strategizing in uncertain times

The ancient Stoic philosophers believed that it was essential to be prepared for downturns—whether contemplating war, shipwrecks, torture, or exile, the “premeditation of the evils and troubles that might lie ahead” was a way to manage life’s inevitable disasters. Modern leaders may be unlikely to endure shipwrecks, but they are beset with uncertainty of all kinds, from geopolitical upheavals to global supply chain shocks. Operating in a near-permanent state of uncertainty may require its acceptance in ways that traditional strategists may not be prepared for.

Get comfortable with discomfort

“Imperfectionism sounds like a bad thing, but what we mean is accepting the ambiguity of not having perfect knowledge before making strategic moves,” says investor and McKinsey alumnus Charles Conn in an episode of our Inside the Strategy Room podcast. In a world marked by disruptions, conventional approaches to strategy can “yield either incomplete or misleading results,” he says; instead, dynamic, real-time, and nonlinear actions have a better chance of success. Adopting a few different mindsets can help leaders go with the flow rather than wait for certainty. For example, an “Ever Curious” mindset “starts with an audacious question or a long-term vision” that leaders should encourage their teams to cultivate, Conn suggests. “Your people have fantastic ideas, but there’s nothing more boring than being told to stay in your lane. You need to change incentive structures so that people aren’t penalized for working on the side.”