We recently connected with Reggie Jeffries and have shared our conversation below.

Alright, Reggie thanks for taking the time to share your stories and insights with us today. Parents can play a significant role in affecting how our lives and careers turn out – and so we think it’s important to look back and have conversations about what our parents did that affected us positive (or negatively) so that we can learn from the billions of experiences in each generation. What’s something you feel your parents did right that impacted you positively.

I’ve never thought about this aspect of entrepreneurship until this question. I think my parents did so many things to help prepare me for this wild ride called entrepreneurship. Simply put, they taught me resilience.

Both of my parents grew up poor, simply stated. They didn’t have a lot and that obviously shaped the way they approached life. Growing up, my brother and I were fortunate not to share their same experience, but they still tried to instill in us the same life lessons that helped them overcome a multitude of challenges. It wasn’t until adulthood and now as an entrepreneur that I truly appreciate what they were trying to teach me all those years ago.

For most of my life, I attributed my resilience to my sports background. I played organized sports much of my adolescence and was fortunate enough to even play collegiate football. During my sports career I experienced a lot of success and also my fair share of failures. Regardless, I always believed in myself and knew I could do even better the next play/practice/game/season/etc. I was never satisfied with my performance no matter what the scoreboard said. That drove me try to be the best version of myself possible in that moment.

That same mentality has proven to be invaluable as an entrepreneur. I quickly learned that I had to stop trying to be perfect and just be better than I was yesterday. What I didn’t realize is sports allowed me to become laser focused on that reality. However, it was my parents that set that foundation in me throughout my childhood. I think back to the countless situations where I couldn’t figure something out as easily as I would’ve liked. My father always pushed me to keep working at it and not to give up. They never yelled or made me feel less than. Instead, they provided me with a gift that I can never repay them for…..belief in myself. My mother would also tell me things are not always going to be easy, that whatever I wanted in life, I was going to have to not only work for but work hard for to get it. Decades later and I can still hear their voice in my head, encouraging me, supporting me, believing in me. It almost gave me this unbridled optimism about my abilities.

It may seem silly, but that all culminated in an event that I still think back to today when I start to have any self-doubt. I was very fortunate and was able to attend overnight camp during the summers of my middle school years. We did a lot of adventurous activities, but one particular event pushed me further than I’ve ever been pushed up until that point in my life. We were whitewater rafting in West Virginia and had the opportunity to repel off a cliff during a daytime hike. I was the second person to go. The first person couldn’t take that literal leap of faith off the cliff that would suspend them roughly 200 feet in the air before repelling down to the ground. They came back up, took off the harness while crying and handed it to me to go next. That obviously didn’t ease any nerves I also had about this activity. Once they got out of the harness and I was up, I don’t think I’ve ever been more nervous to do something in my entire life, even to this day. Long story short, with the help of the guide telling me to believe in him (that’s a whole another story), I finally took that leap of faith, and it was one of the most remarkable moments in my life. I hung there approximately 200 feet above the ground and at the request of the guide yelling down from the top, looked around at the valley that surrounded me. I was not only proud of myself for being the first person to do it, but quickly realized the payoff was a view well worth the fear of taking that faithful step off the cliff. This whole experience is 100% attributed to my parents. Throughout my childhood they helped me do things I never thought I could do on my own; they pushed me past my limits, made me finish things I started and helped me understand that what I was afraid of wasn’t that bad in hindsight. All those lessons came rushing back to me on the side of that cliff and they consistently keep rushing back to me now as an entrepreneur. But, thanks to my parents (and my sports career) I’m able to take a leap of faith almost daily knowing that there’s a view worth taking in and I’ll appreciate it so much more when I do.

Thanks mom and dad (and my older brother)!

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I worked in corporate America for almost 20 years and well over 20 years in the workforce in general. The majority of my corporate American employment was spent at a Fortune 15 telecommunication company. The rest of that time was spent at another telecommunication behemoth. During my employment in these corporations, I’ve been lucky to work in several different business segments. My time as a productivity analyst, manager, Business-to-Business (B2B) salesperson, corporate/leadership trainer and performance leadership coach has given me such a unique outlook on leadership. I’ve worked for a growing organization in a down economy, I’ve worked for an organization during rampant organizational downsizing, I’ve worked in collective bargaining environments and started my career working for startups. I’ve seen and done a lot over the 20+ years of my work career. Like a lot of folks, all of those experiences (good and bad) have shaped who I am today. Additionally, these experiences drove me to start my business, Management Masters Academy.

