Leading with Authenticity: Leadership and the Future of Work
Host Jake Cuthbert of Educo Advisor Group welcomes Stephanie Masters (Nonprofit Sidekick) for a candid conversation on leading with authenticity, building healthy culture, and navigating the future of work—from higher ed and nonprofits to corporate life and entrepreneurship.
From art teacher to HR leader to executive coach, Stephanie’s journey shows that great leadership isn’t about titles—it’s about clarity, candor, and caring enough to have the hard conversations.You’ll learn:🧭 Authentic Leadership: How to be real (not performative) while setting clear expectations.
🤝 Culture over Policy: Why misalignment between boards, execs, and teams breeds dysfunction—and how to fix it.
🏢 Hybrid & RTO Reality: Why many top performers resist the office—and how leaders can keep them visible and growing.
🗣️ Radical Candor 101: Caring personally and challenging directly; avoiding ruinous empathy and obnoxious aggression.
🧠 Strengths Tools: Where CliftonStrengths, Predictive Index, and Kolbe each shine—and how to use them together.
🚀 Accidental Business Owners: Start with why, know your gaps, and find a “who” (coach/partner) instead of forcing every “how.”
“Move from being nice to being kind. Kindness tells the truth because it cares.” — Stephanie Masters
If you’re a founder, people leader, or anyone building teams with purpose, this episode delivers practical frameworks and real-world examples you can use today.
Listen now on YouTube or your favorite podcast platform.
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Securities and advisory services offered through LPL Financial, a Registered Investment Advisor. Member FINRA/SIPC. This content is for educational purposes only and not personalized financial advice.
