Born and reared in the Nation’s Capital, Natalie May, was fully active in DC’s summer youth programs. These organized programs planted seeds of confidence, leadership, initiative and work-ethic that blossomed into her adult career. Today, she is the Principal/CEO of Chaise Management Group, LLC, (CMG) a leading, woman-owned management consulting firm founded in 2013 established on the idea that successful businesses require smart leadership, sound management practices, direction and purposeful commitment to empower the U.S. economy.

Sheen recently caught up Natalie to talk about her leadership and evolution in entrepreneurship:

When you left corporate America, we’re you convinced that you would pursue entrepreneurship permanently or were you just “testing the waters?” Talk about what that transition looked like for you?

It was a daunting decision. For some time, I couldn’t get past being afraid of the “what if something goes wrong and how will I financially sustain life for my kids and me?” I knew I wanted to start my own business but was always too afraid of not having or knowing everything required to start and grow a business.

I worked within the corporate and non-profit sectors for several years and throughout that time, I learned important aspects of operations, programs and management. I decided to stop daydreaming and started working on a transition plan. Having learned from various management and operation practices, I utilized my current knowledge, skills and drive as a catalyst for starting my business. I studied the industry, market and other aspects of business to help support my overall plan. The vision became clearer and from there, the transition easier.

Now that you’ve been in business for over 6 years, how have you’ve grown as a leader?

  • Understanding my strengths and leveraging my weaknesses to position for growth.
  • Broadening my capacity and knowledge made allowance for me to consistently expand and grow. I’ve also learned that management and smart leadership are not about “knowing everything” – it’s about surrounding yourself with people that do.
  • Having the “mindset” and being intentional in my actions.

Have there been times when you wanted to throw in the towel? If so, can you elaborate on what you did to pull yourself through hurdles?

Yes! I often would say, “I didn’t read the fine print in this business ownership thing!” There were and still are challenges but because I BELIEVE in my vision and mission, I’m motivated by those challenges to work harder and do better to get to where I want to be. Without challenge, there’s no growth and learning from my failures, at times created opportunity.

In your industry, are you seeing more diversity of gender, race, age? Do you think that there’s an underrepresentation of African American females in the government contracting space?

Yes and yes! The growth of businesses owned by black women continue to make gains and that’s awesome. However, leveling the playing field for our businesses to grow and thrive in this market still needs work.

I believe we play an integral role in helping shape policy and creating shifts to how to get access to opportunities and win business by voicing our challenges and the solutions that will allow businesses to flourish in this space.

I pay acute attention to legislation and policies that impact my business and industry. I also follow organizations such as WIPP (Women Impacting Public Policy) whose mission is to advocate on behalf of women entrepreneurs by strengthening their impact our nation’s public policy, creating economic opportunities and forging alliances with other business organizations.

What is your guiding philosophy as it relates to executing as a successful CEO?

To create and cultivate positive relationships, from my employees to my clients. To provide guidance, direction, leadership and an environment that allows the people that we support (employees and clients) to thrive and win.

As a role model to other “brown skin girls” including women and teens, what is your message to us?

  • Be your authentic self and not someone else! Learn what the definition of “being you” and build on the positive qualities and characteristics of that discovery.
  • Be inspired and learn from successful individuals and role models and be inspired
  • Be confident and empowered to become the best version of yourself.

As a single parent, what advice can you offer to other single parents who are still working, traditional day jobs but aspire to stepping out into entrepreneurship?

Study, Prepare, Plan and Execute.

Have the “mindset” for business ownership and be intentional. Leadership and business acumen occur through practical experiences and day-to-day responsibilities and challenges [and this can happen working a day-to-day job].

  • Study and draw from those daily lessons by leveraging insights and apply them to accomplishing goals or steps that better position you for success. Entrepreneurship is about wearing many hats – most women master that naturally in our personal and professional lives daily so don’t be afraid to pursue your vision and execute your course.
  • Don’t be afraid to master new competencies, and be well-rounded in the industry or space that you work in.
  • Have a vision, well-defined strategy and FAITH!
  • Be ambitious and start small (never despising small beginnings.) 

What is your favorite quote(s)?

“Successful people do what unsuccessful people are not willing to do. Don’t wish it were easier; wish you were better.” – Jim Rohn

“Success seems to be connected with action. Successful people keep moving. They make mistakes, but they don’t quit.” – Conrad Hilton

Visit Chaise Management Group’s official website today!

Connect with Chaise Management Group on Instagram, Facebook, LinkedIn, Twitter



Photo credit – Delores Holloway, A Little Bit of Whimsy Photography

Makeup – Takia Ross, Accessmatized