Guest: Lesley Young, CRO of Gem

Lesley Young’s favorite book is “The Obstacle Is The Way,” in which Ryan Holiday argues that the process of working hard to achieve something is more important than the achievement itself. When you find yourself in a position of leadership, the Gem CRO says, “you realize there’s a lot of wisdom that you’ve gained in those experiences that you’ve had.” One of her passions is helping other people develop in the careers, which includes convincing them that “that hard yards are going to be the ones that are gonna grow them the most.”

In this episode, Lesley and Joubin discuss speaking vs. observing, meeting your heroes, the Great Depression mindset, developing people, Workplace by Facebook, the power of discontent, choosing to show up, controlling the controllable, repeatable success, being “open for business,” getting fired up, remote work, “only the paranoid survive,” and hard feedback.

In this episode, we cover:

Prepping for public presentations (00:59)
Meeting Salesforce CEO Marc Benioff and working with Snowflake CRO Chris Degnan (04:44)
Fear of everything evaporating, and becoming resourceful (09:28)
The “purpose statement” Lesley wrote for her career, and why she loves to learn (14:16)
Choosing to not be *the* leader all the time, and taking a risk on Facebook (20:35)
Her relationship with her parents and being motivated by unfinished work (25:45)
Ryan Holiday’s “The Obstacle Is The Way” and the journey to the achievement (29:32)
How to work with founders such as Box CEO Aaron Levie (35:58)
Former Segment CEO Peter Reinhardt and asking the right question (41:03)
Why Lesley joined Gem on the eve of a hiring downturn: The long-term play (47:26)
Why Gem CEO Steve Bartel is an “amazing recruiter,” and the return of in-person collaboration (52:14)
The toughest feedback Lesley has ever gotten about herself (59:42)
Why delivering tough feedback is harder than receiving it (01:03:49)

Links:

#126 CRO Gem, Lesley Young: Hard Yards

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#126 CRO Gem, Lesley Young: Hard Yards