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June 6, 2025 36 mins

Meg Crosby and Howard Cleveland co-founded PeopleCap Advisors in 2012 to empower leaders and elevate organizations.

Prior to PeopleCap, Crosby worked as an HR leader for companies of all sizes, including a small tech start-up as a sole HR practitioner, and at Google, where she led acquisition integration. Her corporate work, consulting practice, and board experience have established her as an expert in organizational culture, people strategy, and high growth.

Cleveland began his career as a labor and employment attorney, guiding leaders through complex employee issues and fostering cultures of trust. Now a sought-after coach and advisor for leaders spanning five continents, Cleveland is known for his strategic insights, leadership expertise, and intuitive understanding of human dynamics.


In this episode, Jason, Meg, and Howard discuss:

  • Discover the story behind PeopleCap Advisors and their new book, Running the Gauntlet
  • Key leadership challenges during high-growth phases and how to overcome them
  • Explore six key imperatives for successful high-growth leadership
  • How to develop a "self-replicating talent machine" within an organization
  • The importance of culture in leadership and how to define, demonstrate, and defend it


Key Takeaways: 

  • Building a strong foundation for long-term success often stems from leveraging complementary skill sets. Their dynamic partnership highlights how diverse perspectives can enrich leadership strategies and drive growth.
  • As high-growth companies expand, leaders must transition from being generalists to specialists. This evolution requires continuous learning and the ability to adapt one's skills to meet the demands of a more complex organizational structure.
  • Sustainable growth hinges on creating robust systems for hiring, training, and talent development. Implementing consistent practices ensures that successful leadership traits are reproduced throughout the organization, fostering long-term resilience.
  • Letting go of long-time employees who no longer fit the evolving structure is not just necessary but beneficial. This intentional liberation can open new opportunities for both the individual and the organization, fostering alignment and renewed momentum.
  • Effective leaders know that culture is not just established but maintained through intentional actions. Defining, demonstrating, and defending cultural values is essential to preserving accountability and ensuring sustainable progress, even during rapid growth.


“That's one of the great things about having a strong culture. It will attract the right people and repel others. It doesn't mean that the people it repels are bad; it just means they're not a fit for the culture.” - Meg Thomas Crosby


Connect with Meg Crosby & Howard Cleveland:

Website: https://www.peoplecap.com/ 

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