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The phrase "a difficult conversation with" is correct and usable in written English.
It can be used when referring to a challenging discussion or dialogue that one needs to have with someone else.
Example: "I need to have a difficult conversation with my manager about my workload."
Alternatives: "a tough talk with" or "a challenging discussion with".
Exact(33)
Facing a difficult conversation with an underperforming employee?
I expected a difficult conversation with my boss, but nothing like what I got.
With the help of a partner, Ms. Newsom practiced having a difficult conversation with a colleague.
Tilley says: "For a young person that might be a difficult conversation with their parents and friends.
Torre knows he will soon have a difficult conversation with the starter he removes from the rotation.
You probably didn't want to have a difficult conversation with your aunt whom you knew was voting for Trump.
Similar(27)
We've come up with a Difficult Conversations Checklist that you can literally read point by point during any difficult conversation -- with nearly miraculous results.
One caveat: Although there are many good reasons to get a difficult conversation over with, there are a few situations where it might be best to wait.
You know, however, that's a difficult conversation to have with families who have lost loved ones – about how important it is to make a lot of money playing football.
"It was a very difficult conversation with him for a number of reasons," McGinley said of his decision to overlook Donald.
"With Lee [Westwood] there was a real sense of pride he had made another team, very gracious and very humble, and Ian Poulter is a bundle of energy, you can feel the energy coming down the phone". Paul McGinley on Luke Donald's omission: "It was a very difficult conversation with him for a number of reasons.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com