I'm in the UK and coming up to retirement and have been in a management role in various businesses for years now. Not sure of the rules where you are but:
I think a fair, legally safe (UK wise), business‑sensible response is:
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Explain that overseas remote working is not permitted, especially during probation. Explain that the time‑zone makes it impossible to meet the needs of the role if they were hoping to work whilst abroad. If appropriate also advise this affects the insurance for the laptop and data protection is a consideration.
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Decline the request for a month’s leave, whether paid or unpaid, because the business cannot absorb the absence.
Or, Offer him the choice:
*cancel or shorten the trip
*or take it as unpaid leave
if you can tolerate it (sounds like you can’t)
*or accept that going ahead may end his employment
This is firm, fair, and entirely reasonable.
Going forward, make sure that you have employment contracts that clarify your stance and something along the lines of (depending upon the laws in your country):
Annual Leave Requests All annual leave requests must be submitted through the approved leave‑request system and authorised by management before any commitments are made. Commitments made without prior approval may not be honoured, and any resulting loss will be at the employee’s own expense.
Anticipating Leave Permanent employees may request to take annual leave that has not yet been accrued (“anticipated leave”) only with prior management approval.
Employees in their probationary period may only take annual leave that has been accrued unless management gives explicit prior approval. Probationary periods cannot be shortened or bypassed by anticipating leave.
Any anticipated annual leave taken will be recovered from final salary if the employee leaves the Company before it is accrued.
Leave on Termination All accrued annual leave must be taken before the employee’s final working day unless management approves payment in lieu. Payment in lieu of holiday is at management’s discretion.
Maximum Length of Leave Employees may take a maximum of 10 consecutive working days of annual leave at any one time, unless exceptional circumstances apply and written approval is given by management.
Pre‑Booked Holidays at Recruitment Where an applicant has declared pre‑booked holiday in writing before an offer of employment is made, the Company will honour that booking. All other leave will be subject to the rules above.