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Leading from the Steep Side of The Learning Curve - CEO of Pinnacol Assurance, Phili Kalin
Episode 461st June 2021 • The CEO Sessions • Ben Fanning
00:00:00 00:48:57

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Phil Kalin is President and CEO Pinnacol Assurance in Denver, CO where they protect nearly a million workers and 60,000 businesses.

Phil has also served as a senior executive at Mt Sinai Medical Center in Cleveland, Rose Medical Center in Denver, Custom Med Solutions, and Henry Ford Health System in Detroit.

Phil Kalin has a bachelor’s degree from University of Iowa and his master's degree in health services administration from the University of Michigan.  

Phil’s LinkedIn Profile:

Pinnacol Assurance: 


  • Phil’s first job in his family’s “Five and Dime”, and how it influenced his career.
  • The moment he hiked in the snow to his customer’s house to take care of them.
  • A powerful lesson he learned, at 17 years old, when he needed to run the family business.
  • Why it’s important that you stay on the “steep side of the learning curve”.
  • Advice to leaders who want to grow in their career.
  • Pinnacol’s success strategies from facing the Pandemic.
  • Why Pinnacol celebrated the one year "shutdown anniversary".
  • Why their NPS score increased during the Pandemic.
  • The pros and cons of having your team working remotely.
  • Thoughts on the long-term impact of remote working on corporate culture.
  • The two ways that leaders should be creating content on social media.
  • The two traits he'd instill in every employee… curiosity and constant learning.
  • The big questions he asks his employees.
  • When Phil had an unexpected twist in his career, and how it led to his success.  
  • 3 success strategies that all employees need to understand.


Traits Phil would instil into each employee:

  • Curiosity
  • Being a constant learner


Advice from his father, “The customer is always right”.  

“I love change. I love being on the steep side of the learning curve.”

“‘Are you all in?’ ‘cause if you’re not, then this is probably not the place for you because we are now going forward and as fast and hard as we can.”


Pandemic Lessons for the Workplace, Phil Kalin 

Atul Gawande


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