How to Propose Telecommuting to Your Boss

Earlier I wrote wondering why there is such a dearth of telecommuting jobs in IT. A recent search on Dice resulted in only about 600 telecommuting jobs. There’s a robust infrastructure available that could enable us to work remotely, so I keep wondering, why can’t more of us do it?

Over the last decade, we’ve watched the industry mature from PCAnywhere to Citrix Remote Desktop to Xen and AnyConnect. Like a lot of change, it’s come at a pace faster than workplace and social norms accept.

I think it would be hard for a company to hire someone cold to telecommute for two reasons: First, next to no one is doing it. Second, new employees are such a wild cards, you want to see them working on a regular basis.

Yet workers world-wide are ready for telecommuting. Many don’t even need their desktop to work effectively. A Cisco survey found “most employees don’t believe they need to be in the office to be productive and reported on their ability to access corporate information remotely.”

If you’re looking to telecommute, your best bet is to propose it at your current job. That way the change comes from within. Prove the concept to yourself and your supervisor first. Bill Jensen and Josh Klein, who wrote Hacking Work: Breaking Stupid Rules for Smart Rules propose introducing the concept by doing it on the weekends. They tell of one employee who did just that.

Rather than ask for it up front, he started taking on projects which would occasionally require weekend work, which he did from home. He documented every success, and after a few months presented his case to his boss by highlighting how effective he was. He was awarded two days per week of telecommuting because he already proved that it could work.

Two days a week might be just right.  Any more than that and people forget about you. You may be a productive, model employee, but you also may just be forgotten and a less productive employee who laughs at the boss’s jokes might move up the ladder quicker.

— Dino Londis