So I did what any good big sister interested in productivity would do: I offered to set her up with something a little easier to use. Nothing fancy, of course: I was thinking of introducing her to Remember the Milk. I like RTM for a lot of reasons, although I know a lot of other people have their preferences — the fact that I can use plugins to integrate RTM with both Google Calendar and GMail do a lot for my productivity.

My sister’s response? An immediate no. She relies on paper, not some fancy online gizmo. She proceeded to explain that she only goes online every couple of days, mostly to check her Hotmail email account. It was like an arrow straight into my Web 2.0-loving heart. Somehow, I survived and suggested that maybe a new planner — a bigger one — might be in order. I even offered a trip to the bookstore. I was again shot down, with a whole list of counter-arguments: she’d have to transfer everything over, she’s used to this particular planner and this planner was free, whereas a new one would cost money.

I don’t consider myself some sort of productivity evangelizer; I just think that her system could be improved upon, if only to protect her eyesight. It’s her schoolwork: she’s more than welcome to organize it however she wishes. I managed to keep my advice down to a short suggested reading list and making her promise to consider this whole newfangled internet thing.

I did start thinking, though, about other situations where a person can be forced to adopt a productivity system that just flat out doesn’t work for her, and how to maybe work around it. It’s happened to me before, and I certainly didn’t like it. One of my past employers required us cubicle-dwellers to use a custom system based on Excel spreadsheets accessible across the network to track not only our ongoing tasks but our time cards, accomplishments and a host of other information. I was the employee who constantly forgot to update the spreadsheets and had to be reminded where to check for a given piece of information on a regular basis. It wasn’t a case of my not having the necessary data — I had everything my manager wanted at any given time — but I didn’t translate it into the company’s system very well. We finally managed to slip into an arrangement where I used my own methods to track my work and then filled out my spreadsheets once a week or so.

I’ve heard plenty of horror stories about calendars, task lists and other imposed time tracking and productivity systems (a surprising number of them include required use of Outlook, often in ways it wasn’t intended to be used). Most seem to boil down to the fact that a worker views the ‘productivity’ system as creating hours more work than he otherwise might face. A bad time-tracking system can quickly become as much of an aggravation as a payroll screw up.

I’ve heard plenty of work-arounds, as well: there was the guy who wrote himself a little piece of software to translate between his employer’s task management system and his own, the girl who just refused to play along at a system that didn’t work for her and the guy who convinced his manager to change the whole company to suit his needs. There were varying degrees of success — the girl who wouldn’t knuckle under to her task manager wound up in a new workplace very quickly.

It seems like the best most of us can do with an imposed productivity system is to try our best to make it work for us — and often we can’t do much better than pretending to find it useful. My personal experience shows that most people have to find their own way of implementing time management — whether by adapting GTD to their lives or writing their own handbook. It’s a matter of knowing what solution works for your specific situation. Nobody else will face the exact same time management issues that you do, making your personal touch a necessity when implementing some sort of productivity system.

For companies or organizations looking to create some sort of time management system, however, there is still hope. Bringing the people who will be using the system in on its planning can avoid a whole list of common problems: micromanagement interfering with work, requirements for recording minutia into the system taking up time that could be better spent on projects or poorly integrated systems that require time to shift between. Whether you’re tracking productivity, or just trying to make it easier for employees to get their work done, the employees will be the only people able to tell you if your system will help or hurt them.

And my sister? I managed to convince her to try out GMail since we both agreed that her 2cute4words Hotmail address might not impress college admissions offices.