The first critical step in planning your trip abroad is to book time off work. For this to be successful you must be smart about which dates you propose to your employer and you must present your boss with a clear plan for covering your workload during your absence.

Follow my two step guide below and you will be one step closer to embarking on your dream trip.

Step 1 Picking Your Trip Dates

 I have found that travel dates that meet at least one of the following criteria have the greatest chance of getting approved. However, if your dates can meet all three of the following criteria that is even better!

Dates Occur During a Slow Work Period

 Many, if not all, industries have a slow period during the year. This is the best time to book your vacation. Traveling during this period typically means you will not have to rely on co-workers to cover your work, there will be less unanswered emails awaiting your return, and you will not miss any big deadlines or meetings.

Dates Occur When No One Else Has a Vacation Booked

 Try to find a week when no one else in your department has a vacation booked. By doing this you make it easier to find someone who can cover your responsibilities while you are away. It also leaves qualified personnel in the office to handle any unexpected happenings while you are gone.

Dates Occur When Your Boss is in the Office

 When your boss or manager is traveling they tend to rely on you and other staff members more; they need you to answer phone calls and email them any pressing information. For this reason, try and choose travel dates that do not overlap with your bosses vacation time or business trips.

Step 2 Preparing Your Proposal

 Once you have carefully chosen your travel dates it is time to put together a proposal for your boss or manager. While some companies may already have a formal vacation request process it is still a good idea to provide the following information to your manager in written form:

  • Your proposed travel dates
  • Alternative travel dates
  • A list of your current projects and what you will have done prior to your trip
  • Who will cover your work while you are away
  • How you will catch up on missed work when you get back
  • Who can attend meetings in your place (if needed)

Make sure your proposal is clearly and simply written. I suggest keeping it to one page, utilizing headings, subheadings, bullet points, and or charts. Avoid lengthy paragraphs, multiple fonts, and visual clutter. Your manager should be able to scan your proposal in two minutes and have all the relevant information he or she needs to make a decision.

Remember this is just a proposal. Make it clear to your boss that you are open to suggestions and feedback.

Now that you have your travel dates scheduled it is time to pick a destination for your trip!

How do you schedule your vacation time at your current job? Is your boss flexible or do you have a ton of policies that need to be followed? Comment below.

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This is really interesting and I have a lot of friends who talk about this. My company culture is very different and as a manager, I have never declined a request for vacation time. We see it as the employee’s time to do as they wish. Of course, it helps that I have a team of 9 people with the same function so they can all fill in for each other. This is one of those things you can’t really ask about in a job interview, but hope you can get some insight to company culture before accepting an offer!


Hi Leah,

Thanks for the comment. It is nice to hear that your company has a welcoming culture around vacation time. I too work for a company where vacations are encouraged and its awesome. Other’s however, are not so lucky. And I agree this is something that is hard to get a handle on in a job interview. I also think that it depends on which country your are working in. As some countries mandate that employees receive vacations and other do not. I think that this can be a fundamental difference and can effect company culture and policy.

Glad you enjoyed the post 🙂


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