Aug. 6, 2024

Living the dream with the founder and CEO of Wynter Rich Enterprise and executive coach and leadership consultant Kisha Wynter

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In this episode of Living the Dream with Curveball, host Curveball sits down with Kisha Wynter, an executive coach, leadership consultant, and the founder and CEO of Wynter Rich Enterprise. With over two decades of experience working with Fortune 500 companies and developing leaders in over 50 countries, Kisha is a trailblazer in women's leadership and strategy. She shares her journey from corporate HR to launching her own coaching business, and discusses the cultural nuances of leadership across different countries.
www.yourpowerunleashed.com
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> Curtis Jackson>Welcome, to the living the Dream podcast with Curveball. if you believe you can achieve Chee Chee, welcome to the living the dream with Curveball podcast, a show where I and a few guests that teach, motivate, and inspire. Today I am joined by Arthur by executive coach and leadership consultant and founder and CEO of, Winter Rich Enterprise, Kesha Winter. Keisha has over two decades of experience with Fortune 500 companies.

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> Curtis Jackson>She has an amazing track record of training and developing leaders in over 50 countries. And as I said, she's a trailblazer in women's leadership and strategy, and she wants to make everybody thrive, no matter what culture. So we're going to be talking to her about everything that she's up to.

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> Curtis Jackson>She also has a book coming out pretty soon. So, Keisha, thank you so much for joining me today.

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> Kesha Winter>Thanks for having me, Curtis. I'm so excited to be here.

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> Curtis Jackson>Why don't you start off by telling everybody a little bit about yourself?

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> Kesha Winter>Yeah, you said it all. I'm a leadership development consultant and executive coach, and I work with, corporations, mainly big organizations, but small one as well, to help them develop both their leaders and employees so that they can create transformative cultures where people of all background can just thrive and contribute and live out their full potential, making their biggest impact at work. That's my vision.

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> Kesha Winter>That's what I do.

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> Curtis Jackson>Okay, so tell us how you got your started as an executive coach and leadership consultant.

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> Kesha Winter>So I had, 20 years of, human resources experience in corporate. So I've been doing my own business since 2020. So it is four years now. But I'm not new to the practice because I was in leadership development in corporate, corporate, in HR for 20 years.

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> Kesha Winter>And so I, you know, I was in organizations, and I realized that a couple of things that were taking place. One, this consistent feedback that leaders would give around individuals in the organization, that they were, you know, really good at their jobs, deep domain expertise. But when they got to a certain level within the organization, a lot of times it was middle management or breaking into their first executive level position.

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> Kesha Winter>You would hear that this person has all the domain expertise, all the skill set needed to be successful. But the one thing they don't have is leadership or executive presence or even the ability to influence and communicate well.

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> Kesha Winter>These are the soft skills that a lot of people don't have to get to the next level.

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> Kesha Winter>And they would boil it down, especially if we talk about women. Oh, you just need to tell this person to be more confident. And I said to myself, I said, well, that's not really helpful. Just to tell somebody to be confident so that they can get to the next level. What are the tactical and the practical steps that they can take to show up in their power, to show up in their presence? really just demystifying what it takes to get to the top. And so I decided while I was in corporate, there was a problem, and I decided to figure out how to solve it. And I thought to myself, well, I went through this in my life, how did I overcome these things?

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> Kesha Winter>And I developed an entire program for the leaders within the organization that I was working with. And these leaders were considered high potential, but it's that feeling of self doubt, fear, and imposter syndrome that was getting in the way of their effectiveness. And as a result of me doing it was so impactful and great within the organization. I actually had a, ah, c suite executive tell me when I was preparing to speak on stage and at an event in that corporation that says, well, forget about this company, you need to go do a TED talk, which I will do in the future. and also you need, you know, you need to go out and, you know, share this with the world. And so I thought to myself, I said, well, not only will I do a TED talk and share it with the world, but this might be a really good business concept. And so I decided that when I was still in working in corporate, I would start coaching people on the nights and the weekends, and people were able to get results from it. And so in 2020, January 1, 2020, I decided to take the leap out of corporate and start my own practice and business, helping leaders thrive and get to their next potential. And my book that's coming out, which will eventually talk about, specifically talks about how women do it, but really, I market to women. But the truth is, all these principles are applicable to people of m all backgrounds, regardless of gender. I coach men, I coach women and all of that. So while I may refer even in discussion, to impostor syndrome, self doubt, fear, it's not a woman's issue. Everybody goes through it. And so the principles apply to everyone.

