Was he American or British or another nationality ? There is often a difference in the frequency of the use of "to" and "with" in BrEng and AmEng (and undoubtedly other varieties) when it comes to expressing the concept of saying something to someone.
So, for example , after the verb "talk". I checked with a
concordancer, and a search of an AmEng corpus brought up examples of both, while a search of a BrEng corpus gave examples only of "talked to". So :
BrEng -
I talked to my husband about it
AmEng -
I talked to/with my husband about it
That doesn't mean that no British person would ever say "talked with", but "talked to " is certainly the norm.
I found no examples of "raise a question" on the concordancer, but plenty on Google. And it was clear that both varieties of English may use both prepositions.
This one was from a BrEng site :
Mr Chisholm agreed to raise a question with Cabinet secretary Fiona Hyslop ...
and this on an AmEng site :
Any number above 10 % might raise a question with the rating agencies.
This one was BrEng :
To raise a question to Ofsted, FIRST login and go to
And this one AmEng :
every member is free to raise a question to the entire group at any time
What is not possible to decide by looking at Google is the relative rate of frequency between the two varieties. It may be that both prepositions are alternatives in both varieties and are equally used. But it may be that one is more frequent in BrEng and the other in AmEng. And the nationality of your source may be pushing him to prefer "with".
However, notice that he is giving an old-fashioned "prescriptive" rule. He has "decided" that one is better, rather than looking at what people actually say and giving a descriptive rule. This (ie prescription) is the origin of ridiculous rules like the one that a preposition should never end a sentence - which, as George Bernard Shaw said, is a rule "up with which I cannot put".