Vacation Time Manager Challenges

It is every managers’ nightmare: An employee who has been working hard all year puts in a PTO request weeks before her long-planned family reunion. What she doesn’t know is that you’ve already approved two requests for that same week.

Your response could be: “That’s really not a great time. We already have two people with PTO approved for that week and it is the end of the month. Can you reschedule?”

This scenario plays out in offices everywhere. Maybe you’ve been on the manager side and maybe you’ve been on the employee side. Either way, this is a classic challenging dialogue.

This conversation touches on everything from fairness and trust to business needs and personal boundaries. When handled poorly, these discussions don't just affect individual employees—they ripple through entire teams, eroding morale in ways that can take months or years to repair.

Start with Curiosity

Curiosity is one shift that opens up space for real conversation. Maybe it's Grandma's 90th birthday (non-negotiable). Maybe there is flexibility in the dates. Maybe the "bad timing" is actually about your expectation around vacation time and not about their request.

You won't know until you ask.

Three Ways to Help

Norms for Proactive PTO requests: At your monthly team meetings ask, "As we look ahead, what time off is important to each of you? How can we plan our workload around these needs?" This gets employees thinking ahead about vacation and prevents the crisis mentality where every PTO request feels like an emergency.

When a Request is Made: Meet with person to begin working together to plan for coverage. Don’t make assumptions. Ask what good coverage would look like? Who do they think has the skills and resources to cover urgent items. And identify what can wait until they return. Make coverage planning collaborative, not burdensome.

After they return: Check in and ask "How was your transition back? What would make future time off easier for everyone?" Take every opportunity to close the loop and improve your process.

When It Gets Messy

Sometimes, despite our best intentions, these conversations get tense. I've been there, caught between someone's legitimate need for time off and legitimate business concerns.

Start by acknowledging the difficulty:

"This is tough, and I can see we both have valid concerns."

Then focus on what you both share:

"We both want the team to succeed and for people to take time off without stress."

From there, you can explore options together rather than defending positions. The key is keeping it collaborative, not adversarial.

What This Is Really About: Trust

Every conversation either strengthens or weakens your relationship, and trust, with your team.

When you avoid these discussions, or handle them poorly, you are potentially leaving people with the idea that you don’t care about them as humans.

But when we lean into the dialogue with genuine curiosity and care for both business needs and human lives we build something more valuable than any policy: trust.

And trust is what makes teams resilient enough to handle real life happening alongside work.

The vacation conversation doesn't have to be the one everyone dreads. With the right approach, it becomes the conversation that makes everything else work better.

P.S. Are you facing some conversations that feel impossible? Or feel at risk of leaving people with the wrong impression or breaking down trust? I can help. Let’s chat: https://NCDsolution.com/beth