September 26, 2011


Your mini-vacation to Vegas to celebrate insert-big-event-here with your friends is quickly approaching.

Your flight is purchased, the hotel suite is booked, and you’ve added some hot new heels to your collection that you can’t wait to show off. But there is one lingering conundrum that you haven’t addressed – letting your boss in on your big summer plans. In fact, even though you had lunch with your boss twice last week and have attended several meetings together, you’ve been deliberately avoiding the conversation.  As Lauryn Hill said, “It could all be so simple, but you’d rather make it hard….” Why is this? Why is it so difficult to request the time off that, quite frankly, you deserve for all of your professional dedication and efforts?

You are not alone in feeling this anxiety that causes you to delay this inevitable conversation.  I have been in the HR field for over seven years, and I still get nervous about requesting to use the annual vacation time that was promised to me when I signed my name on the dotted line of that offer letter. Everyone needs time off now and then—even your boss.  Still, it is never an easy task to have that awkward discussion. It all boils down to how you handle the situation, which is also a direct reflection of your level of professionalism.  

The following is a step by step guide to getting time off the right way: 

Notify your boss as soon as possible.   If you ask for time off the right way, your employer will have ample time to make the necessary arrangements for someone to cover for you in your absence.  

Enlist someone to help out.  Limit your boss’s anxiety about your departure by taking the initiative to identify someone in your department who can assist while you are M-I-A.  

Wrap up loose ends.  Complete as many projects as you can prior to your last day in the office. For any projects that you can’t finish, create a detailed list or spreadsheet clearly outlining their statuses and what will need to be done in your absence.  Review this document with your supervisor as well as with any co-worker(s) who will have your back while you are drinking mai-tai’s on the beach. God love them. 

Let everyone know. By spreading the word, you are also managing the expectations of everyone else.  If they have a question or concern about a work-related issue, they can be sure to get it addressed prior to your departure.  

Set an Out of Office on Email/Voicemail. These notifications should detail the dates you will be away and the contact with whom people can follow-up.  Demonstrating this level of preparedness is a great way to express your loyalty and dedication to your employer.  

Check in Occasionally. While we all dread checking the infamous Blackberry while vacationing, it is a good idea to check your email and respond to a few.  This will really convince your boss that you’d much rather be working than sunbathing on the beach.  Okay…maybe that’s a stretch, but at least it will show how much you value your role.  

Come back ready to work. Showing up a little early to the office on the day you return will allow you to catch up on emails and greet all of your colleagues with sun-kissed skin and a smile.  This will also give you the perfect opportunity to share some photos and brag about the amazing time you had in paradise before getting back to the grind.

As a professional, you’ve done your part in disclosing all information to your boss, so you can rest-assured that your time off schedule is confirmed.  Now you can focus on flirting with that fine bartender while relaxing at the pool with a clear “work free” conscience. Bottoms up!


Published in Career