Bwahahahahahahaaaaaaaaaaa
As for the actual topic...I'm going to give you all a slightly different take on it.
If we assume Calista knew they would both at some point, somehow, be 'summoned' for the Gambit (assuming she was fully aware of Alexander's plans to have a gambit, which I think she was)...then it is entirely possible as Stan pointed out, that it may have been a condition of his.
However, if we look at this from a logical and rational perspective, knowing how brilliant of a mind Calista had, knowing about Alexander's real true final wishes (male heir), then Calista would have known that whatever happens to Kane, as was mentioned before, he is the Neo of this story in a way, especially on the dom path. All the sisters know how important he is, many of the staff also and many even bring this up. On the dom path, he is almost an untouchable God in a way who 'will' rise the ranks. Because, ultimately, he is the single only person who can realise Alexander's wishes (if we forget Seth for a moment, who may or may not actually be Calista's son).
Olivia on the other hand...is just another sister ultimately and completely not required for the Gambit to be successful, there are five other sisters available to bare a male heir with Kane (whether he on the sub or dom path is irelevent to him making babies). So if we continue that particular train of thought, surely (as far as Calista is concenred) it is far better, more logical and far more beneficial to train Olivia up to a standard where she can 'compete' with her half-siblings, given how ruthless, cut-throat and downright dangerous they can all be (yes, even your fave soft-freckled red head lol).
Kane really has a free pass to baby making heaven with a sister (at least for those board members actively trying to achieve Alexander's ultimate wishes) providing he doesn't royally fuck it up for himself. He doesn't even need to be made of aware of this, as everyone else is.
Olivia...she is very much on her own really against the rest of them....
