Executive Strategy Leader: How to Build Teams That Win for Generations

Summary

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Podcast Summary: Living Your Legacy

Episode: "Executive Strategy Leader: How to Build Teams That Win for Generations"

Host: Rudy Mawer
Guest: Dr. Cedric Howard, CEO of Howard Executive Consulting
Date: December 9, 2025

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Main Theme & Purpose

This episode explores the critical shift from being a hands-on entrepreneur managing daily tasks to stepping into the role of a visionary leader who builds teams that succeed over generations. Rudy and Dr. Cedric Howard dive into how to define and communicate the “North Star” of an organization, recruit and develop the right talent, and foster cultures that transcend time. Dr. Howard draws on his decades of leadership in higher education and corporate consulting, offering practical strategies, personal stories, and actionable advice for business owners striving to leave a legacy.

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Key Discussion Points & Insights

1. The Transition from Entrepreneur to Visionary Leader

• Why many entrepreneurs get stuck at small team sizes:
  • They excel at execution and getting their hands dirty but struggle when required to delegate, envision, and lead strategically.
    • [00:00] Rudy: “So many people never got past the 10–20 employee side...when it became more the leader visionary, they struggled.”
• The effort and mindset required:
  • Leadership is an intentional, ongoing effort. Entrepreneurs often resist the discomfort of learning new skills or reorganizing their roles.
    • [03:15] Cedric: “You have a desire, you have a vision, but it also requires effort...oftentimes we don't want to go through the effort.”

2. Building Teams with the Right Values and Culture

• Attracting Talent:
  • The process of interviewing and hiring is rigorous; only a fraction of candidates will align with the company’s vision.
    • [04:08] Rudy: “We might interview or invite 200–300 people for a job...then I’ll hire two or three of those and maybe one will turn out okay.”
• Culture as a Differentiator:
  • Start with purpose and vision, infuse work with ethics, emotional intelligence, and competencies.
    • [04:16] Cedric: “You gotta start with the purpose and a vision...you’re also creating a culture.”

3. From Manager to Visionary—Defining the North Star

• Leadership at Scale:
  • There’s a purposeful transition from “mom and pop” operation to business, and ultimately to corporation. It all starts with a clear North Star.
    • [04:46] Cedric: “What is your North Star? If you want to be a small organization...that is okay. But then you’ve got to transition...and then transition your business into a corporation.”
• Continuous Learning:
  • The most successful leaders learn (and unlearn) constantly as the business scales.
    • [05:03] Cedric: “You have to be willing to learn and learn and relearn what you're doing as you develop in each stage...”

4. Learning Leadership Versus Experiencing Leadership

• "School of Hard Knocks":
  • Unlike other disciplines, most entrepreneurs learn leadership by doing, making mistakes, and adapting.
    • [05:43] Cedric: “Most successful leaders have learned how to fail...we’ve learned how to fail so we don’t become failures.”
• The Power of Failure:
  • Failure is framed as necessary for growth—using the baseball analogy: succeeding 3 out of 10 tries puts you in the Hall of Fame.
    • [06:07] Cedric: “If you hit 3 out of 10 times, you’re considered...a Hall of Famer. But often we don’t see the seven times you missed and had to adjust.”

5. The Four Pillars for Building Teams That Win

Cedric distills his philosophy into four actionable areas:

1. Determine Your North Star (Vision)
   • Think in “bold, bodacious goals” and set aspirations on a generational scale.
     • [08:05] Cedric: “In Asia...they have 500-year plans for their companies. Not just five or ten year—they have five hundred.”
2. Develop a Successor Pipeline
   • Succession planning is often neglected; leaders should train others for roles beyond their current scope.
     • [11:35] Cedric: “Many companies fail because they haven’t developed a succession plan...are you training that next level of leadership?”
3. Surround Yourself with Value-Aligned People
   • Your network profoundly impacts your net worth. Seek strengths different from yours.
     • [13:59] Cedric: “Your network determines your net worth...It can’t be your friends—you’ve got to have some strengths very different to you.”
4. Be Proactive, Innovative, and Reflective
   • Innovate rather than imitate (blue ocean strategy). Learn from your errors, and plan ahead for transition and asset protection.
     • [15:37] Cedric: “How are you preparing yourself to learn from your mistakes? That’s being proactive rather than reactive.”

