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
When Everyone Starts Looking to You for Answers | Kate Coelho
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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 about:
• Why "keep your head down and work hard" isn't enough
• The importance of advocating for yourself
• Balancing leadership, motherhood, and life outside of work
• Why growth and discomfort almost always arrive together
If you've ever wondered whether you deserve your seat at the table, this conversation is for you.
Pull up a chair, grab a drink, and join us Court-side.
Connect with Courtney
💛 LinkedIn: www.linkedin.com/in/courtneycheadley
💛 Learn more about Center Court Collective
🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial
About the Podcast
Court-side Conversations is a podcast about leadership, self-trust, and the moments that shape us.
Each episode features a candid conversation with remarkable women about the experiences that helped them trust themselves, navigate challenges, and move forward with confidence and integrity.
Hosted by Courtney Headley, founder of Center Court Collective.
New episodes released every other week.
The Moment You Realize You're the Leader in the Room
SPEAKER_00I think when you're early in your career, you're not expected to know anything, right? You're expected to listen, ask questions, absorb everything and learn. And then there comes this point which I don't think anyone ever really tells you you're in it and it shifts. And then suddenly you're the person in the room that people are asking the questions. And that for me is when I experience the most self-doubt. You know, like why are people asking me? Do I deserve to be here? Do I know the answers? So I always have to just also try to remind myself and trust myself, like you, you've been doing this for a long time. You know what you're talking about. You deserve to be here. You deserve this.
SPEAKER_01Hi, and welcome to Courtside Conversations. This episode is for the woman who's now realizing she's the leader in the room. I hope you enjoy. Today I am joined by Kate Cualho, who is a woman that I admire because she is just a very genuine, authentic person who is incredibly empathetic and might possibly have the best laugh of all time, which I tire tirelessly try to make her laugh. So Kate, thank you so much for joining me.
SPEAKER_00Thank you for having me, Courtney. I'm excited to be here.
Meet Kate
SPEAKER_01Kate, can you, for our listeners, can you just tell them a little bit about yourself?
SPEAKER_00Of course. So hello, I'm Kate. I'm a wife. I'm a mom of two little girls and a dog named Mati. And I live in Redmond, Washington. And I would say I'm in a very full season of life right now, trying to balance my marriage, motherhood, my career, and then trying to figure out myself in the midst of all of it. And I think so much of us are in the trenches day to day and we don't really talk about it enough. So I'm really excited to be here, Courtney. Thank you for having me. And let's dive in.
SPEAKER_01Yeah, I'm thrilled. Thank you. I'm so excited you're here. And Kate, how do you and I know each other?
SPEAKER_00Well, we worked at Equinex together. I think our paths cross when we are working on the future of work. And then, you know, I've I think I'm sure I've told you this, Courtney, but I admire you so much. Your energy, the way you command a room, and just your moral compass that you bring to work every day. But then since Equinex, you know, I call you a friend, we talk just as much professionally as we do text about secret lives of Mormon Wives or the random, messed up TV shows we're watching. So super grateful for our friendship, Courtney.
SPEAKER_01Yeah, likewise, you are one of the many gifts that Equinix gifted me. And I'm so grateful that our paths crossed. And y'all, Kate has given me like a list of TV shows to watch, and I am making my way through it. So I are honored. I love it. And then do you have a drink? What are you drinking today?
SPEAKER_00I am drinking just plain old ice water, trying to get more H2O in.
SPEAKER_01I too. I'm drinking sparkling water, but I'm joining you in that. So there's my friend. Okay. And then can you tell everyone a little bit about your career journey?
SPEAKER_00Studied marketing and organizational behavior in school. I've always been really fascinated by people and their habits, mindsets, beliefs, why do people do the things they do? And after college, I started my career in consulting, doing a lot of program management and change management. And that's where I learned that I really love helping people go through change and experience change in a way that's meaningful for them. There came a point where I was, I eventually wanted to start a family and was looking for more stability. So I left consulting and since then have been helping to drive organizational change across different transformations at tech companies. And then the past two years, I've been really leaning in and driving AI change. And how do you feel about that? What's that like for you? It's so interesting. It's so overwhelming. It's something that we we're experiencing personally and professionally. And there's so much emotion tied to it, like good, bad. And so really understanding where people are at, meeting them where they're at. And then also like I'm going, I'm going through at the same time you are, and leaders are. So I think it's it's fascinating.
SPEAKER_01I selfishly am thrilled that you're in a leadership position in this because I just love how you hold the human aspect like so dear to you. I just love your perspective and how you think about AI change and the human piece of it all.
SPEAKER_00Thank you.
SPEAKER_01Okay. When
The Reality Behind a Successful Career
SPEAKER_01someone looks at your career, maybe like on paper, what are they not seeing?
