Episode Overview

In this engaging episode, we explore leadership through the lens of trust and vulnerability with John Fly, CTO of FirmPilot. Using LEGO® Serious Play® methodology, John shares powerful stories from his 25+ years in technology leadership, revealing how his approach evolved from technical perfectionism to collaborative partnership.

Through hands-on building exercises, John demonstrates key leadership principles including taking responsibility for failures while sharing credit for success, the importance of direct communication about trust, and why understanding your team members as individuals is crucial for effective collaboration. The conversation touches on everything from DIY projects and parenting moments to AI’s impact on hiring, all while building physical models that bring abstract leadership concepts to life.

This episode is perfect for technical leaders, engineering managers, and anyone interested in building stronger, more trusting teams through authentic leadership practices.

Episode Timeline

[00:00:01] – Introduction to Herding Squirrels podcast and guest John Fly, CTO of FirmPilot[00:00:26] – Discussion of John’s favorite LEGO builds, including Star Wars AT-AT walkers built with his son[00:01:00] – First LEGO build: John creates a model representing his life journey outside of work, focusing on continuous growth and DIY passion[00:02:12] – Deep dive into John’s DIY projects, from irrigation systems to car restoration, influenced by his father’s encouragement to fix things[00:03:23] – Second LEGO build: John’s best team experience, building a bridge model representing leadership vulnerability and team support[00:05:04] – John shares the origins of his leadership philosophy, stemming from negative experiences with unsupportive managers, including a supervisor who called him at the hospital[00:08:49] – Transition to exploring barriers to teamwork rather than worst team scenarios[00:09:22] – Third LEGO build: John creates a “ruler/king” model showing how individual kingdom-building undermines teamwork[00:11:07] – Discussion of partnership vs. zero-sum thinking, using technology/sales collaboration as an example[00:13:33] – Sports team analogy extension about individual excellence within team success[00:14:20] – John’s evolution from “tech purity” mindset to “how do we win together” approach over 20+ years[00:16:39] – Impact of AI on hiring practices, with developers using AI during interviews[00:17:03] – John’s direct approach to building trust in leadership, including examples from joining FirmPilot[00:19:01] – Discussion of trust maintenance and vulnerability in leadership relationships[00:20:13] – Current use of AI in leadership for adapting communication styles to different team members[00:22:41] – Fourth LEGO build: John’s advice for new technical leaders, featuring a flag, resources, and multiple paths model[00:24:02] – John’s reflection on the LEGO building process being more challenging than expected due to constraints[00:24:27] – Wrap-up and contact information for John Fly

Key Themes Explored

* Trust-Based Leadership: Direct communication about trust needs

* Servant Leadership: Taking responsibility for failures, sharing credit for success

* Partnership Mindset: Moving beyond zero-sum thinking

* Adaptive Leadership: Continuous learning and flexibility

* Communication Adaptation: Tailoring style to individual team member needs

Notable Quotes

* “If we fail, it’s on me… if we win, it’s the team that did it”

* “I wanted to be the manager I wished I had”

* “Don’t pick a solution before you really understand the problem”

* “We’re going to win this game together or lose this game together”

Where to Find John Fly

Website:JohnFly.comLinkedIn:linkedin.com/in/johnfly

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit herdingsquirrels.substack.com