Mike Does this amount of leave fall within the contractual entitlement, if yes, and if he hasn;t used any of his entitlement so far it's perfectly legitimate to request such a vacation. Please note that HR should ensure that if such a leave is granted for one employee then everyone who has accrued such leave and has requested it should be granted as well. Otherwise you may face discrimination charges. I did not understand what did you mean by high-performing employee, irrespective of their performance all employees are entitled to their contractual leave entitlements. If you have concerns with their performance you need to mange it under the company's performance procedure. Hope this helps.