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Convincing your boss is one thing, convincing the orgranization is another. I'm in the gov't space and we have a small shop. We've done testing of teleworking with great success, however, there are other hurdles like HR and Risk Mgmt and the liability of working out of the office and potential worker comp issues. Couple that with the 'old guard' who do not understand today's employee, especially today's IT employee, and don't see value in working from home because it's not what they would do and it's difficult to shift the culture.

I see a lot of value in most of the points and agree that you can be more productive. What has to happen is managing your employees a bit more closely with respect to accomplishing tasks each day and week. When these are met then justifying telework is easy.

States like Arizona have had a very successful teleworking program for more than 10 years. It started with a committment from the top and policies and guidelines were developed to protect the org as well as the employee. Link: http://www.teleworkarizona.com/