So I need a little advice. I just started a new job (I've been working for about two weeks now), and now I need to ask for five days off so that I can go on a trip that my friends and I have been planning for about a year. I'm definitely still the new guy in the office and don't really know anyone really well yet. What can I say that will give me the best chances of getting the time off without leaving a bad impression? Anybody here have any experience in this area?

You should have probably negotiated that before you started the job by telling them that you already had this planned.
I'd try to ask one of the guys around to see if the manager(s) is cool or not. Or go to the manager tell him/her the situation; the manager can't say worse than "no".

If I managed an employee who came to me 2 weeks into their job tenure requesting 5 days off (have you accrued this vacation time yet?) I would counter: Why didn't you tell me this during the interview/hiring process?

In other words, managers in many industries expect that an organized & responsible employee would have planned far enough in advance to make "new job" and "paddling vacation" coordinate effectively with one another. It's about setting management expectations, in this case.

I have no idea what industry you work in, though, and your industry may be quite different than mine. My suggestion as a business person, however, would be (assuming you like your job) that you either a) reschedule the paddling vacation for another time or b) ask to speak with your supervisor, admit you should have had this planned out in advance / announced your intentions to take a vacation early in your tenure during the hiring process and ask what needs to be done so you can take this time off. Couch the communication in terms of: What, manager, can I do so my unanticipated time away has minimal impact on our team's performance? Etc.

Good luck!

Sarah

Ask a coworker for a suggested approach, or just come out and ask. Without knowing the decision maker I doubt anyone here will have a better idea than a coworker.

As the others point out- the fact that this was prescheduled won't mean too much, since it wasn't mentioned during the hiring discussion. I wouldn't emphasize that aspect too much.

+1 on the excellent advice provided by Sarah.Simon

To echo others: this is pretty bad form, unless the job has predictable lulls that correspond to your vacation. When we had projects with deadlines, I had to state my intended vacation times months in advance. One boss wouldn't let you take an extra day off unless you made up the time after hours, before the vacation. I was always upfront before I negotiated for a project, even telling them about work-related obligations, such as planned attendance at conferences months in the future.

MoapaPk wrote:One boss wouldn't let you take an extra day off unless you made up the time after hours, before the vacation.

Sounds like a crappy guy to work for.

MoapaPk wrote:To echo others: this is pretty bad form, unless the job has predictable lulls that correspond to your vacation. When we had projects with deadlines, I had to state my intended vacation times months in advance. One boss wouldn't let you take an extra day off unless you made up the time after hours, before the vacation. I was always upfront before I negotiated for a project, even telling them about work-related obligations, such as planned attendance at conferences months in the future.

Deadlines kept me unable to take vacations almost every quarter. More than once my vacation was denied even when given a year in advance. With my current job I advised them during the interview process that a week off would be needed 3 days in to the new job. Asking for time off in your situation will not reflect well on you.

kayakerSS wrote:So I need a little advice. I just started a new job (I've been working for about two weeks now), and now I need to ask for five days off so that I can go on a trip that my friends and I have been planning for about a year. I'm definitely still the new guy in the office and don't really know anyone really well yet. What can I say that will give me the best chances of getting the time off without leaving a bad impression? Anybody here have any experience in this area?

This has happened to me a few times. I'm always up front when interviewing for the spot.

If you really like this job and there is opportunity for advancement, don't even ask. There are worse things than a "no" answer: a "no" and a lasting impression on your supervisor that "this guy doesn't have very good judgment even asking in the circumstances". First impressions are lasting.

Should you ask and get a go-ahead, you risk frosting your colleagues with your seeming audacity.

Since you planned this one year in advance, I'll agree with mstender

mstender wrote:You should have probably negotiated that before you started the job ....

kayakerSS wrote:So I need a little advice. I just started a new job (I've been working for about two weeks now), and now I need to ask for five days off so that I can go on a trip that my friends and I have been planning for about a year. I'm definitely still the new guy in the office and don't really know anyone really well yet. What can I say that will give me the best chances of getting the time off without leaving a bad impression? Anybody here have any experience in this area?

If you do any kind of work that immigrant labor does, chances are pretty good that you'll have a job when you get back:

Picking seasonal crops
De-boning chickens
Sex-slave
House Cleaning
Yardwork
Roofing

On the other hand, if nobody really gives a shit about what you do:

Journalist
Hospital Ethicist
Political Pundit
Environmental Engineer

...then you probably won't have a job when you get back.

I prefer my sex-slaves provide a bit more notice. I cut the gardeners more slack.

As others have said, you should have informed the employer during interview or hiring time. It's not likely to come across well when the guy who just started now wants to take two weeks off.

That said, it's done, and Sarah Simon's advice is probably the way to go.