Why Playing It Safe Is the Riskiest Strategic Choice

In the current era of digital disruption, the pace of change has dramatically accelerated, leaving traditional risk management wisdom lacking. Across a variety of industries, technology-enabled disruptors have changed the rules. Many brands that moved cautiously have dramatically increased their risk of irrelevance or set themselves on a path to extinction. The author thus argues that playing it safe is in fact the riskiest choice. He illustrates this with the example of traditional brick-and-mortar retail companies that chose a “timid transformation” — as well as those that effectively pivoted and avoided that fate. Moving faster doesn’t mean being reckless or endless moonshots, but cultivating a culture of experimentation and finding ways to “shrink the change” so that companies can better deliver value to customers.