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How can I handle conflicting vacation requests, especially if they are with my boss?

Elaine Varelas advises on navigating scheduling conflicts at work.

Q.  Recently, I had an issue with my boss about taking a vacation day. She didn’t approve the vacation request as she said she MIGHT be off the same day. I don’t do any of the work she does, and she doesn’t cover my work when I’m out. She was worried about appearances if someone were to walk into our department and see two people missing. I went to HR about this, and she got wind of this. She told me that I shouldn’t go to HR as they have no idea of how our department works. I thought that having an HR department was to also help with employee relations.

A. You must be disappointed on multiple counts. Not getting a day off approved, but more importantly learning that your manager somehow found out that you went to HR with what could be considered an employee relations problem. You didn't say that your boss denied the request, just that she didn't approve it. You could have had a conversation with you manager prior to going to HR to learn more about her reasoning for not approving your time off. You could have discussed with her what specific concerns she had with you both being out the same day, what appearances would be, how your department works, etc. This would have been the ideal opportunity for you to learn more about what motivates her and to better understand her position. Perhaps you have tried to discuss issues with her before and it didn’t go well.

Going to HR clearly upset your boss, as it sounds like she felt you were either going over her head or that you had been treated unfairly, which may have led to a reprimand on her part. I am curious if HR gave you suggestions on how to deal with a situation like this.

Your first interaction should always be with your manager or boss to try to deal with any scheduling conflicts (or any type of conflict) directly. You may have let your boss know how important this specific day was to you. She may have asked you if you had any flexibility. You could have asked her if she had any flexibility.

There are many factors and questions to consider. For example, is your boss at any kind of risk in terms of her role at the organization? Has she gotten feedback that her department is not responsive? Are there people who back you up or back her up when you take time off from work that are no longer there? Recognize that having a clear understanding of how your department works and your bosses’ issues are the most important parts of figuring out where this conflict lies. Try to understand her responsibilities to the organization and how having two people out at once might impact your team.

HR is there to support employees by helping resolve workplace conflicts and helping to address employee concerns. The way they do that is to find out more about the situation and offer insights into questions you might ask your boss, ways to communicate with your boss, and how the two of you might be able to work this out. It's unfortunate that she found out that you went to HR, since this typically would have been a confidential conversation.

You might take the opportunity to explain to your boss that you didn’t go to HR to get her into trouble, but to get guidance on how to have a conversation with her about the situation. Perhaps you're not comfortable with conflict. Perhaps you were looking for insight into how important appearances are for your department.

It sounds like there is some initial conflict going on in your relationship with your manager that drove you to HR and there may be more than meets the eye about this kind of a situation. Learning to communicate through conflict is vital. And reminding HR of the need for confidentiality when you are looking for support matters as well.
  Boston.com