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> Kesha Winter>So that's how I got started in my field.

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> Curtis Jackson>So. And you are so impactful that you have trained, and developed leaders in over 50, ah, different countries. So kind of tell us about that and kind of how it might have been different from country to country.

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> Kesha Winter>Yeah. So really and truly, when I started out in this field, when, I was again back in corporate, when I designed the program, it was a global organization to begin with.

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> Kesha Winter>And so I was already working with people that were global. And it's funny, right? It's interesting because a lot of times we look so much at our differences as individuals that we don't really recognize that we have a lot of things in common, right? A lot of people, most people want to belong. They want to have a sense of belonging. They want to feel like their contributions are valued. And a lot of us have this feeling of insecurity, that we're not good enough, that we're not smart enough.

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> Kesha Winter>Regardless of all of our credentials, regardless of everything that we've accomplished, when we're stepping out of our comfort zone and trying to play big, this self doubt, this fear comes up and it causes us to shrink. So, for me, the feeling that people get is across the board, regardless of nationality and background.

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> Kesha Winter>Having worked with people from so many different nations, however, how people are assessed in terms of effectiveness and what we decide is effective, as at an organizational level, it doesn't always take into consideration different cultural ways of doing things. So, perfect example. This is maybe one of the most powerful examples or clear examples that I can give. a lot of times, most of the organizations that I work with, they're headquartered in the US. And so even if it's global, they're assessing people based on western driven values. And, for example, in a lot of western. In the US, we talk about leadership presence as the person who is, you know, the most outspoken, sometimes the loudest in the room, the person that is the most assertive and can own a room and own the stage, and, you know, the person who is communicating the most. But in other cultures, when I work with people from different asian countries, for example, just the opposite is valued. It is the person that's quiet, that's listening, that has deep thoughts that they can share, but it is not necessarily done in a loud or, even sometimes what I would say, a boisterous way. And so when we assess these people in organizations, we put them to our standards and into our values and not ask the question whether or not it's a stylistic thing or whether or not they're actually being effective. And so that is where I see the difference. I don't think the feelings of belonging and wanting to feel like you're accepted changes by culture, but it is about how each culture considers what is effective.

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> Kesha Winter>And that is what I work with organizations and leaders on. Like, it's not so much your style. That is the question.

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> Kesha Winter>Because, frankly, everybody has to learn to flex their style based on the situation that they're in. It could be in order to influence somebody in a specific organization, you have to be more assertive, like we talked about. On the flip side, being confident and assertive is not the thing that will swing everybody. It could also be that you need to be able to present data. And some people, let's say you're an engineer or, somebody in finance or accounting background, all the confidence in the world doesn't matter if you don't have data and information. On the flip side, people may be feeling so demoralized that you could give them all the data in the world, but you need to have an inspirational style to bring the morale up. And so what I say to people, it's not about right or wrong in terms of how you influence. It's actually identifying what is needed for the situation that you're in. And be able not to just use your default way of showing up, but flexing your style in order to be effective for the situation that you're in. And there's, a very popular Harvard business review article called what's your influence style that I love to refer people to around this topic, because it really breaks down five different ways of influencing and saying. There's no right or wrong. It's about how effective are you at, not going to your default, because we all have defaults. How effective are you to flex the style based on the situation that you're in in order to drive the outcome?

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> Curtis Jackson>So what's three ways that people out there listening can go from invisible to credible at work?

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> Kesha Winter>Okay, I love this question.

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> Kesha Winter>Well, I'm going to say, first of all, in order to be invisible to credible at, work, it's about communicating with impact.

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> Kesha Winter>And so one of the things that I tell people all the time, in order to communicate with impact, you have to be clear about what the message you're trying to get across.

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> Kesha Winter>Clear and even confident. That's the first thing. The second thing that you have to do in order to be effective is that you've got to slow down. Sometimes we speak so fast that people are not able to process what it is that we're saying. And using pregnant pauses is what I call slowing down your speech so that people can keep up with you, so that they can process, so that you're not overwhelming them with too much information helps credibility to be in place even beyond the confidence which I just talked about.

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> Kesha Winter>Right. So that silence is really, really important. And the third thing is speaking in bullet points. And I just did it.

