Are you someone who has received so many accolades for your work, and you constantly perform at a high level, so from all appearances, you’re crushing it? Like people are always impressed by your job, the things you’ve done, and wonder how you do it all?
But inside, you still feel like it’s all a bit of a sham, that perhaps you don’t deserve the titles and positions, and you’re secretly worried that some day you’ll be found out?
Then this is the episode for you!
Today, Kisha Wynter, an experienced executive leader and coach, shares what it’s like to overcome imposter syndrome, how to reclaim your own power in tough work environments, and how women in particular can advance their career and still feel fulfilled.
We discuss some of the most common self-sabotage patterns, laid out in Wynter’s new book, “Your Power Unleashed: How Savvy Women Use Courage to Get Promoted, Get Paid, and Find Fulfillment,” and how to get over patterns like procrastination.
“The legacy we leave behind is shaped by the stories we tell ourselves and the actions we take. People like Connie Chung inspire us to recognize our power and use it to create lasting change.”
“To move beyond our limiting beliefs, we need to examine the narratives that hold us back and restructure our time management to integrate what matters most without compromising our responsibilities.”
“Accountability and community are pivotal in overcoming inaction. Just like in physics, it’s hardest to start, but once you find momentum, staying in motion becomes so much easier.”
“Women, especially in corporate settings, often feel pressured to adjust their communication styles to be effective. We must learn when to adapt and when to leave environments that don’t appreciate our contributions.”
“Self-worth isn’t just about recognizing your own value; it’s also about advocating for yourself in the face of systemic barriers. As women, especially women of color, we need to learn to communicate our brilliance without feeling like we’re bragging.”
NICOLE
Hello, friends! Welcome back to another episode of the School of Self-Worth. I’m your host, Nicole Song. This week, we have a fantastic guest, Kisha Wynter, who is here to discuss her new book, Your Power Unleashed: How Savvy Women Use Courage to Get Promoted, Get Paid, and Find Fulfillment. Kisha speaks directly to the heart of what I’m passionate about. As a leadership consultant and executive coach, she brings a wealth of knowledge from her extensive experience in corporate America, particularly in HR. She has so much wisdom to share with all of you.
I’m really excited to have her on the show. Before we dive in, if you are a high-achieving Asian American corporate leader looking to break through invisible cultural barriers and step into your full power, DM me “power,” and let’s chat. Okay, friends, let’s get into this amazing conversation!
Welcome to the School of Self-Worth, a podcast for ambitious women who know they are worthy of an astoundingly great life. Join us weekly as we align with our intuition, redefine success, and reclaim our self-worth. I’m your host, Nicole Tsong, an award-winning journalist who left it all behind to become a bestselling author of three books and a work-life balance expert, helping ambitious women unlock their intuition and step into a life of fulfillment and radical joy.
Every week, I bring you diverse and meaningful conversations with successful women from all walks of life, sharing insights about what it takes to be brave, joyful, and authentic every day. Each episode is thoughtfully designed to leave you feeling empowered with tangible tips and advice that will lead you to your next breakthrough.
Kisha, thank you so much for being on the School of Self-Worth. Welcome!
KISHA WYNTER
I am so excited to be here, Nicole. Thanks for having me!
NICOLE
I’m thrilled! I’ve been reading your book and truly loving what I’m discovering. Kisha and I were connected through another guest on the show, and as I read your book, I felt you were such a perfect fit for our discussions about self-worth, especially for women in their careers. My focus is specifically on Asian American women, but your work aligns beautifully with what we do here. I’m excited to have you with us!
KISHA WYNTER
Yes! I’m excited to share, and I’d love to hear what resonates with your audience or what might be different for them. I see this as a great exchange.
NICOLE
Absolutely! Can you start by telling us a little about yourself? Give us an introduction to who you are and what you do.
KISHA WYNTER
Sure! My name is Kisha Wynter, and I’m a leadership consultant and executive coach. In just two days, I’ll be a published author, so by the time this airs, I will have released my first book!
NICOLE
Amazing!
KISHA WYNTER
I know you have three books already, but this is my first, so I’m just beginning this journey, which is incredibly exciting for me. I spent 20 years working in Fortune 20 companies in various roles within human resources, including organization talent development, compensation and benefits, and HR business partnering. Most of my experience is in financial services, but now, as a leadership consultant, I touch all sectors.
I live in Stamford, Connecticut, which is about 45 minutes north of New York City. I’m originally from Jamaica, and I’ve spent most of my life in the U.S. So, here I am on your podcast!
