What would you do differently if you had it to do again? CIOs and other executives reflect on the lessons they missed, so you don't have to.

Youth is wasted on the young, said George Bernard Shaw. That sentiment is widely shared by senior technology executives. When I asked several execs to talk about mistakes and gaffes they’d made early in their careers, the responses usually began with, “How many hours do you have?”

As you might suspect, there were common threads. Most of these accomplished experts began their careers with an unshakeable belief in the power of technology to solve any and all problems. Initially, they either misunderstood or downplayed the role of humans in the loop.

“The early part of my career was heavily skewed toward resolving the issues of the day: software and networking. That meant religiously following SDLC and OSI models for best outcomes. Of course, when you have a hammer, everything looks like a nail,” says Yuri Aguiar, a senior partner and former CIO at Ogilvy & Mather Worldwide.

“I have a vivid memory from many years ago of standing in front of a whiteboard in an office in Hong Kong, staring at our handiwork: a sophisticated regional network diagram with boxes, circles, databases, connectors, and lightning bolts,” says Aguiar. “And then it struck me—we hadn’t drawn any stick figures showing the people who would use it.”

It’s about creating a culture where people understand the destination and the vision, and then supporting that with a communications process that shows them how their accomplishments are helping us get to that destination. Eric SchrockCTO of Delphix

Recognizing the need to design for humans doesn't necessarily mean you know how to do so. Timothy Campos, who served as Facebook’s CIO from 2010 to 2016, says it took him a long time to realize that “what you say can be very different from what people hear.”

Earlier in his career, when Campos was CIO at KLA-Tencor, a provider of process control and yield management systems for the semiconductor industry, he gave a presentation at a meeting of the company’s senior executives.

“I was last in line after all the business groups. I talked about stability, fault tolerance, high availability, disaster recovery—all the great technical stuff we were doing,” Campos recalls. “At the end of my presentation, the chief of procurement shook his head and said, ‘It sounds to me like you just want to buy a bunch of shiny new servers.’ I probably had three or four of these types of interactions before I finally realized that I had to speak in the language of the people that I am speaking to if I want to maximize the probability that what I’m trying to say is what they will hear.”

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Leave the comfort zone

Most technology executives have engineering or science backgrounds. They spend the initial phases of their careers focused on hardware and software. When they are promoted into senior posts, however, they are forced out of their comfort zones.

For many, that’s a sink-or-swim moment. If they’re close-minded and resistant to change, their executive careers will be short. If they’re flexible and can learn new skills, they survive and thrive.

“Leaving your comfort zone often leads to the greatest rewards,” says Shelley Leibowitz, former CIO at the World Bank. Prior to joining the World Bank, an international financial institution headquartered in Washington, D.C., she had worked at major banks in New York. “Taking a role at the World Bank was definitely stepping out of my comfort zone,” Leibowitz says. “The World Bank was new and different for me—I had not worked in the development arena, or in a public-sector environment. If you have the opportunity to do something incredibly exciting, how can you not do that?”

Part of Leibowitz’s decision was based on the self-confidence she acquired over years spent in the financial services industry. She might not have had the self-confidence required to make a similar leap earlier in her career. “I’ve learned over time that the hardest, newest, most challenging things are also the most rewarding,” she says.

Patty Hatter, former CIO at McAfee, learned how important it is not to second-guess your decisions. “I definitely second-guessed myself early in my career. I’d replay meetings in my head, thinking about every word, everything that happened,” she says. “I wish that I’d learned earlier to make a decision, do the best you can, let it go, and then just move forward.”

Trained as an engineer, she consciously “retrained” herself to avoid wasteful cycles of self-analysis. “When you stop second-guessing yourself, it’s really very refreshing and empowering. It takes a weight off your shoulders,” says Hatter, who now advises startups.

The importance of taking calculated risks is another lesson Hatter wishes she learned earlier. “Take risks when you can,” she advises. “The opportunities that are most different from what you’re currently doing are the ones that you will learn the most from. Figure out how to embrace risk and take advantage of it. Because you really just don’t know when opportunities are going to come along, and you need to be ready when they appear.”

Not long after Hatter began her technology career at Bell Labs, she was offered an opportunity to set up a new business in Europe. “The sum total of my previous experience in Europe was a four-day vacation in Germany," Hatter says. "But I decided to put one foot in front of the other. What’s the worst that can happen? It doesn’t pan out, and I come back to New Jersey. As it turned out, setting up a business in Europe was one of the biggest and best learning experiences of my life, and it really helped me widen my world view.”

Learn more people skills

Many of the executives interviewed for this article said if they were offered the chance for a do-over, they would put more effort into developing their social skills. “I wish I had learned two things that are very much interrelated: the importance of your network and the importance of relationships,” says Tim Crawford, CIO strategic advisor at AVOA, a strategic advisory firm.

“Technology folks tend to focus more on technology and less on relationships. That’s a mistake, because the relationships are often essential to the success of the technology,” Crawford says. “Relationships also help us build our networks, which become valuable sources of insights that can strengthen our success as technologists.” In Crawford’s case, that relationship-building extends to social media; for instance, he was ranked as one of the Top 100 Most Social CIOs in 2016.

It’s easy to become “overly enamored” with technology, says Mike Kail, co-founder and CTO at Cybric and former CIO at Yahoo. That can cause you to overlook the most significant part of your role, which is “making sure that technical decisions have a direct correlation to the business and driving revenue.”

Kail also urges tech executives to keep their eyes on their organization’s “political landscape and power dynamics.” They are often more difficult to comprehend than the status of the IT systems you’re responsible for running, he points out.

One key lesson that Eric Schrock, CTO of Delphix, learned is the importance of communicating technology strategy clearly and continuously across the organization. “Strategy is really hard to communicate because it’s not a one-and-done thing,” he says. “You cannot simply have an all-hands or write a Google doc, and say, ‘We’re all done.’ It’s a continuing conversation. It’s about creating a culture where people understand the destination and the vision, and then supporting that with a communications process that shows them how their accomplishments are helping us get to that destination.”

Several of the CIOs wish they had learned to "speak the language of business” earlier in their careers. Leibowitz agrees that it’s important to speak in terms that non-technical executives can understand.

But what’s even more important—and harder to learn—is making sure that what you say aligns with the context of other leaders in the organization. In other words, Leibowitz says, tech executives need to speak about topics and issues that non-technical executives care about. “As tech people, we love to talk about cloud and agile, and all the other bells and whistles," she says. "But the technology itself doesn’t move the dial. So you need to explain to people why the tech is relevant and why they should care. That’s what most of us wish we’d learned earlier.”

CIO career planning: Lessons for leaders

The technology skills that got you to the corner office do not necessarily prepare you for the skills you need when you arrive.

Develop people skills, and build your personal network. You never know where the next opportunity may come from—and that’s relevant to more than your next career step.

Take a chance. Get outside your comfort zone.

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