It’s Gonna Get Ugly Before it Gets Good




Meet Kathie Chao. She’s a Managing Director and Head of Digital Retail at Charles Schwab. Never one to back down from a challenge, her role has changed almost every year for the past decade.

In 2021, her scope shifted dramatically. She realized her anxiety about work was tipping into an unhealthy point. She started working with a coach and learned how to use those signals of anxiety to focus her attention on critical areas rather than overwhelm her, ensuring the anxiety and confusion she encountered was ultimately productive vs. limiting.

Kathie, a Harvard and Wharton Business School alum, is never going to stop attacking increasingly complex problems at work. She can’t stop, won’t stop. But if she wanted to get better at facing bigger, messier challenges, she realized she had to accept that along the way, she might not get an A+ at every turn.

In order to achieve her ambitious goals and thrive in senior roles, Kathie learned the most important relationship she could manage, is the one with herself.

Tune in to hear Kathie’s journey, peppered with a ton of humor, pop culture references, and really practical ways she upped her game as a senior leader.

4:34  “It’s hit an unhealthy point” Sifting through anxiety to understand herself and her context

6:07 “Are you driven by excitement or fear?” What the root of your momentum might tell you about how things will likely unfold.

9:55  Kathie uncovers a “status trigger” and how it shows up for her and others at work

18:29  Spoiler: Senior leaders are fallible, operating with their own fears and anxieties! Self-management is critical to scaling well.

27:09  Confusion as a learning tool: Kathie opens up a candid convo with a partner about a confusing remark he had made. Result? Deeper trust and a richer understanding of the risks and opportunities they were facing together

33:47  How Kathie prioritizes what confusion to dig into: “Does it get in the way of me accomplishing the goal?” If YES, must address.

Transcript of this episode available here

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