NICOLE
I love it! That’s awesome. I was just in New York and left Long Island on Friday. It’s a big journey across the country from Seattle, so it’s fun to connect this way.
I have so many questions for you, but I’d love to start with a question I often ask my guests about their self-worth journey. You focus heavily on the experiences of women in the workplace. What would you say was your pivotal moment? In your book, you discuss being in higher positions in HR and helping women advocate for themselves. Where did your journey begin?
KISHA WYNTER
I have a key moment to share. I’ve worked in corporate settings, reaching senior leadership roles. You might look at my journey now and think, “Oh, she has her own company, coaches leaders from over 50 countries, and has a book coming out.” But when I started in corporate, I never thought leadership was in the cards for me.
When I looked at the top of organizations, the people there didn’t look like me—they didn’t sound like me or share my personality. I consider myself more of an introvert. Most people had parents who graduated from college; I’m the first in my family to do so. As the oldest, I didn’t see any representation at the top, which made me feel unworthy and like I didn’t belong. Many times, I was the only one in the room with my background.
A specific moment stands out. I was in my twenties when a senior executive approached me. He had a large team, and I was his HR business partner. I was still fairly new to the organization and the role. He asked me to come to his office for a deep dive on his staff and provide an assessment of each person. I was shocked by his request. I thought, “What can I tell you that you don’t already know?”
As I walked into his office, my palms were sweating, and my heart was racing. I thought he would listen for five minutes and then kick me out when he realized I didn’t know what I was talking about. Despite feeling nervous, I pushed through because that’s what we do—we learn to push through our feelings.
To my surprise, he was keenly listening and furiously taking notes. I thought, “What is he writing down? I’m not saying anything mind-blowing!” This made me realize how often we underestimate our own experience and brilliance while simultaneously placing others on a pedestal.
Fortunately, after that meeting, I heard him credit me for my insights. He was literally repeating some of the things I said to senior leaders and even the CEO. That day, a light bulb went off—I realized I was good enough, I belonged at the table, and I was capable of influencing and leading it.
I also recognized that I wasn’t just ready to talk to the boys’ club; they could learn a thing or two from me. The real imposter wasn’t the feeling of inadequacy; it was the voice in my head telling me I wasn’t good enough. I had to figure out how to turn that inner critic into an inner mentor or coach and own my inner brilliance.
As I overcame these challenges, I began to notice that many people, especially women, were shrinking from their brilliance and power. I developed a passion for helping women in the corporate space stand in their unique brilliance. That’s a bit about my journey.
NICOLE
Thank you for sharing that! I love hearing stories about pivotal moments and how you start to recognize your divine light and inner power. It’s often not about others’ perceptions, but rather about owning our worth first. I appreciate how your book addresses systemic issues while emphasizing the importance of self-recognition.
KISHA WYNTER
Exactly! It’s about agency. While there are systemic issues, there are times when we have no control over those factors. My focus is on how to validate myself. If I’m not receiving external validation, how can I nurture my self-confidence and self-worth? That’s where true power lies. If you can maintain that sense of self, despite external circumstances, you’re on the path to being unstoppable. Ultimately, we all have choices about where we work and live.
NICOLE
I completely agree! I’d love to discuss the unique challenges faced by daughters of immigrants, particularly in the workplace. Many of my Asian American women clients encounter interesting blocks. Can you speak to that experience? Growing up in one culture while navigating another can be tough.
KISHA WYNTER
Absolutely. There are two significant factors. First, there’s the value of humility. I was raised to be humble, to put my head down, and to believe that hard work would speak for itself. This was instilled in me: execute, deliver results, and you’ll be recognized. However, in corporate America, that’s not always the case. If you don’t advocate for yourself and bring visibility to your work, you may get left behind.
Coming to terms with this was difficult for me. I would go home every day thinking, “I just worked hard; why aren’t people recognizing me?” Meanwhile, someone who wasn’t working as hard might be golfing with the boss and getting promoted simply because of their connection. This cultural value was a challenge for me.
The second factor relates to my childhood. I came from a country where I was in the majority, where everyone looked like me. Arriving in the U.S., I didn’t see myself as a minority; globally, we are not the minority. Initially, I had more confidence, but entering the workplace made me aware of societal narratives that suggested I was a woman of color and wouldn’t be able to reach the top. The statistics are stark—only 7% of women of color hold C-suite positions. I had to unlearn many beliefs I had adopted.
