Asking Your Boss To Work From Home

Imagine a workday where you didn’t have to sit in rush hour traffic, stressing out about whether you’re going to make it on time and being cut off at least once before making it to the office. Your wallet would be full and happy after saving on expensive gas, you could work in your pajamas (or whatever you want to wear, really), take breaks as you please, work during the times of day that are best for you, easily eat a delicious and inexpensive lunch at home, and more. It sounds like the ideal situation, right? On the surface, telecommuting is the perfect way to get the work-life balance you’ve always wanted!

Of course, nothing is all sunshine and roses all of the time. The following downsides may come up while you’re working from home.

  1. Interruptions From Anyone Else Who’s Home: If you have family members who are also around during the day, expect inevitable interruptions with family matters while you’re trying to work.
  2. Interruptions from Deliveries or Door-to-Door Salespeople: You may be surprised how many people ring your doorbell during the hours that you’re usually out of the house and in the office. These interruptions can add up and break your focus.
  3. Isolated from Office Communication: What’s the scuttlebutt in the office? You have no idea! While you can still communicate with your coworkers regularly, it takes more effort to do so while you’re telecommuting you may feel isolated from office communication and information, which could potentially put you at a disadvantage when it comes to raises and promotions.
  4. Can Get Lonely: If you’re an extrovert or just someone who is used to being surrounded by people all day, telecommuting can take a bigger toll than you might expect and leave you feeling lonely.
  5. Your Discipline is Taxed: Your house has a lot of cool or even mundane distractions that you’re far away from while working in the office. When you’re up close and personal with these potential distractions, your discipline will be tested and taxed.
  6. Your Boss’ Discipline is Taxed: Your discipline is stretched further when working from home but so is your boss’! Why? Because it takes more discipline for your boss to keep up with what you’re doing. You’re out of sight, out of mind.

For those who are disciplined enough and able to fight the loneliness and various distractions, working from home can actually be more productive. If you feel like you fit into that category, it’s time to ask your boss if you can work remotely. Depending on who your employer is, this could be an uphill climb or a walk in the park. What are some of the downsides an employer might see?

  1. You’ll Get Less Done: Some managers will have a hard time believing you can get as much (or more) done from home than you can while working in the office.
  2. Less Disciplined Coworkers Will Want to Step into Your Shoes: Maybe a manager isn’t as concerned about you working from home but they worry that your less disciplined coworkers will want to do the same.
  3. If There’s a Question or Urgent Meeting, You Won’t Be Around: If you can’t be reached right away for a question or there’s an urgent meeting that you miss, your boss won’t be happy and will blame the inconvenience on the impracticalities of telecommuting.
  4. Out of Sight But Always on Their Mind: Some employers will worry that they’ll forget to check on you, and others will worry for the opposite reason. Like dropping off their kid at college for the first time, they’re extending you a lot more freedom than you’ve ever before. They may find their mind occupied with what you might be doing or working on, which will distract them from their own busy days.

As you can see, your boss has a very different point of view on telecommuting than you do. And the 4 challenges above are only scratching the surface. Here are a few other common concerns employers have about telecommuting:

  1. Fear you won’t work.
  2. Your boss will have to do extra work to monitor you and your work.
  3. Information may be less secure while you’re off the company’s servers and using your own internet service provider.
  4. Trusting that you’re not working two jobs at the same time.
  5. Inability to reach you quickly during business hours.
  6. Inability to collaborate with coworkers as needed.
  7. Concern that this will spiral into every employee wanting to work from home once they see you doing it.
  8. The feeling of a loss of control.

Ultimately, it’s good to know what these fears are because you’ll be able to address them when asking to telecommute. Very few employers will be gung-ho on your transition from working in the office full time to telecommuting full time but there are a few ways you can ease each other into the process, test the waters, and prove that you’re productive while telecommuting.

  1. Trial period.
  2. Start with only 1 or 2 days a week.
  3. Exceed expectations and potentially work extra hours during the trial period to show how productive you can be.
  4. Schedule check-ins to keep your boss informed while you work from home
  5. Set project deadlines and meet them.
  6. Focus on the needs of the company and your boss, not yours.
  7. Remain flexible even if the company wants you to take baby steps because this may be a big step for them.
  8. Write up a plan that integrates well with the company’s scheduled work hours.
  9. Prepare some positive facts about telecommuting. This article ( can help you get some ideas and any further research will be beneficial.

Now that you’re prepared with a few ways to ease into the telecommuting process, it’s time to approach your boss. The best, most effective, and most professional way to do this would be to set up a meeting and submit your request in writing ahead of time. Need some help writing a letter or email that will win them over? Feel free to use one of our sample letters below!


Sample Letter 1:

Subject Line: Request to Telecommute

Dear NAME,

In the past, I’ve been able to work a few hours from home on an occasional basis. During this time, I’ve found that my productivity has increased and I’m able to focus well on my work without running into as many distractions as I do while working in the office.

Because of this, I was wondering if I would be able to work from home regularly, meeting in the office on an as-needed basis? Let me know if this is a possibility and I look forward to our continued collaboration.

Thanks for your time and for your consideration,



Sample Letter 2:

Subject Line: Eager to Work Productively From Home

Dear NAME,

We have lots of exciting projects in the pipeline, don’t we? I’m gearing up for a lot of planning and writing for this year’s revamped conference and while I’m excited to get to work, I know it will be quite the undertaking.

In the interest of increasing my productivity and staying focused, I was wondering if I might be able to work from home two days a week during the lead up to the event? I know what you’re thinking, telecommuting comes with a lot of challenges and distractions. In the past, I’ve found that I can work well from home while remaining completely flexible and coming into the office for important meetings or face-to-face time. I would be available by phone and email while working from home, in case anything comes up, and would ideally like to work remotely Mondays and Tuesdays as there are no regular meetings or collaborations scheduled on those days.

I look forward to hearing your thoughts and concerns. Thank you for your time.