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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About the Author

Joaquin Lippincott, CEO

Joaquin is a 20+ year technology veteran helping to lead businesses in the move to the Cloud. He frequently speaks on panels about the future of tech ranging from IoT and Machine Learning to the latest innovation in the entertainment industry.  He has helped to modernize software for industry leaders like Sony, Daimler, Intel, the Golden Globes, Siemens Wind Power, ABC, NBC, DC Comics, Warner Brothers & the Linux Foundation.

As the CEO and Founder of Metal Toad, an AWS Advanced Consulting Partner, his primary job is to "get the right people in the room".  This one responsibility is cross-functional and includes both external business development functions as well as internal delegation and leadership development.

A UCLA alumni, he also serves in the community as a Board Member for the Los Angeles Area Chamber of Commerce, the Beverly Hills Chamber of Commerce, and Stand for Children Oregon - a public education political advocacy group. As an outspoken advocate for entry-level job creation in tech he helped found the non-profit, P4TH, an organization dedicated to increasing the number of entry-level jobs in the tech industry, and is in the process of organizing an Advisory Board for the Bixel Exchange, a Los Angeles non-profit that provides almost 200 tech internships every year.


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