How to handle awkward PTO request

[Anonymous]

My direct report, who is experienced, asked for PTO for one week. I told her the proposed dates were fine and to submit the dates through our tool so I could approve, and also to email the admin to record on our team calendar, with me in cc.

She sent the email, but after a week of not seeing the request to approve the time off, I reminded her at our next 1:1 in case she had forgotten. She said something about not having access to the tool but she expected to have the issue resolved soon.

When I finally got the approval request, it’s for the week after the original proposed week. Immediately after, I get an email. She had sent an update email to the admin where I was cc’d saying she had to change these dates dates, hope it’s ok.

She addressed the email to me and the admin. She’s based in Europe and I am in the US. The week she now wants is the same week as Thanksgiving which she is well aware of. We won’t have coverage on our team for the 2 days the US team is off, or more if others take the week off.

I need to address this because I feel she should have handled this differently. For starters, she should have come back to me asking to switch the dates instead of submitting the new dates via the tool where the only options are to approve or deny- no comments. Also, the admin doesn’t approve her PTO so why would she send the email to both of us asking if it’s ok to change the dates?

What’s the best way to handle this?

[Anonymous]

I would ask directly why they need to change the dates, pointing out that it's Thabksgiving in the US and you were expecting her to cover the dates while the US team members were out. It may be something beyond her control (family event others are in charge of, close family member's surgery, etc).

Address the process later

[Anonymous]

Write back, drop the admin from the email chain. Say that the week of Thanksgiving is challenging as there will already be many vacations already granted.

[Anonymous]

How aware would they be of US Thanksgiving? Could they have not realized that the switch would be a big deal? I think you are justified in denying.

[Anonymous]

Is the date actually a problem? Or are you just unhappy that the employee changed it without asking you first?

If the new dates don't work, then deny the vacation time and explain why.

If the dates are not the problem, then, in your next meeting with said employee, explain that the change of dates caused confusion, and suggest following the agreed-upon process next time.

[Anonymous]

I’ll ask her the reason for the change, but I can’t get past this feeling that she did this intentionally. Like she knew all along that she wanted the thanksgiving week off but handled it this way instead. The reason I feel this way is, when she originally raised the subject, she mentioned that the time could be during Thanksgiving. When I asked her for the dates, I told her it was fine, it wasn’t during holiday. Then for her to do this? It makes me feel…like I’m being manipulated.

[Anonymous]

Anonymous wrote:I’ll ask her the reason for the change, but I can’t get past this feeling that she did this intentionally. Like she knew all along that she wanted the thanksgiving week off but handled it this way instead. The reason I feel this way is, when she originally raised the subject, she mentioned that the time could be during Thanksgiving. When I asked her for the dates, I told her it was fine, it wasn’t during holiday. Then for her to do this? It makes me feel…like I’m being manipulated.

Barring a surgery or medical procedure, you can tell her that you approved the prior week specifically because it wasn’t going to overlap with coverage, but won’t be able to do the same for her new proposed week. Luckily, you have it in writing.

[Anonymous]

She probably just f-ed up the dates when she asked you the first time. I would 1000% do that.

OP, I just don’t think the world works like this. And even if she did somehow engage in an elaborate Thanksgiving Date Caper, why get your panties in a twist? The answer is the answer and the policies are the policies. You should be responding the same way no matter what.

Just be kind and firm on whatever your answer is. It doesn’t matter if the admin is CCed. It doesn’t matter if she just messed up the dates or spaced or was trying to pull a fast one.

You can’t live or manage like this, running circles in your head.

[Anonymous]

Anonymous wrote:She probably just f-ed up the dates when she asked you the first time. I would 1000% do that.

OP, I just don’t think the world works like this. And even if she did somehow engage in an elaborate Thanksgiving Date Caper, why get your panties in a twist? The answer is the answer and the policies are the policies. You should be responding the same way no matter what.

Just be kind and firm on whatever your answer is. It doesn’t matter if the admin is CCed. It doesn’t matter if she just messed up the dates or spaced or was trying to pull a fast one.

You can’t live or manage like this, running circles in your head.

Agreed. This isn’t an awkward request at all. Just deny and tell her that you can approve her original request but not the updated one. I doubt she has some master plan to get a week off that is inconvenient for the rest of the team

[Anonymous]

Anonymous wrote:She probably just f-ed up the dates when she asked you the first time. I would 1000% do that.

