Honing your job-search skills

Hank Leingang was interviewing for the CIO post at a major company when his internal alarm bell went off. He realized that the other executives were engaged in an ongoing debate over what the CIO role should be.

“They couldn’t articulate what they expected from the CIO, and they were also clearly not interested in having an ‘impact CIO’ in the organization,” says Leingang. “I remember leaving the interviews, going back to the airport, calling the headhunter and saying, ‘No way.’”

Discerning what your prospective boss wants from you is a survival skill everyone should have, particularly in IT, where duties, responsibilities and expectations are frequently underdefined or unarticulated.

It’s not always easy to learn, but you can get the information you need by asking the right questions of the right people, seeking out insiders for unfiltered perspectives and using the whole interview experience to get an accurate view of what the position really entails.

You can get the information you need by asking the right questions of the right people.

“Based on the information you gather, you’ll have to do your own assessment: whether what’s needed in the organization is something you can deliver, if it’s doable, if you can build the team to do it,” says Leingang, now president and CEO of ITM Software Corp.


The stakes are high.

Jerry Luftman, associate dean at Stevens Institute of Technology’s School of Technology Management, recalls a colleague and proven IT leader who took a CIO job without conducting due diligence. He soon found that the company’s culture was too formal and that the scope of work was too broad for him to succeed. He quit within a year.

John Chambers, president of JCC Executive Partners, an executive consulting firm, tells of a colleague who was recruited by a friend to join a company as head of engineering. But he quit after six months because he was turned off by the abrasive culture and an impending downsizing.

“Even though you might be recruited by someone you trust, it’s still incumbent on you to talk to everybody and understand the vision at that organization,” Chambers says. “It’s to ensure that this is the right fit.” Executive search firms often get descriptions of IT jobs that are only three sentences long, so it’s essential for candidates to push for more details, says Al Guibord, chairman and founder of The Advisory Council Inc.

For insight into what the company really thinks of a position, find out to whom it reports, he says. For instance, a CIO who reports to facilities is likely not in the same universe as one who reports to the CEO. Then clarify any doubts by asking why the position reports to that particular group.

Also determine the membership of the management team, how long they have held their current positions and what each did previously. Such details can help you understand whether this is a long-standing, cohesive team built internally or a newly formed one brought in from the outside to shake things up. “It helps you understand the culture of the company, so you know what you’re walking into,” Guibord says.

Executive coach Suzanne Bates worked with one CIO who had learned his lesson the hard way. He took the job with the understanding that the CEO wanted him to drive change. But he soon learned that in his position, he didn’t have the same status as other executives, making change impossible.

“When we ask things like, ‘Will I be on the executive team?’ we hear just the ‘yes.’ But you need more,” says Bates, author of Speak Like a CEO (McGraw-Hill, 2005). “Request a job description to go along with the job offer to spell out the roles and responsibilities, so when you walk in the door there is a common mind-set about why you’re there and what your role is going to be.”

Dean Drougas, CIO at Extreme Networks Inc., a provider of Ethernet infrastructure, says that when he considers a new job, he focuses on how the leadership views IT. Is IT considered a differentiator? A strategic asset? Or is it there just to keep the lights on? He likes to hear answers not just from leadership but from IT staffers, too, so he can see if the views are consistent.

Leingang says it’s important to move beyond buzzwords and get into details. For example, executives often say they want IT aligned with the business. You need to get them to spell out what that means. Leingang suggests that questions like these will get the answers you need:

• Does the organization want me to develop strategies, or does it expect me to deliver technology on plans that others have fleshed out?

• How will I be evaluated?

• How does the organization define success for this position two years and five years out?

• How does it define failure?

Harish Ramani, CIO at Constellation Brands Inc., an international alcohol producer and marketer, says that when he is considering a position, he insists on meeting with a diverse group of people, including those from IT, executives in other areas, and workers two or three layers down.

Moreover, Ramani says, it’s important to understand the company’s business dynamics, the key business drivers, business needs and how IT relates to each of those. He also likes to ask prospective bosses to define business problems – to talk about what’s broken and needs to be fixed.

By asking these kinds of questions, you may discover that those interviewing you lack a clear vision of the position. That’s often a deal breaker, but not always. Although taking a new job amid vague expectations can create difficulties, you can sometimes turn the situation into an opportunity to carve out a role that suits your own vision. “It’s important for you to go in with eyes wide open,” Bates says.

And it helps to open them before you go in. That’s why it’s important to do your homework. “It’s not just about having the right skills [for the job], but having the right interviewing skills,” says Luftman.

To prepare for the interview, talk to people who previously held the job and personal contacts at the company as well as vendors and consultants to find out what’s really going on, says Luftman. He notes that membership in professional organizations, such as the Society for Information Management, where he is an officer, helps in building contacts who can give you the inside scoop.

“It’s an interesting dance,” says Drougas of the job search experience. “You’re interested in being there and they want you there because they have a need to fill. There’s this courtship dance, and you don’t want to show all your warts – as a candidate and as a company.”

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Mary K. Pratt is an IT journalist based in Waltham, Mass.

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