7 Ways To Convince Your Boss To Let You Telework

Seven Ways To Convince Your Boss To Let You Telework

If someone paid you to go on vacation, would you take the deal?

It seems like a no-brainer, but a study by the Travel Effect shows that 40 percent of Americans won’t use all of their paid leave.

That’s right.  Almost half of the people paid to take vacations are like, “Nah.  That’s okay.  I’d rather read email.”

And while it’s baffling, I explored their reasoning hoping to get a better understanding.

There Is No Good Reason Not To Use Your Vacation Time

Forty percent of respondents didn’t want to return to a pile of work.

You ever notice as soon as you pay a bill, the next bill lands in your mailbox?  The same is true for work assignments.  They are a relentless stream of to-dos and if you’re lucky, they excite and energize you.

Who wants to stare at an empty inbox for eight hours?

Humans work better when running against a deadline, so take a vacation and scale your mountain of work with a smile.

Thirty-five percent thought no one else could do their job.

Are you taking AT LEAST 3 overseas trips a year? If not, I'll send you my FREE travel guide. Get more travel in 30 days with these easy steps!

Seriously?  Someone did the job before you and someone will do it after you.  There are many people who can do your job and some will do it for cheaper.

You shouldn’t worry about that.

Here’s a better way to use your energy: find a young professional who could use a chance and share the workload.  Sure, you’re still responsible, but with guidance, they will excel at the job like you did.  Plus, f you ever quit working to travel, your replacement will be ready!

Twenty-two percent didn’t want to seem replaceable.

You aren’t replaceable – at least not to your mom.  To almost everyone on this planet, you are expendable.  And you will be replaced now or later.

Don’t become a “work martyr” in exchange for a false sense of security.  Take time off and spend it with family – those who really value you and think you’re irreplaceable.

Although these aren’t good reasons to skip a vacation, I understand how important it is to feel secure in ones job.  So, while I advocate unplugging, I will meet folks halfway by offering tips on working from anywhere in the world.  By working remotely, you can travel more often while maintaining a handle on your job.

How To Convince Your Boss To Let You Telework

There are many benefits to working virtually.  For me, the best benefit is the ability to work from so many beautiful locations in the world.

Here’s a rundown of how to get your telework request approved.

1 | Manage current assignments

How are you handling your current work assignments?  No matter what forward-thinking Richard Branson is doing, many employers are still uncomfortable with extended time away from the office.  And the fact that they don’t actively encourage vacations keep more employees from requesting time away.

Your first duty is making your boss totally comfortable with your work in the office.  He’ll be more willing to give you a chance at working away.

If you’re already working your buns off, bravo.  Keep it up.

For those catching up on Twitter during work, don’t you dare ask to telework until you do a better job in the office.  This is important.  You don’t want to do poorly while working remotely and mess it up for others in the future.

Don’t put that smear on your travel karma.

2 | Know the facts

Know the facts about working virtually.  Taking a vacation not only benefits your health, but the health of the organization.  A study found that for every 10 hours of vacation, productivity jumps by 8 percent.

Take some time to research the benefits of telecommuting before going to your boss.  Have a few examples of relatable business where it’s going well.

Have your scientific proof – who can argue with science?

Make sure you can quote the best studies and reasons it’s applicable to you and your industry.  If you’re able to explain these facts to your supervisor, you increase your chances of getting to yes.

3 | Check technology

Do you have the technology needed to be accessible and productive?  The last thing you want to do is make promises you don’t keep.

Check internet connections, power sources and phone service upfront to make sure you can connect when needed.  Make sure work sharing and communications systems and processes are in place before you need them.

Tell your team how you will keep track of your workload.  Ideally, this information should be available to your team and boss at all times.

Start using these systems before teleworking to make sure folks understand how they work and are comfortable with them.

4 | Practice teleworking at the office

Occasionally, work in another location in your building to break the habit of your boss and coworkers seeing you in the same place every day.

When you ask to work remotely, your boss doesn’t only think about your ability to do solo projects.  They are also considering your ability to work on a team when you’re not physically located near them.

Your boss and team must know that if they need you, they can reach you in a variety of ways – even if you’re not in front of them.  By working in remote locations around your building, you create this understanding.

5 | Prepare for the challenging questions

This is where your friends or a mentor will come in.  Ideally, you should role play with those who manage employees or teams so you get an honest perspective.

Ask them to give you a hard time about your request and practice the exchange several times.  You’ll feel more prepared and confident if you know what your boss would potentially ask and you have already practiced how to answer.

6 | Propose different scenarios

During your telework discussion, you’ll need alternatives if your first proposal is denied.  How about teleworking on days you don’t have meetings?  Or ask for one day of working virtually per week and increase the number of days based on your performance.

The key is to ask for your dream telework agreement first, followed by a great telework agreement.

If your dream proposal gets a yes, you’ll win big.  If it gets a no, you’ll have another proposal that would still make you happy.  Compared to your dream request, the second request will sound more realistic and be easier to approve.

7 | Ask for a trial period

Ask your boss if you can try working remotely on a trial basis.  It’s easier to say okay when there is a way out.

That’s why company’s offer trial periods for their products.  If you love it, you’ll keep it. If not, you say this didn’t work and things will go back to normal.

Give your boss that same security and he’ll be more likely to approve your request.

Your trial period is your time to shine.

Ask coworkers for feedback and constantly improve your performance.  Go over expectations beforehand and only promise the minimum.  When possible, give your project more than you agreed to.

Become a pro at time management.  As these skills increase, so will your productivity.

Although taking a legit, no-one hears-from-you trip is on your wish list, working remotely is a step in the right direction.  To recap:

  1. Manage work assignments in the office
  2. Know the facts about working remotely
  3. Check your technology for accessibility and productivity
  4. Avoid always working at your desk
  5. Prepare for challenging questions in advance
  6. Create different scenarios for approval
  7. Ask to work virtually on a trial basis

As you’re creating the life of your dreams, telecommuting is a great way to see the world and keep the folks at work happy.  Remember: no one lies on their deathbed wishing they had worked more.  So start here and work yourself up to vacation without cords.

Get out there.  And send me a postcard.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
Last year, I had the telework conversation with my boss.  I always have to push myself into that small, ten second burst of courage needed to ask for what I want.  You know if you don’t ask, the answer is always no.  So, I started the request with my dream proposal which was teleworking on Thursdays and Fridays.  This would give me longer weekends to spend time at new locations. I could also fly on Wednesdays after work to cash in on cheaper fares.  He turned down my proposal.  I countered with a more flexible request – that I work remotely on a case by case basis.  He agreed and it has worked like a charm.  Many times he no longer requires that I gain approval beforehand and teleworking has become a part of my weekly routine.  Find me on Twitter for more about this and other travel topics.
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
Photo by Glorgio Montersino