Her CEO Wanted More Time With Her. She Thought She Was Failing.

Jackie Hendy’s CEO asked her to hire VPs so she could spend more time with him thinking about the business and its strategy. She worried it meant she wasn’t performing. She was delivering. Her team was delivering. But letting go of the work still felt like admitting she couldn’t handle it. Sound familiar? Jackie worked her way from receptionist to Chief Human Resources Officer. In this episode of Court-side Conversations, she shares the experiences that challenged her confidence, the career advice she refused to follow, and what changed when she learned to delegate. We talk about: • Why success doesn’t make you immune to self-doubt • Having a seat at the executive table without feeling heard • Being told to change her hair to be taken seriously • The advice she never forgot after delivering a devastating layoff • Letting go of work without questioning your value CHAPTERS 00:00 She Thought She Wasn’t Performing 00:56 From Receptionist to CHRO: Meet Jackie Hendy 04:31 A Seat at the Table, but Do You Belong? 07:48 “The Day That Gets Easy, Step Away” 09:10 Change Your Hair to Be Taken Seriously? 10:54 Self-Doubt, Doing It All & Learning to Delegate 16:57 Truth-Telling, Little Jackie & Finding Joy 💛 Have you ever interpreted someone’s request as a sign you weren’t doing enough? Share your experience in the comments. Subscribe for candid conversations with women about leadership, self-trust, and the moments that shape us. CONNECT WITH COURTNEY 💛 LinkedIn:   / courtneycheadley   💛 Center Court Collective: https://www.centercourtcollective.com 💛 Join Center Court Connections: https://www.centercourtcollective.com... 💛 Coaching, speaking, or podcast inquiries: courtney@centercourtcollective.com 🎧 Listen on your favorite podcast platform: https://www.centercourtcollective.com... ABOUT THE PODCAST Court-side Conversations is a podcast about leadership, self-trust, and the moments that shape us. Hosted by Courtney Headley, career coach and founder of Center Court Collective, each episode features a candid conversation with a remarkable woman about navigating challenges and moving forward with confidence and integrity. New episodes every other week. #womeninleadership #selfdoubt #leadershipconfidence #CourtsideConversations Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/all-good-folks/g... License code: 6OMN2JS8MHGTKY5U