The risks can escalate the longer you wait. "I see a lot of companies that are still highly mainframe-based because they've never gotten away from their core software," Weeks says. "The problem now is finding people to support that environment. I don't think there are a lot of people coming out of college saying, 'I want to support mainframes!'"
"Someone early in my career said to me that part of the role of the CIO is knowing which frogs to kiss," Meilen says. "You have to try out some new things. But if you're not clever about which ones, you're going to waste a lot of time and not get much from it. It can't be chosen at random. It's an important element of what we do that we will take some risks on new technology. That's part of our responsibility within the enterprise. There aren't a lot of functions that own responsibility for taking risks, but IT and the CIO do."
And so, he says, it's imperative to keep trying new things, even if some of them wind up as failures. "By playing it very safe, you're not serving your enterprise as fully as you could be or should be."
How to handle tech mandates from the CEO
"Hey, I was just reading an article..."
Those six words strike fear into the heart of many CIOs. It happens like this: The CEO or CFO reads an article about an interesting new technology and directs you to implement it -- without knowing any of the details. What do you do if you know it's not a good fit?
"CIOs struggle with communicating both upward and downward," says Jason Cohen, CIO at Diversified Agency Services. "Some CIOs I talk to tell me, 'The CEO dropped it in my lap and I have to do it.' I say you aren't doing your organization or your CEO justice unless you fully explain the pros and cons."
The secret is to carve out pieces of information the CEO can understand. Cohen says he'd approach it this way: "I might say, 'I read that article, too -- about transferring files through the cloud. But did you know the average file size for an advertising agency is much larger than for a manufacturing company because of the large graphics? That's why that doesn't work for us.' "
Bring-your-own-device mandates can be particularly challenging. "Executives always ask, 'Can I use my iPad?' " says Pete Lee, engagement manager at SWC Technology Partners, which provides IT services to midsize businesses.
BYOD programs offer many advantages. "But they can kill IT staff, because they have to manage so many different things," he says. "If you implement BYOD, there will be more cost for managing those devices and more licensing costs."
The best approach is to make sure upper execs understand those costs. "Every executive responds to ROI," he says. "If you can compare the return on investment with what it will cost to implement BYOD, they can make the right decision."
Knowing that an article that a CEO has read could land on your desk at any moment should serve as a motivator to stay informed yourself. "The best approach is to stay ahead of it," says Rachel Dines, an analyst at Forrester Research. "You need to be reading the same magazines, so when the CEO drops an article on your desk and wants to implement this whiz-bang thing, you'll already have looked into it and talked it out with your reports. You'll be ready to say, 'Yes, we've been thinking about suggesting this,' or 'No, we can't, and here's why not.' The worst thing is to be blindsided."
And, she says, make sure you're not doing the same thing to your own IT organization. Make sure you get buy-in from every segment of IT before committing to a project. "When I see an implementation go wrong, it's usually because someone from above mandated it," she says. "I see that more than you might imagine. Something is brought in all of a sudden, and the infrastructure folks are saying, 'I wish someone had asked me because this doesn't jibe well with the technology we have.' "
-- Minda Zetlin
Zetlin is a technology writer and co-author of The Geek Gap: Why Business and Technology Professionals Don't Understand Each Other and Why They Need Each Other to Survive. Contact her at firstname.lastname@example.org.
Read more about management in Computerworld's Management Topic Center.
This story, "The best tech investment I never made: Four CIOs' tales" was originally published by Computerworld.