You have a horrendous commute. Maybe it's multiple modes of transportation followed by a long walk requiring you, your laptop, and your lunch to brave whatever conditions Mother Nature has cooked up for the day. Or maybe you've developed a relationship with your car that is far more intimate than you ever imagined. You two know each other well after hours and hours in stop-and-go traffic during which you change the radio stations so rapidly out of boredom and frustration that you're not even sure what song was playing.

A bad commute can make an otherwise agreeable job miserable. If you're in this situation and wanting to telework, initiating a thoughtful conversation with your boss is the first step. Perhaps you've asked your boss before and she said no. Maybe you haven't yet tried. Either way, here's an email that you can share--or convert to talking points for your next face-to-face meeting to make your case for working from home. This message aligns with the tenets of building leadership buy-in shown in this graphic.

Dear Boss -

I'd like to work from home and wanted to get your thoughts on how this might work for our business and team. As you know, I really enjoy my work. A big part of that is the opportunity to work with you. I've always found you to be a thoughtful, forward-leaning leader and one open to new ways of doing things that don't compromise what's most important--the health of our group.

Our business is, of course, very important to me. I've been inspired by you to grow in many ways and have learned so much during our time together. One of the things I've learned is that it's important to challenge the status quo and our traditional ways of thinking about things.

I've done some research and found that typical businesses that adopt telework policies save an estimated $11,000 per person per year. Further, studies have found that teleworking employees are 25 percent (or more) more productive than their in-office colleagues.

Years ago after some high-profile policy reversals at places like Yahoo and Best Buy, I wouldn't have believed that working from home was as productive or engaging as coming to the office. Those businesses are in trouble but we're not like them. Today, we have lessons learned from these early, struggling adopters and better understand how professionals in our industry are making work-from-home options wildly successful.

  • We have all of the tools we need. With my laptop and phone, I am securely connected to you and our team. While we might want to explore some other free or low-cost collaboration solutions, no additional financial investment is needed. In fact, overhead costs will be reduced because I'll no longer need space at the office.
  • I'll be more productive. I know, it's hard to believe that's possible, right? Kidding aside, the four to five hours* I spend now getting to and from work each week can be partly reinvested in my projects and I'll be less prone to the typical interruptions that happen in the office.
  • Our performance management tools are in-place. Annual reviews and impromptu meetings won't change. I'll be a phone call away when you have a question or concern on how something is progressing.
  • Incorporating a work-from-home option reflects the kind of innovative, high-trust organization we are and strive to be in the future.

Intrigued? I hope so. What's next? I have some ideas on how we might make this work.

  1. I'd appreciate a chance to meet with you to discuss the specifics of how you and I would remain closely connected.
  2. Next, if you're interested in exploring this more broadly for the office, I'd be happy to lead or support a working group to develop the parameters of who's eligible, when face-time is required or expected, or what we do if performance slips.
  3. Then, we pick a date. In advance, we'd agree to success criteria. We'll know working from home is successful when... (i.e. deadlines are met or exceeded, customer service is improved, morale and engagement goes up, etc.) I'm open to a trial period if that would make you more comfortable to start. However, I'll tell you that I'm confident that I can make this work well for both of us and our business.

I'd like to have a chance to talk with you in person once you've had a chance to read this. Thank you for your consideration.

To make it a painless one, you have to first get into the right mindset and believe that your boss will be open to a logical argument. Next, your key points must be focused on the benefit to her and the business, as opposed to, leading with the obvious benefits to you personally. Stay open-minded and flexible as you listen to her response. If she seems intrigued but non-committal, ask what additional information would be helpful. In this case, it's likely that she'll suggest either a trial period or set number of days per week to see if telecommuting works. It's up to you whether or not you take less than what you're seeking upfront. I believe 2 days per week (for example) is a great starting point and something you can build from in the future. Before you finalize any agreement to a trial period, make sure you get clear on what success looks like.

If you get turned down flat, ask if you can revisit the topic in 6 months. For bosses that really dig in and say something like "not now, not ever," then you move to Plan B. You'll have to decide if the commute is something you can live with or if now is a good time to start looking for other employment opportunities with companies that are either closer to home or do already have telework policies in place.

For more ideas on how to get the support you need from your boss, check out my book Flock: Getting Leaders to Follow.

*25 minutes is the average one-way commuting time in the US. Calculate your total weekly commute time and replace this average before sending the email for greater impact.