Ex-Oracle executive: How to take smart risks at work

Courtesy of Wiseman Group

MPW Insider is an online community where the biggest names in business and beyond answer timely career and leadership questions. Today’s answer for: Describe one make or break moment in your career–how did you navigate it? is written by Liz Wiseman, president of Wiseman Group.

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.

An outside consultant whom I deeply respected said, “I highly advise against this. Keep the team on track.” My team members noted that this was more than just high-stakes learning–this was “you-must-be-high kind of stakes. The senior executives couldn’t be reached, and I was the closest thing to adult supervision. Should I choose the safe path or take the rockier road that could pave the way for greater progress?

I decided letting them wrestle with the company strategy and walk in the shoes of senior executives was actually the best way to hone their strategic thinking skills. So I told the group that they were free to redefine their work, but with freedom came obligation. “Be creators of value, not just critics of the status quo,” I cautioned. I then scrambled and called each of the three executives at home. It was too late to ask for their permission, so I shared my rationale and asked that they keep an open mind. Yes, they were slightly annoyed but they were also intrigued.

The group worked through the night and delivered a compelling presentation–analysis and answers. Having been readied, the senior executives responded brilliantly. There were a few uncomfortable moments, but the ripples stirred by these emerging leaders became a wave of change that delivered a clearer, more compelling strategy. The would-be mutiny was transformed into a movement because we took the unpaved path. To make new discoveries, we have to abandon the well-worn tracks. We might need to go off-road for a bumpy thrill ride or sit in the “splash zone.” But, if you take the unpaved path, don’t do so blindly. Take smart risks and pave the way for success:

Acknowledge the risk: Recognizing the threats prompts us to take precautions, keep our ear to the ground and watch for signs of trouble.

Set boundaries: Be flexible but clear on what you expect from others.

Take the risk out of risky moves: Clue people in and make it safe for everyone to venture into new territory.

Sure, stepping into a zone of discomfort can feel unnerving. Yet, when we venture out, we discover that our comfort zone expands. And then our influence does as well.

Read all answers to the MPW Insider question: Describe one make or break moment in your career–how did you navigate it?

Build-A-Bear CEO: How to navigate difficult career decisions by Sharon Price John, CEO of Build-A-Bear Workshop.

Why I gave up everything to start a career in Singapore by Perry Yeatman, CEO of Perry Yeatman Global Partners.

Why I choose to put my children before my work by Lauren Stiller Rikleen, president of Rikleen Institute for Strategic Leadership.

How this Google executive handles stress at work by Margo Georgiadis, president of Americas Operations at Google.

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