Throughout my 20 years in corporate America, I noticed one consistent thing at almost every level; you were taught about the company’s products, services and at times even the company culture. However, I never saw an emphasis on learning true communication skills for leaders. What became more perplexing about that fact was I observed how effective communication was a differentiator between good and bad leaders. Moreover, the leaders that mastered the art of communication were more effective in their role, had better productivity, developed their people better and had a better team culture. It boggled my mind why there wasn’t more of a focus on the “soft skills” (I call them “critical skills”) for managers of people. As I transitioned into leadership training and coaching, it became evident there was a thrust for this knowledge from people leaders. Luckily, I got my bachelor’s and master’s degrees in Communication Studies and was able to lean on that initially to help people improve their communication ability. Over time I continued to invest in honing my understanding of leadership communication to share with my internal stakeholders and clients. After a few years I realized I wanted to have a greater impact and decided the one way I could do that is by starting my own business focusing on helping leaders learn and master their communication abilities to be more productive, reduce turnover and make their day-to-day lives less stressful. Management Masters Academy is designed to help leaders solve these problems.

At Management Masters Academy, we believe that effective communication lies at the heart of exceptional leadership. That’s why our program is specifically designed to help enhance core leadership competencies through a comprehensive curriculum that emphasizes communication excellence.

Our program goes beyond traditional training methods. We bring together a cohort of motivated leaders who share a common goal: to become masterful communicators and influential leaders. Through interactive workshops, immersive simulations, and collaborative group activities, we create a stimulating environment that encourages active learning, engagement, and real-world application.

At Management Masters Academy, we are laser focused on equipping leaders with the essential communication skills needed to excel in today’s dynamic business landscape. From effective storytelling and persuasive presentations to active listening and conflict resolution, our program covers a range of core competencies that will elevate your leadership capabilities and help leaders navigate any professional challenge with confidence.

Can you tell us the story behind how you met your business partner?

While I worked in corporate America as a trainer, I wanted to be the best trainer I could be. I studied the craft and was thirsty for feedback from my managers and peers. I studied the experienced trainers to learn what they did that was effective. I picked the brains of my leaders to understand how to not just be good but to be great. Just when I thought I mastered the skill of facilitation, I met Dave Florie.

Our regional corporate training organization in the company downsized and we started to partner with other regional training teams from across the country to maximize resources (people). That’s when I had the opportunity to partner with trainers from all over the country. During that time one name kept coming up repeatedly as one of the best trainers in the company; Dave Florie. Eventually I had the opportunity to partner with Dave and that’s when I realized the hype was real. Dave quickly became somebody I looked up to and my bar for facilitation excellence was raised to a different level. Dave and I worked on several different projects together and quickly became friends who admired each other’s skill and ability. We both loved the art of facilitation but approached the craft from different angles. Dave was very detail oriented and meticulous about his approach to facilitation. I relied more on my ability to ad lib and figure things out as I went. I know Dave made me a better facilitator and I’d like to think I made him a better facilitator too. As the years passed, it became evident our time working together was going to come to an end one way or another. Long story short, we agreed that one day we would venture out on our own and start a business where we could continue to help leaders become the best versions of themselves but do it in a way that was free from corporate restraints. That day finally came in 2023.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

“Don’t let perfect be the enemy of the good”. This is a phrase I’ve heard repeated many times over the past several years. I’ve even expressed this same sentiment in one way or another during a training or coaching session. However, it didn’t become truly meaningful to me until I became an entrepreneur.

My managers over the course of my time in corporate America would always remind me that things didn’t have to be perfect to be impactful. Usually I didn’t listen and instead spent more time after work hours working on a project to make sure it was just “right”. As an entrepreneur however, this was a luxury I couldn’t afford. I found myself obsessing over every little detail because now my name was attached to this product and not just the corporate company name that may or may not really mean anything to me. I thought <insert any Management Masters Academy customer facing material> was a reflection of me and my abilities as a learning and development professional. If my product wasn’t seen as great, then I wasn’t great. If something I put out there bombed, then I was a failure. That’s simply nonsense. With the help of my own coach and mentors, I was able to realize that I needed to keep moving forward even if something (my website, my content, my social media post, etc.) wasn’t exactly perfect (however I defined perfect). The reality is my clients are the ones that will tell me if it’s perfect or not. And if they tell me it’s not perfect, it’s not the end of the world, I just need to go back to work and make it better next time. That’s the exciting part about entrepreneurial work, it’s truly an iterative process.

I can’t say I’m perfect at this mentality by any means. I still find myself scrutinizing the smallest details sometimes. However, I’m trying not to let perfect be the enemy of the good when it comes to not letting perfect be the enemy of the good.

Contact Info:

• Website: www.managementmastersacademy.com
• Linkedin: https://www.linkedin.com/company/managementmastersacademy/
• Vimeo: Management Masters Series – Our interview sessions are focused on talking to leaders about their leadership challenges, how they overcame them and how those challenges have made them a better leader/the leader they are today. Link: https://vimeo.com/showcase/10500536