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> Kesha Winter>I gave you three things right. And this is a big trick that a strategy, I should say, that people are able to use is that if you want people to actually listen to what you're saying and your push, like, there are three things that I have to say.

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> Kesha Winter>They're going to stay to the third point because they don't want to miss out on the last thing. So it's speaking in bullet points and not just throwing out all the information.

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> Kesha Winter>Because when you throw out all the information, you lose people.

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> Kesha Winter>Right. One of the ways not to lose people is to slow down, but the other way is to speak in bullet points or highlights. It's just like thinking about reading a newspaper article versus a paragraph. You remember the highlights.

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> Kesha Winter>And so what are, like, we talked about, what are the three ways? Here are the three ways. And so that's the third. That's the third way. Speaking in bullet points and not in paragraphs. So those are the three ways to go from invisible to credible at work.

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> Curtis Jackson>Well, I know everybody wants to get paid. They want to get the promotions and find fulfillment at work. So what are some of the best practices or tips you can give people to be able to do that?

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> Kesha Winter>All right, so the first thing, because it's paid promotion and fulfillment, right. Those are the three things we just talked about. And I'm going to start with the fulfillment first because I really just started with this idea of overcoming self doubt and fear.

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> Kesha Winter>And I'm going to tell you a little bit of story about myself on, even why I was able to write this program for women in organizations and people of all background in organizations is because when I entered into corporate at an early age, I didn't feel good enough. I didn't feel smart enough.

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> Kesha Winter>And so I had this, you know, even now, you hear talking about, oh, you run an organization. You've coached people from over 50 countries globally. You have a book coming out. Wow, that's so impressive. But it wasn't always this way for me. The thing that got me really, was when I stepped into corporate, I was the first person in my family to graduate from college. So when I looked up, I didn't think that I was the type of person that could be in a leadership position. And then I thought about, oh, my gosh, like, you, you're a woman, you're a person of color, but. And you have an accent and all the things. You're an introvert, which I am. And the people that are in leadership are the most extroverted people out there. And I don't know if your audience identifies with any of it. You just think that you fall below the standard. And it came to a pivotal point for me one day when I was going to a leader's office, he asked me as a c suite executive again, I was early in my career to give him an assessment of the people in his organization.

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> Kesha Winter>And in my mind, I started thinking, you know, am I going to be able to add any value to this person? Is he going to think that I don't know what I'm talking about? You know, that impostor syndrome was really attacking me in my head. And I went to the office scared, but I pushed through, and I thought, he's not gonna.

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> Kesha Winter>He's just gonna dismiss me. He's not gonna listen.

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> Kesha Winter>But his response took me by surprise. Cause not only he was listening to me as somebody that was early in her career, but he was furiously taking notes. And then after the meeting, I heard him quoting me in meetings. And you know, what stood out to me that day was that sometimes we undervalue our own brilliance because it comes easy to us, and we. We don't recognize that it's absolutely game changing to someone else. And that was the day something in me shifted that my difference, is not a liability. It's an asset. It's a differentiator. And not only was I good enough to sit at the table, I was capable enough to lead it. Not only was I ready to play with the big boys, as they would say, but they can learn a thing or two from me, just like I was learning from them. And that is why you asked me in the beginning why I do what I do. That's why I now work with corporate professionals to help them really turn that inner critic into their inner coach, to learn how to stand in their unique brilliance and really to own their power and unleash it, which is the topic of my book.

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> Kesha Winter>And so, going back to this, the first thing that you want to do to find fulfillment is really understand your worth, really understand the value you bring to your table. To the table. It's one thing I was just telling a client just before this call, it's one thing to try to get other people to validate you. But when you're not getting that validation externally, brothers and sisters, sons and daughters, you've got to learn to validate yourself. So that's the number one thing I would say on the fulfillment piece.

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> Kesha Winter>The biggest piece is the fulfillment. And then the final piece, I'm just going to give you, you know, one quick tip around salary negotiation, because it's promoted, paid, fine, fulfillment. I started with fulfillment first.

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> Kesha Winter>The point I'm going to make around getting paid your worth. The first step, I already said, you've got to know your strengths, you got to know your values, you got to know what you bring to the table, and you have to own it, because if you don't own it, you're not going to feel comfortable and confident to go in and ask for what you want. Once you make a list of the strengths and also the impact that you bring to a company, the impact could be that you save the company money through efficiency and productivity. It could be that you increase morale if you're in an HR function or you're a leader, you know, it could be that you brought in revenue if you're in sales, marketing, or some commercial role, but be able to quantify the benefit that you've brought to the company so that you can initiate a discussion with leaders and organizations to say, okay, I'm not asking for charity here.

