How to talk to a worker who asks for additional time off

Welcome to our regular HR advice column, Ask a Resourceful Human. Here to answer all of your burning questions is Massella Dukuly, the head of workplace strategy and innovation at Charter, a media services company that aims to transform the workplace. Dukuly has trained over 10,000 leaders at startups and global enterprises, including Squarespace and the New York Times. Sign up for Charter’s free salary transparency playbook.

What happens when workers need more time off than policy allows?

There are many different reasons an employee might need additional time off, and it’s important to diagnose effectively before jumping in with a “no.”

As HR leaders, we have a responsibility to support employees and our organizations. Ideally, that support is mutually beneficial, but there are times when it can feel challenging. On one hand, we want to ensure fairness for all employees, and naturally, there has to be someone (*cough, cough, you!*) who enforces policy. On the other hand, the rigidness of a set number of days off doesn’t consider the fact that every employee is different and may need different support. And while some workers might require more time, many others might not even be fully utilizing the PTO they have.

Ultimately, I recommend putting on your investigative hat and being clear with the employee about why you’re doing so. Start by sharing, “I understand that you’re asking for a period of time off that, if approved, would be more than our policy allows for. As an organization, it’s important that we’re fair and consistent with all team members, so I’d love to understand more about the time needed so that we can support you.” Follow that up by emphasizing, “Of course, you don’t need to share any specific details, as your personal time is exactly that. That being said, if this time is being used to support your well-being or caretaking responsibilities, it may be seen differently to a vacation. How do you see it?”

Understanding what’s at stake for this employee will help you determine the best course of action. If what they share is related to well-being, for example, there should be flexibility. Perhaps they should be using another form of PTO. Will this be recurring? Are there other flexible ways to support the time they may need away from work? Getting clear on as much as you can will put you in a position to come up with a high-impact solution. In many cases, the answer doesn’t have to be a binary yes or no.

Should you approve the PTO for any reason, be clear about the process going forward. Share something like, “We understand that every employee has unique life circumstances and we want to support you. However, in the event of leisure PTO, you have exceeded our policy, and to remain fair to all employees, we’ll need to discuss future approval. How do you feel about that?”

And if you do need to say no, be sure to share why. The conversation isn’t always comfortable to have, but it keeps everyone aligned and ensures equity for all team members.

Last but not least: Don’t forget to do an org check. Are your time-off policies flexible and generous? This might be time to check in with your team. Let’s remember that butt-in-chair doesn’t automatically equal high performance. You have a team of adults—be clear about what they need to accomplish and allow them the flexibility and autonomy to get there.

Good luck! Let me know how it goes.

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