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Six Practical Tips for Asking Your Boss to Work From Home

We working moms want to know how to find more balance as a mother. We seek ways to make work, motherhood, and domestic duties flow better. That’s why so many of us look for work-from-home positions.

Did you know that telecommuting employees are more productive and tend to be more loyal to their company? In addition, telecommuting reduces stress. However, approaching your boss about working from home might feel intimidating. I understand because I’ve done it twice. My experience taught me how to approach a supervisor about the subject of working from home.

Unfortunately, some supervisors struggle to see how telecommuting employees benefit their business. You may have to convince your boss (who will have to convince their boss) that telecommuting is good idea.

Motherhood Prompted My Transition to Telecommuting

After the birth of my first child, I worked as a billing analyst. Our main client was a Fortune 10 company and the job was fast-paced and exciting. I returned to work six weeks after my baby was born, but I struggled to balance the needs of my newborn with the demands of my job. When my baby refused the bottle at daycare and spent the day hungry and crying I knew something had to change quickly.

Immediately I knew that telecommuting would be the perfect situation for me.  Since no one else in my company worked from home I didn’t know if my request to telecommute would be approved.

I summoned the boldness that only youth can lend (I was 23 at the time) and requested a meeting with my boss.  I asked him if I could work from home and, after talking to corporate, he said yes. My boss asked me to attend the weekly status meeting in person and to be available by phone and email during business hours. I gladly agreed and began working from home.

My First Telecommuting Experience

For over two years I enjoyed the best of both worlds. I loved balancing my days between full-time motherhood and a full-time career. Then, two weeks after the birth of second son my boss left the company. His temporary replacement wanted me to return to the office at least part-time. He said I could work part-time for a few weeks after my maternity leave. Then I needed to be in the office full-time.

I declined and left that job to become a freelance writer and a family therapist. For several years I happily set my own hours and homeschooled my children.

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My Second Telecommuting Experience

Eventually I left the field of therapy and became self-employed. I didn’t want to obtain debt to grow my small business, so I decided to return to work part-time as an administrative assistant to earn extra money. The plan was to work part-time for a couple of years and then leave to focus on my own business.

Again, I fell in love with my job and the company I worked for. However, the job that started as a four-day-per-week, part-time gig quickly turned into a full-time, salaried human resources position. I knew I was taking on more than I could balance over the long term, but the work was fulfilling.

After a couple of years the domestic side of my life began to fall off the rails. As my own business (which had become businesses, plural) grew, I struggled to stay focused at work. I wanted to give my all to each area of my life, but I was stretched too thin. (See How I Work Full Time and Homeschool for evidence.)

I needed to give up my job, but I wanted time to plan a smooth exit. After I lost a caregiver and a virtual assistant in the span of a few weeks I came up with a quick plan.

I asked my boss if I could work from home two days a week. This plan saved me several hours each week that I could use for my domestic and small business responsibilities. He went to bat for me with the owners and I, gratefully, transitioned to a more balanced life.

Still, I knew I needed to give up my day job. I planned a slow, six-month long exit to make the transition smoother. Without the ability to work from home for those last six months I likely would have had to leave my job abruptly or ignore my businesses. I’m ever grateful to have had the chance to tend to both responsibilities completely.

How To Ask Your Boss To Work From Home

Neither company I worked for had a telecommuting policy in place before I began working from home. Asking my bosses for what amounted to special treatment felt intimidating. I had to think quickly of the best way to present my case to my bosses. I’m glad to be able to share what I learned from my experience so other moms might find the work-life balance they need.

If telecommuting is a common practice in your company, then asking your boss to work from home is a fairly easy process.  However, if you’re among the first in your company (or in your position) to work from home, you may have a few hurdles to jump before sealing the deal.

Here are my best tips for asking your boss to work from home.

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What’s In It For Your Boss or Your Company?

If telecommuting is rare or non-existent in your company, you’ll be setting a precedent.  Your company’s senior management focuses on profits and productivity – as they should.  If you can’t tell them how your telecommuting is good for their company, then they may hesitate to allow something outside of the norm (read: outside of what’s currently working; see also: if it ain’t broke, don’t fix it).

When I returned to work after my maternity leave, my son and I struggled with our nursing relationship.  I spent an hour of my work day pumping milk for him but he refused the bottle at daycare.  Within a couple of weeks I had to actually leave work to go nurse him at daycare, which took more than an hour of my day.  I was exhausted and most certainly less productive than I had been.

I considered quitting my job before coming up with the telecommuting solution.  My boss didn’t want to lose me and I still wanted to do my job.  Telecommuting was the perfect solution.  It may be the perfect solution for you, as well, if your work-life balance issues will be solved by working at the office less.

Even though your boss may be sympathetic to your need to work from home, ultimately you  have to show your boss how working from home is best for the company.  Will you be more productive?  Will you help the company achieve greater profits?  If you work for a smaller company, even things such as using fewer company resources (electricity, water, printing supplies, etc) may be important to note when talking with your boss about working from home.

Start With a Trial Period

When you ask your boss to work from home, start with a trial period.  Ask to work from home just one or two days a week at first.  You may find that telecommuting just a couple of days per week is enough to achieve optimal work-life balance.  Working from home can be isolating, especially if your co-workers all work from the office.

Decide which days are best for you and be prepared to start with just one day per week if your boss is hesitant.  Make sure you’re more productive on that day than you usually are in the office (which won’t be difficult if you currently work in close quarters with your co-workers.)

Have a Plan for Communication and Accountability

It’s important to your boss that he or she be able to measure or track your productivity.  Both you and your boss need know if telecommuting is working.  In my first telecommuting job, it was a weekly status meeting with my boss and no complaints from corporate about my work that let him know that telecommuting was working out. (I worked more closely with corporate in another state than with the site director, though he was my immediate supervisor.)

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Find out what will make your boss the most comfortable.  Will it be weekly face-to-face meetings?  Will it be projects completed earlier than the due date?  Be willing to negotiate and compromise to show your willingness to cooperate and make working from home a good experience for everyone.

Consider Those You Manage

If you’re in a management position you not only have to consider your boss, but also your employees.  How will you manage them from afar?  Will they, too, want to telecommute?  How you do feel about them working from home?

Have a plan to present to your boss outlining how you will manage your team remotely. Don’t leave any legwork for your boss to have to do. Think of as many variables and obstacles as you can before meeting with your supervisor and have solutions ready.

Stay Flexible

Even if you and your boss agree to a set schedule of work-at-home days, be flexible enough to attend meetings in person with short notice.  Always be available via phone and email during your agreed-upon working hours.  Be prepared to work from the office when there are big projects requiring a team effort.

What If My Boss Says No?

If your boss says no to working from home, but your work-life balance is suffering, offer another solution.  Maybe you can work four days per week instead of five.  Maybe a shorter workday is in order.  Or half-day Wednesdays or Fridays might be the answer. (Obviously, this solution might come with a paycut.)

I believe most employers want their employees to be happy and healthy. Happy, healthy employees are more productive employees.  Don’t be afraid to ask for what you need. Don’t give up if you are told no the first time. Continue to look for a solution that benefits both you and your company.


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