It’s Been a Sweet 16: The Middle School Years (2018-2020)

Growing a business is a little like raising a child. From the early days of worrying if you’re going to inadvertently harm your “baby,” to the stressful highs and lows of navigating the changes that come raising a successful business, we’ve had an eventful 16 years at The Roundtable. In celebration of our anniversary week, we thought we’d take the opportunity to look back at a few of the milestones along the way and share some of the lessons learned.

The Middle School Years (2018-2020)

Middle school is an awkward time. A time of braces, pimples and growing pains. It’s no different in a business. As you grow, the warts start to show up in your processes and you find your talent starts to get stretched to areas where they’re no longer as competent as they need to be. And then, of course, there’s the things that hit you sideways that you don’t see coming like the when your first crush dumps you or, in the case of The Roundtable, a global pandemic smacks you in the face.

Milestones:

  • I Became an Author. My first book – Did I Really Sign Up for This?!? was published as part of our 10th anniversary celebrations. Two years later, my second book – The Grassroots Leadership Revolution – came out during lockdown. I never really wanted to be an author, but I just came up with a new book idea so you may see a third one coming your way in 2025.
  • WBE Certification. We proudly became a certified Women’s Business Enterprise (WBE) certified business and joined an amazing network of dynamic women business leaders. In 2021 we won the WBE Rising Star Award.
  • Our Community Gains Momentum. Roundtable clients aren’t clients, they’re members. We value connection, community and celebration. We had the biggest posse at the RBC Women of Influence Awards, hands-down. I’m forever grateful to our community of members who have helped us co-create our programs over the past 16 years and love celebrating all our milestone wins together.

Lessons Learned:

  • If You Don’t Ask, You Don’t Get. When I told my coaching mentor Marshall Goldsmith that I’d written my first book he said, “Why don’t I endorse it for you?” And then he said, “Why did you wait until the end of the day to tell me about your book? Do you think a man would have done that?” It was a great lesson that I’ve never forgotten.
  • Play the Long Game. Between March 2020 and July 2020 we sold a total of zero programs. I had many of our clients reach out to me to tell me to hang in there but I honestly thought we might lose the business. I’ll always be grateful to our core team at the time – Shelby, Susan and Leah – who locked arms and helped me pull us through that bleak time. These relationships – within our team and clients – didn’t happen overnight. Business is a long game not a short sprint.
  • Stay Agile. Unlike many leadership companies, our organization had always been agile so flipping over to Zoom during Covid was fairly stress-free. I’ve always liked the idea of flexibility within frameworks which allow you to adapt and pivot without needing to reinvent.

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