6. Keeping Vision Alive Within Teams

• Constant Reinforcement:
  • Repetition and affirmation are key—teams quickly forget long-term vision unless reminded regularly.
    • [10:44] Rudy: “Most companies only ever share it once a year...every Monday we do our all staff and the first ten minutes, we actually go back through all of our yearly goals and our vision...”
  • Cedric uses “Setting Notes” with small rewards to reinforce core values.
    • [11:25] Cedric: “A person gets a Setting Note. They also get a $5 Starbucks coupon...which reaffirms what we’re hoping to do.”

7. Building a Multi-Generational Legacy

• Thinking Decades Ahead:
  • True legacy is about establishing financial AND educational foundations for descendants you might never meet.
    • [17:18] Cedric: “How do I build wealth that my great grandkids are benefiting from? ...A person dies twice: when you physically die and when they’re forgotten.”
  • Ensuring your name is remembered is a core motivator for Dr. Howard’s work.
    • [17:54] Cedric: “I want to make sure that for decades and generations to come, they’re always calling my name.”

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Notable Quotes & Memorable Moments

• On Learning Through Failure
  • [05:43] Cedric: “Most successful leaders have learned how to fail...we’ve learned how to fail so we don’t become failures.”
• On Vision:
  • [08:05] Cedric: “They have 500-year plans for their companies...That’s thinking multiple generations.”
• On Succession:
  • [11:35] Cedric: “Are you training that next level of leadership for the job you desire for them to have? Remember, learn, unlearn, relearn.”
• On Network:
  • [13:59] Cedric: “Your network determines your net worth.”
• On Legacy:
  • [17:49] Cedric: “A person dies twice: when you physically die and when they’re forgotten. And one day, the last time they called your name.”

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Timestamps for Important Segments

• 00:00–03:15 – The entrepreneurial struggle: tasks versus vision
• 04:08–05:03 – Recruitment, culture, and leadership at scale
• 05:43–07:03 – Failing forward; the necessity of learning by doing
• 07:15–15:37 – Cedric's 4 pillars: vision, succession, network, and innovation
• 10:44–11:28 – Keeping vision “alive” with constant reinforcement
• 17:18–17:54 – Defining and building a lasting legacy

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Conclusion

This episode offers both inspiration and direct, actionable strategies for listeners who wish to move from effective managers to legacy-minded executive leaders. Dr. Cedric Howard’s experience and storytelling make abstract principles real, from the importance of the North Star to the day-to-day reinforcement of values, hiring well, developing successors, and thinking beyond your lifetime. Listeners are left challenged to envision not just what they can achieve, but what they can establish for generations to come.

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Find more from Dr. Cedric Howard:

• LinkedIn: Dr. Cedric Bernard Howard
• TikTok: Cedric B. Howard

"Keep building a legacy." — Rudy Mawer [18:28]

Transcript

[A]

I know so many people that never got past the 1020 employee side because they were great entrepreneurs. They were great at getting their hands dirty and doing all the work. But then when it became more the leader visionary, they struggled. Why do so many entrepreneurs struggle with that?

[B]

Well, I think part of it is they have a desire, they have a vision, but it also requires effort and oftentimes we don't want to go through that. Dr. Cedric Howard is a strategic visionary leader and, and the CEO of Howard Executive Consulting. Recognized for redefining leadership across higher education and beyond. His work has shaped leaders across industries, earning him a reputation as a trusted voice in excellence and innovation. I think the most important thing is surround yourself with people who have the same values as you. Your network determines your net worth. Most successful leaders have learned how to fail.

[A]

Yeah, yeah, yeah.

[B]

We've learned how to fail so we don't become failures. And I think one of the most.

