My boss asked me to work on vacation

How to handle it is a new series where I share my answers to your questions about office encounters and corporate etiquette. Click here to ask a question that could be featured in an upcoming post.

Before we begin, I thought I would mention that thankfully, this scenario was not based on my work experience. It did, unfortunately, happen to a friend.


Tickets are booked, reservations made and the countdown to your vacation is on. You’re already mentally packed for this trip and visualize the umbrella in your drink while someone takes roll during your afternoon conference call. Then, you snap back to reality when you see an email come across from your manager asking if you wouldn’t mind taking your laptop with you while you’re gone. You know, in case of an emergency.

The thing is, you do mind, and your laptop from work is the last thing you want to be packing in your carry-on bag. The office joke that it’s only Pretend Time Off, though sometimes true, is not that funny at its core.

My advice on how to handle it

  1. Set up a meeting with your manager to review all of their concerns prior to your departure and assign a proxy to handle each issue while you are out of the office. Sample high-impact questions to ask:
    • Would you be willing to review my out of office plan to ensure all the bases are covered during my time off?
    • What else can I do to give you more peace of mind while I’m gone?
    • (Hard ball bigger picture convo) What does this say about our company culture if we aren’t empowering each other to step away, no strings attached and truly take a break from work? I think this is an opportunity to use this situation to model the culture we want for our company. Change has to start somewhere. Will you be my advocate?
    • Going forward, would you be willing to address any questions you have when you approve any vacation time I submit so we have more time to plan and proactively address these concerns?
  2. Set up individual meetings with your proxies to make sure they are comfortable with the items they are taking on. Write a thank you note and offer to return the favor when you get back. (Starbucks helps convey gratitude, too.)
  3. If indeed, you are the only person in your company who is capable of handling an issue that comes up and your job is on the line, negotiate to get your vacation days back for any time you worked. Here’s how to say it: I will agree to bring my laptop and will respond to any urgent issues but upon my return can I count on your approval to submit any hours worked as paid overtime? Another consideration: Expensing international data plans and hotel wifi.

My friend ended up pushing back when their manager asked by simply replying, “You know, I’m really not comfortable with that,” and their boss completely backed off and said, “Ok, I understand.” Keep in mind, this may be a conversation better had in person or over the phone than by email so you can ensure the message is delivered with respect and can better manage the overall tone.

Vacation time is important not just for you, but your family as well. Consider this excerpt from a study done for Project: Time Off:

“The majority of adults (62%) say their earliest memories were of family vacations taken when they were between ages 5 and 10. Half (49%) of adults describe their memories of childhood family vacations as “very vivid.” These memories are significantly stronger than their memories of school events or birthday celebrations.” (Harris Interactive)

Have the confidence to stick up for yourself and what you know is right. Then, be sure you follow-through and tie up any and all loose ends before you sign off. Remember,
“You teach people how to treat you by what you allow, what you stop, and what you reinforce.” – Tony Gaskins

I hope you have a wonderful vacation!

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