We were lucky to catch up with Kisha Wynter recently and have shared our conversation below.

Alright, Kisha thanks for taking the time to share your stories and insights with us today. Let’s start with the story of your mission. What should we know?

Whether we like it or not, work takes up a significant portion of our lives. Many of us spend the majority of our waking hours at work, so if we are unhappy there, it means that we are unfulfilled in a significant part of our life. My purpose is to help corporations and leaders create inclusive coaching cultures where all talent thrives, regardless of background, this helps everyone feel fulfilled and that they are unleashed to contribute at their highest potential

I spent many years in corporate HR, specializing in talent management and organizational development. As I climbed the corporate ladder and participated in numerous performance reviews, I repeatedly witnessed a troubling pattern: talented, hardworking women, particularly those from diverse backgrounds—whether based on race, age, religion, national origin, personality, socio-economic status, etc.—were often overlooked for opportunities and advancement due to a perceived lack of confidence or leadership presence.

What troubled me most was that despite their strategic thinking, strong performance, and exceptional work ethic, these women were often dismissed with the all-too-common critique that they lacked the confidence to “own the room.” I share this story in my forthcoming book, Your Power Unleashed: How Savvy Women Use Courage to Get Promoted, Get Paid, and Find Fulfillment. My frustration peaked during one particular performance review discussion where yet another brilliant woman was on the verge of being passed over for a promotion. As I listened to the misinformed conversation, I decided I had enough. Enough of hearing how brilliant women were living below their potential. Enough of leaders misdiagnosing the root cause of their timidity. Enough of their worth being summed up and discredited by one overly simplistic phrase—”lack of confidence.” And finally, enough of being told to “fix her”—as if she were broken. There was a huge disconnect. I realized that the issue wasn’t with these women—it was with the misunderstandings of various styles, a lack of deep relationships, and structural biases within the corporate structure.

Determined to make a difference, I decided to step away from working within organizations to create a boutique leadership consulting firm dedicated to addressing these issues. Through cultivating understanding, exposing evaluation blind spots, and garnering organizational support for women and anyone else who feels misunderstood or unseen, we aim to create real change.

As a coach, I believe that principles such as establishing rapport, creating psychological safety, providing a container of support, being curious, collaborating, and holding others accountable are not just nice-to-haves—they are essential for creating strong and healthy cultures at work.

I also believe that if we are ever going to create truly healthy cultures as leaders, we must have the courage to look within and lean into our own healing journeys. This self-reflection helps ensure that we don’t perpetuate trauma in the workplace. The more I engage in this work, the more I realize that dismantling oppressive systems is both an internal mindset endeavor and a matter of external systemic and cultural change. As the saying goes, “hurt people hurt people,” and in environments like this, no one truly reaches their full potential. However, I firmly believe that once the most powerful people tenaciously commit to doing the work, everything can and will change for the better.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I have already explained why I started my business, but how I got started in Human Resources was a matter of happenstance. As an immigrant and first-generation college graduate, I had no idea what to expect working in corporate. My first full-time job out of college was at a Fortune 50 company, and I will never forget when they decided to move our department from Stamford, Connecticut to NYC without giving us any warning. I found out on a Monday morning that we were moving the following Monday, which turned my 10-minute commute into a 90-minute commute.

I didn’t know much about corporate America, but I knew that how the situation was handled didn’t sit right with me. After commiserating overnight with my family, I notified them the next morning that I was going to resign. Yes, I gave them 4 days’ notice because they gave me 5 days’ notice of such a big move.

It was then that I was connected to my HR Manager for the first time. The way she handled the situation—apologizing on behalf of the leaders, listening, explaining, and even providing me with severance pay—made a profound impact on me. I decided in that moment that I wanted to work in HR so I could be an advocate for employees. And as they say, the rest is history.

At Wynter Rich Enterprises, we offer a range of services to help individuals realize their potential and help organizations create inclusive cultures. Our services include executive coaching, training, workshops, keynotes, and leadership programs.

What differentiates us is our holistic, heart-centered approach to leadership development. We don’t just focus on business metrics; we focus on the whole person. We believe that business provides the perfect platform for mission-driven and compassionate leaders to make an impact by doing more good in the world. The catch for leaders is that this good work starts with their own healing journey and the courage to look within. Transforming workplaces starts with the individual, and we create experiences through our training, workshops, and coaching for that reflection and action.

Seeing our clients thrive and knowing that we’ve helped create more inclusive, supportive workplaces is what drives me every day. Our work proves that being good to people is indeed good for business, and nothing makes me happier than witnessing the success of those we’ve had the privilege to support.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

My business started when I worked in corporate and saw a problem that the organization wasn’t able to solve: helping women succeed and advance through the leadership ranks. As a woman who had experienced similar issues that leaders were not handling well, I took it upon myself to create a solution. I developed a leadership program for women and coached their managers on how to lead and develop them. The program was a huge success, and I thought to myself, if this can work inside my company, why not see if it will work with people outside of my company?

I set up a blog, YouTube channel, and started posting on LinkedIn to attract coaching clients. In 2019, I launched my first group coaching program outside of my workplace. I coached the participants at night and even worked on weekends. Once I tested the idea and received raving reviews from the participants, I realized this was indeed a viable business idea.

Initially, I thought I would just coach individuals, but only a few months into my business, an organization overseas reached out to have me bring my coaching program to their company. I realized that by bringing this program into organizations, rather than only working with individuals, the impact could be multiplied.

Now, hundreds of people across the globe, from individual contributors to executives, have gone through my coaching programs. With all the learnings and experiences, I have decided to take the next step and put them into a book, “Your Power Unleashed: How Savvy Women Use Courage to Get Promoted, Get Paid and Find Fulfillment which has been a lifelong dream of mine.

How’d you build such a strong reputation within your market?

The results speak for themselves. From the very beginning, my focus has been on delivering tangible outcomes for individuals and organizations. Whether it was the initial success of the leadership program I created within my corporate role or the raving reviews from my first group coaching participants, the consistent positive impact of this work has been the cornerstone of my reputation.

Clients have seen real, measurable improvements in their careers, confidence, and workplace cultures, which has led to word-of-mouth referrals and a growing demand for my coaching programs. I left working inside organizations five years ago, and even this week, it blows my mind that someone I previously worked with reached out to me for coaching.

I have learned that when people feel seen, understood, and cared for, and you supplement this with effective strategies, they remember for years to come. By consistently helping clients achieve their goals and overcome challenges, I’ve been able to build a strong reputation based on trust, effectiveness, and genuine transformation.

Contact Info:

• Website: https://www.yourpowerunleashed.org/corporations
• Instagram: https://www.instagram.com/kishawynter/
• Linkedin: https://www.linkedin.com/in/kishawynter/
• Youtube: https://www.youtube.com/@KishaWynter

Image Credits

The personal photo then images 2 and 3 from the second page are Hector Pachas Photography.