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> Kesha Winter>I really enjoy the opportunity of working in this company because you want to start positive on a positive note. And I want to discuss with you what are the ways to be considered for a salary increase, because here's the data on the impact that I've made. And so really knowing the value that you bring, being able to communicate it so that you can present a business case on why it makes sense for you to get a salary increase, that's a data driven, business case driven way to negotiate your salary and promoted.

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> Kesha Winter>I'm going to give you one tip on the last point, which is, how do you get ahead and advance professionally in corporate?

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> Kesha Winter>It's really when I was raised as somebody from a working class family growing up, I don't know about you, Curtis, but you might have been, taught the same thing.

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> Kesha Winter>Just your hard work will speak for itself.

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> Kesha Winter>Put your head down and just get results.

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> Kesha Winter>And, you know, that's good if you want to get the job and not get fired. But that strategy alone is not going to get you promoted. And what's going to get you promoted. First of all, you have to read the whole book to understand all the steps. But I'll give you one step right. It is that you have to be able, in addition to communicate the value that you bring, you've got to build a strong network with people that can mentor you and teach you the ropes to get ahead. And also, people that are going to be advocates for you that can, they're in positions of power. They can open doors for you that you cannot open for yourself.

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> Kesha Winter>Those are the people. And, you have to build relationships. And even with coaches like me, that will teach you and help you get out of your mental block and your limitations and help you to break your limiting beliefs so that you can reach your full potential. I would say you would have to, have at least three of these people on your crew, I would say, or a professional way of saying it is your advisory board. It is a mentor, a coach, and an advocate or sponsor that can help you get ahead because the days of the Lone Ranger are over. If you really want to get ahead professionally, you've really got to understand it takes a, strong network to help you get there.

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> Curtis Jackson>Well, you know, we all face it at work, politics or possibly toxic work environments. So talk to the listeners about how to navigate those situations and issues strategically.

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> Kesha Winter>Yeah, it builds upon everything that I just said. If you want to navigate organizational politics, first, of all, you got to deliver results and do good work because if you're in a toxic environment and you're not performing, guess what?

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> Kesha Winter>You could be the first want to be let go and the first one to be cut. So you got to make sure you're delivering results, executing. You have a high say do ratio doing what you say you're going to do, right? That's the number one thing.

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> Kesha Winter>But it can't be the only strategy. The second strategy, I'm not going to expand too much upon it because we just talked about it. It's building that advisory board. The one point I'll add, in addition to what I said about, mentors, sponsors and coaches is you've got to build this board before you need it, this crew that's going to have your back. Because if you try to get an advocate after a situation has gone sour, for example, with your manager, it's going to be too late. You've got to build a friend or get friends before you need them. And one example I give you, I was in a toxic situation many years ago where a leader told me that he was going to support me to take another job in another part of the organization, which, would have been promotion for me to my face. But then the hiring manager for that role called me and said, you know what, behind your back, your manager is saying that they're not going to let you go because they need you. So basically he lied to my face.

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> Kesha Winter>But you know what? You know what worked for me? I had a very strong relationship with his boss, so I didn't use the relationship all the time. But that was one example, I was just like, okay, if I try to go head to head with him, I'm going to lose. But if I go to his boss, if I go over his head, like, he can't get in the way of me winning at work. And so I had a conversation. I said, hey, I don't necessarily want you to have this conversation, but I'm applying to a job. And, you know, this person is trying to block me. And I know my performance is strong. She's like, forget it, I got you. And she made the call. She talked to the hiring manager of the other role, and I was hired. He couldn't stop me. Right? Some of us, we try to fight our battles ourselves, and that's not going to always work. And that's why I think it's really important in order to navigate organizational politics, you got to have a strong crew. My last point I'll give you on, this is that you also have to be visible, because even if you do the best work in the world, if nobody knows about it, you're going to be the best kept secret in town. And if you're the best kept secret in town, you're not going to have anybody to advocate for you because they're not going to know how great you are, and so they're not going to advocate for you. Right. So those are some of the things that I would say that you've got to be very savvy in order to navigate organizational politics so that you can thrive and win at work.

