Shawn K. Woods: Helping leaders reach their full potential

“[Vistage] taught me the power of not going it alone. No business leader should go at it alone.”

Editor’s Note: This profile is part of a series highlighting Vistage Chairs — executive coaches who help guide CEOs and leaders of small and midsize businesses to make better decisions for their companies, families and communities.

At just 42, Shawn K. Woods was set to retire. Undeterred by a failed business, he launched a real estate company that grew to $10 million in 36 months. All the profits were liquid cash.

The 2008 recession hit, and he lost it all and was homeless.

“I wish I had a Vistage group to learn from then,” he says.

Vistage Chair Shawn K. Woods

This wasn’t the first time Shawn turned obstacles into opportunities. Growing up on the West Side of Chicago, drugs, gangs and violence were part of daily life. Some of his teenage decisions cost him multiple full-ride scholarships to play Division I football.

He had two choices: Continue down that path, or he could redirect his energy.

Shawn chose the latter, wanting to be part of the solution to those problems. He pursued a career in law enforcement and became a highly decorated detective. He performed exceptionally well in various roles, including stints as a narcotics officer, a homicide detective, and a crisis negotiator before earning his MBA. Shawn then moved into the corporate world and later became a successful serial entrepreneur.

The next part of his journey

After his real estate company collapsed, Shawn again redirected his energy. This time, he was on a mission — to help individuals and organizations reach their full potential. He began executive coaching, facilitating soft skills and leadership development workshops and delivering motivational speeches as CEO of Shawn K. Woods and Associates.

“Motivational speaking is just the start of what I provide,” he says. “Through additional mentoring, training, and leadership development workshops, along with executive, life, and career coaching, my clients have the tools, strategies, and guidance to revolutionize people, processes, and organizations.”

Working with leaders of all levels has allowed him to travel the world delivering presentations at more than 2,500 conferences, including keynote presentations for Fortune 500 companies, associations, small businesses, government and non-profit organizations.

While speaking, coaching and facilitating on his own, he discovered Vistage. The more he learned about how the organization brings together high-caliber CEOs and executives, the more he knew it was the next part of his journey. “The group dynamic allows you to get to know members better and develop deeper relationships,” he says. “I also appreciated that Chairing a Vistage Group added to my legacy of transforming people, processes, and organizations to reach their full potential.”

Shawn with founding members of his CE group

Shawn began his Vistage journey after launching a CEO group in June 2022. The timing coincided with suffering from COVID-19 and becoming a caregiver for his mother.

“Shawn would be on Zoom with me taking calls back from candidates, and he could barely talk,” says John DeBord, senior vice president for the Central Region at Vistage. “But he overcame it with optimism, energy, desire, and belief in this journey.”

Shawn’s tenacity and determination to keep going despite the professional and personal challenges earned him the 2022 Les Whitney Award for Perseverance, an annual award for Vistage Chairs who have overcome adversity.

“The starting line to build and launch a group begins well before the first interview with an executive recruiter, before attending Academy and engaging the first member candidate,” DeBord adds. “Shawn successfully overcame barriers, roadblocks and challenges that few in Vistage have faced. Shawn is a force for good; his first CEO group includes diversity in gender, race, age and the LGBTQ community in addition to the diversity of industry.”

‘The power of not going it alone.’

Serving as Vistage Chair combines Shawn’s unique experiences as a crisis negotiator, detective, coach, facilitator and speaker. The critical skills he developed for negotiations including interviewing, interrogating and understanding the psychology of human behavior help him support and strategize his approach to issue processing as a Chair, he says.

But best of all, Chairing allows him to get to know members personally and intimately.

“Vistage offered additional opportunities in the form of community,” he says. “Vistage puts a business leader in a room with 15-17 other high-caliber individuals and myself to help them solve their greatest professional challenges. It taught me the power of not going at it alone. No business leader should go at it alone. We are a Vistage family.”

Shawn with his grandchildren

Shawn says he is blessed beyond measure to live a fulfilling life that is rich in purpose, which includes enjoying his four kids, and 15 grandkids, dining in Chicago restaurants and rooting for the Pittsburgh Steelers alongside the opportunity to pair, coach and mentor top executives daily.

“Chairing is one of the most fulfilling roles I’ve ever had,” he says. “I help navigate business leaders to fulfillment by allowing me to connect the dots for members.”

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If this coaching story interests you and you’d like to see more, learn more about Chairing and how it could lead to the next chapter of your life.

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