Leadership sounds empowering—until you're navigating chaos, clunky systems, and a team giving you major side-eye. Amy and Kim talk with Stephanie Chung—trailblazing exec, leadership strategist, and accidental trust-builder—about the messy reality of stepping into high-stakes roles. Stephanie gets candid about what it’s really like to walk into a company mid-crisis, how to lead teams that don’t look, think, or operate like you, and why asking the right questions beats having all the answers. From decoding broken sales processes to building authentic relationships, her approach blends Radical Candor with radical curiosity. Her book Ally Leadership isn’t just a guide—it’s a wake-up call for anyone ready to lead with heart, backbone, and an open mind. If you’ve ever doubted your instincts or feared saying the wrong thing, this episode is your invitation to lead anyway—and lead better.

Get all of the show notes at ⁠⁠⁠RadicalCandor.com/podcast⁠⁠⁠.

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Chapters:

(00:00:00) Introduction

Kim and Amy introduce leadership expert Stephanie Chung.

(00:01:31) Leading Through Change: Where to Start 

The process of evaluating and addressing organizational challenges.

(00:05:43) Diagnosing Sales Challenges 

How process inefficiencies—not people—often hinder sales teams.

(00:07:21) Building Trust as a New Leader 

Strategies for establishing trust with new teams from day one.

(00:10:07) Transforming JetSuite: From Commodity to Luxury

Lessons from leading cultural and brand transformation.

(00:11:46) Feedback & Self-Awareness in Leadership 

The importance of vulnerability and inviting radical feedback.

(00:17:50) Ally Leadership & Generational Diversity 

Why curiosity is key to leading across generations and identities.

(00:24:20) Being an Underrepresented Leader 

Navigating workplace bias and building allyship in leadership.

(00:30:11) Courageous Leadership & Using Your Voice 

The importance of speaking up and building leadership muscle early.

(00:33:27) Neuroscience of Bias & Rewiring the Brain 

How to overcome in-group bias through exposure and curiosity.

(00:38:13) Asking Questions to Build Trust

Using questions to uncover personal connections and build rapport.

(00:40:26) Listening to Understand, Not to Respond 

Tactics for active, empathetic, and observant listening.

(00:43:07) Where to Find Stephanie

Leadership legacy, travel tips, and connecting with Stephanie.

(00:47:08) Conclusion

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