If you want to work from home, but aren’t the freelancing or entrepreneurial type, you’ll have to educate your boss or join one of the growing number of companies that have work-at-home jobs.

Excerpted from Undress For Success—The Naked Truth About Making Money at Home (Wiley, 2009)

“If your first reaction when you think about teleworking is ‘Oh, my boss will never go for it,’ you aren’t alone,” Cali Williams Yost told us. She’s a work-life flexibility consultant and author of Work+Life: Finding the Fit That’s Right for You (Riverhead/Penguin Group, 2005). “In fact, I’ve helped tens of thousands of people use flexibility to find their work-life fit, and the top fear they all express is the fear that the answer to their proposal is going to be no. How do you get past this very common fear? Ask yourself, what’s the worst thing that can happen? The worst thing that can happen is that the answer is no. Then where are you? You are no worse off than when you started. And from my experience, nine times out of ten, if you are a good employee, the answer is going to be yes to some version of your well thought out plan for at least a trial period. So what do you have to lose?”

So let’s work on that well thought out plan. Before you start to actually write, spend at least a couple of weeks cataloging what you do on a daily basis. The more specific you can be, the better. For example:

7:00       Left for work.

8:00       Arrived at work.

8:20       Arrived at desk after getting coffee.

8:40       Finished checking voice mail.

10:00       Checked and responded to e-mail until George stopped by with gossip about the merger.

10:30       George left and I went back to e-mail.

And so on. You may want to change the names to protect the guilty, or better yet, create categories for how you spend your time, but the point here is to gain a clear picture of how much of what you do could be done from home. Along the way, you’ll find some office time wasters that may help your pitch as well.

Next, you want to show management that you understand they may have a concern about not being able to monitor your activity. If your company already embraces results-based management, you’ll have a head start. Look at your job description and compare it with the work log you’ve been keeping. Indicate the extent to which each of your job activities can be done remotely.

Finally, list a measurable result next to each element of your job. You and your boss will want to finalize these jointly. For example, an auditor might be measured on completed audits:

• No more than five errors per month are found on audits.
• For at least 10 weeks per year, no audits are more than 30 days old.

A salesperson might be measured on quotes and proposals:

• Ten calls made, resulting in four meetings and two requests for proposal.
• Proposals are submitted with two days.

A technical support person might be measured on client satisfaction:

• Calls answered within 45 seconds.
• Case settled, on average, within six minutes.
• Customer satisfaction score of at least 9.0.

Armed with clear understanding of your job, and how your performance can be measured, you can start to pull together a proposal for your manager. Remember: Think about things from his or her perspective, and don’t forget to deal with the company-wide picture.

Here are the broad issues your proposal should cover:

• Your reasons for wanting/needing to telework.
• The benefits for your company, your manager, your co-workers, and your customers. There’s an extensive summary of the pros and cons on our sister site, the TeleworkResearchNetwork.com as well as free downloadable white papers that summarize the bottom line benefits of telework for companies.
• Any challenges or concerns you anticipate from your manager, co-workers, and customers.
• Specific strategies for how you will address or resolve the issues. Be realistic—saying there won’t be any issues is naïve.
• An explanation of why you’re a good candidate for telework (see Chapter 3 of Undress For Success—The Naked Truth About Making Money at Home and take our telework self-assessment/readiness quiz here).
• A time frame for when you would like to start teleworking, how often you want to do it, and how long you would like the arrangement to last. (Proposing a test period offers employers a safety net.)
• Specifics about how and when you propose to have the success of your telework trial measured and under what conditions the arrangement can be terminated prematurely.
• A schedule you plan to keep, and what your manager and co-workers can expect in terms of your availability.
• Details about how and how often you’ll stay in contact with your manager and co-workers.
• A description of your home office—it’s not unreasonable for your employer to want to pay a visit.
• Details about what equipment, software, technologies, and office supplies you’ll need and who you expect to supply them.
• Details about how your home computer will be safeguarded and backed up.
• How you propose to deal with data security and privacy issues.
• A plan for how you will handle technology problems.
• A plan for how you will access company information systems, hard copy files, and internal and external mail.
• If you have small children at home, a plan for how you will keep them from interrupting your work.
• Information about whether you will be available for on-site meetings or an emergency and what notice you’ll need if you’re wanted in the office.
• An understanding about work-related travel expenses. If you expect to be reimbursed for the times you come into the office, be sure to discuss that.
• A discussion of any labor union issues that may apply.
• A checklist for compliance with safety- and/or OSHA-related issues.
• An understanding of who’s responsible for at-home injuries. Some teleworkers have sued their employers for nonwork injuries: A neighbor assaulted one when she opened the front door for him; another claimed injuries she sustained on the way to the lunchroom—her kitchen. Both lost in court, but they add a new worry for telework employers.
• How you intend to comply with company policies, rules, and procedures while teleworking. Federal labor laws apply to home-based staff as well. Believe it or not, even an employee’s after-hours use of a Blackberry can violate federal overtime laws.

While a minority of companies that offer telework have written policies in place to govern the arrangement, we think getting it in writing will reduce conflicts for both you and your boss. Even if your boss is your best friend, who knows what tomorrow will bring—a new boss? New ownership? A formal agreement is your best protection against future unknowns. Sample telework policies, agreements and other documents are available at our sister site, TeleworkResearchNetwork.com.

Other resources:

Sample Telework Proposal to Management

What are your telework prospects - quiz