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> Curtis Jackson>So tell us about that book coming out in September. Tell us the name, where we can get it and what listeners can expect when they read it.

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> Kesha Winter>Yes. So it is called your power unleashed. So that's the title of the book. The subtitle is how savvy? Savvy is politics.

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> Kesha Winter>Women can use courage to get promoted, paid and find fulfillment, which everything we just talked about is basically what I talk about in the book. With more strategy, more detail, I get into how do you build confidence? How do you validate yourself at work when nobody is validating you? How do you live life according to your value so that you can feel at peace and fulfilled and not just burnt out?

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> Kesha Winter>And that's the fulfillment piece. But then the strategy is what we talked about, the network. We talked about the salary negotiation and also how to communicate effectively. You asked me one of the questions, how can we go from invisible to credible at work? It is about how you communicate and how you build that leadership, influence and executive presence. I talk about that in the book.

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> Kesha Winter>And how to even be an, effective coach to your employees. So it covers a lot. It comes out September 17, and you can get it by going onto my website, yourpowerunleashed.org.

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> Kesha Winter>it will be available for pre order a month before the book comes out. So around August 17.

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> Kesha Winter>But until then, you follow me on LinkedIn. It's my favorite place to be. You have to go under Keshawinter. K I s h a w y n t e r is how you spell my name. I'm always on LinkedIn. Dm m me m. I say, everybody. I love to talk to people in the DM's only on LinkedIn. so those are the two places that you can find me, and you will find more information about my book.

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> Curtis Jackson>But tell us about any other upcoming projects that you're working on that listeners need to be aware of.

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> Kesha Winter>That is my big focus. It's about seven weeks away, so my solid focus is getting the book out and doing podcasts. So listen to my podcast tour. I'll be all over Spotify and Apple podcasts on various podcasts and just really promoting the book and doing speaking engagement.

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> Kesha Winter>So you'll have to follow my by me on LinkedIn, as on my website, even on Instagram if you want, so that you can get the latest information on where I'll be speaking and, how you can connect with me in order to help you succeed in business and in life.

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> Curtis Jackson>Throw out that website again and close us out with some final thoughts as well. Maybe if that was something I forgot to talk about that you would like to touch on or just any final thoughts you have for the listeners.

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> Kesha Winter>Yeah, it's, So my website, it's actually the name of the book, your power unleashed. So.

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> Kesha Winter>Unleashed.

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> Kesha Winter>Pastence.com.

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> Kesha Winter>and that's my website.

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> Kesha Winter>And my final thoughts for you is, I think about this all the time. We spend the majority of our waking hours at work.

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> Kesha Winter>And so many people live their life for the weekends. The weekends is two out of seven days of the week, or they live their life for vacation, which is two weeks or if you're lucky, even four weeks out of the year. So therefore, we're spending the majority of our lives, the majority of our waking hours at work or running our business. So if we are unhappy in those areas of our life, it simply means we spent a significant portion of our lives to be unhappy. And so I say, find something that fulfills you, that you are able to make an impact, a difference in the world.

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> Kesha Winter>Bring also, obviously bring financial provision for your family and in an environment that nurtures you and supports you. And if you're not in a place like that, develop the leadership, the communication, the emotional intelligence skills to be able to build relationships in your company so that you can have that fulfillment. And if you can't do it with your current company, then believe you me, you're going to be able to find it somewhere else. So find a place where your talent is going to be valued and nurtured so that you can bloom where you're planted. That is the thing that I leave you all with today.

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> Curtis Jackson>That's why we do it. Ladies and gentlemen, Miss Keisha Wender, yourpowerunleash.com dot. Please be sure to check her out. Follow her on LinkedIn Instagram like she said, pick up the book when it comes out. Follow Rate Review share this episode to as many people as possible we all have to work and we can all thrive and learn from what Kesha has taught us today. If you have any guest or suggestion topics, Curtis Jackson, 1978 T.net is the place to send them. Get on that favorite podcast app of yours and give us a follow rate review us.

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> Curtis Jackson>Check it out. Thank you for listening and supporting the show. And Keisha, thank you for joining us and sharing your expertise.

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> Kesha Winter>Thank you so much, Curtis. It's been a pleasure talking to you and being on your podcast.

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> Curtis Jackson>For more information on the living the Dream podcast, visit www.djcurvefall.com.

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> Curtis Jackson>until next time, stay focused on living the dream.

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> Kesha Winter>Dream.