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“So, general, tell me what went awry.”

This is what I’ve been hearing from government and industry leaders who invested heavily in information technology to improve organizational performance but didn’t see the returns they expected. Some chief executive officers implemented instant messaging software across their organizations to improve communication flow, but because users were not convinced that communications were secure, instant messaging was ignored. In other situations, both leadership and staff were uncomfortable with social networking tools because they were used to communicating through other people—not with more direct, less formal means.

Today’s information technology leaders face myriad challenges in making their organizations effective and relevant. These range from bureaucratic, financial and outside challenges; to building secure information networks where information is managed and readily accessible; to driving cultural change.

I faced more than a few challenges when I was an active-duty general. Here’s a snapshot of three of them:

Following the terrorist attacks of September 11, 2001, the Pentagon burned for three days. Our greatest challenge was keeping vital communications online. But critical systems in the Pentagon basement were threatened by fire hose water that was pouring down into the basement. Our military and civilian work force did a great job of covering equipment with tarpaulins to keep national-level communications functioning, and these people worked with industry to swing vital voice, data and video communications to various locations throughout the Capital area—places to where senior Pentagon Army and Navy members had evacuated. At the same time, as manager of the National Communications System, I had a mandate from the White House to set priorities for restoring 5.5 million voice and data circuits knocked off the air from the attacks on the World Trade Center. Wall Street chief executive officers and other members of the President’s National Security Telecommunications Advisory Committee volunteered the resources of their firms to help restore government and financial markets. Through incredible coordination, the stock and bond markets were back in service only six days after the attacks.

Managing the year 2000 (Y2K) rollover was a special U.S. Defense Department challenge because we wanted to ensure that computers controlling national security systems would stay online, that systems involved in managing nuclear missiles did not malfunction and that people did not misinterpret any computer-generated data. We also were concerned that systems used by Russia in managing its nuclear arsenal needed to be upgraded to roll into the year 2000 smoothly. As a precaution, Russia assigned military and political leaders to address potential glitches with the United States near the Cheyenne Mountain Complex in Colorado Springs, Colorado. But, on the morning of January 1, 2000, matters were complicated by the announcement that Vladimir Putin was replacing Boris Yeltsin as president. This leadership change came as a surprise, and at the same time Russia was launching missiles into a neighboring state. Fortunately, we quickly determined that these missiles were tactical Scuds and that they were not being launched because of any Y2K-related computer glitch. But these events created high stress and complicated my role as Defense Department spokesman for Y2K on January 1.

When tasked with developing communications for the Joint Chiefs of Staff during the 1991-1992 Gulf War, we realized there was limited infrastructure in the region and that we needed to use satellites extensively. We faced considerable delays working through the Pentagon’s approval and funds appropriation processes, but we needed to do this to acquire commercial satellite services. And, while we were running through the Pentagon hallways shuffling paperwork, the news media and others were quickly buying up limited commercial bandwidth so they could cover the war. In the end, leadership within the Joint Chiefs of Staff prevailed over process, and we acquired needed capacities. However, we were uncomfortably close to having to commandeer bandwidth through the National Security Emergency Preparedness program.

Guaranteeing information technology leadership success is a different type of challenge. Unfortunately, there are no good “how to” books on being a successful chief information officer (CIO) or chief technology officer. So, how can government and business leaders ensure that they’re armed to deliver on tomorrow’s greatest information technology challenges? Certainly, a prerequisite for success is leadership vision. But in today’s Web 2.0 world, CIOs also need to embrace several key points. First, they must understand that we are moving into an “age of interdependence” in which organizations rely more on others to do jobs from virtual locations. They must ensure that network users embrace network-centric services and social networking tools. CIOs must appreciate that e-mail volume has grown so much that it is becoming an ineffective communication vehicle. And, they must promote “intergenerational harmonization” throughout their organizations by building a team that capitalizes on the best characteristics of each age group in their work force: Baby Boomers (digital immigrants), Generation X (digital hybrids) and Generation Y (digital natives).

Meanwhile, chief executive officers and boards need to ensure that their CIO is experienced, capable and “at the table” for driving change in the organization; is able to work with members of the board to improve performance across the organization; and is able to apply meaningful metrics and is held accountable for demonstrating return on investment.

In the end, information technology success stories will result from effective government, industry and international relationships.