Managing time off

When I worked at a Fortune 500 company, I had a staff of 14 people. The director issued an edict that we could not have more than 10% of our team out on approved time off for any given day. Taken literally, that meant I could only approve one person to be off each day. What a silly rule.

One of the many joys of management is the requirement to manage time off for staff. My general rule is that if someone asks for time off, I grant it no questions asked. I am an admitted workaholic, and I know I don't take enough time off. I don't want that to be the case for team members. 

The holidays present a challenge for managing time off because many people enjoy taking time off around Thanksgiving and Christmas/New Year's. It got so bad that in January, some people would put in time-off requests for that year's Christmas. We implemented a process in which we would ask for everyone's planned time off for the holidays on October 1st. This way we had everyone's requests for Thanksgiving and Christmas and could plan accordingly. 

Management is responsible for ensuring that there are no single points of failure. If there is only one person who does a particular task, what happens when that person is out of the office? There should always be backups who can take over to ensure business continuity. 

With my current team, I used the same process of asking for everyone's holiday PTO requests in October. The problem is that I'm still getting requests, and now I have to consider the time off that is already approved and team coverage. I have two people who perform similar functions who have requested the last two days before 12/31 off. Thankfully, there is a third backup, but I need assurance that the backup is up-to-speed on everything so that nothing stops. Usually, there is some major end-of-year crisis, and I do not want to get caught with my pants down.