How to Take Smart Risks at Work

By Liz Wiseman

April 28th, 2015

Originally published on

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.

To read the rest of this article in it's entirety, please click here, or visit

  • “Wiseman (co-author: The Multiplier Effect: Tapping the Genius Inside Our Schools, 2014, etc.) provides a big boost for first-time employees and others who refuse to be bound by arbitrary limits. . . .An exciting promotion of lifelong discovery and enthusiasm as answers to routine and business as usual.”
    Kirkus Reviews
  • “Agility, resilience, grit, and a growth mindset—these are the attributes effective leaders need in a changing world. Rookie Smarts shows leaders at every age and at every stage of their careers how to master these skills.”
    University of Michigan professor and author of Leadership Sustainability
  • “Wiseman masterfully shows why novices can outdo veterans, expertise blinds us to fresh ideas, and the brilliance of newbies remains untapped. With sage insights and fascinating examples, Rookie Smarts is a must-read.”
    Wharton professor and author of Give and Take
  • “If you want to be a learning machine, improving and growing every year, this is the book for you.”
    SVP of People Operations, Google, Inc.