Aug 20, 2026

The Leadership Pressure No One Talks About in Tech | Keith Corbin| The Cyber Savvy Woman| EP 143

In this episode of The Cyber Savvy Woman, Rachele Schainker sits down with Keith Corbin, founder of Evolution Coaching, for a thoughtful conversation about leadership, workplace systems, and the realities leaders face in technology and product roles. With a background spanning engineering, product management, partnerships, and leadership in hyper-growth tech companies, Keith brings a perspective that goes beyond traditional leadership advice.

Together, Rachele and Keith explore why leaders often mistake the friction and limitations of their roles for personal failure. Keith explains how organizational structures, competing expectations, and the responsibilities that come with management can create contradictions that leaders need to recognize rather than simply try to eliminate. They discuss why middle managers in particular can feel caught between the needs of their teams and the demands of the organization, and why what worked at one level of leadership may no longer work at the next.

The conversation also looks at Keith's approach to coaching, including his ideas around frames, positions, patterns, and understanding the systems people operate within. He shares why organizational dysfunction can sometimes serve a purpose, how recognizing the underlying reasons for a problem can create new possibilities, and why leadership is not simply about individual traits but also about understanding the larger system.

Rachele and Keith also discuss AI and technology, including the value of keeping some friction in our work rather than automatically removing it. Keith explains how he thinks critically about technology, why human connection still matters in his coaching practice, and how leaders can use technology intentionally instead of simply choosing whatever is easiest.

Whether you're a technology leader, middle manager, emerging executive, or someone navigating the complexities of leadership, this episode offers a grounded perspective on working within imperfect systems, understanding the realities of your role, and making more intentional choices about how you lead.