Holidays and time off for remote contractors

Decide the model before the offer

There are three common approaches for full-time contractors:

• Paid days off: a set number of paid days a year, written into the agreement. Simple, and attractive to good candidates.
• Unpaid days off: the monthly fee is reduced for days not worked. Cheaper on paper, but people then avoid taking holidays and wear out.
• A fee that already allows for time off: a somewhat higher fee, with the expectation that the contractor plans their own holidays with notice.

Whichever you choose, write it into the offer and the agreement. Candidates ask about it, and the answer says a lot about how you work.

Public holidays: theirs and yours

Ukraine, Georgia, Armenia and Kazakhstan each have their own public holidays, and several fall on dates that differ from US or Western European ones, such as Nauryz in March in Kazakhstan. Your public holidays do not automatically apply to the person, and theirs do not apply to you.

• Ask the person for their country's public holiday list at the start of each year.
• Agree which days they take off: their public holidays, yours, or a fixed number of days to place as they like.
• For support roles, plan cover for days when your customers are active and the agent is off, and the other way round.
• Put all of them in a shared calendar at the start of the year.

A simple request process

1. The person requests time off in the tracker or by email, with the dates and who covers what.
2. You confirm within two working days.
3. The days go into the shared calendar, and an out-of-office reply is set.
4. The week before, the person sends a handover note.

Agree notice by the length of the absence, for example two weeks for a few days and a month for a longer holiday, and apply the same rule every time.

Cover while they are away

For an assistant, most work can pause for a week if it is planned: the calendar is set, the inbox has an out-of-office reply, and you know where things are. For support, someone still has to answer customers.

Options for support cover are a second part-time agent who trains alongside the first, an overflow service for peak weeks, or reduced hours with a clear message on your contact page. Our coverage guide has the shift options.

Sick days and emergencies

Agree how the person reports being ill (a message before the shift starts is enough), whether sick days are paid, and what happens during a longer illness. Keep it humane and simple; asking a contractor for medical notes for a day or two rarely helps anyone.

In Ukraine, power cuts and air-raid alerts can interrupt a working day. Agree what the person does then: a message as soon as they can, a backup place to work if they have one, and catching up later. Ask about their backup set-up in the interview, without making it a reason to reject anyone.

Writing it into the agreement

• The time-off model: paid days, unpaid days or a fee that allows for them.
• Which public holidays apply.
• Notice for planned absences, and how to report illness.
• What happens to unused paid days at the end of the year, if anything.
• How time off works during a trial period.

Whether paid leave affects how a contractor relationship is classified depends on local law, so ask your adviser. Our contractor agreement checklist covers the other clauses.