Global CIO: 13 CIOs Describe Their Biggest Mistakes

When InformationWeek editors drew up questions for our ongoing CIO Profile series, we included one asking about the "Decision I wish I could do over." I was ready for a lot of job interview type responses, of the "my biggest fault is trying too hard" variety.

Instead, I've been blown away by the candor, humility, and perspective these leaders have shared. CIOs have discussed genuine mistakes--hold the sugar coating, with a side of lesson learned. They've relived problems with vendor contracts, outsourcing, and project management. They've lamented letting a troubled project drag on. Many are intensely personal looks back on career missteps, including chasing dot-com riches.

It's leadership by example. Of course we all know it's OK to make mistakes--in concept. The hard part is staring down the real thing. Here are some "Decisions I wish I could do over" that your CIO peers shared during the past year, with links to their full CIO Profiles:

Michael Manchisi , CTO, MasterCard Global Technology and Operations: As a financial officer earlier in my career, I saw all the signs that a project was heading south, but I kept it going longer than I should have. I learned the importance of failing fast and redirecting resources and dollars to more mission-critical projects.

Peter Whatnell, CIO of Sunoco: At one company, we were looking at a major legacy replacement project and a number of the executives didn't want to "go to the trouble" of defining a business case, arguing that it was an obvious business infrastructure investment. Against my better judgment, I was convinced to go along with that view. Of course, 10 months later, the project was killed.

Ed Trainor, CIO of Amtrak: When I was CIO of Paramount Pictures, a subsidiary of Viacom, the CIOs of the major Viacom business units launched a company-wide infrastructure outsourcing initiative that ultimately failed, primarily because the result/reward structure was overly unbalanced in Viacom's favor, as we didn't construct a true win-win situation for both parties. One lesson I learned was that there has to be sufficient benefit for both parties to make it truly successful. I also learned that outsourcing is simply another way of many to accomplish your business objectives and that it isn't a general solution to be applied to all problems.

Mark Greenlaw, VP and CIO of Cognizant: 2003 was a tough year for me when the startup I worked for was acquired, and I was laid off. I took a job that wasn't right for me. I stayed only a short time and felt I let down the person who hired me.

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Amin Kassem, Executive VP and CIO of SHPS: A major software vendor tried to change a software licensing model on already licensed software in order to charge higher fees. After we obtained bids from competitors, it quickly stopped its efforts to change the licensing model, and I kept the software. I wish I'd replaced the vendor, as it wasn't serving as our business partner. Thankfully, its technology plays a less critical role in our current technology strategy.

Ann M. Harten, VP of Global Information Services and Human Resources at Haworth: When I first got into IT in 1993, we implemented a pilot of a new ERP system with a very small (read: too small) team. The result was several months of mind-bending work that consumed very long days and was quite draining. I learned early the importance of properly staffing any system implementation and the hypercare that follows the pilot launch. It was a great experience, with a terrific group of people, and I am fortunate that they still speak to me.

Laxman Kumar Badiga, CIO at Wipro Technologies: I wish I'd never taken a personal trip to Kuwait during the Iraq invasion in 1990!

Jason Harrison, Worldwide CIO Of Mediabrands: Seven years ago, I was managing the implementation of an investment tracking system for Johnson & Johnson by a small software company. We were 90% done when issues started cropping up--functionality gaps, data incongruities, and promises broken. We spent an enormous amount of time trying to execute that last 10% when we should have had the courage to simply walk away from the colossal failure. Lesson learned.

Marty Colburn, Executive VP and CTO at The Financial Industry Regulatory Authority: The biggest one was taking on leadership of an Internet startup. It was almost impossible to turn around.

Kirk Gutmann, CTO of General Motors: I wish I'd developed more staff in the Asia-Pacific region quicker. The growth rates there have been five to six years faster than all the forecasts.

Patti Reilly White, Senior VP and CIO of Darden Restaurants: Darden has offered employees the opportunity to rotate into other parts of the business to grow and develop broader skills. It never seemed like the right time in my career to take advantage of this, but I wish I had. I believe it would make me a stronger CIO today if I had worked in a key area, outside of IT, for one of our brands.

John P. Burke, CIO of Ambit Energy: I was working as a consultant in the '90s when a customer asked me to become a VP over their IT group. I agreed, but continued working with the customer on a part-time basis because I was committed to other clients. I discovered you can't earn trust as a leader in a part-time role. I should have turned down the offer or rejected having direct reports.

Marc Probst, VP and CIO of Intermountain Healthcare: Leaving Ernst & Young to help a startup business during the dot-com revolution. If you learn from your failures, then this gave me my Ph.D.

It's striking how many of these are from years ago. I know I still think about the phone briefing I took with the top executives of a growing, $200 million-a-year company called Infosys in 2000, just months after I'd started with InformationWeek. I fundamentally underestimated how much and how fast India's IT sector would change the global industry -- or that Infosys might grow to a more than $4 billion-a-year company. In 2000, with IT budgets still flush, I missed the simple power of a lower-cost option.

The tough mistakes stick with us. We live with them, we learn from them, we might even learn to laugh at them, as these leaders have. But like them, we also don't forget them.