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Have you ever negotiated paid leave or PTO for an extended vacation, 1+ months(s)?
How did you go about it? I’d like to take some time after a wedding for traveling and an extended honeymoon next summer!

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I love your advance planning skills! I’d wait until a couple months beforehand and then just ask for a month PTO and see what they say. If it’s anything like my firm it’s actually less headache from a back office system standpoint to simply pay you during your time off instead of finagling unpaid time so they may just say “Go, have fun, and don’t advertise within the firm that we’re paying you more PTO than others” or they might just offer for you to exhaust your allotted PTO/take a little bit of unpaid PTO.

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I've never heard of a person successfully negotiating additional PTO. My buddy who is a wily negotiator tried to bump PTO from 3 to 4 weeks at his boutique. They went up to a 25% salary increase but would absolutely not budge regarding PTO for some reason.

I havent personally, but have had friends that negotiated unpaid time but were able to keep insurance and benefits during that time.

On the job, I negotiate pto for all the overtime I work

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