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September 16, 2025 55 mins

Episode Overview

In this episode, John sits down with Kristyn Drennen, founder of Transform CXO, to dive deep into leadership, scaling, and the power of fractional executives. They explore how business owners can break through growth ceilings, leverage the Entrepreneurial Operating System (EOS), and free themselves from solopreneur chaos.

From the difference between visionaries and integrators, to how fractional COOs help real estate teams scale without overextending, this is a masterclass in leadership clarity, accountability, and sustainable growth. Kristyn shares her unique perspective from working across multiple industries, showing why the right frameworks and talent can transform both businesses and lives.


What You'll Learn in This Episode

The Power of Operating Systems

  • Why Scaling Up often overwhelms smaller businesses

  • How EOS provides clarity and simplicity for real estate teams

  • Why consistency, not complexity, drives growth

Fractional Executives Explained

  • What fractional COOs and integrators actually do

  • Why "fractional horsepower" beats hiring too early

  • How to know if fractional talent is the right next step

Visionary vs. Integrator Roles

  • The difference between creating ideas, executing, and managing

  • Why many team leaders get stuck wearing too many hats

  • How to free yourself into the visionary role without losing momentum

Leadership & Team Development

  • Why most growth challenges come down to people or process

  • How to use Working Genius to identify strengths and frustrations

  • Why leadership development gets pushed aside—and why it shouldn't

Scaling with Intention

  • Why loyalty can cap your team's growth

  • The importance of building an accountability chart

  • How to hire people who've already been where you want to go


Resources & Mentions

  • Traction by Gino Wickman – The foundation of EOS

  • Scaling Up by Verne Harnish – Framework for larger businesses

  • The Motive & The Advantage by Patrick Lencioni – Must-reads for leaders

  • The Six Types of Working Genius by Patrick Lencioni – Productivity assessment for leaders and teams

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