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By Christy Schutz

Maybe you have been lurking around the site, reading up on all the pros and cons involved with working from home, evaluating whether you have the temperament to succeed, or judging whether your particular work can even be done from home. But the truth is, that kind of work arrangement seems very implausible for you right now. How would you even start? Would it involve leaving your current role and looking for a new job? Not necessarily. There are a lot of people who were successfully able to make that telecommuting transition without leaving their current employers. What can you do to explore that option? One way is to create a telecommuting proposal and pitch the idea to your boss.

Here are five things to consider when writing your proposal:

1. Start with a Trial Period

Your ideal situation may be you in PJs working from home five days a week starting next Monday, but if telecommuting roles are not a part of your corporate culture, you are going to need to ease into it. Your best bet is to recommend a trial period to your boss. That way, he or she can opt out of the arrangement if certain expectations are not being met. Carefully outline a determined period of time (30 days, 90 days, etc.), the days of the week you plan to try working from home (1 to 2 days a week during the trial), what hours you plan to be online/accessible, and any other details that will be important to establish all that the trial period entails.

2. Spell Out Success

For many bosses, the misconception is that telecommuters will ultimately end up parked on the couch watching daytime TV, folding laundry, or goofing off instead of getting their work done. So it is essential to spell out the way your success will be measured during the trial period. Set goals that are comparable to what you are expected to do when you are in the traditional office. Your goal will then be to meet, or better yet, exceed your productivity goals during your work-at-home trial period.

3. Talk About Tools & Environment

Another concern for most bosses is that it will require equipment and resources to work from home. Will it require an investment on the company’s behalf? Do you have WIFI, an established working space in your home, dedicated phone lines, software platforms, or need special access, etc.? Get detailed, so they have a full idea of what is going to be involved in accommodating your request.

4. Outline How You Plan to Stay Connected

Communication with your boss, colleagues, and other internal customers can be a tricky thing to figure out when you are working from home. Carefully map out how to plan to navigate those scenarios. Maybe it includes regular meetings or conference calls, using tools like Skype that allow you to have face-to-face contact, and other ways you can maintain communication with the people who are critical to your success.

5. Anticipate Objections & Provide Research

There are probably other hot-button issues surrounding a possible work-from-home arrangement that will be important to your boss. Take some time to think those things through and outline your suggestions on how you will mitigate those challenges. It is also helpful to do a little research and include statistics that showcase how telecommuting arrangements improved productivity, reduced costs, boosted morale, or whatever else you think will resonate within your corporate culture. The bottom line is that it is important to address the objections head on and outline how BOTH you and your organization will benefit from the arrangement.

The next thing to do is to make plans to present your proposal. It is best to do this in person if at all possible. That way you can carefully go over your proposal, answer any questions, and address concerns. In the event your boss needs more time to consider what you’ve proposed, it is a good idea to go ahead and make plans to reconvene at a later date before leaving your meeting. If they decline, you could suggest a more limited trial (e.g., one day a week vs. two), or suggest telecommuting to complete specific tasks (like completing reports one afternoon a week, etc.). If none of those things tip the scales in your favor, don’t lose heart. It just may not be the right timing.

If they accept your offer, now is the time to shine. Show your boss how the reduced commute, added flexibility, and simply the benefit of the doubt are all components that will make you a happy, engaged, productive employee. Keep specific stats and make plans to meet again after the trial to talk about the results. Assuming it is a success, you may have to start the process over again, with a new, extended trial, how you will measure results, additional details on tools or resources you need, added ways you plan to communicate, and any additional objections that came up along the way.

Anyone else who's made this transition and have something to add? What did you include in your telecommuting proposal? What particular objections did you face? If your boss said “no” initially, how did you get them to reconsider?

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Christy Schutz is a communications professional and freelance writer focused on topics like employer/personal branding, career management, personal development, women in the workplace, and female entrepreneurs. She enjoys putting 16+ years of experience in the advertising, recruitment marketing, employee/internal communications and special events industries to good use by helping others to discover, develop and market their own distinct calling or mission. This Tampa Bay, FL-based Mom also keeps herself busy by raising 4 kids, caring for her husband & doting on her dogs Petey and Daisy!