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Dear Anna,
How do I ask my manager about taking annual leave? I’m a graduate and my busy manager can be a bit tricky to approach.

Early in your career is a great time to build a good approach to discussing annual leave. It’s an area that often creates tension when it doesn’t have to. Here are some things that can make the process smooth for everyone involved. 

Timing: Attempting to ask for leave in the middle of a busy period isn’t a good idea. Raise your request in your regular catch up (note my optimism!), in the morning when they are fresh or at the end of the day when they are ready for a change of pace. If your team is working to a remote pattern, I’d recommend a call or webinar chat on the days your manager is working from home rather than back-to-back meetings on their office days. 

Format: There are two things most managers hate in my experience: surprises and being told what to do. Most of the time your leave request will be both.  Use a format that gives advance notice of the request and the request itself. At the “anything else?” point of a normal conversation, say “yes, I’d like to take some annual leave in the next two months. How do you like that to work in our team?”  Raising the request in this way puts them in control and acknowledges that your leave has an impact on the whole team. Your manager can now start planning for your absence and guide you on their preferred approach. 

Merge into the traffic: Just like peak hour traffic patterns, there are peak times of the year for personal preferences around key religious holidays, sporting events and the constraints of the school term. A friend’s wedding date rarely fits conveniently with a litigation calendar.  Advance notice is the key to ensuring you can book leave at the best time for everyone. If you are combining annual leave with study leave, give your manager and team as much notice as possible.

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