NICOLE
Thank you for sharing that. It’s interesting how many women feel they should just work harder instead of learning to advocate for themselves. But when you do that, you often end up working less if you learn to work smart!
KISHA WYNTER
Exactly! Working hard is important, but working smart is crucial. Women often become the “worker bees” and end up with more execution tasks instead of being involved in setting strategy or leading. They hit a ceiling where they are seen as dependable, but not as decision-makers.
NICOLE
And then they miss out on leadership advancements. For Asian American women, that number is even smaller than 7%. How do we start to shift that?
KISHA WYNTER
That 7% includes all women of color, and I believe it’s around 2% for Asian American women.
NICOLE
Right, which is shockingly low. You mentioned humility, which resonates with me. How did you reconcile the need to be humble and nice while also advocating for yourself confidently?
KISHA WYNTER
Initially, I didn’t frame it as power. I thought about it practically. When I’m excited about something—like a movie or a book—I’m not shy about sharing that enthusiasm. I realized I could bring that same energy to my work without feeling like I was bragging. I was simply sharing my excitement.
People are receptive to genuine passion. If my motive is authentic, people respond positively. For example, I developed a program called “Own Your Power” in corporate settings to address challenges women faced. Sharing the success stories of women who embraced their power helped others see me as someone who could solve problems.
As someone more introverted, I found it exhausting to be outgoing all the time. Instead, I would have one-on-one conversations with people in positions of power to naturally share what I was working on. This consistent engagement helped them become my advocates when I wasn’t in the room.
NICOLE
Thank you for sharing that insight!
KISHA WYNTER
That’s the second strategy I employed—to ensure I communicated my work to influential people and leveraged them to gain visibility in spaces where I wasn’t present.
NICOLE
You have so many great tips in your book! One challenge for women is finding the balance between confidence and the fear of being perceived as aggressive. What would you say to women navigating that line?
KISHA WYNTER
It really depends on the scenario. I’ve experienced how passion can sometimes be misinterpreted as aggression. I recall a meeting where I was discussing budget needs, and a leader commented on my smoothie, saying I was “like the Incredible Hulk” and needed to calm down. I wasn’t angry at all!
In situations like that, I focus on effective communication. I identify what’s important to the other person and frame my message accordingly. Instead of saying, “We won’t meet the budget,” I might say, “I know it’s important for you to present well to the CHRO, and this news may not be what you want to hear, but…” This approach helps the other person feel supported and receptive to my message.
NICOLE
It’s interesting how often people want to place blame elsewhere. But you can shape the conversation to work in your favor.
KISHA WYNTER
Exactly! It’s important to assess your goals. There are times when I challenge the system, especially when I see bias in promotion discussions. I’ve pointed out discrepancies when similar behaviors are perceived differently based on gender. However, it’s exhausting to fight that battle daily.
Ultimately, we need to adjust our communication styles to be effective in our environments. I had a leader who struggled during an international assignment because he didn’t adapt his style to the local culture. You have to read the environment and adjust to be effective.
If you feel you can’t adjust or influence the organization, sometimes the best option is to find a place that appreciates you for who you are. We all have choices to make.
NICOLE
I appreciate that perspective. You’re choosing to be in your current situation, so you can either fight against it or focus your energy on where you want to be.
I used to be a journalist, and I remember feeling miserable toward the end of my time in newspapers. I had to choose to accept my circumstances while I figured out my next steps. Once I accepted that, I found peace in my situation instead of resisting it.
KISHA WYNTER
Exactly! When it no longer worked for me, I made the choice to leave.
NICOLE
I love that. I wanted to pivot to something I found fascinating in your book: self-sabotage patterns. You identified several, including indecision, disorganization, overthinking, rigidity, playing small, and procrastination. I thought, “Wow, you’ve listed everything!”
I’m curious how you frame these patterns. For example, instead of just labeling someone as a procrastinator, how can they recognize they might be in a self-sabotage pattern?
KISHA WYNTER
Great question! I often ask myself, “Why am I not doing this task? It might take me 20 minutes, but I’ve been thinking about it for two days.” I encourage my clients to ask themselves what they’re afraid of. If the answer involves fear of failure, looking bad, or making a mistake, then it’s likely a self-sabotage mechanism.
Procrastination often serves as a coping strategy for stress, which stems from fear. I don’t believe anyone is inherently a procrastinator.
NICOLE
I’m glad we’re discussing procrastination because I can relate to it, especially with my next book. When I ask myself what I’m afraid of, I realize I fear my business failing if I focus on the book, or that the book itself will fail to meet my expectations.
