Preparing to Take Time Off During the Holiday Season

There is an intense pressure to stay connected to your work throughout the holiday season to ensure “no balls are being dropped” at work.

And I’m here to release you from that pressure. I’m here to remind you that taking time away from work is the best tool to reconnect with your humanity. And I’m here to help you prepare for and communicate your boundaries and expectations around time off during the holiday season. 

First things first, create a working document that you can share with colleagues and clients

  • Within this document, include the following: the dates you will be out, the projects currently in flight, any potential due dates, as well as any outstanding tasks and who owns them

  • By creating a working document, it communicates transparency and accountability while you are out.

Next - communicate it early, communicate if often

  • - When you have planned PTO on the horizon, start communicating the dates you will be OOO as often as you can. 

  • - This can include adding your upcoming OOO dates to your email signature, concluding every meeting with a reminder about the upcoming dates, and by sharing your working document ahead of time. 

  • - It can look like this in action, “Hey all, before we wrap today’s meeting, just a reminder that I will out of the office all of next week. Please refer to the working document I created as the source of truth while I am out”

Starting today, end every meeting with a reminder of the dates you’ll be out of the office in the month of December. 

Lastly, be prepared to have conversations around holiday time off confidently. 

Below are a few templates to use when approaching conversations around holiday time off -

  1. When you need to ask for time off,

“Hey xx,

I am planning on taking [xx date - xx date] days off.

I am aware this is a busy time of year and this is how I will set the team up for success before and while I am out: [action item # 1, action item #2, and/or action item #3].

How else can I help make sure I'm able to fully disconnected during these days off to relax/explore/be with my family during those dates?”


2. When you need to set a boundary around saying NO to additional work before year end, 

“Hey xx,

I recognize this is a need for the business at this time.

I’m currently working on wrapping up ABC before the end of the year.

With a tight timeline, and only a couple weeks left in 2023, do I need to re-prioritize what I’m working on? I can’t take on any new work but I can shift focus if needed.”


3. When you need to communicate expectations around time off,

“Hey team,

Now that we are in the thick of the holiday season and the busiest time of year, the goal of this email is to ensure expectations around time off and work related projects are communicated.

- Expectation # 1

- Expectation # 2

- Expectation # 3

What else can I help with before we all take some well deserved time off?”

Before I wrap up, I also want to recognize that the holiday season can be incredibly sad, isolating and hard. I’m here to recognize that sometimes you may just need some space and a little note of support when you’re in need. Not everyone has family to spend the holidays with and not everyone has fond memories as the end of the year approaches. 

Here’s a template for when you suspect the holiday season is tough for people,

“Hey xx, I’m not sure if and how you may celebrate the holiday season but if you ever need support or space in the coming days, I am here to help”

Recognizing every workplace and every individual has different experiences in the holiday season, Career Civility is here as a resource to help you communicate expectations and boundaries around time off in the workplace – even during the busiest time of year.

Jenna Rogers

Founder + CEO of Career Civility

A passion for changing the conversation in the workplace

https://www.careercivility.com
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Writing an Effective Out Of Office Message

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Communicating Boundaries at Work - Even During The Busiest Time of Year