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I have a bit of a conundrum. I'm currently employed, but I'm job-searching and I have two final interviews scheduled close to each other (driving distance), but very far from me (plane travel distance). I have already scheduled time off of my current job to take the first interview (I didn't tell my current employer it's for an interview, just that I need time off), but I just got notice of the second. Would it be acceptable to ask for an additional day off so that I don't have to make two plane flights? Additionally, I know the first company (who I've already scheduled with) moves very quickly, and, if I pass, I would expect to have the offer a couple days later; waiting even a week for the second company could skewer my chances with the first company (the second company moves much slower, although I can push them to move quickly).

A compounding factor to this is that I've been sick all week and been working from home. I've had periodic calls with my boss and he knows I'm sick (I have a cough now), so whether I'm sick or slacking is not in question (as far as I know). However, my boss wants me to report to the office as soon as I'm better, and I told him I would be returning to the office on Tuesday (today is Friday) after my interview on Monday (which he doesn't know about; he just knows I'm taking vacation time). If I was to tell my boss I need to take Tuesday off as well and report to the office on Wednesday, would that be a reasonable request given the circumstances?

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    If you have the ability to take the time off, I would do so to give you breathing room in your schedule. It would be easier to take the time off now than go back to work, get back into your tasks, and then later take more time off. – JRodge01 Nov 15 at 17:38
  • @JoeStrazzere More or less, yes. Especially since my boss is asking me to be in the office on Tuesday. – Ertai87 Nov 15 at 19:00
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The definition of PTO is useful start point. It can vary based on location and company, but in general, it includes:

bank of hours in which the employer pools sick days, vacation days, and personal days that allows employees to use as the need or desire arises

In your situation, you have a personal need, that just became present (second interview). You are absolutely free to use your designated time-off hours for that.

Please, don't clump together different issues of taking time for interviewing (which can be really any other activity: going to a rare theme park ride, spending 24hrs in line for that rare chicken sandwich or whatever) with the issue of being sick and sick time. You are not in business of trying to trick your boss, there is no need to justify time off beyond what's written in employer's handbook.

Be honest, and provide enough details with "I would like to take extra day off, is that OK?"

If you still need some extra "it is OK and professional", here are your two options:

  1. take extra day off, fly once, get back to work
  2. take extra day off some time later, fly twice, increase the risk getting sick on plane and lose productivity
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You are requesting a day off. It may be denied.

Tell your boss that you need another day off and would appreciate it if he would approve it.

If you feel the need to address your current circumstances, you can add something like, "I am aware that I have been sick and working from home this week, but some things have come up and I will need to take another day off soon. Tuesday is probably best, but if it isn't Tuesday, it will probably need to be later in the week or the following week. Seems like getting this done now would be less trouble for everyone rather than spreading out my days off." Or something to that effect. It's honest, it indicates your concern for how your request impacts the business and it does not require that you disclose the nature of the time-off request.

If your boss asks about what you are doing, a simple, "I would rather not say," is probably sufficient. There are innumerable personal matters that should not be disclosed (e.g. "I'm having a cyst removed from my xyz" is inappropriate to share with your boss; but perhaps if he presses further you can use it as an example..)

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