IT: Don't let the CEO wonder what you do all day

If there's no catastrophic system failure or major software deployment to work on, CEOs might wonder what IT does all day. Here's how to make sure your contributions aren't undervalued when things go smoothly.


Robert Handler, an analyst at Gartner, will never forget one of his earliest consulting jobs. "I was asked to gather enough data on a CIO to fire him," he recalls. Handler dutifully began researching the CIO's current and past activities but could find no obvious missteps. In fact, the man in question was the best CIO he'd ever met.

Eventually, he returned to the CFO who had given him the assignment to ask why the CIO was to be fired. The CFO answered, "'He's spending a lot of money, and everything seems to be working just fine,'" Handler recalls. "And I thought, 'I don't ever want to be a CIO!'"

Handler had encountered one of the paradoxes of the IT world: Technological achievements often result in things not happening -- bad things, like outages, lost data or network breaches. "On a good day in IT, nobody knows you're there," says Joe McLaughlin, vice president of AAA Western and Central New York, a Buffalo-based not-for-profit that provides emergency roadside assistance and other services to its 880,000 members.

Worse, top executives may know that you and your staff are there, but they think you're updating your Facebook profiles while waiting for requests for help. Like the CFO who Handler encountered, they may assume that if they don't see new technology being deployed or major problems being repaired, there's nothing much going on. But in reality, a good IT person will, for example, "be constantly looking at resources to find out about zero-day attacks and other threats," says Mike Vitale, CTO at TalkPoint, a New York-based webcasting provider that facilitates about 20,000 webcast events per year. "If there is a threat, the provider will put out a patch quickly. But then I have to find out, if I install the patch, will it stop part of the website from working? People don't know about the blocking and tackling that goes on every day."

"There's this misconception that you stand up your servers and then they run in perpetual motion from that point forward with no care and feeding involved," adds Chris Brady, CIO at NextGear Capital, an inventory finance provider for used-car dealers whose 75 branches serve 9,000 dealerships.

That misconception is easy to understand. Corporate executives may think enterprise IT systems are like home computers: You set them up and they keep running with little or no intervention as long as security updates and patches are set to automatically download. It's hard to argue with the logic that servers costing $50,000 or more should have at least the same capabilities as the $1,000 Macs or PCs sitting on their desks at home.

The same goes for the functions they're accustomed to using easily in the cloud, such as email across many different devices. "A lot of IT teams for the past 10 years have been supporting Microsoft products," Vitale says. "Then -- boom! -- overnight this executive has an iPad and wants it to work on the network. People are getting rid of BlackBerries and want to use Android or iOS devices. It sounds easy to them, but it's not. They just expect it to work, and if it doesn't, there's a good deal of anger."

Indeed, IT often goes unappreciated unless and until something fails to work as expected. "I've seen a lot of companies where business units can overrule IT," Vitale says. That philosophy holds, he says, unless an important tech function fails. "Then they're waiting for the IT team to swoop in and save the day. It's the most thankless job in the world right up until something goes wrong."

But while it may be tempting to deliberately break something or allow it to fail so as to gain the recognition that comes with fixing a business-impacting problem, deliberately doing your job badly will not be beneficial to your department, your employer or your career. And there are better ways to get IT's value across to top executives, even when things are running smoothly.

Let them know what you're doing

"There is this conception that if I'm concentrating on BYOD, all the old stuff like server patching and firewall configuration can take a back seat. But those things need to be taken care of as much as the new shiny projects do," says Joel Dolisy, CTO (and top IT executive) at SolarWinds, an Austin-based network management company with annual revenue of $269 million. The solution, he says, is to provide regular updates on what IT has accomplished. For example, he says, "I have a meeting with my CEO today to talk about the latest things we've achieved in Web development, and that people are not twiddling their thumbs all week waiting for problems to happen."

"Executives are sensitive to money and to the total head count devoted to the IT department. Providing that information on a regular basis is primordial, because otherwise people think the money is going into a black hole," Dolisy says.

That's not a good situation. "There's a clear danger that if IT is not communicating well with the rest of the executive team and providing transparency into day-to-day operations, a lot of mundane tasks will be trivialised," Dolisy says. "At that point, it's difficult to deal with. The only thing that comes from the rest of the executive team is pressure to downsize the budget and downsize the number of heads, and only work on the new shiny projects. That's a recipe for disaster."

And Vitale wonders, "How many jobs have been outsourced just because the IT team did a poor job of explaining what they do on a daily basis?"

Keep it short and sweet

While many CIOs agree that it's essential to let upper management know about IT's activities and accomplishments, they warn that the task must be handled carefully because of the many competing demands on top executives' attention, and the danger that they won't fully listen to a presentation about technology operations, much less read a report about it.

For McLaughlin, the solution is to give the CEO a written report -- but a brief one. "It's very simple and executive-level, and it's one page," he says. "Basically, the question is: Are we winning or losing? If we're winning, maybe the executive can move on to something else. System availability was 99.89%. Do we care about the 0.11%? Maybe not."

Brady tries to casually mention to the CEO whenever her team completes a substantial project. Let's say they've just updated the company's mail servers to the latest version of Microsoft Exchange. "No one's going to see anything other than that the mail server has changed," she says. "But that's a pretty big project for the infrastructure team. So if you take your high-level project plan and explain why you're doing it and the effort involved, they'll see that there's a substantial project your team is doing."

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