How to Take Smart Risks at Work

By Liz Wiseman

April 28th, 2015

Originally published on www.Fortune.com.

Mike Tyson once said, “Everyone has a plan until they get punched in the mouth.” Our defining moments are often the ones when we toss out the plan and roll with the punches.

While at Oracle, I was charged with developing a flagship executive development program to hone the strategic thinking skills of our senior leaders. The participants would spend two days learning about the company’s strategy and then have two days to tackle a real, mission-critical project using what they’d learned. On day five, they would present their work to the top executives. It was a high-stakes, action-oriented approach to learning.

At first everything appeared to be going well, but mid-way through the work projects, I detected rumblings of dissent. The class leaders pulled me aside and clued me in. The group felt that rather than working on the assigned project, they could make a far greater contribution by giving the top executives feedback on how to improve the company strategy. This was more than a slight change in plan. We had invested substantial time and resources into preparing the work project, and the top executives were expecting solutions the next day. Plus this was a dangerous deviation. While improving the company strategy seemed noble, this could easily spiral into a gripe session and exposé. Top executives rarely appreciate surprises.

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