The One Where I Lie To The CTO

This was several years back. Keep in mind that early in my career, my father had told me that doing a good job often meant doing what needed to be done in spite of your boss. And by that he meant that you can either make your boss successful and happy or you can run every decision by your boss. In which case no one is successful or happy.

I was working at the time for a Fortune 500 company and our CTO had signed up to deliver a big project for an important client with whom he had personal connections. He also decided to outsource a key part of it to a large tech services firm who claimed they had a product that would do most of the heavy lifting for us.

As has been typical in my career, when the vendor said they had a product, what they really meant was they had something vaguely resembling a product that vaguely matched what we needed, and with heavy customization they could torture it into doing what we needed. Of course by customizing their “product” we cleverly combined all the downsides of vendor software with all the downsides of custom software. We simultaneously achieved the holy grail of bad ideas: an inflexible vendor package that would have to be forced into doing something it wasn’t designed to do but would also be forked from their main product codebase - guaranteeing sooner or later it would be end-of-lifed once the vendor realized how expensive it was to keep maintaining. We grumbled to each other about what a horrifically bad idea this was, especially considering the vendor’s proven track record in not delivering anything on time.

Because the CTO had a yearly turnover of his direct reports, every status call about the project took some variation of “great idea, boss” even though literally no one involved thought it was even a good idea. Or even a mediocre idea. It was a bad idea.

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