The only thing more dangerous than an alcoholic short-term-memory-challenged non-technical throw-you-under-the-bus IT director with self-esteem issues that are sporadically punctuated by delusions of superiority is one who fears for his job. Submitted for your inspection: a besotted mass of near-human brain function who not only has a 50 person IT department to run, but has also been questioned by the business owners as to what he actually does. So he has decided to show them. He has purchased a vendor product to replace a core in-house developed application used to facilitate creating the product the business sells. The purchased software only covers about 40 percent of the in-house application's functionality, so he is contracting with the vendor to perform custom development on the purchased product (at a cost likely to be just shy of six-figures) so that about 90 percent of existing functionality will be covered. He has asked one of his developers (me) to scale down the existing software to cover the functionality gaps the purchased software creates. There is no deployment plan that will allow the business to transition from the current software to the new vendor​-supplied one without significantly hurting the ability of the business to function. When anyone raises this issue he dismisses it with sage musings such as, "I know it will be painful, but we'll just have to give the users really good support." Because he has no idea what any of his staff actually does, he is expecting one of his developers (again, unfortunately, me) to work with the vendor so that the Frankensoftware will perform as effectively as the current software (essentially as a project manager since there will be no in-house coding involved). Lastly, he refuses to assign someone to be responsible for the software: taking care of maintenance, configuration, and issue resolutions after it has been rolled out. When I pointedly tell him I will not be doing that (because this is purchased software and I am not a system admin or desktop engineer) he tells me, "Let me think about this." The worst part is that this is only one of four software replacement initiatives he is injecting himself into so he can prove his worth to the business owners. And by doing so he is systematically making every software development initiative akin to living in Dante's Eighth Circle. I am at the point where I want to burn my eye out with a hot poker, pour salt into the wound, and howl to the heavens in unbearable agony for a month, so when these projects come to fruition, and I am suffering the wrath of the business owners, I can look back on that moment I lost my eye and think "good times."