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.
Episodes
16 episodes
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.
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 mappe...
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 d...
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 abou...
.png)
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 a...
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 ...
.png)
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...
.png)
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 ...
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 followin...
.png)
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.<...
.png)
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 on...
.png)
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 wit...
.png)
