Do you think he would regret having a woman as his boss?
Is this sentence correct?
I don't know if "regret" is the right word. You regret things that you do. If you do not have responsibility for the decision (to have a female boss), I don't think you can regret it.
What about tense?
DO you think he WILL regret...?
DID you think he WOULD regret...?
I can't make the do... would combination work in my head.
I'm not a teacher, but I write for a living. Please don't ask me about 2nd conditionals, but I'm a safe bet for what reads well in (American) English.
We're just working with the material we have to work with in the original question. I don't believe it was an indication of his personal opinions.
It's certainly not the first time a grammar question was centered on a statement I don't believe and it won't be the last.
I'm not a teacher, but I write for a living. Please don't ask me about 2nd conditionals, but I'm a safe bet for what reads well in (American) English.