[A]

Important lessons to learn is most people listening have small teams and they're managing.

[B]

Yes.

[A]

How do you transition from managing day to day managing tasks to becoming a visionary leader?

[B]

The very first thing is.

[A]

It spans.

[B]

The globe like a super high cold Internet. Elvis Preston, 5:3.

[A]

Today, Apple is going to reinvent the phone.

[B]

It's not over until I win. The Living youg Legacy podcast. For those who live to leave a legacy that's extraordinary. The impossible. Oh, that is sensational. Jordan Open Chicago with the lead. Usain Paul is the fastest man on the planet. You can live your dream.

[A]

Hello and welcome back to another episode of Legacy Makers tv. Today we're going to talk about how to go from a great manager to a visionary leader. A lot of you listening are probably in that transition period. Cedric's joining us today. No one better to talk about that topic and how you can be the best version of yourself when leading your teams. Welcome to the show. Thank you.

[B]

Thank you for having me.

[A]

So let's talk about you. You know, obviously we're going to dive into the leadership element, which I know everyone's going to love. But before that, how did you get here? What's your story?

[B]

Thank you, Rudy. So for the first 31 years of my professional career, I worked in higher education as a college administrator. 28 of those years I was a vice president. And so it was my goal to establish leaders from students into corporate leaders. The last couple years since COVID I've been really working with corporate leaders in order to make them more resilient and to enhance the effectiveness of their organization.

[A]

Yeah, love that. I think there's so many entrepreneurs that are great entrepreneurs but aren't great. Like, they don't know how to be leaders. You know, I grew my company to 100 staff. And you know, to get to 100 staff, you have to be a good leader and CEO. But I know so many people that never got past the 10, 20 employee side because they were great entrepreneurs. They were great at getting their hands dirty and doing all the work. But then when it became more the leader visionary, they struggled. Why do so many entrepreneurs struggle with that? I guess is my question.

[B]

Well, I think part of it is they have a desire, they have a vision, but it also requires. It requires effort. And oftentimes we don't want to go through the effort. The cycle of despair.

[A]

Yeah, yeah.

[B]

We get to the part where we're energetic, we're entrepreneurial, we're really focused, and then we hit the first role barrier.

[A]

Especially with the team side. Like, I was, I was doing a live call yesterday. Someone said, rudy, how you find so many great hires? And I go, well, you know, we might interview or invite 2, 300 people for a job, and we'll shortlist that to, you know, the top 10, 20, 30%. Then we'll do interviews, and then I'll review the top people in that interview or do second interviews. Then I might even meet with the final person. Then I'll hire two or three of those and maybe one will turn out okay. So. And it's like that process most people don't want to go through.

[B]

Yes. Yeah. Well, I have found, especially in my world, you got to start with many, but also you got to start with the purpose and a vision.

[A]

Yeah, yeah.

[B]

Because what you also creating is a culture.

[A]

Yeah, yeah, yeah.

[B]

And that's an important ingredients as a part of the process.

[A]

Yeah.

[B]

And so, you know, it's important for my team for you to have ethics, emotional intelligence, and be smart.

[A]

Yep, yep. And it's fine. It's hard to find all those.

[B]

That's certainly the case.

[A]

But let's talk about. So let's talk about the. Most people listening have small teams and they're managing.

[B]

Yes.

[A]

How do you transition from managing day to day managing tasks to becoming a visionary leader?

[B]

The very first thing is what is your North Star? If you want to be a small organization, what we call a Mom and pops, meaning organizations, that is. Okay. But then you got to transition to being a business and then transition your business into. Into a corporation.

[A]

Yeah, yeah.

[B]

And that's very intentional. But what is your North Star? And you have to be willing to Learn and learn and relearn what you're doing as. As you develop in each stage of that particular process.

[A]

Well, talking about learning, what's funny is you can go learn marketing, you can go learn sales, you can go learn tech. But. And of course, there are leadership courses. But I feel most entrepreneurs, no one ever, they never learn leadership apart from learning by doing. Right. But like, you know, marketing, they might go take a Facebook ad course and study it Right. By monamine or something.

