The Leadership Skill Nobody Teaches (But Every CEO Needs) | Richard Yep

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Richard Yep, Vice President of Vetted Solutions, to talk about the real challenges of leadership—especially the difficult transition from being someone’s peer to becoming their boss.

Richard brings decades of leadership experience from nonprofit organizations and executive search, sharing hard-earned insights on building inclusive cultures, hiring the right people, and making values-based decisions even when they come at a cost. This conversation explores what worked, what didn’t, and what every entrepreneur, CEO, and emerging leader needs to hear as they grow their organization.

🎧 What You’ll Learn in This Episode:

• How to navigate the awkward but essential transition from peer to boss without losing trust
• Why hiring for passion over perfect qualifications attracts the right talent to small businesses
• How to balance finances with growth—and why patience often matters more than speed
• How inclusive leadership improves decision-making and organizational effectiveness
• When to delegate, how to let go, and why listening is a leadership superpower
• The real cost of values-based decisions—and why they define organizational integrity
• Practical advice for entrepreneurs preparing to scale

⏱️ Episode Timestamps:

• 00:00 – Introduction
• 02:54 – Navigating the challenges of leadership
• 05:53 – Hiring and attracting talent in small businesses
• 08:54 – Balancing finances and growth
• 11:55 – Common challenges for CEOs and nonprofit leaders
• 14:53 – The importance of communication and inclusivity
• 17:47 – Delegation and letting go
• 20:35 – Values-based decision making
• 23:35 – Building an inclusive culture
• 26:39 – Pivots and new ventures
• 29:24 – Advice for entrepreneurs
• 32:36 – Conclusion and resources

👤 About the Guest:

Richard Yep is the Vice President of Vetted Solutions, bringing decades of leadership experience from nonprofit organizations and executive search. He specializes in helping organizations navigate leadership transitions, build inclusive cultures, and make strategic decisions that align with core values.

Connect with Richard Yep:
LinkedIn: https://linkedin.com/in/richardyep

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