何度も聞いてすみませんって英語でなんて言うの？

If you want to be very formal in this slightly awkward situation, you can begin with "Apologies..." Although not grammatically correct, you can begin a question with "Sorry to bother you again..." and then immediately follow it with "..., but can I ask you about..."

When talking about doing something many times then you can use 'so much' or 'many' a simple way to express this is 'sorry to bother you so much'

This can be a difficult situation. You need something to happen and your boss is pushing it off or not listening. In American business culture, all three of these sentences would be ways of apologizing for returning to the same subject, while also saying you are going to keep bringing it up. To "pester" someone is to bother or annoy them. You could also say "I'm sorry to keep harping on this." or "I'm not trying to beat a dead horse." "Beating a dead horse" is a phrase that is commonly used when you do something over and over with little chance of changing anything.

You can say: I'm sorry for asking so many questions, which is a more polite way of saying I'm sorry for bothering you. I apologise for all the interruptions is also a good alternative. Interruptions means when you stop someone, like your boss, from doing their usual activities.

"I'm sorry to bother you again" to bother someone is almost to 'get on their nerves' to irritate them. bother, bothering and bothered. "I apologize" a very formal and politer way of saying sorry