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Ryan Westwood has six executives who've worked with him for 10+ years. Most CEOs burn through leadership teams every 18 months. In this episode, he reveals why he only hires one executive per year, how he uses physical activities to bypass polished interview performances, and the single question that reveals everything about a CEO's leadership quality. In this conversation, Ryan shares his frameworks for building stable executive teams, vetting M&A targets, and accelerating executive onboarding. He breaks down how board composition reveals company dynamics, why he maintains a decades-long spreadsheet of talent observed in authentic contexts, and his approach to creating aligned economics that keep executives engaged long-term. CHAPTERS 00:00 Introduction 01:08 Ryan's Background and Fullcast 02:02 The M&A Playbook: Vetting CEOs Before Acquisition 04:44 Mental Barriers and Company Growth 06:46 Decisive Integration Strategy for M&A Success 07:53 Managing Multiple Executives from Acquisitions 11:08 The Advantage of Long-Term Executive Teams 12:41 One Executive Per Year: The Compounding Effect 14:54 The Repeat Executive Question for Vetting CEOs 16:33 Equity Alignment and Executive Motivation 19:27 How to Find Executive Talent: The Observation System 25:43 Diligencing Companies Through Board Composition 29:31 Psychological Safety and Team Dynamics 31:31 Interview Tactics: The Question That Reveals Everything 33:36 Background References and Timing 34:25 Physical Activity Interviews: Walking and Fly Fishing 36:47 Executive Onboarding: The CEO Operating Rhythm Document 39:18 Closing Thoughts ABOUT ANDY Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating. CONNECT WITH ANDY / amowat ABOUT HOW I HIRE How I Hire is a podcast in partnership with Whispered and Front Lines where Andy Mowat talks with senior GTM leaders about how they find, vet, attract, and grow exceptional talent. Subscribe for more insights from GTM leaders on building high-performing teams!