How to Convince Your Boss to Let You Work From Home

your boss who you need to convince to let you work at work

So you want to work from home? Well, you have to convince me first.

Ok. Maybe not me exactly, but I am a business owner and for years I successfully ran my business with the mom-and-pop mentality that if I could see my employees in their seats, they must be working. If I sent employees home, who knew whether they would goof off or not? Most businesses start with this mentality and many never get past it, however, at our company we changed course and have not only improved morale, but also gotten more efficient as a result.

This is a post on how we did it, and (more importantly) how can you convince your boss to let you work from home. Here's the five-step process:

  1. Broach the subject
  2. Articulate the objections
  3. Find alternatives
  4. Establish a baseline
  5. Review & experiment

Broach the subject

This may sound silly, but you don't get what you don't ask for. At my office it was one or two employee that voiced interest in being able to work from home a few days a week, but when we brought it up at a company-wide meeting almost everyone was interested in it. If you want to work from home, talk to your boss about it.

Articulate the objections

If you don't already have a work-from-home policy, chances are your boss will say "NO WAY!" to your first request. At this point it's very important to find out why the answer is no. Everyone is different, but here were my concerns:

  1. I didn't want to lose visibility.
  2. I wanted people to be able to stay in touch
  3. I didn't want people to get distracted

These concerns, while they are valid, are not necessarily solved by working in an office:

  1. At a company with 20+ people, I really don't have as much visibility as I think I do.
  2. People in the same office don't always talk.
  3. People get distracted at work (8 hours of meetings anyone?)

That said, the concerns still have to be addressed. That brings us to the next step.

Find alternatives

Now that we know the objections, we can propose better ways to measure worker productivity and facilitate communication:

  • We track our time using Harvest.
  • We track our code commits using GitHub.
  • We graph our productivity (billable vs. non-billable time, etc) using Google Visualization.
  • We use Yammer to help people keep in touch.
  • Everyone sends an email indicating what they will be working on when they are out of the office

As a result of this increased communication, everyone actually has more insight into what people are doing and communication barriers can be overcome.

Establish a baseline

No matter what your metrics, it's important to establish a baseline. These are numbers you can refer to once a work from home experiment goes into effect. This also has the added benefit of helping to identify employees that may be key contributors that are not being properly recognized and can help make sure that the tradeoffs (more communication and tracking) are things that you are prepared to do.

Review & Experiment

Once you have these new numbers and metrics, review them with your boss to get his (or her) take. Chances are they will be so impressed and reassured by their new business metrics that scheduling work from home days will be no problem. As you start to work from home, you also have real practical numbers you can look at to make sure you are being as productive as you are in the office.

Final Tips

Here are a few final tips, based on our experience:

  1. In our experience work-from-home days are best when they are optional company-wide days. This means people can come in to the office, but if they are going to work from home, everyone does it at the same time. This can help avoid the problem of being the odd-person-out.
  2. We like our work-from-home day to be once a week. This allows for a co-working experience as well as a little heads down productivity.
  3. It's important to realize that not everyone works well from home. Working from home is a privilege that requires additional responsibility. Metrics are an important and impartial way to identify workers that shouldn't be allowed to work from home.
  4. Good luck! Be sure to share your experience with us.

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I think a small part of what made this work for us was the decision before we implemented this policy to reduce morning stand-up to fewer days a week (instead of everyday) and lean on those communication tools more. I think that got people used to using those channels of communication and increased the overall level of trust.

Good point, Robbie. I think when it comes to daily stand up meetings, the size of the team really matters. Once you pass 10 people it gets really hard to keep daily meetings from wasting people's time.

On the other hand, two days a week feels just right for us at 20+ people.

It's also important to note that we're talking about company-wide meetings. I think the daily check ins is still pretty important on projects with multiple developers.


I love the approach you took in this post, outlining a manager's natural reaction to working from home, and how to address their concerns.

I would love to see a follow-up post in a few months time with what you've learned, and what (if anything) you would do differently.

In my opinion, not enough managers and employers are willing to write honestly about their motivations and concerns with situations like this, so this kind of post can be incredibly valuable. Nicely done.


Thanks, Scott! We've actually been doing this for several months and it's been very successful. Our specific metrics center around time tracked (trust-based), and GitHub commits (impartial/numeric). Not only has this switch improved morale, but by paying attention to time (billable vs. non-billable, etc) we've also helped improve our efficiency. My only regret is that we didn't switch sooner.


At our company we have a day long event for everyone that's out of the office or on vacation. It's wonderful to be able to look at the top of our google calendar and instantly know whether I should expect to find people in the office or not.

Half of our staff is remote though and while it does have its own problems, we've been able to grow much more rapidly than otherwise and our customers love having us spread out over the timezones.

But seriously, sounds like metaltoad is making lots of great strides towards happy employees. That has to feel great!


It is difficult to convince boss to let me work home. With your tips it's not more difficult. I'll try it on my boss. Thanks for sharing.

About the Author

Joaquin Lippincott, President & Founder

Joaquin is a modern technology veteran. Throughout his career he has built successful digital strategies with a wide assortment of transformative technologies and platforms, helping clients identify a clear path for success.

Over the years he has worked with industry leaders such as DC Comics, the Emmys, Intel, Technicolor, Verizon Wireless, Habitat for Humanity, Limewire, the Linux Foundation, Sony Pictures Television, Mercy Corps, and Cisco as well as numerous small businesses, advertising agencies and internet start ups. With over 14 years of experience in his field he is still as passionate about technology as ever.

Joaquin is a graduate from UCLA with a degree in design and has also served on the AIGA Portland chapter board as President.

Twitter: @joaquinlippinco