Episode 311: Build a High-Trust Team - Even If Growth Is Testing Your Culture w/ Meghan Popoleo

About the guest: Meghan Popoleo is the President of The O’Connor Group, where she has spent the last decade helping organizations grow through strong people strategy, culture, and leadership. She came into the business from the nonprofit world, openly admits she did not start out loving HR, and has grown into a values-driven leader known for vulnerability, execution, collaboration, and people-first leadership.

About the episode: In this conversation, Steve sits down with Meghan to unpack what it really means to be “growth ready.” Megan shares why vulnerability is not weakness, but a leadership advantage, especially when you’re scaling a company, building culture, navigating succession, leading hard conversations, and raising a family at the same time. For founders, executives, and high-performers, this episode is a practical reminder that sustainable growth starts with values, trust, and the courage to ask for help.

Key Takeaways:

• Why vulnerability is essential for personal and professional growth
• Megan’s journey from nonprofit leadership into HR and people operations
• The partnership between Megan and founder Marsha O’Connor
• How hard conversations strengthen leadership tandems
• Protecting company culture during growth
• Why “teammate” matters more than “employee”
• Women in leadership, motherhood, and asking for help
• The tension between saying yes, learning fast, and avoiding overwhelm
• Building new service lines without losing core values
• Why relationships are a true growth lever
• Creating communities that support female leaders and entrepreneurs

Links and resources mentioned:

• The O’Connor Group: www.tocgrp.com
• The O’Connor Group on LinkedIn
• 57th Street Partners 
• Shadow Her

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