Courtney Headley

Court-side Conversations with Courtney

Business EN ↓ 10 episodes

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 wa...

Author

Courtney Headley

Category

Business

Podcast website

www.buzzsprout.com

Latest episode

Jul 4, 2026

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Episodes

When Everyone Starts Looking to You for Answers | Kate Coelho 04.07.2026

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 the loudest. In this conversation, Kate Coelho shares what it was like navigating that transition, why advocating for yourself matters just as much as d...

Know Your Strengths, Trust Yourself More | Jocelyn Guite 20.06.2026

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 than 15 years of experience across multiple industries. We talk about: How Clifton Strengths changed the way she views herself and others  Why asking for help is a st...

She Looked Confident. She Was Secretly Second-Guessing Everything. | Angelique Bui 05.06.2026

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 in corporate America, to talk about the self-doubt that followed her throughout her career, even when others saw her as confident, capable, and strong. Angie shares what...

Finding Joy in Everyday Life | Jamie King 22.05.2026

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 conversation about career growth, self-doubt, motherhood, stress, confidence, and finding joy in the middle of real life. Jamie shares what it looked like to leave a job witho...

Choose Your Pain: Trusting Yourself Instead of Playing the Game | Marlenne Johnson 08.05.2026

This episode is for the woman who feels like she has to change who she is to succeed. I’m joined by Marlenne Johnson, someone I’ve known for years and deeply admire for her honesty and self-awareness. We talk about what it actually looks like to navigate environments where you don’t feel like you belong… and the choice so many women face: Do I play along…or stay true to myself? Marlenne shares her...

Get Out of Your Head and Trust What You Feel | Ashley Watkins 24.04.2026

If you’ve been living in your head… second-guessing, overthinking, trying to “figure it out”… this episode is for you. In this conversation, I’m joined by Ashley Watkins, a former teacher turned coach, who built her career not by following a plan… but by following what felt right. We talk about what it actually looks like to trust yourself in real life. Not in theory. Ashley shares how she makes d...

If You’re Not Growing, You’re Rotting | Allison “Allie” Germain 11.04.2026

This episode is for any woman who feels stuck… and knows something needs to change. In this conversation, I sit down with my friend Allison “Allie” Germain to talk about fear, growth, and what actually keeps us from taking the next step. We talk about:  What it feels like to be in a role that doesn’t fit   The difference between comfort and growth   How fear shows up when you're thinking abou...

When Everything Feels Split | Jessica Johns 27.03.2026

Some seasons of life don’t fit neatly into categories. You’re not all in at work. You’re not all in at home. And no matter what you choose, it can feel like something is getting less of you. In this episode, I sit down with one of my closest friends, Jessica Johns, to talk about what happens when your identity shifts, your priorities change, and the way you’ve always measured yourself no longer ap...

A Conversation with My Mom | Chris Johnson 13.03.2026

Some of the most meaningful insights in my life have come from simply sitting across the table from someone and asking a few thoughtful questions. For the first episode of Court-side Conversations , it felt only right to start with the woman who has had the greatest influence on my life, my mom, Chris Johnson. In this conversation, we talk about the moments that shape us, the quiet confidence that...

Trailer: Welcome to Court-side Conversations with Courtney 05.03.2026

Welcome to Court-side Conversations with Courtney. This podcast 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 navigating the workplace can feel isolating sometimes. And it helps to hear...

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