TPO Consultant Spotlight: Cindy Winters

January 16th, 2014
Written by: Admin

Meet Cindy

Cindy WintersDespite her last name, Cindy Winters says she doesn’t miss the cold temperatures in New England where she built her career. After attending college in New Hampshire, she remained in the Northeast to work as an HR executive in the finance and biotechnology industries, and later as a principal and founder of an HR consulting firm. But the Granite State’s loss has been TPO’s gain. Cindy joined the firm in 2007 and today works with TPO’s financial services, technology, professional services and non-profit clients.

From Infrastructure to Investigations

Cindy brings her clients a broad range of experience including management coaching and development, strategic planning, employee relations, and HR infrastructure implementation. As one of TPO’s go-to HR investigators, she also works with law firms and private companies to perform independent investigations of employment-related legal complaints. She’ll interview the employee complainant and the accused, assess the circumstances surrounding the complaint, and provide a report of the key findings.

The Safety of a Sounding Board

Much of Cindy’s work entails one-on-one collaboration with CEOs and executive directors, for whom she acts as an executive sounding board. “It’s often difficult for CEOs to admit to their inner circle that they don’t know how to handle a situation,” says Cindy. “And that’s what’s so great about TPO. Our consultants act as trusted confidants to business leaders who need to talk through their challenges and brainstorm solutions in a safe environment. I love encouraging CEOs to think about their challenges in new ways, and helping them become better leaders in the process.”

Mind Mapping the CEO

This day-to-day work has granted Cindy a keen understanding of the realities facing today’s CEO. “They’re trying to deal with the external, the internal and the unknown,” she says. “And uncertainty is underpinning all of it.” Cindy finds that ambiguity in the economic and political environments is making it difficult to formulate a one-year strategic plan, much less a five- or 10-year vision. So she feels it’s her job to support and empower business leaders and help them identify new ways to accomplish their near-term goals for growth. “No one is doing things the way they always did them,” she says. “And if they are, they’re out of business.”

Lighting the Way

For Cindy, the best part of her job is when she succeeds in helping a client see things in a new and different way. “I love seeing the light come on,” she says. “It’s a wonderful feeling for me, personally, when someone helps me see a challenge and solution more clearly, so I find great joy in doing that for others.” But she’s quick to point out that she “gets” as much as she “gives,” which is the beauty of the collaborative relationships she forges with her clients.

Why She Loves TPO

Cindy enjoys the dynamic, knowledge-rich environment that is TPO’s trademark. “It’s an organization that attracts extremely talented people who are able to leverage their talents in support of our clients’ business goals,” she says. But TPO’s consultants aren’t the only ones with the brainpower. “I love the fact that my TPO colleagues are smart and savvy—and that my clients are just as high-caliber.”


Cindy’s passions outside of work revolve around travel, sailing and her family, which includes a daughter and son-in-law, two step-children and five grandkids. As members of the Sailing Club of Washington, she and her husband have spent time sailing in the British Virgin Islands and are considering a future sailing excursion in Belize. Cindy claims there are valuable life—and consulting—lessons to be learned through sailing. She once attempted to moor a 42-foot sailboat and managed to back up over the dingy in the process. The lesson according to Cindy? “It’s best to look around before changing course.”


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