Work from Home Jobs: How do I ask to work remotely?

I worked remotely for a Fortune 500 company for 8 years.  It started in 2010, when I moved to the opposite coast from the corporate headquarters to be near my extended family.


One of the most frequent questions I am asked is “How do I ask my manager to work from home”.  Here are seven tips on how to give yourself the best chance to get a ‘Yes’.


1. Understand your audience

  • Find out if your company has an established flex work program.  
    • Check with HR, that department usually runs this type of program.
    • If there is not an established flex work program, think about how open your manager, or your company, is to remote work arrangements.  Is there precedence? If others have done it at your company, go to them for advice.  If you will be a first for your company, you will need to be even more prepared to make your case.
  • Identify your decision makers and your advocates.
    • Virtual Work Insider can help you develop your key stakeholder map to determine where the barriers might be and who can be your advocate.
  • Plant the Seeds in advance.
    • Don’t drop your request on your manager with an urgent need for an answer.  Starting this discussion informally in advance of your request is your best chance to understand what the barriers to “Yes” will be, and that information will enable you to put together your plan.  To your best ability,  start feeling out your manager in advance before it gets to a point where it might start feeling like an ultimatum i.e. avoid a discussion like “I would like to work from home or I will leave the company.”

2.  Understand Yourself

Think about if working from home is a good fit with your personality and the way you like to work. The flexibility of working from home might seem intoxicating at first, but there are downsides to consider as well.

  • Introvert or Extravert
  • If you are an extravert, what’s your plan to get the interaction you need to draw energy from being around others?  How will you feel when you can’t be at happy hour or a co-worker’s baby shower or birthday celebration?
  • If you are an introvert, how comfortable will you be with inserting yourself via video or phone call with your team members and senior leaders?  How willing will you be to do the extra work to influence your work groups, manager, and leadership from a distance?
  • Managing your time and workload independently
    • While it’s been proven that productivity improves with working from home, overwork is also a downside – often it’s harder to have the boundaries between life and work if you work from a home office.  Are you willing to put in the extra effort to making the virtual work situation seamless?  Especially at the beginning it will take extra time and forethought to set yourself up for success.  And on the flip side, will you know when to turn it off and walk away from your desk?
    • Are you a self-starter that can have the diligence to work and hit your deadlines without the constant oversight of your manager or team?

3.  Show you are indispensable 

For many companies, remote employees can be viewed as a risk.  Lower the barrier to Yes by proving your worth and showing your skills in advance of asking to work from home.   Companies have an incentive to retain strong employees.  Show them that you are worth retaining.


4.   Have a plan for the short term

Think through how you would do your work and stay connected to your manager and teams.  Usually if you have solid plan that anticipates all of your manager's concerns it will help you get to Yes.  Virtual Work Insider can help you develop that plan so that you get the flexibility you are looking for and also make it seamless to the business.


5.  Test it out

If you are still having trouble convincing your manager,  think about a low risk way to test a remote work situation.  For example, ask to work remotely around an upcoming holiday when there is less high profile work happening.  Or ask to work from home one day a week for a month.  It will allow you to try out your short term plan and show your manager how you will stay connected.


6.  Consider your long term plans

Think about if your career path as a virtual employee would be any different than if you were located at the headquarters.  Many companies that do not have an official flex work program have not yet planned out the career paths for those who are remote and may require the employee to move back to headquarters to get promoted.  For fully remote companies, this is not an issue.  While it is not necessary to have it all worked out before you go remote, it is good to think ahead a little to make sure this move is setting you in the right direction for your longer term career and life goals.


7. Don’t give up at the first no 

Timing is everything with this type of request.  If your manager is not an advocate for virtual work, are there other managers that might be?  Think about what other roles might be more open to this type of work.  And, in the future, there could be corporate changes that would open up a new window to ask again.


You no longer need to spend time searching for work from home jobs.  You can do the job that you are currently doing from home if you have the right plan to influence the right people.


Do you have a story about when you asked to work from home?  Would love to hear what worked or didn’t work for you. Just email sacha@virtualworkinsider.com

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