedback revealed he was making conversations about himself when trying to show empathy. Josh reveals Skylight's "say the thing" principle for psychological safety, why they measure velocity by setting aggressive roadmaps they can't hit and aiming for 80-90%, and why hiring engineers just to write code leaves half their value on the table. From understanding stakeholder success metrics to avoiding pet agendas, Josh shares battle-tested frameworks for creating environments where brilliant engineers with low egos ship customer-delighting products at high velocity. Key Topics: Why "run to the inevitable" means having hard…

People in this episode

Host: Bill

Guest: Josh Carroll

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Mentioned in this episode

Organizations: Skylight

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