I've had the opportunity over the last several weeks to spend time with a number of current and former CIOs to just listen to their stories: about their careers and about their personal characteristics and outlooks on life, and how those shaped their career choices and outcomes.

One of those people is Charles Lee, who has a long track record at a number of companies, most notably as the former CIO of Taco Bell during a time of strong growth. As we spoke, a certain phrase kept coming up again and again. As Lee described his career path, he referred to points in which he was offered a job that he was unqualified to take.  

"I would always start by wondering what they were doing." Lee said. "I didn't know anything about that job. But then I would stop and think to myself, 'I'm a smart guy. I can figure it out.' And I would dive in."

Those points represented the greatest turning points in his career. As we spoke, it occurred to me that I had taken a similar path. The times in which I had my greatest successes were when I was put into a situation I was almost fully unprepared for (at least I thought). But I was able to not only survive, but thrive. As I spoke with a number of other executives in the weeks following my conversation with Lee, I saw the same pattern repeated.

[Are you connecting the dots? See CIOs: Always Be Strategizing.]

Furthermore, it became clear there was a two-part equation. First, we were willing. Like Lee, we knew we were smart and were confident we could figure things out. Second, we were all given tremendous opportunities by people who trusted us beyond what our mere experience demonstrated. People could see something in us that we could not fully see in ourselves, and they were willing to take a chance on us so that we could rise to our potential.

As Lee and I were talking, I characterized this common experience as being like novice swimmers repeatedly thrown into the deep end of the pool. It also struck me that this experience is becoming less and less common. And that's a real problem.

As our IT organizations have become more politically charged, and as our technology domains have become more specialized, the risks of trusting someone enough to put them into this kind of situation have grown significantly. As a result, we have an entire generation of IT professionals who haven't had the same kinds of opportunities we had. Large numbers of IT pros have spent their entire careers within a single domain. Because they've never been thrown into leadership roles and challenged to just figure things out, they've become ensconced within the insular culture of their organizations, and they're reluctant to expand their knowledge or experience base outside of their domains.

As we enter a new era for IT organizations -- as I describe in my book The Quantum Age of IT: Why Everything You Know About IT is About to Change -- I believe that this risk aversion will prove to be a massive liability. As I discussed this issue with Lee and the other IT executives, we realized that those "deep-end" experiences taught us the most. During those times we learned to trust ourselves and our teams. We learned how to learn and make sound decisions. Organizations that don't have leaders with those experiences are in trouble.  

So the questions for you: Are you comfortable with the deep end of the pool? Are you prepared to throw yourself into it, to volunteer for positions far beyond your experiences? You must overcome the desire for job security and begin pushing the envelope.  

And if you're an IT executive, you had better get comfortable investing in, and trusting your teams enough to create, these kinds of opportunities. It's a huge risk. But the risk of not doing it is much greater. The future of our IT organizations is at stake.  

Get comfortable with the deep end. The water can be turbulent and a little scary, but I promise the experience will be rewarding. Jump in!

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