Begin by planning ahead. If you have yet to ask your employees about their holiday plans, do this immediately. To plan accurately, you will need to begin the planning phase no later than the end of summer / early autumn. Try having a calendar (virtual or paper, whichever fits your business needs best) available for time off requests that has dates 6-12 months out from the current time period. Weddings, anniversaries, baby showers, and holiday plans are usually planned months in advance so if your employee is attending something important, chances are they have already begun planning.
Getting the request in writing will be a short and long term benefit for everyone involved. (Another benefit to having a time off calendar available for employees to write requests on!) Additionally, having a form accessible for employees to fill out will help with consistency. Relying on your own memory is relying on a detail to be forgotten or a message to be misinterpreted. This form should have the employees name (and identification number if your business location uses which), the date they are putting in said request, the date(s) the employee will be out of the office, who they report to, and (if applicable) any allotment of PTO/Sick/Vacation time to be used.
Does it seem like everyone in your office wants the exact same day off? Unless you plan to have your business closed that day, make certain days “Premium Time Off” as a privilege. Reserve this “Premium Time Off” for high-performers or employees who have made significant sacrifices during the rest of the year or constant team players. Reward their good actions and they will continue to contribute well to the success of your business.
Lastly, make sure employees fully understand the business needs and goals. Do not be afraid to black out certain dates when projects are typically due for completion or high business traffic happens.
When these steps are put in place and your employees are fully aware, you will have a successful plan in action for meeting business needs and giving your employees the vacation times they request.