[B]

But.

[A]

But it's very rare that they buy a leadership course or read a leadership book and they learn just in the school of hard knocks, right?

[B]

Absolutely. But most successful leaders have learned how to fail. Yeah, yeah, yeah, we've learned how to fail so we don't become failures. And I think one of the most important lessons to learn is to realize that you're going to fail often. And it's part of the growth process. It's that tension that you need in order to propel you forward.

[A]

Yeah, I like the learn how to fail. Yeah. Talk about that a little more.

[B]

So, as you know, I use the baseball analogy. If you hit 3 out of 10 times, you're considered to be, you know, a Hall of Famer.

[A]

Yeah.

[B]

You know, but oftentimes we don't see it is the seven times that you actually swung the bat and miss the ball and make the adjustment to know how to hit the ball. Just three times.

[A]

Yeah. And I think that's a great reminder because you're talking about the very best in the world.

[B]

Yes.

[A]

Hidden successfully three times out of ten.

[B]

Yes.

[A]

To win championships.

[B]

That's right.

[A]

You know, a lot of people go in and expect to win, swing nine out of 10 or 10 out of 10 times, and they get upset when they don't. Yeah.

[B]

And that's not including all the times you're spending, you know, in the research and development phase of things. And that's really where you learn how to fail. Oh, that's not working well. Or that is working well. But this is not seasoned for you to do this particular project or this particular process. You got to move to next season.

[A]

So next question for you on that, we're talking about learning, leadership, going from manager to leader and visionary. What. What are like three or four, four key points that people should focus on?

[B]

One, determine your North Star to realize that you have to develop a team around you that's going to promote you. And the process. The process. Determine the product that you produce. Number three, be proactive. Realize who's doing what you're doing well. And Learn from them. And third and most important things, don't be afraid to be innovative. We got a number of people that are doing the same thing. Red ocean concepts. Don't be afraid to create a blue ocean.

[A]

Yeah. So I want to break all four down quickly. A couple of minutes on each. Number one North Star. That is your vision, where you're all going and you're aligned and focus on that shared vision and get into that, that, that big thing. Right?

[B]

Yes. I also say. So I spent some time in Asia.

[A]

Okay.

[B]

And when I was in Asia, one thing I learned is that they have 500 year plans for their companies.

[A]

Oh, wow.

[B]

Not just five year tenure, they have 500 year.

[A]

That's crazy.

[B]

They're thinking in that way.

[A]

That's crazy.

[B]

And so I thought, okay, what is my bold, bodacious goal? What is my bold goal? To become.

[A]

Why? Why do you think they do? Because I think over there they pass down in generations more. Right. Is that why they think generation? That's crazy.

[B]

Most do not.

[A]

Yeah, yeah, yeah.

[B]

One generation may be two.

[A]

Yeah.

[B]

Not multiple generational.

[A]

That's great. Yeah. Because I've only ever thought about until I die. Right. What my legacy is and. Correct. Yeah, yeah, yeah. Expand on that a little. Give me an example or how you learned.

[B]

So a great example of it from my perspective is even most successful organizations, you're going to go through different iterations. And so are you preparing the next leaders to take on once, you know, able to take on. So we look at Howard, executive coaching. I'm preparing that next generation. My son is 23. He served in the military to become a leader.

[A]

Well, that's good because I think you learn so many core skills that most of society lack these days in the military. I like hiring a lot of ex military because they show up on time and they make their bed and they're dependable. Yeah, yeah, yeah, yeah, they do.

[B]

But he's also learning how to be a leader on a global scale. Dad has done a tremendous job of starting this company. Dad has done a tremendous job of working with corporate and educational leaders. Now it's time for you to take international. So his goal is what are the languages I need to learn in order to scale this into a multinational corporation? That's thinking multiple generations. Yes.

