Podcast Appearances

Thought-provoking conversations with leaders, experts, and change-makers.

Imagining Bridges to Better Leadership

Meg Crosby and Howard Cleveland: People Are Capital: Transforming Leadership Through Strategic Talent Development

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

  • Developing and retaining talent
  • Relational vs. transactional leadership
  • The importance of people strategy in organizational success
  • Preparing high performers for leadership roles
  • Building trust and authentic connections within teams

Key Takeaways

  • A thriving partnership isn’t about sameness — it’s about balance. When Meg and Howard combine their unique backgrounds in law, HR, and organizational development, they create a powerful approach to leadership that transcends individual expertise.
  • Talent is the most critical capital in the knowledge economy. Leaders who invest in developing, valuing, and sometimes liberating their employees create organizations that are more innovative, resilient, and successful.
  • Relational leadership transforms transactional management. By focusing on trust, understanding, and individual potential, leaders can create environments where people feel genuinely valued and motivated to excel.
  • Purpose drives performance more powerfully than control. When leaders shift from monitoring tasks to developing people, they unlock creativity, commitment, and sustainable organizational growth.
  • Leadership is a skill that can be learned, not an innate trait. By providing clear frameworks, ongoing development, and time to lead, organizations can transform high performers into exceptional leaders who build thriving teams.

“Everyone deserves to find a place where they are valued, where they feel valued, and where they can add value.”

Meg Crosby

“Delegation is often viewed as a transaction, but to be effective, it’s a relationship, and it takes time to develop and it takes time to explain.”

Howard Cleveland

The Nice Guys on Business

Meg Thomas Crosby and Howard Cleveland: Growth, Grit, And The Magic Of Getting People Aligned With Purpose

Meg Thomas Crosby 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. She has worked for companies of all shapes and sizes, including for a small tech startup in Los Angeles as a sole HR practitioner and at Google, leading acquisition integration.

Howard Cleveland is a coach and trusted advisor to CEOs, executive teams, and senior leaders. In his roles as a Labor & Employment attorney, growth advisor, and certified leadership coach, Howard has partnered with leaders for over 25 years to help them understand and unlock the strengths of themselves, their teams, and their organizations.

Howard serves leaders whose circumstances have temporarily outpaced them. Many of his clients are:

  • In the midst of significant personal or professional transitions
  • Struggling to meet the current expectations of their position
  • Struggling to gain traction
  • In complex, fast-changing situations
  • Having difficulty getting their team to perform
  • Struggling to stay at the right level and delegate
  • Not comfortable holding their team accountable

Howard serves as an experienced thought partner and confidential sounding board to help leaders gain clarity, confidence, and a clear path forward that is aligned with their personal and professional goals.

The Leadership Code

Why your people strategy is just as important as your financial strategy: with Meg Crosby & Howard Cleveland

Today’s episode is all about a topic that separates the companies who thrive from the ones who stumble: Why your people strategy is just as important as your financial strategy.

I’m thrilled to welcome two powerhouse guests who know this terrain inside and out: Howard Cleveland and Meg Crosby, co-founders of PeopleCap Advisors.

Howard is a recognized executive coach, people strategist, and growth advisor. With over 25 years of leadership, consulting, and coaching experience, he’s been a trusted partner to leaders navigating challenges at every stage of growth — helping them gain clarity, confidence, and alignment between people and business goals.

Meg is a master of scaling high-growth companies. With deep experience working alongside private equity firms and portfolio CEOs, she helps build high-performing, sustainable organizations ready to tackle the pressures of rapid expansion. Before co-founding PeopleCap, Meg led Google’s HR M&A team, overseeing people-related due diligence and integration on more than 35 global acquisitions. She’s also the co-author of the forthcoming book, Running the Gauntlet: Proven Strategies for High Growth Leaders, coming out April 2025.

In this conversation, we’ll explore how aligning people and financial strategy isn’t a “nice to have” — it’s a make-or-break leadership responsibility. You’ll hear insights on scaling, culture, leadership bottlenecks, and how to future-proof your organization for long-term success.

Let’s dive in.

The Transition Bridge Podcast

“Running the Gauntlet” – Proven Strategies for High-Growth Leaders with Howard Cleveland and Meg Crosby

“The single biggest way to impact an organization is to focus on Leadership Development,” John Maxwell

Whether you are in the midst of significant personal or professional transitions or want to take your company to another level, this episode is for you!

Transitions in the marketplace can be challenging, whether you are being promoted into a leadership role or you want to understand how to scale your company, team, culture, and capacity.

Howard Cleveland and Meg Crosby are strategic leaders in this industry.

Howard is a trusted advisor and professional coach for CEO’s, founders, executives, and leadership teams of purpose-driven businesses.

Meg is also a strategic advisor to CEO’s, boards, and investors, and is a recognized thought leader in People Strategy.

Their book, “Running the Gauntlet,” can be found on Amazon and is a significant tool for leadership growth.