Run to the Inevitable: High-Trust Engineering Teams | Josh Carroll
Author: Bill
February 6, 2026
Duration: 52:53
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 conversations immediately, not later
How 360 feedback and discovering ADHD transformed Josh's leadership approach
Skylight's "say the thing" principle for creating psychological safety
Why hiring engineers just to write code wastes half their problem-solving value
The three-sprint maximum rule: forcing teams to ship iteratively and learn fast
Measuring velocity without silly metrics: aggressive roadmaps at 80-90% completion
How past company dysfunction creates self-fulfilling prophecies at new companies
Why Josh rarely shares his solutions anymore, even when he's seen the problem before
Building high-trust, low-ego teams: avoiding pet agendas and command-and-control baggage
Connect with Josh Carroll:
LinkedIn: https://www.linkedin.com/in/josh-carroll-83637912/
Company: Skylight (MySkylight.com/careers - hiring 20+ engineering roles!)
Skylight is actively hiring Ruby on Rails, TypeScript/React/React Native, and Android Kotlin engineers. Check out their careers page if you're looking for a high-trust, low-ego engineering culture that values autonomy, rigor, and care.
Subscribe for more conversations with engineering leaders who understand that leadership is a series of humbling lessons, and growth means constantly discovering new mistakes to work on.
I hope you enjoy this episode! Give it a like, share, and subscribe to not miss the content coming your way weekly. – Bill and the 40 % Better podcast team
Connect with Bill on LinkedIn: https://www.linkedin.com/in/wblennan/
Visit the 40 Percent Better website here: https://40pb.com/
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#40PercentBetter #BillLennan #Leadership #TeamPerformance #EmployeeEngagement #PsychologicalSafety #BusinessGrowth #Kaizen #EngineeringLeadership #Coaching The 40% Better podcast with Bill Lennan unlocks previously unheard-of performance levels in teams and leaders. Bill Lennan, founder of 40 Percent Better, interviews experts on employee engagement, psychological safety, engineering leadership, and actionable mental models. Learn how to foster high-performing teams, improve team productivity, and achieve sustainable success in business through a focus on human-centered systems.
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