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I'm curious about how you found yourself in a position of both hating a piece of software and having to defend the decision to use it.

Why did you have to defend something you hated? Where I work if something doesnt have an advocate, it stops being a product offering.

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Just a guess, but probably the sunk cost fallacy. Lync licensing is not cheap, and once you've put in the time to buy it, provision the ridiculous amounts of hardware necessary to run it, deploy it, push the client to end-users, train up on how to use it, it represents a significant investment.

You also forgot "it's probably not his/her choice".

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