Dear People Ops:
I work for a small tech start up and we don't have set leave time. The agreement is that we just ask and give them ample notice. I started at the company in January of this year and already had a 2 week trip booked in March. I then took a week in July off, I've had a few long weekends here and there and I have just requested 2.5 weeks off just after Christmas. I take more leave than other people but my boss has never said anything other than go for it. Do you think I should follow the culture of my company when asking for time off, or just ask for what I want and see what my boss says? I don't want to seem unprofessional, but I want to enjoy my life.
Unlimited vacation? Sounds awesome, right?
WRONG! (Sorry, it was kind of a trick question)
I openly advocate against "unlimited vacation" policies because it leaves too much room for misunderstanding. What seems appropriate to one employee may seem outrageous to their coworkers or boss. The result, an otherwise talented employee is faulted for something they didn't even realize was wrong - asking for too much vacation.
My first advice. Go. For. It. As long as your work is getting done, your absence is well planned for and isn't leaving your coworkers to pick up the slack, and you're hearing positive feedback from your manager there is no reason you shouldn't be able to take advantage of this awesome benefit. Working for an early stage startup may mean you're paid below industry average, so utilize every benefit you can.
That being said, you'll want to tentatively probe how your time off is being perceived by your manager and teammates if you plan a future with the company. Its unfair that you may be judged as "not committed" for taking advantage of a company benefit, but it's a risk.
First, make sure your absence isn't impeding the work of your colleagues. Once that's been covered, gauge how those around you are responding to your vacation. When you walk out the door are you getting passive aggressive grumblings from co-workers, or does no one notice? Reading the tone of those around you can tell you a lot about a company's culture toward vacation and how you are being perceived.
And then the next time you request time off, try something like "I'd like to request X time off. Based off our conversations it sounds like my work is exceeding expectations and I'm fulfilling all the responsibilities of my job, but I wanted to check in before taking this vacation". I wouldn't highlight that you take more vacation than other employees. The goal is to create a space to have a conversation with your manager about if, in their eyes, your work is getting done because that's all that should matter when considering vacation requests.
And if you're a manager - avoid that gut reaction to say no. There is a reason your company has chosen to implement an unlimited vacation benefit. Perhaps it's to combat areas where they can't compete for talented employees, like salary. Allowing, and even encouraging your team, to utilize this benefit (within reason) will keep your employees happy, engaged and ideally with your company for years to come.
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