For the last three years I’ve been running our 25 Top Information Manager listing, an annual project where we cherry pick and profile top CIOs and IT-related execs for readers. It’s a four-month process of dozens of one-on-one interviews that include identical questions about leadership, pressures and priorities. It’s probably my favorite job and always a humbling learning curve, a fast download on big issues from the people who are calling the shots.

At this level of authority, leaders never start out by describing details of budding technologies. They’re more likely to seek passionate reasoning and dispassionate evidence in pursuit of business success. Their greatest concerns are timing, risk and opportunity, not project scale or feature functionality. Whether the issue is big data, mobility or cloud, their daily decisions are typically about when they should leap, how far and why.  

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