Court-side Conversations with Courtney
Court-side Conversations: Bold women. Strong voices. Real talk.
Court-side Conversations brings women together for honest conversations about work, confidence, and finding their voice…without the corporate speak.
Each episode centers on real stories, lessons learned, and the advice women embraced (or intentionally left behind) along the way.
Because when navigating the workplace feels isolating, it helps to hear from someone who’s been there too.
When women share their experiences openly, we learn faster, feel less alone, and lift each other up in the process.
These conversations happen the way all good ones do…over drinks, in good company.
Pull up a chair and join me, Court-side.
Court-side Conversations with Courtney
Latest Episodes
Learning as You Go: Intuition, Mentors & Entrepreneurship | Maggie Williams
What if you didn't have to have everything figured out before taking the next step?In this episode of Court-side Conversations, Courtney Headley sits down with entrepreneur and commercial real estate professional Maggie Williams...
When Everyone Starts Looking to You for Answers | Kate Coelho
There comes a moment in your career when something shifts without you noticing.One day you're the person asking the questions. The next, everyone is looking to you for the answers. And for many women, that's exactly when self-doubt gets ...
Know Your Strengths, Trust Yourself More | Jocelyn Guite
What if the key to moving through self-doubt isn't fixing your weaknesses, but better understanding your strengths?In this episode of Court-side Conversations, I sit down with my longtime friend Jocelyn, an HR leader with more t...
She Looked Confident. She Was Secretly Second-Guessing Everything. | Angelique Bui
What if the people who seem the most confident are also questioning themselves behind the scenes?In this episode of Court-side Conversations, Courtney sits down with Angelique Bui, a leader with more than 30 years of experience ...
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Finding Joy in Everyday Life | Jamie King
What happens when you stop trying to be perfect and start trusting yourself a little more every day?In this episode of Court-side Conversations, Courtney sits down with one of her closest friends, Jamie King, for an honest conve...
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