How to Ask to Work Remotely Over the Holidays

December is when many people want to be somewhere other than their usual desk. You might be traveling to family for two weeks with only five days of leave left, or simply want to avoid an empty office between holidays. Asking to work remotely for part of the period is common, and most managers will say yes to a well-written request.

The key is to make it easy to approve: specific dates, a clear plan for availability, and an honest answer to the question every manager will have, which is whether anything will slip.

Ask Early And Put It In Writing

Ask at least a few weeks ahead, before the team’s holiday schedule is finalized. A written request also gives your manager something to forward if they need approval from someone else. If your team has already published a holiday schedule announcement, check it first so your request fits the plan.

Be Specific About Dates, Location, And Hours

Vague requests get vague answers. Name the dates, where you will be, and the hours you will work, especially if you will be in a different time zone.

Before:

Hi Jen, I was wondering if it would be possible for me to work from home or remotely over the holidays since I will be visiting family. Let me know if that is okay.

After:

Hi Jen, I will be visiting family in Toronto from 14 to 31 December. I would like to work remotely from 14 to 23 December, then take leave from 24 to 31 December as already booked. While remote I will work 9am to 5pm Toronto time, which overlaps with London from 9am to 12pm Toronto time. I will be on chat and join the Monday and Thursday team calls. Is that okay with you?

The second version answers the questions before they are asked: when, where, what hours, and how the team can reach you.

Address Coverage And Risk

If your role involves anything time-sensitive, say how it will be covered. Mention deadlines that fall in the period and how you will meet them. If you need equipment or access (VPN, a second screen, a company phone), say so. If your work cannot be done remotely for part of the period, offer a solution rather than leaving it for your manager to solve.

Check practical constraints too. Working from another country, even briefly, can raise tax, immigration, or data security questions for some employers. Ask HR if you are unsure, rather than assuming it is fine.

Know Your Formal Options

Some countries give employees a formal right to request flexible working. In the UK, for example, the government’s guidance on flexible working explains the process and what employers must do in response. A short holiday request rarely needs to go through a formal process, but it is useful to know the rules if you are asking for something longer.

Make It Easy To Say Yes, Or No

End with a direct question, and accept a no gracefully if it comes. If your manager has concerns, offer a compromise: fewer remote days, a different date range, or a trial for part of the period. Set your out of office message for the leave days, and keep your status accurate on the remote days so colleagues do not assume you are away.

A Context For Requests To Your Manager

A Wrivio Context for requests to a manager could say:

Rewrite this as a short, polite request to my manager. State the dates and what I am asking for in the first two sentences. Then cover working hours with time zones, how I will be reachable, and how my work will be covered. End with a direct question. Keep every date, time, time zone, location, and name exactly as written. Do not add commitments or conditions that are not in the draft.

Press Ctrl+Shift+Space, paste your draft, and check the diff for dates and time zones. A request that accidentally offers availability you did not intend is hard to take back once approved.

Common Questions

How do I ask my boss to work remotely over the holidays?

Ask in writing a few weeks ahead with specific dates, your location, working hours with time zones, how you will be reachable, and how your work will be covered. End with a direct question.

Is it okay to work from another country over the holidays?

It depends on your employer and the countries involved. Short stays are often fine, but some employers have tax, immigration, or data security rules, so check with HR before you book.

What if my manager says no to working remotely?

Accept it politely and ask whether a shorter period or different dates would work. A compromise is often possible once the specific concern is understood.

How far in advance should I ask to work remotely in December?

At least three to four weeks, before the team’s holiday coverage plan is finalized. Earlier is better if you are traveling internationally.

Download Wrivio for Windows to turn a vague holiday request into a clear message your manager can approve quickly.