The path to the CIO's office: Real-world challenges required

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The key was starting out small, with projects like Visual Voice, which translates traditional voice mail messages into a form compatible with IP-enabled devices and software. "We prototyped it in our spare time," says Rodrigues. Kheradpir worked with the marketing department. And slowly but surely, a product-development group blossomed. Since then, the group has developed dozens of consumer products, including mobile handsets and fiber-optics based video, voice, and data services (marketed as FiOS), generating hundreds of millions of dollars in revenue.

"With Shaygan's support, we were able to build this from small successes rather than him going to senior management right away to invest in it before we knew if it would work," says Rodrigues. The CIO gave Rodrigues the time to prove the value of the product-development mind-set and the support necessary to build it into a successful enterprisewide program.

Mentoring is critical for these stretch assignments. "If someone's a little over their head," adds Finnerty of Applied Materials. "I make sure I surround them with expertise." People who have done the work before, or at least some piece of it, are there to provide advice.

Terry Dinterman, JetBlue's vice president of technology services, had just a few months to negotiate an infrastructure outsourcing contract for the airline to address system-availability concerns and pave the way for a new reservations system. He'd set up application development deals before, but nothing with such a great impact on the enterprise or with such a tight deadline. However, the Ones to Watch honoree had backing from the airline's senior executive team and its board. CIO Joe Eng joined Dinterman in meetings with board members, invited him to speak at senior leadership forums to build awareness of the project, and served as Dinterman's trusted advisor.

"Joe always made himself available to discuss the approach and progress of the RFP and negotiations," Dinterman says. That not only gave him the confidence to nail down a deal in eight months, but also the authority to handle vendors who tried to circumvent his RFP process by going to Eng and other JetBlue execs.

Dinterman walked away not only with an enterprise win but also with a wealth of leadership know-how. "Simply the experience of going through a very visible and challenging project generates leadership development," he says. "You cannot underestimate the value of new relationships that get established with senior executives, key business leaders and even business partners when navigating an enterprise project."

He's now worked closely with executives from finance to legal to sales. And because the infrastructure outsourcing contract was only one of the big projects on his plate -- he also negotiated contracts with Microsoft and EMC, relocated part of his workforce and managed a dozen other enterprise projects -- "I had no choice but to develop my ability to discern when to trust [my] team and when to dive into the details."

Give Them Room to Grow

There's a fine line between having a supportive CIO and becoming suffocated by oversight. Having space to make mistakes is essential to moving ahead, says Dinterman. He's probably his own harshest critic, but he has a long list of things that he now knows he could have done better on the infrastructure outsourcing deal.

He should have staffed up the project office more instead of assuming technical leaders could also provide full oversight. He should have created a more comprehensive communication and change-management plan to jump-start adoption of technology such as new teleconferencing capabilities. He should have realized earlier that he needed deeper expertise in some technology areas than he had on staff and brought in consultants sooner.

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