Taking risks may be the smartest way to advance your IT career

Risk assessment is a huge part of IT. It’s also a huge part of an IT professional’s career.

Risk can stop you in your tracks or propel you forward, but no matter how things work out, taking a risk can be the wise thing to do.

We asked IT professionals to tell us about the biggest career risks they ever took. Their stories show that taking risks, even those that don’t pan out, can have big payoffs — and that risk-taking can be habit-forming.

Going for broke

Back in 1999, Marc Mallow had a vision. He saw a new way to deliver creative technical and multimedia services using a virtual network of workers. But companies weren’t yet comfortable using virtual resources, broadband penetration wasn’t high enough to support such services, and existing applications couldn’t meet his business requirements.

So Mallow turned himself into a programmer, using his free time over the next few years to build the application that he knew could be the core of his business. “I had a goal I wanted to accomplish, and there was no off-the-shelf software to get it done,” he says.

Then, in 2006, shortly after the birth of his second child, Mallow gambled big on his software: He borrowed US$400,000 to start his company.

Today, Mallow is the CEO of OnIt Digital LLC in New York. He uses software he developed himself to manage the schedules of all his full- and part-time employees. His bet has paid off with an expanding business that counts Fortune 500 companies among its clients.

Being the first to try a new technology is always a gamble, and Don Curt says he knew that. Still, as CIO at a global manufacturing and distribution company, he opted to try a vendor’s new Java-based version of an ERP system when it came out in 2001.

The new system promised increased capabilities, but because of the risk inherent in trying a new product, Curt limited the implementation to just 10% of the company.

Good thing. The move to the newer model didn’t go as well as he’d hoped. There were problems with bugs, transactions and connectivity. A year later, having spent $1 million, Curt aborted the initiative and moved everyone back to the vendor’s older version.

“The whole thing became a black eye,” Curt says. But because people were happy to get back on a system that worked and he was able to cover the $1 million through savings in other areas of IT, “the consequences in this case were minimal,” he says.

But he learned a valuable lesson: “If you’re going to be first, get lots of assurances, understand where you’re at, and that [vendors] need to give you extra services at their cost — which wasn’t the case with me.”

The experience didn’t sour Curt on risk-taking, though. He is currently managing partner at Alpharetta, Ga.-based CIO Services LLC, a company he started.

When Eileen Strider was vice president of IT at a large insurance company, a planned consolidation of several data centers didn’t go smoothly. The company president asked Strider to explain the situation to the unhappy business people at an annual sales force meeting. Strider knew the usual PowerPoint presentation wouldn’t go over well with that audience.

“They didn’t really want to know the technical details, so I was trying to figure out how to do this without making it sound like I was blaming other people,” she says.

She decided to take a risk and use humor to explain — and diffuse — the tense situation.

“I could have totally bombed,” she says. “But my intuition was strongly telling me to do this, that it would be OK. And it couldn’t be worse than boring them with PowerPoint and having them walk away saying, ‘I still don’t understand.'”

She dressed for her presentation in a bulletproof vest, lightening the atmosphere immediately. She used a volunteer from the audience to portray the fragile application that had to be moved to Chicago. She piled him up with a huge stack of three-ring binders and added multiple bright pink Post-its to represent the policies, patches and fixes made to the system over the years. Then she used a rubber coil to link him with another volunteer, who played a new system that ran the application, and she had them attempt to shuffle together toward another volunteer who represented Chicago.

Strider’s risk helped her audience understand why the move had been rocky. It improved IT’s image and enabled everyone to lighten up. She is now president of consulting firm Strider & Cline Inc. in Kansas City, Mo., which she co-founded.

In the early 1980s, Kavin Moody was 18 months into his job as a systems planner for sales and marketing at The Gillette Co. He proposed building a system to extract information from the operational system and feed it into a different environment, where it could be analyzed and combined with much better report-writing capabilities.

In short, Moody wanted to build a business intelligence system, but this was years before anyone had put that name on it.

“It was criticized by the IT people as being redundant,” Moody says. “And if it had failed, I would have been gone; no question about it. But it was the right thing to do. I knew it would have a big impact, and I felt obligated to the business managers who hired me.”

He worked hard to get the CIO, an IT director and a sales division leader on board. Then he found money in the existing budget to build a prototype, which he used to convince the sales department to invest in the project. In the end, the project not only succeeded but also eventually expanded into a multidivisional system.

The success propelled Moody to build and lead the systems research department. That role put him on the path to CIO, a position he held at Gillette for five years. Today, Moody is executive director at the Center for Information Management Studies, a forum for IT management issues at Babson College in Wellesley, Mass.

Naomi Karten remembers colleagues telling her that she’d make a good consultant. But at the time, she was an IT manager at a national insurance company, where she had job security. And in 1984, job security meant something. The idea of going out on her own wasn’t on her radar screen.

Then, a few things got her thinking. She facilitated consensus-building between two camps that were bumping heads. She realized she didn’t like the company’s “toxic” work environment, and she wasn’t inspired by the thought of going somewhere else and doing more of the same.

The idea of becoming a consultant clicked, and she made the leap, giving herself just one year to succeed.

“The idea of working without a boss or the security of a job was outside the scope of anything I had ever conceived of,” Karten recalls.

She learned as she went. “Sometimes, what you don’t know can help you,” Karten says, explaining that if she had known then what it took to run a consulting business, “it would have been overwhelming.”

Networking and serendipity helped her build her business, and today she is principal at Karten Associates in Randolph, Mass. “Often, we are capable of so much more than we give ourselves credit for,” she says. “It’s only by taking a chance that we find out what we’re made of.”

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Lauren Mackler, a personal and executive coach at Lauren Mackler & Associates LLC in Newton, Mass., and co-author of Speaking of Success (Insight Publishing, 2007), has a simple system to help assess risk.

1. Write a list of pros and cons regarding the action you are contemplating.

2. Assign each a rank from 1 (lowest potential benefit/harm) to 10 (highest potential benefit/harm).

3. Add the scores to find out whether pros or cons dominate.

“The pros-and-cons exercise puts out in front of you where your values are,” Mackler says. “It really makes you think about your priorities.”

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