Would

AlpheccaStars

anonymous

Clive

Then don't use 'would' here. Say it another way.

I could say the following.

When will you be leaving New York?

When are you leaving New York?

When would you be leaving New York?

The reason I am not using "will" and "present continuous" is because it sounds direct to me since the person that I am asking the question is my boss. I figured using would makes the question less direct. Am I correct?

The tone of voice carries far more weight than the use of the modal "would." It is a matter of culture and business environment.
Some bosses prefer non-nonsense business questions. In some countries and cultures, though, bosses expect their subordinates to speak deferentially and subserviently.

Thank you for your response. So you mean the following below is correct?

Azaz: Ma’am, when would you be leaving?

Ma’am: I will be leaving in two weeks.

or,

Azaz: Ma’am, when would you be leaving?

Ma’am: I would be leaving in two weeks.

both conversations are correct and interchangeable?