Podcast

Leadership Lessons in Empowerment

  • Aug 03, 2026
  • 2 min read

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– Mike Ryan, CIO of Wintrust Financial Group, shares his career journey on CEO Tech Live Season 2.
– He discusses how empathy and resilience shape leadership lessons throughout decades of experience.
– The episode explores why employee empowerment drives innovation across organizations.
– Ryan reflects on how digital transformation creates lasting business impact.

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CEO TECH LIVE - Season 2

In Season 2 of the CEO Tech Live Podcast, host Ben Fanning speaks with Mike Ryan, CIO of Wintrust Financial Group, about his career journey and decades of leadership experience.

Ryan shares how empathy and resilience shape his leadership lessons, why employee empowerment drives innovation, and how digital transformation creates lasting impact.

Key Highlights

  • How taking risks fuels employee growth and innovation
  • Why learning from failure strengthens leadership at every level
  • What empathy and empowerment deliver in business transformation