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 trustWhy hiring for passion over perfect qualifications attracts the right talent to small businessesHow to balance finances with growth—and why patience often matters more than speedHow inclusive leadership improves decision-making and organizational effectivenessWhen to delegate, how to let go, and why listening is a leadership superpowerThe real cost of values-based decisions—and why they define organizational integrityPractical advice for entrepreneurs preparing to scale⏱️ Episode Timestamps:00:00 – Introduction02:54 – Navigating the challenges of leadership05:53 – Hiring and attracting talent in small businesses08:54 – Balancing finances and growth11:55 – Common challenges for CEOs and nonprofit leaders14:53 – The importance of communication and inclusivity17:47 – Delegation and letting go20:35 – Values-based decision making23:35 – Building an inclusive culture26:39 – Pivots and new ventures29:24 – Advice for entrepreneurs32:36 – 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🚀 Ready to Make Your Business Official?Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.👉 Register here: https://www.igotnext.co/training👉 Grab your FREE Legal Guide at:https://www.topemployermistakes.com🔗 Stay Connected with Sedgwick AndrewsFollow us across all platforms for legal tips, business strategy, and boss-level motivation:👉 https://linktr.ee/Sedgwick_Andrews_LC