Move Coaching from Theory to Practice, with Jason Weeman Coaching for Leaders

Jason Weeman: Upwork

Jason Weeman works to build meaningful relationships by creating experiences that are inspiring and transformational. He has worked for some of the top brands in the world, including Apple, LinkedIn, and Upwork. Today, he is the head of corporate learning and development at Upwork. One of the key areas of focus for his team and him is building a coaching culture.



In this conversation, Jason and I discuss how his team was a catalyst for coaching culture at Upwork. We discuss what worked to influence culture in this way, what didn’t work, and the lessons they learned along the way.

Key Points

Be lazy, be curious, be often. -Michael Bungay Stanier



Organizations are trying to create a culture for coaching, but not giving the feedback. The stronger that we develop a sense of common language on feedback, the better we get on quality.

People sometimes don’t believe it should be so simple…so they try to make coaching development too complicated.

Resist the urge to focus too much on data and tracking.

Significant buy-in from executive leadership is critical for the success of a coaching program like this. Also, having a culture of “we” being in this together makes all the difference.



Resources Mentioned



Life at Upwork

The Coaching Habit workshop

The Last Feedback Workshop You’ll Ever Need



Related Episodes



These Coaching Questions Get Results, with Michael Bungay Stanier (episode 237)

How to Get the Ideal Team Player, with Patrick Lencioni (episode 301)

How to Create an Unstoppable Culture, with Ginger Hardage (episode 350)



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