Thanksgiving turkey? Check. Sophisticated Black Friday game plan? Check. Premature holiday decorations you’re not ashamed to put up in mid November? Triple check.

While everyone has their own holiday checklist, the surefire most important one on everyone’s list is getting their vacation time. The end of Q4 is a gift from the corporate gods to get us through the end of the year hump, and between Thanksgiving, Christmas and New Year’s everyone’s looking to maximize their holiday travels.

But what exactly is the best way to ask for time off? After all there’s still work to get done in the office in between trips to Bermuda and Tahoe – everyone can’t just abandon ship. Plus, with companies offering different types of vacation, from traditional PTO to unlimited, making sure requests are appropriate can feel...nuanced. For new and younger employees, stressful.

Luckily, every company has to deal with vacation time, and barring any unique circumstances, you and your company should be good following a few basic guidelines.

How Much Time Off Is Acceptable Should Be Clear

There’s nothing worse than not knowing what’s an acceptable amount of time to take off.

For employees, it’s useful to keep in mind the average American worker gets 10 days PTO, and 10 federally recognized holidays. Roughly half of companies will offer some additional days off, usually close to Christmas.

Using this guideline, it’s best to not allocate all your time off towards a single stretch. While you’re entitled to use days off how you like, companies likely aren’t expecting everyone to take two consecutive weeks off. We’d recommend putting no more than half your PTO towards one vacation. However you and your manager should be mindful of exceptions, such as the case with international relatives, where using vacation days together makes sense.

On the employer side, if there are stipulations around vacation time, don’t rely on a “you should have known” passive aggression. No one is going to remember their employee handbook, and it’s useful to send reminders around the holiday season about what your policies are. This is particularly important for companies who have unlimited time off, as that definition is ambiguous by nature. Managers should set a precedent by proactively communicating with their employees about vacation time, and employees should respond with being upfront about their intended vacation time off.

Over Communicate

We repeat: over communicate vacation plans.

For employees, this means checking in early and often with your manager, team members, cross functional partners, and anyone who could possibly need you for something work related during your vacation time. Send emails with your vacation dates highlighted in bold text and in included in the subject line (Example: Michael Out Of Office December 23-January 2nd).

If there are any shared work calendars, mark your vacation dates on there as much in advance as possible, and for good measure bring them up with your manager in any 1 on 1’s you have. This is especially important if you plan on taking an extra long vacation, or one that doesn’t coincide with larger company wide vacation times (August and December being the most common ones).

For employers, don’t leave the onus to your employees. Establish commonly used channels for planning vacations, and make it clear where and how employees should make their plans known.

Be Clear On What ‘Time Off’ Means

This one’s tricky. On one hand, vacation is meant to be time for employees to recharge and get away from work. Studies have even shown that relaxing away from work actually boosts attitudes in the workplace. On the other hand, it can be really frustrating to have a project stalled because a key person can’t respond to a slack message.

To balance the two, we’d recommend creating some sort of safety valve system. Employees can choose a method they prefer (Gchat or slack or text etc), and establish who can contact them and how, should there be something truly urgent. No one should have to feel like refreshing their email constantly on a vacation, but it’s not unreasonable to ask for some sort of check in system, particularly for long trips. This is nuanced by design, and will require healthy communication between team members; instituting an official policy runs the risk of overreaching into someone’s vacation.


Take Vacation Time

This one’s for both employers and employees: vacation time is important.

So don’t make taking vacation a stressful thing. Study after study have shown that PTO is good for a number of things, including employee productivity, morale, and retention (these tend to go together). Fostering a culture where employees feel competitive and unable to take time off is both self defeating and counter productive.

We understand that with small and aggressively growing companies, this can be difficult. Employees understand that as well. But pushing relentlessly through hyper growth stages is as exhausting as trying to gain muscle without resting between workouts. Human beings literally need mental rest away from work.

If you follow our first 3 principles, then partitioning a fluid PTO system shouldn’t feel difficult. Just keep in mind to outline vacation limits, communicate dates often, and to do your best to let vacation truly be vacation. The result will be happy employees, happy managers and happy holidays!

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