SPEAKER_00It probably looks pretty clean, well thought out, sequential. Um, but what they don't probably see is the uncertainty behind it. The so many questions of do I go for this role? Am I getting too comfortable? Am I gonna get laid off? What do I need to be doing? What's going to make me happy? And then most recently, what they probably don't see is me trying to balance being a mom, running the house, and my career. I want to show up 150% to work, but I want to show up 150% and be present with my girls and my family. I think that's probably the biggest thing people don't see right now.
SPEAKER_01While it may look clean and well thought out on paper, it can be quite messy and there's a lot of uncertainty in it. So I love to dig into this podcast with my first question. Can you tell me about a time at work where you felt like you truly belonged or a time when you realized you did not belong?
SPEAKER_00Oh, okay. This is back in my consulting days, and I was working on a major airline merger. And so two weeks post-merger, we ran a 24 by seven command center. And luckily, everything went super smooth, and so there was a lot of downtime in the command center. And I remember it was probably the second or third night shift, and people were starting to get a little loopy, like as one does, right? If you're staying up multiple nights in a row. And I'm talking everyone, BPs, MDs, everyone in a room. And so there was singing like don't stop believing, people were dancing on tables, there was a hair crimper, costumes, candy, and people were having a blast. I was able to let my guard down and really just connect. I wasn't worried about producing the next deliverable. And that's a moment I really felt like I belonged because I built genuine connections and I'll probably remember that for the rest of my career.
SPEAKER_01Yeah, I love that. The sense of belonging because there was real connection. And it sounds like you could let loose and have some fun.
SPEAKER_00Yeah. And you know me, right? It takes me a while to open up just because that's how I'm wired, right? And so I think you can appreciate even more me being able to just let lose and have fun. Were you dancing on tables? Hell no. Damn it. I was gonna be like, I need pictures, or it didn't happen. Definitely, definitely part of the hair crimping.
SPEAKER_01Okay, hell yes.
SPEAKER_00Yeah.
SPEAKER_01I mean, that's like very descriptive. When you were like, there was a hair crimper, there was singing, there was dancing on tables. I'm like, okay, clearly this stuck with you.
SPEAKER_00Yeah, it was fun and definitely relationships that I've carried with me throughout.
SPEAKER_01Sometimes it's those human moments like in between the work that just feel like, yeah, okay, this is this is why I'm here. Okay. Tell me about the best or worst career advice you've ever received and how it has achieved you. Can I do both? Yeah, please.
Why Working Hard Isn't Enough
SPEAKER_00Okay. I think some of the worst career advice I've ever received was to just keep your head down, do good work, and the promotion will come. Is I think, you know, there's truth. Absolutely do good work, right? Do good work, it'll be recognized, people will ask for you, and so on. But you absolutely need to advocate for yourself, like show your worth, show your impact, because no one else is going to do it for you. And I wish that I would have learned earlier on is don't expect people to do it for you, like take ownership. And then I would say some of the best advice I've ever received is pretty practical. One of my account managers early on told me that when preparing or coming for a one-on-one with my boss, I should come with an agenda. And if I have questions, come with a perspective and ask them to react to it. So even though your boss usually owns the meeting, like take some mental load off their plate and take ownership. And so that's something that I've carried with me throughout. And I probably I use some aspect of it every day.
SPEAKER_01I can say that I've seen that in when we work together too. So what I heard from you is do great work, but also be prepared to advocate for yourself because promotions won't just come.
SPEAKER_00Yeah. And ask for it, right? Ask for it. Because, you know, I remember having a conversation with the VP about a promotion. She was like, it's gonna take you two to three years. But then I started having more conversations about it and it was done in a year. So you don't just let people decide for you.
SPEAKER_01That's right. Like just keep keep going after it because you were told two to three years, but it happened for you in a year because you put it out there. Yeah, I think so. And then the other piece of just come prepared to a meeting and if you have a question, come with a perspective.
SPEAKER_00Yeah. How has that served you in work? Nothing specific that comes to mind, but a lot of times if there's weird stakeholder dynamics or like, you know, so and so's not responding to my emails, what do I do? You know, of okay, well, I'm having this challenge, getting a response. I've reached out and done this, this, and this. I'm thinking it might be helpful. Can I draft an email for you to reach out to them?
SPEAKER_01Brilliant. I love that. Okay. So throughout your career, can you tell me when has your inner critic or when has self-doubt shown up for you?
SPEAKER_00When hasn't it shown up? Is how I feel. I think it's definitely shown up in ebbs and flows.
"Do I Deserve to Be Here?"
SPEAKER_00Most noticeably, I think when you're transitioning out of this early career phase. And I think when you're early in your career, you're not expected to know anything, right? You're expected to listen, ask questions, absorb everything and learn. And then there comes this point which I don't think anyone ever really tells you you're in it, and it shifts. And then suddenly you're the person in the room that people are asking the questions. And that for me is when I think I experience the most self-doubt. You know, like why are people asking me this? Right. And then do I deserve to be here? Do I know the answers? So I always have to remind myself and trust myself, like you, you've been doing this for a long time. You know what you're talking about. You deserve to be here. You deserve this.