[A]

Great. It's great. So number one was the North Star and thinking big and long term. I love that. And I love the Asia analogy of thinking big, you know, hundreds of years down the line. But one thing I do want to add to that because I realized after you know, I've led teams for 10 plus years, but big teams for the last seven or eight. And you as the leader always have it. Right. You have that big North Star and you might tell your team about it and do your corporate annual events or quarterly events and retell everyone. But I what I learned is because you got new people coming in and out and people have short term memories, most of them don't actually know about it on a daily basis or weekly basis. They forget. Right. And you might have a poster in the office or whatever if you have a corporate company. So one thing we did is every Monday we do our all staff and the first 10 minutes is we actually go back through all of our yearly goals and our vision and our big. Like our big North Star. Yes. So. So I would love to talk about that. How do you keep the team aligned and focused on that because they get so lost in the day to day and most companies only ever share it once a year.

[B]

Absolutely.

[A]

Yeah.

[B]

The important thing is to use affirmations. So as you mentioning that you have developed an affirmation that as a part of your team development you're going to reintroduce the annual concepts. But what are your company values? They should never change?

[A]

Well, we actually go through those right after. We go for our core values right after.

[B]

And that's where it begins. Also. What are the reinforcements, the positive reinforcements of those values? So for me, my name is Cedric Howard, so I have what are called setting notes. So a person gets a setting note. They also get a $5 Starbucks coupon so they can go to Starbucks, which reaffirmates, reaffirms what we're hoping to do.

[A]

Yeah, yeah. Do you have shares in Starbucks?

[B]

I do.

[A]

Okay, good.

Okay, good. That's number one. All right. What was the second one? Was what second tip?

[B]

The second tip is also as a part of your professional development. Why are you training them? Many companies fail because they haven't developed a succession plan. Are you training that next level of leadership for the job that you desire for them to have? Remember, learn, unlearn, relearn. So how are you relearning to operate? In a way I oftentimes refer to it the difference between Star, Blockbuster and Netflix. You gotta recreate yourself. You gotta recreate your brand to where things are going, not to where things have been.

[A]

Yeah. And that's funny because someone also yesterday on my live asked me, rudy, do you care that you do all these different things and you're constantly changing? I said, I feel you have to at least in my industry now because it's so fast evolving. If I was still selling courses like I was 10 years ago, I'd be bank, I'd be broke, you know, because it's so saturated. So you always have to stay ahead. And I think people get concerned about that because half of the business advice is like, just do one thing, do it well. Don't have shiny object syndrome, which I agree with in some ways. But then also we, because of technology in the Internet, I think cycles evolving a couple of years now versus 20 years like they used to.

[B]

Yes.

[A]

So you have to keep pivoting, changing and adapting or you fall behind like blockbuster.

[B]

One thing I learned, you know, in working with my corporate leaders is that actually it's my first book, Cedric. I have staff who are not financially literate, so they're not good business managers. So can you write a book on what does it mean to be financial literate? So that's what I wrote. Now I have, especially because in currently in corporate America, we're managing four generations from baby boomers all the way to X and y, all as a part of the workforce.

[A]

Wildly different, like I imagine, Right?

[B]

Values.

[A]

Yeah, yeah.

[B]

And expectations. And so they say to me, cedric, hey, can you write us a book that we can work with our, our young professionals to help them understand the importance of leadership and what does it mean to be a leader and transition out of just managing tasks and then as a leader, establishing long term vision?

[A]

Yes.

[B]

And that's a key component of how I am evolving as an author and as a person who is publishing articles. To lead as a thought leader within my industry and within the community.

[A]

Yeah, I love that. Let's go on to the third tip that you gave. What was the third one again?

[B]

Yeah, I think the most important thing is surround yourself with people who have the same values as you. Your network determines your net worth.

[A]

Yep.

[B]

And so what is your network within your corporate entity? And I would say it can't be your friends. You got to have some strengths there that are very different to you. So a great example of that is I am a very, very deep thinker. I overanalyze almost everything. My core partner is shoot from the.

[A]

As you got that you can, you.

[B]

Can see when we're, you know, when we're, when we're interacting with each other, the social introvert is social butterfly. He's out there. The introvert is myself. When we get together, we realize that we have a role to play with each other.

