Episode #66: Dean Owrey, CFO at UPMC

Welcome everyone to another episode of the Learning to Lead podcast. This episode comes from our interview series where I interview seasoned leaders and try to extract from them their best leadership tips and practices.

This month, I had the privilege of interviewing Dean Owrey, who is the CFO of International and Commercial Services & Information Services Division at UPMC in Pittsburgh. Dean is the first interview I’ve done from a referral from someone who in our Learning to Lead group, Paul Matthews, who also works at UPMC. In fact, Dean is one of Paul’s mentors. I really enjoyed my time with Dean and I believe this podcast will add a lot of value to your life.

Episode #66: Dean Owrey, CFO at UPMC


Connect with Dean:

In this episode, you will learn: 

  • How to set yourself apart in an organization
  • How to make an impact in the lives of young leaders
  • How not to be average
  • How to deal with conflict
  • How to balance life and work
  • How to put your family first
  • How to build a great team
  • How to develop leaders

Linked Mentioned in the Show:



  • Tell us about yourself, your family, your passions, and what you do.
  • What is one thing about Dean Owrey that people would be surprised to know?
  • When you think of success, who is the first person that comes to mind and why?

Personal Leadership:

  • Walk us through your leadership journey . . . did you always aspire to be a leader wherever you were? How did you learn leadership? Did someone teach you?
  • Can you name a person who has had a tremendous impact on you as a leader? Maybe some one who has been a mentor to you? Why and how did this person impact your life?
  • What are you doing and what have you done to ensure you continue to grow and develop as a leader?
  • What books have you read that have made a great impact on you that you would recommend? 
  • How do you structure your days and your life so that you are as productive as possible?
  • How do you balance life and work?
  • At one point, you left E&Y and then returned, otherwise known as boomeranging… do you recommend this practice for young leaders? You were a partner at Ernst & Young and left to go to UPMC…why did you do that? What impact did it have on you?
  • Can you tell us about Michael and the impact he had on your life?

Organizational Leadership: 

  • Talk to us about the organizational culture of UPMC, what makes it great? What are you guys working on to make it better? With so many employees, how do you ensure that everyone is bought into the culture you’ve developed?
  • What qualities do you look for in up and coming leaders?
  • In your leadership experience, what have you learned about building a great team?
  • What does mentoring and development young leaders look like in your organization?
  • What have you found to be the biggest challenges that executives face?
  • What do you think is the biggest challenge facing leaders today?


  • What advice would you give young leaders when it comes to picking the “right” career?
  • What can young leaders do to set themselves apart in their organizations?
Closing Questions:
  • What are you most proud of up to this point in your life?
  • What do you want your legacy to be?
  • Any closing advice for young leaders?

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