SPEAKER_01Yeah. For me, I always felt like I was the youngest one in the room. Yeah. And I remember when I was no longer the youngest person in the room. And I was like, holy shit, I'm the leader. It was just like a real mind fuck.
SPEAKER_00Yeah. It's like, I feel like I was in college five years ago.
SPEAKER_01Yeah, no, that really resonates with me. Okay. Well, you know, you said when you move out of your early career phase and you're now like in mid-career, your inner critic has shown up for you. How do you move forward even when your inner critic is talking at you?
SPEAKER_00Well, I feel like this is a hashtag not sponsored promo to Courtney's awesome circle, which I did in May, and I learned a lot of tools to apply this, right? I think what I probably do the most is just name it. Like call it out, recognize it's your inner critic, your self-doubt, and you know, say this is here, and maybe it's here because you think other people have more experience or you don't know, but call it out and then also anchor on the facts. Trust yourself that you're here for a reason. People want to hear what you have to say and to get out of your head. And we've talked about this before. Your inner critic is there, it's like a defense mechanism to protect you, right? If I look back on my career, so much of the growth has been through discomfort. And so much of that growth, my inner critic has been there alongside. So it's like a blessing and a curse, right?
SPEAKER_01I love that. So moving through, you just have to name it, this is what's happening, and then just remind yourself that I was invited to this table. People put me in this position. I deserve to be here, damn it. And the the growth through discomfort. I mean, that's that's how we do it, right? Like that's how growth happens. If you're comfortable, you're likely not growing.
SPEAKER_00Yeah. And I think naming it separates it from you because you can go down spirals so quick. And so recognizing and naming it helps you not spiral.
SPEAKER_01I love it. Naming it gives you the space to be like, I'm not it. That it is its own thing.
The Career Advice She Wishes She'd Heard Sooner
SPEAKER_01Brilliant. Um, if you were to start your career again today, knowing what you now know, what, if anything, would you do differently or try to do sooner?
SPEAKER_00I think I would tell young Kate to just chill. Like, don't don't worry as much that it all works out. In my 20s, I was so caught up of like, I need to be successful and grow my career, and that if I was doing something that that meant success when really I would just tell myself to stop and really enjoy that season more. I love that. So just chill and enjoy, enjoy where you are. Yeah.
SPEAKER_01Well, are you up for a lightning round with me?
SPEAKER_00Yeah, my heart's racing. Okay, let's do it.
SPEAKER_01Okay, here's my rules for a lightning round. Don't overthink. First thing that comes to your mind, there is no right or wrong answer. And everything I'm gonna ask you is related to work in person or virtual.
SPEAKER_00In person, because you always leave in person more fulfilled.
SPEAKER_01Least favorite office jargon.
SPEAKER_00Let's take this offline. Biggest workplace pet peeve. AI slop. Where everyone is just giving you regurgitated AI stuff to review and not reviewing it, and it doesn't make any sense.
SPEAKER_01Does that happen a lot?
SPEAKER_00More than you would think.
SPEAKER_01If you came with a warning label, what would it say?
SPEAKER_00It'll take her a while to open up, but it'll be worth it.
SPEAKER_01I know that to be true. My last question for you, it doesn't have to be a lightning round question. You can let it breathe.
SPEAKER_00What is bringing you joy these days? The sun in Seattle. It's almost summer. When sun comes out, it's like people are on steroids and so happy and coming out of hibernation. So that's what's bringing me joy.
SPEAKER_01Well, Kate, I so appreciate you doing this with me. Thank you. This was super fun for me. Um, one
Growth Lives Outside Your Comfort Zone
SPEAKER_01thing I'm taking away from this conversation is what you said about the recognition of you know you're growing when your inner critic is there. I think that's brilliant. So thank you for sharing that. And what I love to do to close out this podcast is to ask my guest if they have a toast that they would like to share with our listeners. Do you have like a favorite toast or something that you like to do?
SPEAKER_00Okay, I don't, but one of my sorority sisters really good friends from college is Norwegian, and so we obviously did a lot of toasting in college. Yeah. She would always say skull, which in Norwegian is cheers. Okay.
SPEAKER_01Well, let's do it. Okay. Skull. Skull. Cheers, my friend. Thank you.
SPEAKER_00Thanks for having me, Corney. This is fun.
SPEAKER_01Listeners, if anything that you heard today resonated with you, please do share this podcast with a woman that you love. And if you and I are not connected on LinkedIn, please come find me. I would love to say hi. I'm always listening. And yeah, until next time, we'll see you courtside. Cheers, y'all.