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.
When Letting Go at Work Feels Like Failing | Jackie Hendy
You’re delivering. Your team is delivering. So why does being asked to delegate feel like a sign you’re falling short? When Jackie Hendy’s CEO asked her to hire VPs, he wanted more time with her to think about the business and its strategy. She worried it meant she wasn’t performing. In this episode of Court-side Conversations, Jackie shares what she learned about self-doubt, belonging, and letting go throughout a career that took her from receptionist to Chief Human Resources Officer. From f...
10 Oct 2026
Not Speaking Up Is a Career-Limiting Move | Yee May Leong
What if NOT speaking up for yourself is the very thing holding your career back? Yee May Leong spent more than 40 years building a career in tech, often as the only woman in the room. Over the years she learned that advocating for what you believe in, even when it ruffles feathers, is essential to success. In this conversation, Yee May shares why finding sponsors matters, how she's learned to pick her battles, and why self-doubt can actually be a good thing. We also talk about belonging, bein...
26 Sept 2026
Be a Sponge: The Career Advice That Helped Fran Carasco Grow
What if one of the best things you could do for your career was admit what you don’t know? Fran Carasco has built her career by staying curious, building relationships, and learning from the people around her. Her approach? Be a sponge. In this episode of Court-side Conversations, Fran shares why she believes your network is your net worth, why she intentionally does things that make her uncomfortable, and how being willing to say “I don’t understand” has helped her grow. She also gets candid...
18 Sept 2026
Taking the Opportunity Before You Feel Ready | Marci Oates
What if you took the opportunity before you felt completely ready? Marci Oates started her career working in the cafeteria at HP and retired 30 years later as a Vice President of HR. Her career wasn't built by having every next step mapped out. It was built by saying yes to opportunities, taking lateral moves, asking for what she wanted, and continuing to move forward even when self-doubt showed up. In this episode of Court-side Conversations, Marci shares what her career looked like behind t...
29 Aug 2026
When You Know It’s Time for a Career Change, But You’re Scared to Go | Rachael Greenwood
What happens when you know it’s time for a career change, but self-doubt keeps you from making it? In this episode of Court-Side Conversations, I sit down with Rachael Greenwood, a teacher who spent more than a decade in the same school district and admits she stayed about three years longer than she knew she wanted to. We talk about the loyalty and self-doubt that can keep us stuck, what it really means to feel supported at work, and what finally gave Rachael the confidence to make a change....
15 Aug 2026
What I Wish I Would Have Known Earlier in My Career | Tamika Brunetti
What would you do differently if you could start your career all over again? In this episode of Court-side Conversations, I sit down with Tamika Brunetti to talk about the lessons that took years of experience to learn. We talk about difficult feedback, knowing when you belong (and when you don't), self-doubt, self-awareness, the worst career advice Tamika ever received, and why she wishes she had started building something outside of her job much earlier. One of my biggest takeaways from our...
3 Aug 2026
How to Know If You're Making the Right Career Decision | Randi Carlini
Have you ever wondered if you're making the right career decision? In this episode of Court-side Conversations, I sit down with my cousin, Randi Carlini, to talk about what it looks like to trust your talents when life doesn't go according to plan. From earning a biology degree to building a career in hospitality, to stepping away from her career to raise her children, Randi shares the self-doubt, courage, and quiet confidence behind each chapter of her journey. In this episode, we discuss: &...
18 Jul 2026
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 to explore what she's learned from building an unconventional career, investing in opportunities before she felt completely ready, and navigating entrepreneurship one step at a time. Maggie shares why she believes the best opportunities often come from learning as yo...
4 Jul 2026
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 the loudest. In this conversation, Kate Coelho shares what it was like navigating that transition, why advocating for yourself matters just as much as doing great work, and how she's learned to trust herself even when her inner critic shows up. We also talk a...
20 Jun 2026
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 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 strength, not a weakness The role self-doubt played when she first became a manager How she...
5 Jun 2026
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 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 it was like leaving a company after 17 years, stepping into a completely new role, navigating inte...
22 May 2026
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 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 without a plan, return to a workplace that truly felt like home, navigate leadership in male-dominated ...
8 May 2026
Choose Your Pain: Trusting Yourself Instead of Playing the Game | Marlenne Johnson
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 journey through HR, from trying to fit into a male-dominated environment to making conscious dec...
24 Apr 2026
Get Out of Your Head and Trust What You Feel | Ashley Watkins
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 decisions based on her gut, how her inner critic shows up as she builds her business, and why comm...
11 Apr 2026
If You’re Not Growing, You’re Rotting | Allison “Allie” Germain
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 about change Why overthinking keeps you stuck And what it act...
27 Mar 2026
When Everything Feels Split | Jessica Johns
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 applies. We talk about: the tension of motherhood and career learning to make deci...
13 Mar 2026
A Conversation with My Mom | Chris Johnson
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 comes with experience, and the lessons that stay with us long after the moment has passed. Pull u...
5 Mar 2026
Trailer: Welcome to Court-side Conversations with Courtney
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 from someone who has been there too. When women share their experiences openly, we learn faster,...
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Spotify
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