Learning to Repurpose Disappointment, with Jay Woodcroft

"You can do a ton of great things and still find yourself on the wrong side of wins and losses."

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Welcome back for season 7 of the Glass and Out Podcast! For epsiode #226, we’re joined by friend of the pod and Edmonton Oilers Head Coach, Jay Woodcroft.

He is entering his third season as the Coach of the Oilers, with the best winning percentage of any coach in franchise history. Last season, the Oilers were eliminated by the eventual Stanley Cup Champions, the Vegas Golden Knights, in round 2. This season it’s fair to say there is only one goal in the City of Champions.

Listen as shares his philosophy of repurposing disappointment, why it’s important to “walk the talk” when it comes to building culture, and how a similar path in coaching led to a friendship with Miami Heat coach Erik Spoelstra.


  • 0:08 On the new facility in Edmonton
  • 4:47 Recharging the batteries before starting a new season
  • 7:08 How fishing influenced coaching and patience
  • 10:44 Favourite books on coaching and learning from NBA legend Pat Riley
  • 12:27 Expectations for Oilers and keeping things focused on day to day
  • 15:20 Supporting players and letting results take care of themselves
  • 17:44 Learning to repurpose disappointment and Ken Holland’s post-season speech story
  • 22:14 Not overcorrecting a team’s areas of need
  • 26:00 Approaching training camp by focusing on one area at a time
  • 30:13 Selecting details that matter for a team
  • 30:00 Counting days of a season and walking the talk with culture building
  • 37:20 Big moments during a season to celebrate or learn from
  • 39:47 Acquiring Mattias Ekholm and his impact
  • 44:05 Journaling lessons learned from past coaches he’s worked with
  • 49:30 Dream dinner with three coaches
  • 50:30 Friendship with Miami Heat coach Erik Spoelstra
  • 52:30 Raising daughters and the growth of women’s sports

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