How To Ask Your Boss To Work From Home |

How To Ask Your Boss To Work From Home


The COVID-19 pandemic gave employers and employees a glimpse at what it may be like to work remotely full time. And while some employees fully embraced the work-from-home (WFH) life, others were climbing the walls and couldn’t wait to get back to the office.

As more businesses start returning to “normal” operations, you may be mulling over how to ask your boss to work from home permanently. After all, who wants to deal with a stressful commute, restricting schedule, or distracting coworkers interrupting your flow state?

So if your company hasn’t pitched the idea of flexible work arrangements, it may be time to advocate them for yourself.

Don’t worry; you’re not going to get fired for asking to work remotely, especially when you follow the tips in today’s guide.

How To Ask Your Boss To Work From Home

Follow these 5 tips to boost your chances of getting the green light to work remotely:

1. Brainstorm All The Reasons You Want To Work From Home

Grab a notebook and start brain-dumping all the reasons you’d rather clock in virtually.

Is your grueling commute a major drain on your motivation? Are you more productive during “off” business hours? Do you have to take care of kids or relatives?

List all the reasons the call to work from home is so alluring. Then, circle back to frame these in a way that not only benefits you, but your boss, team, and company. For example:

  • My commute is an hour long, and I could be spending that time productively on the clock from home instead of wasting time in traffic.

  • I have more focus between the hours of X and Y, which is when the office is typically closed. I could be working from home and accomplishing more for the team during that time.

  • Our clients on the west coast frequently call/email when our east coast team is already clocked out. I could attend these meetings from home with a split schedule and give the team a headstart on their to-dos for the following day.

Try not to focus on the perks of working from home that strictly benefit you. Your boss and the company won’t care that you like rolling out of bed and working in your PJs. But they may pay more attention to your request when they hear about how much more productive you’ll be.

2. Think About How Your Working From Home Will Affect Your Team

If you’re the first employee attempting to work remotely, your boss may not want to risk removing you from the well-oiled machine. So you must anticipate and prepare for how this change will affect your coworkers and your team’s daily operations.


Write down concrete answers for:

  • Your ideal work from home hours/days

  • How you’ll track your work hours

  • How you’ll set and manage priorities and expectations from home

  • Whether you can be flexible and still meet in the office as-needed

  • When you’ll be available to your coworkers and how they can reach you during work days (via Slack, email, video calls, etc.)

  • How you’ll attend meetings and collaboration sessions

  • How often you plan to touch base (once daily, AM and PM, weekly calls, etc.)

  • How you plan to supervise from afar (if applicable)

  • How you’ll keep your manager in the loop (and vice versa)

  • Which equipment/remote software/apps you’ll use to get your work done

  • Whether you’ll need a VPN or other security measures to keep your work secure off the company network

  • What happens if you encounter problems at home and can’t work there

  • How you’ll continue to interact socially with your team (i.e., attending happy hours, joining volunteer events, etc.)

  • How you’ll continue to exemplify your company culture

Once you have these details outlined, your boss doesn’t have to do any of the legwork to ensure you’re set up for success. You’ve taken the initiative to prepare a cohesive gameplan, making you appear confident in your ability to work remotely.

3. Gather All Your Supporting Evidence

Your managers may have a hard time trusting that you’ll get your work done away from their watchful eye. So it’s best to gather some hard evidence to back up your case.

If you’ve been working from home, you may have stats to compare your productivity in-house vs. from your home office.

For example, did you finish your coding tasks 25% sooner when you weren’t distracted by your coworkers? Did you land a new client by being available off-hours? Did you increase ROI for your marketing campaigns because you were fully immersed in the data?

Jot down any major wins you noticed when you were WFH to use as supporting evidence for why you can handle this new work style. You can also gather:

  • Performance reviews during your WFH time

  • Glowing emails from happy clients

  • Positive feedback or recommendations from coworkers about your work ethic

If you weren’t keeping track of these, you might need to run a little test to snag this data. Call out sick during the week (preferably on a day that’s not too hectic) and work remotely. Keep track of your time working, answer all the emails/messages your team sends, and do all your regular tasks as if you were already a remote employee.


Take notes of all that you accomplished and whether you could have done as much in-house. At the very least, clue your boss into your emails/messages/project updates so they can see you’re being productive even though you’re technically “out sick.”