KISHA WYNTER
That’s a common fear! It’s interesting how putting strategies in place can trigger anxiety about actually following through.
NICOLE
Exactly! We could talk about procrastination all day!
KISHA WYNTER
All day, yes.
NICOLE
But I’m curious. At this point, you see what you’re afraid of. The hardest thing for most of us is getting into action. I have an action strategy from a friend who’s a coach for this particular issue, but I know from experience—both mine and my clients’—that it’s often really hard to move into that action. You address this in your book. How do you think about it when you’re at that point where you need to take action on something you’ve been putting off?
KISHA WYNTER
Right. I think there are a few key points. First, identify the story you’re telling yourself about the situation. You may have the strategy, but sometimes just having a strategy isn’t enough. We all know the basics—like eating less to lose weight or moving more. We know the strategies, but there might be a belief system in place that feeds into our hesitation.
For instance, if you think, “If I don’t write this book, my business is going to fail,” ask yourself why you believe that. Is it true? Did your business fail when you wrote your other books? Reflect on what worked in the past. It’s about recognizing those mindset shifts. For example, if you organize your time properly and dedicate a reasonable amount of time—maybe an hour a day or 20 minutes a day—to writing, will it really impact your business negatively?
Once you identify something that helps shift your mindset, you might need to work with a coach to facilitate that change. Next, consider accountability. Sometimes, even when your mindset has shifted and you’re ready, you still hesitate. Find someone you don’t want to disappoint.
Once you take that first step, building momentum becomes easier. It’s like the physics principle: an object in motion stays in motion, while an object at rest stays at rest. If you’ve been inactive for a long time, starting can be particularly challenging.
NICOLE
Totally.
KISHA WYNTER
So, gather your community, seek accountability, and just get started. That initial step can be tough, but pushing through is essential.
NICOLE
I always think about that. I’m a big advocate for physical movement, and I know that many people struggle to get motivated. I do too. But I often remind myself, “You don’t have to think about how you’ll feel at the end of the workout; just focus on putting your shoes on and leaving the house.” Once I put my shoes on and step outside, it’s hard to back out of going to the gym. By the time I’m there, I think, “Well, I’m here now, so I might as well do the workout.”
It’s about identifying that one thing that helps you swing in the right direction. I love that idea. You don’t need to be a physics expert to understand it; it’s beautiful.
KISHA WYNTER
Exactly! Even in the book Atomic Habits, James Clear emphasizes just taking that first five minutes to get started.
NICOLE
Yes!
KISHA WYNTER
Put on those sneakers and go!
NICOLE
Exactly! I feel like I could ask you so many more questions, but I want to focus on one that I think will help people: defining what power means and how to stand in your power. If that’s the crux of everything you’re teaching in your book, how do you think about power for yourself?
KISHA WYNTER
It really comes down to agency—what’s within your control. I believe that everything we truly want in life is within our control. Often, we give our power away by thinking, “This isn’t going to happen for me.”
For me, I know I would never have been able to advocate for women who were held back in the workplace if I hadn’t first owned my own power. I motivate myself by recognizing that even if I can’t do it for myself, I need to learn how to own my power. There are family members, parents, children, and people I love who I want to see succeed. If I’m not walking in my own power, I can’t share that power with anyone else.
For me, it’s about agency. You have to own it first. If you look at my book, the first section is called “Own Your Power,” and the second part is about unleashing it. You can’t unleash your power if you don’t own it first.
NICOLE
I think about all the women who have owned their power. Where would I be without them? Recently, I saw Connie Chung on her book tour. What if she hadn’t fought against those awful newsrooms in the seventies, where she was often the only woman—and a woman of color? Most of us wouldn’t be where we are today without those choices being made.
KISHA WYNTER
Fun fact: as a child in Jamaica, I wanted to be a news anchor.
NICOLE
Oh, really?
KISHA WYNTER
Yes! Connie Chung was the person I looked up to and said, “I want to be like her when I grow up.”
NICOLE
Totally! Who didn’t? She was so driven. You talked about values in your book too. She was driven by her values and her desire for that job. She faced horrific stories but was determined to succeed at all costs. It was just her and Barbara Walters—there were no other women. They paved the way for us. I often think, if more of us were determined, what could really happen in the world?
KISHA WYNTER
Absolutely.
NICOLE
In this world and life we live, you have to show up consistently. It may look easy from the outside, but it takes effort to show up consistently. I think about my five-year-old niece and other women coming after me. If I keep doing it, it gives them permission to do it for themselves too.
