Interested in starting your own entrepreneurial journey in personal development but unsure what to expect? Then read up on our interview with Sherry Winn, CEO of The Winning Leadership Company, located in Fishtail, MT, USA.

What's your business, and who are your customers?

I own The Winning Leadership Company, which is the spearhead for my speaking, consulting, and writing. The only pathway to a winning organization is through leadership--leaders who empower others. Leaders are in their positions to make the hard easier because other team members cannot. I support leaders to became Olympic-level leaders producing Gold-Medal teams where impossible ideas become realities. I make the hard easier by building cultures where people know that it is their right to question, challenge, and say no. I help leaders to look beyond the evidence to find the answers that nobody else is looking for and to live in the winning leadership zone where they are creators, innovators, and thought leaders.

Tell us about yourself

As a Two-Time Olympian and National Championship Coach, I knew the ways to create and build winning mindsets. I coached college basketball for 23 years, where my teams won a National Title and participated in the Elite Eight three times. Corporate leaders started asking me to share my insights on creating winning teams, so I left the world of college coaching to enter into the corporate world of speaking, facilitating, and consulting. What I learned through being an elite athlete and coach was that people needed support to live to their true potential. Because we have so many challenges, we often lose sight of our brilliance. I find great joy in coaching others to realize the winners that they were born to be.

What's your biggest accomplishment as a business owner?

While I love speaking to groups as large as 14,000 where I can share messages of empowerment, what I have found to be the biggest accomplishments are the leaders that I've coached: the CFO who was on the chopping block because he lost the company 1.6 million dollars and who within three months of working with me helped the company secure 6 million dollars, the executive director who couldn't have tough conversations with her team members and was close to being terminated and who is now an SVP, and the CEO who was at a stalemate with his business and then was able to open a second store.

What's one of the hardest things that comes with being a business owner?

When you own a business, you must learn what the essential parts of the business are. You must train yourself to work on the business rather than in the business. You have to know yourself well enough to know what must be delegated, who is trustworthy of that delegation, and how to delegate the work.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

If you are going to start a business today, be truthful with yourself. Research what it takes to own a business. You cannot lie to yourself about your strengths and weaknesses. Understand that building a successful business doesn't happen in a day or a year. A successful business is ever-evolving, as you must be. To keep your business growing, you must keep yourself growing.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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