Managing People

Like a Boss: “How do I handle a member of my team who abuses our unlimited PTO policy?”

December 19, 2019
November 7, 2023
Jennifer Romolini
Lattice Team

Welcome to Lattice’s advice column for new managers, “Like a Boss.” I’m your host, Jennifer Romolini. I’m an editor, an author (of the career guide “Weird In a World That’s Not”), and, yes, a boss who’s been managing other humans for the past dozen or so years at companies both giant and tiny, at quick and dirty startups and multi-layered corporations, with remote and in-office teams ranging from five to 45. I’m also a speaker who talks about succeeding at work even when you feel like a freak. And, sometimes, I give advice, like right now.  

Dear Boss,

My company has unlimited PTO days, but one of my employees takes a little too much advantage of that benefit. While I know technically the policy allows her to take the time and she does try to work ahead, parts of her job need to be handled in real-time, and — when she’s out — her work has to be covered by someone else. Plus, it’s making others on the team question her commitment and work ethic. How do I handle this conversation and help turn the situation around?

No Clue How to Proceed

Dear No Clue,

‘Tis the season for extra-special managerial challenges: when employees mentally check out during office hours, cross boundaries at holiday parties, and — somewhat understandably — push the limit of company vacation policies in order to get the most out of winter breaks. 

While it sounds like your employee is an evergreen time-off-policy exploiter, the holiday season can bring out the worst in even the most committed and reliable staffers, causing conflict for well-meaning managers who want to be generous with days off, but also need to keep people working in order to meet the needs of the business. Lucky for us, the most effective strategy for managing this issue applies year ‘round.  

Speak the Unspoken: Setting Boundaries Around Time Off 

I’m going to say something now that might be controversial and, at the very least, will suck a little to hear: This does not sound like an employee problem so much as a management problem. 

It sounds like, when your company implemented this unlimited PTO policy, they didn’t set any rules around it. This is a challenge because it assumes that those who work with you will behave in a way you’ve never really told them they have to behave. You (or the company at least) have made an assumption about a “right” thing to do without communicating it, and assumptions, of course, rarely work out the way we imagine they will (if they did, there wouldn’t be that terrible cliché about them turning us into asses). 

Like any good relationship, the one you have with your employees requires well-communicated, mutually-agreed-upon rules and boundaries. These will particularly help in situations like these when the “technical” policy seems to contradict day-to-day expectations. So, if you haven’t yet, set a time to explain to your team that, while the company maintains an unlimited PTO policy, all time off must be requested and approved by you (barring emergencies, of course). And that approval of time off is not guaranteed but is instead dependent on a variety of factors including workload, deadlines, and staff schedules. 

Communicate this policy in writing to all your direct reports. Communicate this policy in a reasonable, non-punitive tone (Don’t be a jerk! They didn’t have any rules to follow so they didn’t follow them!). At this point it doesn’t have to — and shouldn’t — be about singling out one person’s behavior, but instead setting a standard that everyone can adhere to. Know that mistakes were made on both sides and move past the issue by starting fresh with the employee.

If going forward, she breaks the PTO rules you’ve set so coherently and calmly, you’ll stand on firmer ground, have a clear case that she’s abusing your and the teams’ trust, and can find a path to changing the problematic behavior. (I know! The management fun never ends!) 

Now that we’ve solved this, go have an eggnog, listen to Mariah Carey, and plot out what you’ll do on your own well-deserved days off.