Your People Strategy Is Your Business Strategy with Howard Cleveland and Meg Crosby


Ever feel like your org is sprinting toward growth... but nobody packed the map?

Rosie is joined by Howard Cleveland and Meg Crosby, co-founders of PeopleCap Advisors and co-authors of “Running the Gauntlet,” to unpack the real (and often messy) dynamics of leading through change. With decades of experience helping high-growth companies, they reveal the six imperatives every leader needs to scale effectively and stay human in the process.

From the power of context to why process is really just trust in disguise, and how to tell when someone just isn’t a fit for the next leg of the journey, this conversation is packed with sharp insights, personal stories, and practical takeaways you’ll actually want to use.

Whether you're leading a 5-person startup or a 100-year-old org, you’ll leave this episode feeling seen, equipped, and ready to lead with clarity.

Guest Info

About Howard Cleveland, JD, CLC

Howard is the Principal & Co-Founder of PeopleCap Advisors. He is a seasoned strategist who serves as a coach and trusted advisor to leaders navigating complex transitions and high-stakes decisions. Drawing on his unique blend of experience in employment law, executive coaching, and people strategy, Howard helps leaders identify the underlying personal dynamics and strategic opportunities in their challenges, empowering them to lead more effectively. Howard is a sought-after facilitator, helping teams perform more cohesively and productively. Whether coaching individuals or teams, Howard creates safe, collaborative environments where people are empowered to grow and thrive.

 

About Meg Crosby, Principal & Co-Founder

Meg is a recognized thought leader in People Strategy. Meg co-founded PeopleCap Advisors in 2012 to help organizations unleash their full potential through their people. She is a strategic advisor to CEOs, boards and investors, a recognized thought leader in People Strategy, and enjoys asking tough questions. She is also an Operating Partner with SSM Partners, a growth equity investment firm focused on software, services and healthcare. Prior to PeopleCap, Meg’s 20-year career in human resources established her as an expert in organizational culture, people strategy and organizational growth.

 

Key Takeaways:

  • Know your growth stage: Align decisions with your organization's stage of development.
  • Align culture with strategy: Your culture must evolve to support your current goals.
  • Grow leaders to grow the org: Leadership development is essential for scaling.
  • Trust lives in process: Clear systems create consistency and reliability.
  • Right people, right stage: Not everyone will (or should) grow with the organization.

Resources:

Get their book: Running the Gauntlet: Proven Strategies for High-Growth Leaders
Learn more about PeopleCap Advisors

 

Connect with Howard and Meg

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