Convince Your Boss To Say Yes To Your Vacation

Convince Your Boss To Say Yes To Your Vacation

In a perfect world, you wouldn’t need to convince your boss to say yes to your vacation.

She would visit your cubicle with praises of your work and suggest that you take a few weeks off – paid, of course.

In reality, it takes planning to get approval.  These tips make it easy for you by first making it easy for your boss.

Make It Easy

Unless your boss is Scrooge, he doesn’t want to squash your hopes of white sand and blue skies.  Put yourself in his shoes to create a vacation request that won’t cause him heartburn.

Put in your leave slip as early as possible so that it won’t be pushed aside or rejected.  You also avoid the chance of requesting the same vacation days as your coworker.

Before approaching your boss, determine the pros and cons of your request.  This includes picking the right time to go on vacation.  Are you pushing against a project deadline or a busy season?  This may lower your odds of getting your boss to agree to time off.

If you are a popular sales rep, ask a dependable coworker to cover any new or pending requests in your absence.  Offering solutions to the boss before they mention concerns strengthens your argument.

Remind your boss of your accomplishments and she will see that you’ve worked hard for a vacation.

By eliminating reasons for your boss to say “no”, you’ll get a “yes”.

Don’t Accept The First “No”

According to Seth Godin, “no” can mean several things including:

  • I’m too busy
  • I don’t trust you
  • This isn’t on my list
  • My boss won’t let me
  • I’m afraid of moving this forward

Seth also points out that “no” doesn’t mean your boss fully understands what you’re asking or that they hate you.  In other words, get to the bottom of the “no”.

Ask to return at a better time to discuss it further.  Find out if there is anything you can do to get a yes now or in the future.

The more information you’re able to squeeze out of your boss, the better you can prepare for your next vacation request.

Increase Your Productivity

Win your boss over by planning a noticeable increase in your productivity.

I’ve adapted this trick from The 4-Hour Workweek.

You’ll start with a request for two days off.  It doesn’t matter which two days you ask for, but they should be adjoining days – a Monday and Tuesday or a Thursday and Friday.

To make the greatest impact, you’ll need to lower your productivity a tad on the weeks leading up to your vacation.

Gasp!  If this goes against your morals, skip it.  It isn’t a huge part of the trick, but it gives the tactic an extra boost.

When you return to work after the extra days off, push yourself to accomplish more than usual.  Offer to help co-workers with their workload or ask your boss for extra assignments.

Don’t forget to mention the burst of productivity to anyone who will listen.

Sustain this extra work for a week or two.  Your act will make it hard for your boss to ignore that time away from work increases productivity.

Finally, it’s a good habit to update your coworkers on important matters that might come up during your absence.  And don’t forget to bring back yummy goodies for your office.