Use a password manager to generate 16 character strings as answers to each security questions. I guarantee your IT person will no longer remember them.
"Three. Like one-two-three." -> they hear "tree" or "123"
"'D'. Like Able Baker Charlie Delta." -> they hear anything ending in "ee", or "abelbakercharlydelta"
And so on, ad nauseum.
I used to do random characters, but have switch to a string of random dictionary words. Still not perfect (since "a string of random words" could potentially be accepted as a valid answer), but I feel like having it be human-readable makes it less prone to that kind of fuzzing.