By the time we added our 10th retail outlet, the VP of retail sales (I'll call him "Andre") decided that we needed PoS (point-of-sale) software. By now I was IT manager, but Andre never consulted with me about his plans for the software acquisition. Apparently, because IT's primary responsibility was maintaining the warehouse software (the only system software we were running at the time), Andre figured he could buy a PoS package without any input from us. This turned out to be a big mistake.
The vendor he chose, "LMNOP Software," sold other retail system software too, and Andre decided to purchase its warehouse package as well. That way all our stores would be supported by one vendor. By the time the deal closed, we had 25 outlets. We installed the software in every one.
Surprise! LMNOP's software turned out to have some nasty bugs, and its support team was clueless. I made a few phone calls and found my way to "Kaitlin," the only programmer at LMNOP who seemed to understand the software. Unfortunately, she was way too busy to provide day-to-day support. So Andre decreed that whenever something went wrong, the store manager was to call me. Without source code, all I could do was call Kaitlin. And increasingly Kaitlin wouldn't even call me back. I did the best I could, and gradually I began to figure out how the apps worked. Or didn't.
We fade to black -- and fade back in three years later, by which time we have four huge warehouses and 150 stores. Andre finally figures out that LMNOP's software is a total disaster, and the IT department hears rumors that the company will be developing its own in-house system. But (surprise!) no one actually talks to us. Instead, Andre sends me a memo: The new PoS software will be written by ... Kaitlin, who has recently left LMNOP under questionable circumstances.
Her contract states that she must produce the product in two years -- a goal no one in IT considers remotely realistic. Sure enough, two years later, all Kaitlin's got to show is a PowerPoint presentation describing how the project is going to look some day. To the utter disbelief of the guys in IT, Andre rewards her by appointing her VP of Retail IT.
Another year passes, the company president finally realizes that Kaitlin is never going to produce the PoS software. He tells her that her employment will be terminated in three weeks, and offers her a dazzling severance package. Then he tells me to learn everything she's doing so we can take over her job when she leaves.
When I ask her for documentation, she can't produce any. She claims that when she found out she was being fired, she deleted all but a handful of her files "because she was sure we wouldn't need them." Yeah, right. After she walks, the president orders the IT department to "just fix it."
I can find several lessons in this disaster, but I'll mention just one for now: Talk to your IT department once in a while, especially before you invest a ton of money in new software.