Standing on the ledge - Part 3 - Kicking the habit

You can find Part 1 here and Part 2 here.
Two things you must remember about what the Windows world is about. One: Instant gratification. You can do stuff immediately after the install. Or the install itself has been dumbed down to a wizard. Two: Continuous tweaking. Always something new to try or to patch. Something is always changing or being changed. And guess what, you have little control over it (you can if you have the bucks). It is so bad that many people have been conditioned to want change or updates or something new to tweak ever so often. I've had users who moved to the Mac during the heady colored iMac days that asked me "why are they no updates?". I asked them whether something is wrong. The answer is negative. Somehow these users feel that if there are no regular / weekly updates then they must be something wrong. Think about it for a moment. These Windows users are assuming that the computer will always go wrong if not taken care of regularly. Really, they expect that if there no updates, Windows will blow up.
This is the second hardest thing to teach users who are no longer using Windows. Relax, no updates means that everything is ok. Sometimes calm waters are just that, calm waters. Stop focusing on fixing the computer and just use it. Confidently.
What is the most hardest thing to teach to ex-Windows users? It gets worse before it gets better .. and stays that way. This is the opposite of the Instant Gratification thing. No, you won't get everything running in 10 minutes. But yes, once it is up it'll stay up and we don't have to do anything major on it. In fact, as a user, they'll do even less because the model is that there is another person whose job is to take care of everything else. Unfortunately, that could also be you. And users if given the choice between something done in 5 minutes but always require tinkering vs something done in a day and never causing problems anymore will probably opt for the quick fix. The remedy? Make a big fuss about it. Call a meeting to discuss the steps to be taken and the impact on the users etc etc.. If it is a big fuss, users tend to accept that'll it take time. And if you are calling that meeting, why don't you actually do it properly. Who knows, you can even try to implement Change Management.. oooo that's a big word.
In the meeting identify, define and clearly mark the goal. Then plan on how to get from here to there. Make the transition gradual and plan for it to be so. Start with those that make the least impact, computers that offer limited functions or services to users. Then, back-room / supporting services. This is the area where Linux was born and shines. Finally deal with the desktops.
Once users have made the transition and are still a bit sore about the whole change, don't end your plan there. Think of "Now what?" What else can be done to make the experience of having moved better. Find way of making things better the users so that they can see why the journey was made in the first place. Point out open source / linux projects that will help them or that they are interested in. Start with Gimp and move from there.