A reader asks...

KD -

My current company is a mess - I'm currently interviewing and have great traction, but I'm concerned about a vacation I've planned
for late August.  When should I tell a prospective employer that I've got a Disney trip planned?

--Pritesh from Charlotte

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Hi Pritesh -

First, let me say "wow" - Orlando in August?  It will only be 120 degrees, down from 124 in July.

On the vacation front, here's some fodder for you to consider.

1. I followed up with you to learn that you're a marketing guy who expects to make 90K in your next job.  There's never been a 90K person that couldn't figure out a way to still take that vacation when they switched jobs.  If you're in a process with a company that can't help you figure that out (wants to force you to give it up), walk away.
2. You don't tell any prospective employer too early that you've got a vacation on the books.  Doing so makes it seem like you have the wrong priorities.
3. The right time to tell them about your vacation is before you come back for what you understand will be the final round of interviews, which for most companies who employ people at your pay level is going to be round #3.  It's sad that 3 rounds of interviews is the norm, but it's true.
4. Once you confirm that the next round of interviews is probably going to be the last round, you say something like, "Hey - before you put me in front of anyone else, I should let you know that I already have money down for a vacation in late August.  I hope that won't be an issue, but figured I needed to let you know before we go to the next step."
5. Time it like that, and you maximize your chances that the vacation will be covered by company policies.
6. There's some game-playing that can happen on behalf of the company - they might ask you to take it as unpaid time according to their "accrued leave" policy.  Don't even hesitate - if they go that direction during the interview process, ask them to let you go in arrears according to their leave policy or simply ask the manager to work it out with you without involving payroll.

Take that advice, and odds are you'll be taking your vacation, on the new company's leave policy.

Or you could go senior level and time your job change until after your PTO account is empty at your current company.  Your call!