Coaching Real Leaders Coaching Real Leaders

Best of CRL: Why Haven’t I Made it to the C-Suite?

Aug 17, 2026 · 48m

Summary

Host Uriel Wilkins coaches Randy, a Black executive VP, who repeatedly fails to secure C-suite roles despite his qualifications. They explore whether the barriers are internal shortcomings or external biases, helping Randy shift from seeking external validation to defining success by his own values. Randy realizes he has been adapting to fit corporate norms rather than finding environments that align with his purpose. The conversation concludes with Randy considering entrepreneurship to build a legacy grounded in self-defined success rather than corporate approval.

Topics discussed

Sponsors: Capital One Venture X and Saver Cards Episode Intro: Executive Coaching with Randy Randy's Background and Leadership Style The Glass Ceiling and Considering Entrepreneurship Generational Differences and Vulnerability Internalizing Rejection and Social Biases Detailed Interview Experience and Lack of Feedback Analyzing Bias vs. Self-Improvement Sponsors: Quo, Shopify, and Monarch The Frustration of Unexplained Rejection Faith, Resilience, and Adapting to Fit In Blending Identity with Organizational Needs Accepting Reality and Being Selective The Choice to Remain an Outlier Sponsors: NetSuite and Capital One Owning the Choice and Fear of Risk Security Needs vs. Entrepreneurial Risk Conclusion: Self-Belief and Next Steps Outro and Credits
Listen ad-free on Castria