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
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