Preparing for a CIO Role? Stretch Yourself with IT Leadership Challenges

Our Ones to Watch honorees maximize leadership opportunities as they prepare for a future CIO role

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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.

Letting up-and-coming leaders learn doesn’t mean letting go of the reins altogether. Charting a course is exceedingly important when giving your best and brightest a shot at something new. “You have to set up the experience with the takeaways in mind,” says MasterCard’s Reeg. “It’s got to be fundamental to the program that they learn something new.” Reeg wanted Meister to run real-time, mission-critical services and manage a large, global team spread from Missouri to Mumbai.

Though Meister keeps succeeding, he says one of the benefits of new experiences has been learning how to fail. A few years ago, he was struggling to build a website using a new rich user-interface tool. His team was stymied by performance issues in the final days of testing. “Because we had a high level of trust across our organization and with our pilot customer, we were able to switch to an alternate technology, quickly redeploy the site incorporating our pilot customer’s feedback and still hit production in time for our second customer’s implementation,” says Meister.

He witnessed other aspiring leaders refuse to admit mistakes for weeks or months, wasting time and money. “I’ve learned that if you’re going to fail at something—and there is enough trust across an entire team to admit that something is going to fail—then fail quickly. The sooner you take responsibility, the better.” That requires the CIO to create a culture that views failure as “a small setback to longer-term success,” says Meister.

Turns out that advice also applies to the CIO’s task of assigning up-and-coming IT leaders these opportunities. Sometimes a new on-the-job experience doesn’t work out—the environment is too political, the resources aren’t there, the timing isn’t right. “You have to get the balance right when it comes to pulling the plug on a new experience,” says Finnerty of Applied Materials. Too early, and you may shortchange someone who could have been successful. Too late, “and you can burn out a great person or stop a career.”

It comes down to matching the right experience to the right person, providing support while leaving room for growth, and constantly communicating about how things are going. Particularly in the early weeks of a new assignment, says Finnerty, it’s important not just to be available to someone tackling a new experience but also to actively track how the project or role is going and make adjustments when necessary.

Finnerty doesn’t want to smooth the course too much. “Part of the experience is learning that CIO environments are never easy,” he says. But when things truly aren’t going well, “it’s all about being candid and open and saying, ‘Here’s the situation. How can we adjust it?’” says Finnerty. Maybe he needs to provide his protégé with more political cover. Maybe more or different resources are required. Maybe a deadline should be changed.

“I’ll always ask if there’s something I can do. In some cases they’ll say yes. In other cases, they’ll say, ‘Let me handle it, but let’s talk about how to do it,’” says Finnerty. “In most cases, they solve it themselves.”

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Copyright © 2010 IDG Communications, Inc.

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