• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Commentary

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

By
Liz Wiseman
Liz Wiseman
Down Arrow Button Icon
By
Liz Wiseman
Liz Wiseman
Down Arrow Button Icon
April 28, 2015, 12:00 PM ET
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.

About the Author
By Liz Wiseman
See full bioRight Arrow Button Icon

Latest in Commentary

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Commentary

hoskins
Commentaryoffices
Gensler Co-Chair: Hot-desking was supposed to save money. It may be costing you your culture
By Diane HoskinsApril 30, 2026
22 minutes ago
tillis
CommentaryCongress
Thom Tillis: Free markets built American prosperity. Government intervention puts it at risk
By Thom Tillis and John StanfordApril 30, 2026
2 hours ago
iran
CommentaryIran
The Strait of Hormuz is a data problem, not just a military one
By Erik Bethel and Ami DanielApril 30, 2026
2 hours ago
hollywood
CommentaryMarketing
I spent 20 years learning to navigate an industry. Then I built a campaign for the man who’s dismantling it
By Matti YahavApril 29, 2026
21 hours ago
aging
HealthLongevity
We’re the CEOs of Peloton and the Hospital for Special Surgery. Living longer isn’t enough, we need to live better, too
By Bryan T. Kelly and Peter SternApril 29, 2026
22 hours ago
gen z
Commentarydisruption
AI won’t kill your job — it will kill the path to your first one
By Jeffrey Sonnenfeld, Stephen Henriques, Johan Griesel, Andrew Alam-Nist and Peter YuApril 29, 2026
23 hours ago

Most Popular

Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
Success
Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
By Preston ForeApril 27, 2026
3 days ago
‘Take the money and run’: Johns Hopkins economist Steve Hanke on why the UAE quit OPEC
Energy
‘Take the money and run’: Johns Hopkins economist Steve Hanke on why the UAE quit OPEC
By Shawn TullyApril 29, 2026
1 day ago
‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
AI
‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
By Sasha RogelbergApril 28, 2026
2 days ago
Jamie Dimon gets candid about national debt: ‘There will be a bond crisis, and then we’ll have to deal with it’
Economy
Jamie Dimon gets candid about national debt: ‘There will be a bond crisis, and then we’ll have to deal with it’
By Eleanor PringleApril 29, 2026
24 hours ago
‘They left me no choice’: Powell isn’t going anywhere—blocking Trump from another Fed appointee
Banking
‘They left me no choice’: Powell isn’t going anywhere—blocking Trump from another Fed appointee
By Eva RoytburgApril 29, 2026
16 hours ago
More than two-thirds of U.S. schools say they’re unable to afford the cost of student free lunch—and MAHA’s dietary guidelines may make it worse
Economy
More than two-thirds of U.S. schools say they’re unable to afford the cost of student free lunch—and MAHA’s dietary guidelines may make it worse
By Sasha RogelbergApril 29, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.