KISHA WYNTER
Exactly! You’re making the world a better place and paving a path for others. It’s a significant part of our legacy. If it weren’t for women like Connie Chung, we wouldn’t be as motivated today.
NICOLE
Oh my gosh, truly!
KISHA WYNTER
So…
NICOLE
Well, this has been such a fun, powerful, and impactful conversation, Kisha. Now it’s time for rapid-fire questions!
KISHA WYNTER
Yes, I’m ready!
NICOLE
Great! First question: What was the last thing you watched on television?
KISHA WYNTER
Oh my gosh, what’s the name of that show? It’s on Netflix, Nobody Wants This. Have you seen it?
NICOLE
No, I haven’t seen it.
KISHA WYNTER
It’s with Adam Brody. If anyone used to watch The OC, they’ll recognize him. It’s a romantic comedy, and it is so funny and good!
NICOLE
Yeah, I’ve heard about it but haven’t seen it yet.
KISHA WYNTER
I love it! It warms your heart.
NICOLE
Awesome! Next question: What’s on your nightstand?
KISHA WYNTER
I have three books there. One is Atomic Habits, which I keep going back to because I’m always trying to recreate my habits. The second is my own book, Your Power Unleashed, which I keep in front of me because I’m always doing the exercises. Chapter five focuses on being bold, audacious, and courageous. The third is a spiritual book called 100 Days of Believing Big.
NICOLE
Fun! I love book recommendations. I find that I read more than I watch TV, but I think TV can be illuminating in its own way.
KISHA WYNTER
Books are definitely better than TV! I need to spend less time on TV and more on reading. I used to spend whole weekends reading as a kid, but I can’t do that anymore.
NICOLE
Totally!
KISHA WYNTER
Yeah, I just can’t.
NICOLE
You just need a little accountability and motivation. I was doing a book challenge with my local library and read so much, but once it was over, I only read two books!
KISHA WYNTER
That’s a great idea! Join your local library.
NICOLE
Yeah, a little book challenge! Okay, next question: When was the last time you tried something new, and what was it?
KISHA WYNTER
Well, besides writing a book…
NICOLE
Writing a book totally counts!
KISHA WYNTER
Okay, I’ll include that. But I want to mention something else. I’m really focused on taking care of my mind, body, and spirit. I was doing well in 2020 because I was scared of getting COVID. Since then, I’ve started a new way of eating called the nutritarian diet, which focuses on getting a lot of micronutrients through whole food plant-based vegetables and fruits. I feel very energetic, and I’m hoping to stick with it.
NICOLE
Sounds lovely! I love that. Okay, last question: What are your top three most used emojis on your phone?
KISHA WYNTER
Oh, all right! My favorite emoji is the stars—the little three stars. I always think of Rihanna’s song, “Shine Bright Like a Diamond.” That’s one. The second is the red heart; I also use the pink heart sometimes because I don’t want people to think I’m overly sentimental, but I love red. And the third emoji is the laughing emoji—the one where the head rolls over. I just love those deep belly laughs!
NICOLE
Amazing! I love that.
KISHA WYNTER
Joy!
NICOLE
This has been so fun. Kisha, we’ll definitely link your book in the show notes, but what’s the best way for people to find out more about you?
KISHA WYNTER
The best way to connect with me is on LinkedIn; just look for my name, K-I-S-H-A W-Y-N-T-E-R. That’s my main platform. I’m also on Instagram, so feel free to follow me there.
NICOLE
Great! Make sure to check out her book; we’ll link it below. Congratulations on getting it out into the world! It’s like birthing a big child, so good job on that.
KISHA WYNTER
It truly is like birthing a baby! The book is called Your Power Unleashed: How Savvy Women Use Courage to Get Promoted, Get Paid, and Find Fulfillment. You can find it on Amazon.
NICOLE
Make sure to grab a copy! Thank you so much, Kisha, for sharing your wisdom with us on the School of Self-Worth. I am so grateful.
KISHA WYNTER
I am so grateful too. Thanks for having me!
Thank you for tuning into today’s episode. Before you go, if you are a high-achieving woman wanting to uncover your biggest blind spots preventing fast, intuitive decisions, I have a 72-second assessment for you. DM me “quiz” on Instagram at @NicoleTsong.
Thank you for being here and for listening. We read every note we receive about how the podcast is making a difference in your life. Please know how much we appreciate each and every one of you. Until next time, I’m Nicole Tsong, and this is the School of Self-Worth.
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