[A]

Well, it's funny because I think those two are so important strengths. So. And I used to be more like you and I've like trained myself to be more like your partner. So like now I'm half and half. Yeah. I can like switch and be in the middle because you know, I used to be, I was a scientist and chess master, so super analytical and data driven. But then you, you do have perfectionist syndrome and sometimes spend too long making decisions and the opportunity is already gone, you know.

[B]

Analysis, Morales.

[A]

Yeah, yeah, I had that. I had that the other day I was buying a rental property and I thought it was the best one out of all the ones I viewed. But then I still dwelled on it a week rang back, made an offer, he said I already sold it, you know, so. So yeah, I think it's good to have that mix of both. Right. Actually ended up still winning that because then I offered him ten grand more and he came back. Came back, yeah. But it cost me ten grand more. So let's go on to the fourth one. Yeah, Final one. Yeah.

[B]

And I think the most important thing as you begin to focus on these aspects is how are you preparing yourself to learn from your mistakes. That's being proactive rather than reactive. Oftentimes people are reactive because they haven't thought to plan, they haven't thought to establish a plan, they haven't thought to be reflective.

[A]

Yeah, yeah.

[B]

I've oftentimes say your errors, the things that you fell from, the things that you've fallen from, the things, the mistakes that you've made is nothing more than a setup for your future success.

[A]

Yeah.

[B]

Have you taken time to learn from those mistakes in order to grow?

[A]

Well and I think there's some key like business stuff in there within like asset protection. Right. You should also be like doing asset protection. And that's forward thinking, like outside of the day to day business. Most people don't think about that until everything falls apart apart or they get sued, you know.

[B]

Liability insurance.

[A]

Yeah, that's the whole insurance insurance. Yeah, yeah, yeah. Insurances.

[B]

Yeah, it's for what could occur. Now what is?

[A]

Yeah, yeah, insurance and also building to sell. I didn't understand what building to sell meant until I went to sell my first company and the guy got a 60 page due diligence document to fill in and you have to basically show how the company runs without you. And I'm like, well not a lot of it doesn't. So. But now I build my company's to sell in advance. So I think that's good about the proactiveness like on a bigger scale that most entrepreneurs don't think about in the early days because that's when you get into bigger business, you know, tens of millions. That's when that stuff really matters.

[B]

Absolutely. Absolute transition from mom part to business to a corporation.

[A]

Yeah. Good. So, last couple of questions, because I know you obviously shared some more about your story, more of these lessons in the episode, but I want to ask you on the legacy side, what does a legacy mean to you?

[B]

Oh, legacy is everything for me. Legacy is how do I build wealth that my great grandkids are benefiting from. They would never meet me, but they would know my legacy because I've established the financial and the educational foundations for them. I oftentimes say that as a part of this wealth building aspect in my world is my grandfather taught me an important Lester and I tell the story of my grandfather. He said, a person dies twice when.

[A]

You physically die and when they're forgotten.

[B]

And one day, the last time they called your name.

[A]

Yeah.

[B]

I want to make sure that for decades and generations to come, they're always calling my name.

[A]

Yeah, I love that. I heard that one one time. It was a good. It's very good. Yeah. And then last question. People want to learn more about you. Check out the books or learn from you or, you know, geek out on this leadership stuff as they're growing their businesses. How do they find you?

[B]

Yeah, you can always locate me on social media, LinkedIn, Dr. Cedric Bernard Howard, and on Tick Tock, Cedric B. Howard. Anything that said you could be Howard because it's actually trademark.

[A]

Okay.

[B]

You can, you can reach me.

[A]

Good. Love it. Love it. Well, there you go, guys. Another episode in the wraps. How to have more impact as a leader and lead from the front with big vision. I love this because most entrepreneurs don't appreciate this, right? And they're all trying to grow. So I hope you enjoyed the episode as much as I did. Check out, of course, his full TV episode. I'll see you guys soon. Keep building a legacy. Take care.