It is a difficult balancing act for businesses to ensure there is adequate staff coverage while at the same time allowing staff their requests for time off. It is understandable to prioritize anything that encourages cashflow but taking care of staff needs also promotes stability and reduces HR costs. What are some ideas?
1. Clearly communicate expectations to staff well in advance
However you do it, via emails, a policy and procedure manual or via the employment contract, give staff a clear understanding of the ways that you will handle leave applications. Is there a particular time of year when all staff are required to work? During times when staff are most likely to apply, do you have a first come first policy or another way to select who will be successful with their applications? What is your process for applying for leave? Is there provision for staff to carry over unused annual leave to the following year?
2. Maintain good staff records
So as to ensure that staff take their required leave, maintain comprehensive staff files that include what days have been taken and payments that have been made accordingly. There are many software programs available to make this task systematic and user friendly.
3. Develop a staff roster for stretched holiday periods well in advance
A staff roster showing those who are in place to maintain the business during holiday periods will help remaining staff understand the level of coverage they are providing. This same staff roster can then be used to communicate with clients if needed to let them know what staff are available to take care of their needs.
4. Vacation messages
Vacationing staff should be encouraged to record vacation messages that explain the period of their absence and the contact details of the covering staff member. This should be in both email and phone form. There is nothing worse for a client than continuously phoning someone within the business and not understanding why they have received no response to their messages. It is also reassuring for these clients that the business has a backup system in place so that they are not left without service during the holiday period.
5. Back up desk files
With the same goal for continous service, it is recommended that staff, particularly those involved in ongoing management or project development, maintain detailed deskfiles that enable any other staff member to take over the work in their absence. Even better still, staff leaving on holiday should begin to brief the covering colleague at least a week in advance so that any questions about projects that are active can be answered.
6. Plan to have covering staff maintain the general flow of work
There can be a tendency for staff to "clean up" as much as possible before they go on leave with the intention that nothing further will be undertaken until they return from leave. The whole idea of annual leave is to enable staff to become destressed and to rebuild strength. It makes little sense for the staff member to then return from annual leave to be faced by a large mountain of work that has been waiting for attention. Playing catch up at the end of holidays has the potential of undoing all of the good produced by the break. If at all possible, it would be useful for vacationing staff to hand over their work email passwords so that covering staff can deal with any pressing issues that arise. If the business has only a skeleton staff in place during these seasonal times it may be difficult to achieve much extra but at the very least, urgent matters can be dealt with even during a key staff member's absence.

(A side note: The same principle of a regularly updated deskfile enables sound succession planning for all key staff roles. No-one is indispensable in a well-run business. It is sound business practice for each role to have at least one other backup person within the organization who knows at least the rudimentary responsibilities and who can step in as needed.)
7. Plan to ensure key organizational activities are maintained
On a similar note, there are key aspects of the business that need to be maintained, even during the holiday period. Even if you decide to shut down the business during a particular holiday period, there is a need for such aspects as staff salary/wage payments, payments of invoices on time and the dealing of urgent matters. If needed put into place automatic payment options during holiday periods or ensure that at least one person is able to take care of vital financial transactions during this season.
It is a contradiction in terms but holidays are incredibly stressful for businesses. Sound advance planning can reduce that stress and increase customer confidence in the stability of your business.