Unless you already know that your boss is predisposed to letting you telecommute, one the best ways to start a dialogue is to submit a well-written proposal. In your proposal, take a business-case approach, looking at things from your boss’s perspective. Address ‘what’s-in-it-for-the-company’ issues, as well as any concerns or objections your boss might have. Plan to hit your boss with a double-whammy: A written proposal and an oral presentation.

The written proposal enables your manager to more carefully consider your ideas when she has more time.  Plus it can serve as a crucial tool if your boss must obtain approval from higher up in the food chain. The presentation prepares your manager to absorb the points in the written proposal and gives her the opportunity to raise questions or objections.

I can see some of you cringing at the idea of having to write a written proposal. Trust me on this one. By taking a professional business approach to the idea you are increasing your chances of getting an approval from your manager.  This is not a thesis statement or some large written grant.  A one to two page proposal is all you need. 

The four most important aspects of the proposal are:
• The positive business impact to telecommuting
• The schedule with a trial period
• Any equipment or additional costs
• Accountability that you’ll get the job done at home

Deploy statistics and case studies that support the business benefits of telecommuting. Numerous studies support the notion that telecommuting workers are more productive and have higher morale and less absenteeism. Organizations that allow telecommuting have less employee turnover. Provide examples of other companies in your area, especially competitors that allow teleworking.

Propose a schedule. Mondays should not be one of the days you propose for teleworking. I consistently work from home on Tuesdays and Thursdays.  But I have also worked from home on Fridays (where at previous my company there was a moratorium on Friday meetings).  You’ll probably want to pledge to be in the office for all staff/team meetings.

Talk about equipment. Reluctant managers are more likely to say yes if you already have the equipment you need to make it successful.  However, you absolutely must address if there is any equipment you will need.  It is important to stress which equipment the employer will provide and what you already have at home

Build in accountability measures. Suggest ways for your boss to keep tabs on you and be fully informed of your progress. Offer to e-mail your boss a report of your activities for each day of at-home work. Suggest frequent evaluation meetings at various stages of the trial period. Establish a list of measurable goals against which to determine the success of the trial.

After you hammer out your written proposal, work on what you plan on saying to your manager.  We’ll discuss the oral presentation further next week.