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This article was published on June 5, 2016

Why there’s no such thing as ‘unlimited vacation’

Why there’s no such thing as ‘unlimited vacation’
Emily Lentz
Story by

Emily Lentz

Emily is on the marketing team at Help Scout, where she writes about support, company culture and other fun stuff. Emily is on the marketing team at Help Scout, where she writes about support, company culture and other fun stuff.

As much as some progressive companies love to claim “unlimited vacation” among their benefits, there’s really no such thing. If there were, employers would be paying people who never show up.

Even with the most flexible of time-off policies, there still has to be some sort of understanding in place between the company and its workers about what’s reasonable and expected.

Putting guidelines in place will ward off any friction and anxiety that may occur when PTO is otherwise a free-for-all.

Your team isn’t comfy with ‘unlimited’ time off

As a hiring manager, you might think “unlimited PTO” is an attractive benefit, especially for candidates coming from Orwellian organizations that monitored their every move.

And yes, it’s a godsend for folks who no longer need to file paperwork just to visit the dentist, or who fear retribution when their kid is sick and they need to stay home.

The more subtle reality, however, is that the take-what-you-need approach can make your team anxious and uncomfortable.

How much time off is too much — will I get a stern talking-to if I take four weeks off in a year? Five? Six?

Should I feel guilty about putting my team in a tight spot?

What about that workaholic jerk setting an unhealthy precedent by never taking any time off — does leadership secretly wish everyone were more like him?

Open ≠ untracked

why, question
Where the company’s concerned, the primary benefit of an open vacation policy is that no one has to administer that baloney. Leaving it up to individuals means that management can focus on less menial tasks.

But tracking doesn’t have to be cumbersome — most Human Resources Information Systems (HRIS) have time off-request processes built in, or you can use a stand-alone product like TrackSmart.

Even with an “open” policy, tracking is critical:

  • Teams need to be aware of and adjust for when someone will be out. Jeff Hassemer, head of strategy at Integrate, uses iSolved for the calendar view of requests, which allows him to detect any overlap.
  • It helps identify whether a key player will be out at a critical time. Does the project need to be rescheduled, or does the PTO request need to be denied?
  • It prevents people from taking too much or too little time off. “Pay attention to the outliers,” Hassemer says. “While unlikely, you may have someone who abuses the system. More importantly, there are some people that never take a break or sign up for a vacation. . . .they need to take a mental break as well to be a highly effective employee.” What’s more, it’s important leadership models this behavior for everyone else.

How Help Scout handles it

KinHR time-off calendar screenshot

Help Scout’s policy used to be “take time off when you need it.” That changed, as it has with other companies, when folks started asking the People Ops team how much time off others were taking. No one wanted to be the selfish outlier.

Now, to reduce insecurity about what’s appropriate, we encourage everyone to take three to four weeks off per year (plus 10 holidays) as a rough guideline. We ask everyone to get approval from their manager for anything more than a half-day, to minimize impact to the productivity of the team.

We use KinHR to ensure everyone’s vacation is on one calendar and to track time off — which we only do to ensure people are taking enough time off.

We feel strongly that time away helps everyone stay focused and productive when we’re in front of our computers, and some people (leadership included) need a gentle reminder that not only is it okay to step away, it’s sanctioned.

Other approaches to open time off

Jacob Zax, Co-Founder and CEO of Edify Technologies, shuts down the office for 19 specified weekdays per year. “Our company runs religiously in two-week sprints, so syncing up our time off helps us stay productive,” Zax says. “In addition to those 19 days, people can request additional time off (or always take a sick/personal day), but need to explain why and may be denied.”

While it’s not particularly flexible, the pros — clarity, forced work/life balance, minimal team disruption, and the ability to confidently plan trips in advance, among others — outweigh the cons.

Moz offers a flexible PTO guideline of 21 days off per year, which get front-loaded into their HRIS. People don’t have to record their time off (although some managers choose to track it with their teams), and they can take more than 21 days with their manager’s go-ahead.

“We opted not to call it ‘unlimited,’” says VP of HR Rebecca Clements, “because we believe there is benefit to setting an expectation about how much time off is reasonable and supported.”

A handful of heroes like FullContact, Basecamp, and Buffer offer “paid, paid vacation”: Time off plus funding for teammates to take trips. (We’ll get there!)

Treat your team like the adults they are

adult, child, playful
There’s no one-size-fits all approach to a flexible vacation policy; every company handles it differently.

The key is to grant people enough autonomy to make the right decisions for themselves and their team.

“Ultimately for us it is an expression of how we give everyone full trust when they join the team,” says Ryan Sullivan, co-founder and CEO of Parkifi.

“They are trusted to manage their time effectively, to make choices that are in the best interest of Parkifi, and to communicate to the management team if they have issues. The unlimited vacation policy gives us a very visible way of showing that we actually mean those words, and that they have responsibility to be trustworthy teammates.”

If your benefits advertise “unlimited” time off, that’s not a real promise you can make — an open or flexible time-off policy is closer to the truth, and to the understanding you reach with the team you trust to act like adults.

Instead, set some guidelines that allow people the freedom to take what they need while still getting the job done.