Direct Report Going Too Far with Unlimited PTO? Ask Madeleine

November 12, 2022 Madeleine Homan Blanchard


Dear Madeleine,

I manage a team in a large company that recently went to an Unlimited PTO policy. I am glad, because tracking and trying to get people to take their PTO was a pain.

So far, it has worked pretty well. The policy is that people need to request holiday time in advance, mainly so I can cover for people and not have too many people out at the same time. As a team we try to stagger summer holidays and take turns being on call for the big ones that everyone takes, summer Fridays, etc.

My problem is one of my team members—I will call her “S”—who calls in sick almost every Monday. I didn’t really notice it until it started to happen regularly. I also have noticed that she never accepts Monday meetings. Other team members are making jokes about how we can’t have certain meetings on Mondays if S needs to be there.

When S comes in on Tuesdays, I can smell the alcohol on her. I suspect she is partying so hard on the weekends that it bleeds into Mondays and she thinks that is okay. I actually don’t know if that’s true, but something really feels off about this. Thoughts?

Monday Madness


Dear Monday Madness,

Something is off. When other team members start cracking jokes about something, it is your cue that it is long past time to address it.

I can only assume you have an HR business partner, so you need to check in with that person to get the details on the Unlimited PTO policy. Most require the employee to clear PTO with the manager in advance (as you mentioned), and a doctor’s note is required for extended time off due to illness. The whole idea behind PTO is to give people the flexibility and freedom they need to manage their lives and choose how to manage their time to get their work done.

The fact that you and your team are having to schedule around S is an indication that she is using the policy incorrectly—so you must step in. Her cavalier “I just don’t work on Mondays” thing is way out of bounds and you need to put a stop to it pronto. The reasons ultimately don’t matter. If S actually is dealing with an illness, she needs to tell you and work with you to manage her schedule and properly support her in getting the help she needs.

The question of her smelling of alcohol is a separate issue. If she is partying like a maniac, it isn’t really your business unless it keeps her from showing up to work. And you don’t know if that is the case, even though it might seem that way. You can be prepared to share information about mental health and substance abuse support if your company has an EAP program in case S reveals anything that makes that appropriate.

There is a good possibility S is just confused about what Unlimited PTO really means.

Get the facts, get some solid language from HR, practice if you feel shaky, and then say what needs to be said without blame or judgment. Be clear with S about what is required and what is unacceptable. And offer appropriate help if it is needed.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.


About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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