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.
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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.
About an hour later, the link went down again, so I grabbed the keys and proceeded to the network closet for the 15th time that week. I pulled the power cords from the modem and the firewall, waited the obligatory 15 seconds, and plugged it all back up. Fixed!
When I got back to my desk, I had an urgent email from Tom in my Inbox titled, "ISSUE WITH EMAIL!!!" The message started with the words, "There is something wrong with email! Please see the attached." In the message, he had pasted a screenshot of the Outlook send-and-receive failure message, as well as the warning message in the lower-right corner that Outlook could not connect to Exchange.
I wasn't sure whether to laugh or cry -- it was funny yet sad in so many ways. It was also a prime example of why drinking buddies are not always the best choice when staffing senior management for a new company.
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This story, "Go drinking with CEO, get hired as CIO," was originally published at InfoWorld.com. Read more crazy-but-true stories in the anonymous Off the Record blog at InfoWorld.com. For the latest business technology news, follow InfoWorld.com on Twitter.