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15 ways to salvage a troubled digital transformation

Digital journeys are rife with hurdles and setbacks. From reorganizing the ranks to insisting on value, here’s how to reboot a digital initiative gone awry

Source | | Esther Shein

Robert F. Kennedy once said, “Only those who dare to fail greatly can ever achieve greatly,” which may bring some comfort to IT leaders when it comes to digital transformations that stumble.

The reasons why digital initiatives fail are well documented. They include underestimating the complexity of the initiative or lacking consensus on what digital transformation really means. Often officials realize that while they’re busy transforming they still have to run a business, and sometimes, the initiative ends up taking a back seat, says Marty Boos, CIO of event ticket marketplace StubHub.

“What happens fairly regularly is the amount of effort is underestimated and the time to get to ROI is underestimated,” Boos says, adding that once you get started on an initiative, “the marketplace changes slightly or some assumptions you made going into the project turn out to be not completely accurate.”

With any transformation, projects get mired in the fear of the unknown, risk aversion and a misunderstanding of what digital offers, says Rick McNabb, chairman and CEO of consultancy Optimity Advisors. A strategy is set and then maybe IT delivers on 60 percent of what was promised. “So we don’t put the right strategy out there and we don’t deliver on the strategy we intend to deliver,’’ he says.

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