Permanent file/folder delete based on list

I am considering the situation when, for some reason, say death, I want nominated files to be permanently deleted.

Thus, in the case of death an executor, based on instructions contained within the Will, go to the computer start a program select the “death” list and sensitive files are permamently deleted.

Does anyone know of a software program that can carry out such a function. I have done some searching and analysis with no luck.

Barry