OP, I just don’t think the world works like this. And even if she did somehow engage in an elaborate Thanksgiving Date Caper, why get your panties in a twist? The answer is the answer and the policies are the policies. You should be responding the same way no matter what.

Just be kind and firm on whatever your answer is. It doesn’t matter if the admin is CCed. It doesn’t matter if she just messed up the dates or spaced or was trying to pull a fast one.

You can’t live or manage like this, running circles in your head.

Ironically this is my normal approach - give benefit of the doubt, let things go. I am willing to monitor emails over Thanksgiving break and address urgent matter so she can take her PTO. But I wonder if she’ll see me as a pushover and encourage similar behavior in the future. Plus, I’m a new manager so the concern in the back of my head is— I’ve got to make sure to handle this properly.

[Anonymous]

She told you the dates may be during vacation. She very obviously got the dates wrong when she told you them. You can have a conversation with her about the changing dates, but I wouldn't deny her request just so you don't feel like a push over.

[Anonymous]

Anonymous wrote:

Anonymous wrote:She probably just f-ed up the dates when she asked you the first time. I would 1000% do that.

OP, I just don’t think the world works like this. And even if she did somehow engage in an elaborate Thanksgiving Date Caper, why get your panties in a twist? The answer is the answer and the policies are the policies. You should be responding the same way no matter what.

Just be kind and firm on whatever your answer is. It doesn’t matter if the admin is CCed. It doesn’t matter if she just messed up the dates or spaced or was trying to pull a fast one.

You can’t live or manage like this, running circles in your head.

Ironically this is my normal approach - give benefit of the doubt, let things go. I am willing to monitor emails over Thanksgiving break and address urgent matter so she can take her PTO. But I wonder if she’ll see me as a pushover and encourage similar behavior in the future. Plus, I’m a new manager so the concern in the back of my head is— I’ve got to make sure to handle this properly.

You need to tell that voice in the back of your head to shut up. As a new manager, your job is not to think the worst of your employees. You should be going to bat for them as a good manager, not creating strife.

Just don’t respond to the time off system, communicate about the change by email and don’t approve/deny until it is sorted and she knows to approach you with the correct dates in the future. The suspense will be enough to make the point.

[Anonymous]

I would approve it and move on unless your company has a policy of absolutely needing to cover those two days. My huge international company does not require that for holidays like Thanksgiving but each company is different.

[Anonymous]

Anonymous wrote:

Anonymous wrote:She probably just f-ed up the dates when she asked you the first time. I would 1000% do that.

OP, I just don’t think the world works like this. And even if she did somehow engage in an elaborate Thanksgiving Date Caper, why get your panties in a twist? The answer is the answer and the policies are the policies. You should be responding the same way no matter what.

Just be kind and firm on whatever your answer is. It doesn’t matter if the admin is CCed. It doesn’t matter if she just messed up the dates or spaced or was trying to pull a fast one.

You can’t live or manage like this, running circles in your head.

Ironically this is my normal approach - give benefit of the doubt, let things go. I am willing to monitor emails over Thanksgiving break and address urgent matter so she can take her PTO. But I wonder if she’ll see me as a pushover and encourage similar behavior in the future. Plus, I’m a new manager so the concern in the back of my head is— I’ve got to make sure to handle this properly.

I had a bit of a fight (stood my ground) with a manager recently because they wanted to deny leave at a time I had no control over (a significant birthday for a parent) because it was inconvenient to the team. I’d talked to my co-lead on the project months earlier when I thought this might happen and she’d agreed she could cover it, so there was that. But my manager’s issue was basically it could look bad for him and for me if he approved leave at inconvenient times and this became a “trend”. That was the part that made me mad since (a) I’d checked already that my colleague could manage and (b) there is nothing that indicates this would become a “trend.” I’ve been at my job over a decade but have only had that manager for a year.

I’d say find out why it changed, find out whether it has to be those dates, and worry about it happening again if / when it happens again rather than trying to anticipate possible future scenarios now.

[Anonymous]

It’s September. If this happened in early November, I’d deny the request. Approve the request, tell the employee that you appreciate the advanced heads up.