How To Ask Your Boss for Time Off

What is the best way to ask your boss for vacation or time off? Most employees have the luxury of either asking, and gaining approval, when they have time with their boss or perhaps, self scheduling on a team calendar. But not everyone is that lucky. Some have to find a way to ensure the planets align before their request is granted. If this is you, here are three ways to increase your odds for approval.

First, make sure that you make the ask on their terms. In other words, if the best way to garner their full attention is in a meeting, schedule a meeting in the most conducive environment. If there is little privacy, find a time and location when you can have their full attention. Second, come prepared. This isn’t a meeting about the vacation, but that question can be added to the forum. So bring in several talking points to review then add the vacation question. Third, follow up the conversation with an email that confirms that agreement. If they prefer the request in writing, be sure that you guide the communication by not letting it go unanswered.

Sometimes there is a decline of request because of personal or project scheduling conflicts, or someone else has asked for that time in advance. Other reasons for denial would be concerns over workload, performance issues, or yes, a difficult boss.

If you anticipate your request could be denied, work with your coach on the best way to approach your boss. Your coach can help you prepare and practice your justifications along with keeping emotional reactions out of the equation. Preparing for rejection in advance will help you brainstorm talking points to assuage your boss’s concerns and invite them to see the benefits of the timing/purpose of your request, i.e. slow time for business, self-care, engagement, etc. Tap into your negotiation skills to control the dialogue and reach a win-win. And always have a plan B in case the time that you ask for is not available.

If you are continually denied, or there is little justification for the denial, it may be time to speak with human resources. You should work with them to review the terms of your employment contract and enlist HR to help you reach an agreement. Remember, this step doesn’t need to be formal, but HR should be able to offer a facilitated conversation to clarify any misunderstandings or proactively diffuse conflict.

How To Be Career Happy? Make Sure Your ‘Ask’ Is Strategic and Gracious

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