Many leaders fall into the trap of hedging—pursuing multiple, parallel efforts to mitigate risk—believing it to be a strategic safeguard. On the surface, dividing resources across different initiatives may seem like a prudent way to increase the odds of success. However, history and experience show that this approach often signals a lack of technical expertise and strategic vision. The fundamental flaw in hedging is that it disperses focus, dilutes accountability, and ultimately erodes team morale.
A classic example of this failure can be found in Steve Jobs’ turnaround of Apple in the late 1990s. When Jobs returned to the struggling company, he found a bloated product line, with multiple teams working on competing initiatives. Rather than allowing Apple to hedge its bets, he slashed the product lineup from dozens to just four, forcing the company to concentrate its energy on a few great products. His leadership proved that success comes not from trying everything, but from making bold, high-conviction decisions and committing fully.
Hedging also weakens execution because humans are not wired to excel at multitasking. In The One Thing by Gary Keller, the author argues that splitting focus between multiple priorities leads to subpar results. The same principle applies at an organizational level: when teams are asked to juggle multiple, competing projects, they experience cognitive overload, leading to inefficiencies and disengagement. Morale suffers when individuals feel their work is not contributing to a single, unified goal but is instead part of a scattered, unfocused effort.
Another well-documented case of failed hedging comes from Microsoft’s mobile strategy in the early 2000s. Instead of fully committing to a single approach, the company pursued multiple operating systems and hardware partnerships simultaneously, trying to hedge against uncertainty. This lack of focus resulted in inconsistent products, internal confusion, and ultimately, failure to compete with iOS and Android.
True strategic leadership requires conviction. It means identifying the right path and committing to it, rather than spreading resources thin in the name of optionality. Successful leaders don’t play it safe; they make the tough decisions, eliminate distractions, and rally their teams behind a singular, ambitious vision.