I was the catch-all IT guy for a small upstart technology company. The CEO was a brilliant developer-turned-entrepreneur who could write code in his sleep but had the business sense of a can opener. Most of the senior management was close friends of the CEO, so things like skills and qualifications were not a high priority when it came to hiring his inner circle -- for example, the CIO.
This CIO, "Tom," had vast gaps in his IT knowledge but didn't seem to realize it. He was always making suggestions or butting in with highly unhelpful information. Some instances were more conspicuous than others.
[ See what technologies won the InfoWorld 2012 Technology of the Year awards. | Follow Off the Record on Twitter for tech's war stories, career takes, and off-the-wall news. ]
One time, Tom asked if I could install some software on his "PC" while he was in a meeting. He had a laptop with a docking station, monitor, keyboard, and mouse. When I arrived, he had taken his laptop with him to the meeting.
Later that day, I dropped by his office to reschedule the install. Somewhat perturbed, he asked why I was unable to complete it during the meeting as he had requested. When I explained that I couldn't since he had his laptop with him, he pointed to the monitor and said, "But I left my PC here." Facepalm.
On another occasion, we'd been experiencing some intermittent problems with our VPN tunnel link to the secure hosting facility where most of our servers lived. Every few hours, the link would drop, severing our connection to most of our critical servers, including the Exchange server. (Can you say "single point of failure"? But I digress.) If the outage lasted more than a minute, the work-around was to reset the modem and the firewall.
Tom had been on vacation when this started, so on his first day back, I sat down with him to explain what was happening, the business impact, and what we were doing to fix it. As I threw out terms like "WAN link" and "Exchange server," Tom arched his eyebrows, nodded, and occasionally said, "Hmm...," as if he understood everything I was telling him. At the conclusion of my report, he said, "Well, it looks like you have everything under control. Keep me posted on your progress." I went back to my desk and resumed my troubleshooting work.