As an employee, unlimited vacation might sound like a dream come true. 

But, when you're running the company, it sounds as frivolous as nap rooms, ping pong, and a dozen craft beers on tap. Silicon Valley stuff, right?

I wrestled with the pros and cons of unlimited paid time off, but I couldn't help imagining anarchy at the office. Empty desks, piles of work to catch up on, and a come-and-go culture that was too loose to be productive. 

So, for years I've stuck with the same stale paid time off (PTO) policy: 10 days in year one, 12 days in year two -- maybe the same one that you have. With each approved request, employees would see an exact balance of the hours they have left. Like a scarce currency of freedom from the office. 

Is that really the mindset that I wanted to create? A culture of saving up minutes as the hours tick by, in hopes of cashing in the time to escape?


We already somewhat offer flexible schedules, and the ability to work from home as needed, so revamping our vacation policy was the last frontier. Here's why I decided to go unlimited, and why you should to. 

Count results, not minutes.

I never really liked High School. To me, it felt like grown up daycare. We arrived at the same time each day, followed the same routine schedule, and counted the minutes until the bell rang so that we could get on with our days. 

But college -- college was a different story. Not a morning person? Schedule night classes. Like to travel? Front-load your week and take Fridays off. Need to miss a class to focus on something of higher priority? No problem. 

Are you treating your employees like they are in high school, or in college? In the book ReWork, Jason Fried (of Basecamp) says, "When you treat people like children, you get children's work."

So, count the results that someone produces, not the minutes that they log in the office. 

It's getting harder to disconnect.

Disconnecting from the office isn't as black and white as it used to be. In a world of Slack notifications and 24/7 customer support, my employees are going above and beyond their normal working hours to keep the company moving. 

In exchange, they have the flexibility to adjust their schedules as needed during the day. The same philosophy carries over to vacation. 

If you force your team to stay connected at their desk from 9-5 with no personal time, you can expect them to shut you out completely on vacation days. But, as the line starts to blur between time off and time at work, your team is more likely to be there when the business needs them the most.

Less red tape means easier administration

I used to get emails like this: "My cousin is coming to visit, can I take 4 hours off in the afternoon?" And then a few days later, "My cousin's flight was delayed, I only need 2 hours off."

I don't know exactly how much time I spent reconciling PTO balances, but every minute was agony. Thankfully, the unlimited policy means a lot less noise. It doesn't mean no rules, however. 

At Trainual, we ask for two weeks notice to schedule something, and the request must still be approved. This way we can ensure the entire department isn't off on the same day. Employees are still responsible for any deadlines, projects, tasks or responsibilities on their plate. So, they can get more done before leaving, or find someone else to fill in. 

When you opt for unlimited vacation, you're empowering your team to balance their workload and their life, without your micromanagement.

If someone abuses the policy, they aren't a fit anyway

When switching to unlimited PTO, my biggest concern was that someone would abuse the perk. But, consider this -- if someone is consistently absent, difficult to reach, and not completing the work they were hired to do, will they last very long anyway? Not at my company. 

As flexible as our schedules have become, we've instituted a formal 90 day check-in process to keep a constant communication loop with everyone on our team. This is the perfect time to revisit how appropriate someone's time away has been. Did they prepare for any absence appropriately? Were all projects completed as scheduled, and all goals hit? Is there anywhere that we need to course correct in order to meet the requirements of the position?

Don't use a policy like restricted PTO to manage with control. Instead, manage with communication, and let your people manage their time.