Leading (Digital) Transformation From the Inside Out

Change is constant, and going faster than ever. We call it innovation, transformation and continuous improvement. It happens with success, failure, acquisitions and mergers. We can manage the change, or the change will manage—and likely defeat—us. And, if you are reading this column, you like to win.

Last month, I wrote about the how best people to lead your business/digital transformation might be right under your roof. She or he knows the fabric, the culture, the fears and doubts, the org chart as well as the power map. And they have the informal network to get things discussed, debated and done. It takes a team—indeed, usually many teams—to truly succeed.

Transformation is not easy. It takes work, skills and patience. Skillsets and mindsets and tool kits are likely new and different to be successful. Here are some we have seen in our 30 years in the change field – and the last five to 10 in digital transformation.

Have a clear purpose. Know the “why” of the transformation. Yes, there is always the strategic plan—and the purpose of that strategy has to be simple and clear. The leaders of your transformation must understand the “why” deeply in his/her bones—and believe in it.

Meet them where they are. It does not work to have a clear vision and plan if it seems unrealistic, impossible and irrelevant to your people. The great leaders of change have empathy—they know how to connect to the different groups in the business and speak their language, empathize with their circumstances, and their doubts and pains.

Communicate, communicate, communicate. Said another way: share, listen and learn. Effective communication is really not that easy. It means that your leader(s) need to be able to articulate the proposition well, and what is expected—and in the language of the existing culture and mindset of your people (as above). They need to listen to the fears and doubts, challenges and ideas of the people who will have to inform, learn, execute and live with the change (or not). And they need to know you’ve heard them—you’ve learned from them. Keep the dialogue alive, being responsive and engaged.

Accept and embrace failure. Failure is a learning opportunity. Almost all success—even those considered “overnight”—in truth were years of failure (or limited success) in the making. The tools of rapid transformation are no longer top-down. Success never has been a straight path, no matter how neat and clean your plan looks on paper. It is organic, iterative, interactive and fast.  Your leaders need to be able to accept and learn from the failures, and then help others to do the same.

When you have a culture and leaders that have these attributes, then your insider-leader can help your external and new-hire experts be accepted and embraced, and the transformation can truly deliver spectacular results.♦

Stephen Garber is director of Third Level Ltd. Contact him at 561.752.5505 or sgarber@thirdlevel.com.

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Drew Limsky

Drew Limsky



Drew Limsky joined Lifestyle Media Group in August 2020 as Editor-in-Chief of South Florida Business & Wealth. His first issue of SFBW, October 2020, heralded a reimagined structure, with new content categories and a slew of fresh visual themes. “As sort of a cross between Forbes and Robb Report, with a dash of GQ and Vogue,” Limsky says, “SFBW reflects South Florida’s increasingly sophisticated and dynamic business and cultural landscape.”

Limsky, an avid traveler, swimmer and film buff who holds a law degree and Ph.D. from New York University, likes to say, “I’m a doctor, but I can’t operate—except on your brand.” He wrote his dissertation on the nonfiction work of Joan Didion. Prior to that, Limsky received his B.A. in English, summa cum laude, from Emory University and earned his M.A. in literature at American University in connection with a Masters Scholar Award fellowship.

Limsky came to SFBW at the apex of a storied career in journalism and publishing that includes six previous lead editorial roles, including for some of the world’s best-known brands. He served as global editor-in-chief of Lexus magazine, founding editor-in-chief of custom lifestyle magazines for Cadillac and Holland America Line, and was the founding editor-in-chief of Modern Luxury Interiors South Florida. He also was the executive editor for B2B magazines for Acura and Honda Financial Services, and he served as travel editor for Conde Nast. Magazines under Limsky’s editorship have garnered more than 75 industry awards.

He has also written for many of the country’s top newspapers and magazines, including The New York Times, Washington Post, Los Angeles Times, Miami Herald, Boston Globe, USA Today, Worth, Robb Report, Afar, Time Out New York, National Geographic Traveler, Men’s Journal, Ritz-Carlton, Elite Traveler, Florida Design, Metropolis and Architectural Digest Mexico. His other clients have included Four Seasons, Acqualina Resort & Residences, Yahoo!, American Airlines, Wynn, Douglas Elliman and Corcoran. As an adjunct assistant professor, Limsky has taught journalism, film and creative writing at the City University of New York, Pace University, American University and other colleges.