What Breaks Healthcare Transformations Before Technology Ever Does with Ryan Olsen of Hoag Health System
This week, David Wright is joined by Ryan Olsen, Chief Administrative Officer of Hoag Health System, to discuss what it takes to lead large healthcare organizations through complexity, constraint and change. Ryan shares lessons from turnaround leadership, physician alignment and organizational politics, and explains why trust, incentives and discipline matter more than technology alone. The episode also explores the realistic role of AI in healthcare, the pressures facing health systems today and the personal leadership lessons Ryan learned the hard way.
Key Takeaways:
00:00 Introduction.
04:16 Trust is foundational to driving effective organizational change.
07:00 Listening more than talking dramatically improves negotiations and relationships.
10:32 Strong physician partnerships underpin successful growth and operations.
12:04 Using the Stockdale Paradox to lead through brutal turnaround realities.
14:44 Difficult conversations, done compassionately, unlock meaningful organizational change.
17:48 Humility and self-awareness are essential antidotes to executive ego.
25:56 Hoag’s disciplined OKRs drive quality, growth and accountability.
33:36 AI will support, not replace, high-skill clinicians and surgeons.
36:24 Prioritizing mental and physical health makes you a better leader.
Resources Mentioned:
“Good to Great” by Jim Collins
“The Hardest Job in the World” by John Dickerson
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