In the end, your performance should speak for itself.

So if you routinely hand in work late, never respond to Slack messages, or need your coworkers to make excuses to clients about your mistakes, convincing your boss to let you leave the confines of your cubicle may be an uphill battle.

However, if your performance reviews show you’re a natural self-starter, never late on deadlines and deliverables, and communicate effectively even when you’re out of the office, they’ll have more trust in your ability to work from home.

4. Arrange An In-Person Meeting To Pop The Question

You could certainly send an email to your boss with your WFH request and all the evidence proving it’s a wise idea. But it’s better to go the extra mile and schedule a one-on-one meeting to discuss all the ins and outs face-to-face.

Let your boss know you’d like to have a conversation about improving your work environment and increasing your productivity. Give them your available times to chat and sign off by saying you’re looking forward to your discussion.

When you get a meeting time on the schedule, it’s best to create an agenda for how you’d like the conversation to go. This will help you stay on track and show you’re laser-focused on your intentions.

Your meeting agenda may look something like:

Opening statement: I’d like to work remotely to give my full attention to my responsibilities and dive into deep work during my most productive hours of the day.

Go back to the reasons you outlined in step 1 to come up with your own statement that reflects why it’s in your company’s best interest to let you work from home.

Evidence sharing: Over the past X months I’ve been working remotely, I’ve been able to take early morning career development classes, increased sales by X%, and came up with X creative strategies to improve ROI for my campaigns. I attribute these achievements to a flexible schedule, lack of wasted hours commuting, and greater focus from home.

Here’s where you’ll want to share all the evidence you gathered in step 3. Whip out the metrics you recorded to prove your higher productivity levels, happier clients, key performance indicators (KPIs), error-free work, etc.


WFH goals and gameplan: If you allow me to work from home, I plan to exceed my [sales, coding, marketing, etc.] goals by X% this quarter, onboard X new clients, tackle X new projects, etc. In my proposed Work From Home Plan, I outlined [go through all the strategies you considered during step 2].

Once you walk your boss through your plan, they’ll see that you’ve thought of everything for them. Stress that you believe you can perform at a much higher level from home, which will benefit your team and the company.

Suggest a trial run: If you’d like to test this strategy before committing to a permanent work from home arrangement, we can track my performance for one [week, month, quarter] and regroup to discuss what may need tweaking. There’s no pressure to continue if it’s not in the team’s/company’s best interest.

If your boss is one of those I have to see it to believe types, they may not give you the green light until they see you’re a productive remote employee firsthand. A trial run gives you the chance to iron out the kinks in your plan and prove it’s beneficial for everyone involved.

Ask for an evaluation of your performance during that time. And make sure to keep meticulous records about everything you accomplished.

Closing: Are there any questions I can answer for you or concerns I haven’t addressed?

Give your boss time to soak in all the details of your proposal, and reassure them that they don’t need to make a decision immediately. Chances are, they weren’t expecting your request and may need time to consider all the potential pros and cons.

5. Prepare For Pushback

Even if you have a solid, convincing argument for why you should be allowed to work from home, you should also anticipate negative responses. Prepare to answer these ahead of time, and your manager will see that you’ve thought through every possible objection.

The most common negative reactions include:

  • No one else is working remotely; why should you?

  • How will I know you’ll be available?

  • What if I need something handled urgently?

  • How will I know you’re actually working?

  • What if everyone wants to work remotely after you start doing so?

Your remote work plan should outline answers to all these, so go back and explain them in greater detail if they failed to land the first time.

And if others want to join your remote work experiment, tell your boss you can be the guinea pig to prove it either works or doesn’t. Show them why remote work is a perk to keep employees happy and productive, or attract other candidates to the company, making it worth the trial run.

Still a No-Go? Consider Looking For a New Remote Position

Many companies saw the benefit of allowing their teams to work from home during the COVID-19 pandemic, and they’ve continued this trend. If your boss doesn’t let you work remotely, there are tons of 100% remote positions you may want to chase instead. is a job board that specializes in the best marketing, communications, tech, and design jobs in Canada. And many of these fantastic positions are remote!

So if you’re jazzed about the idea of never stepping into an office again, don’t hold yourself back from realizing this goal. Find your next dream job now!


  • Null_n_Void

    She got the negotiation skills