Background: I am part of a team that provides volunteer tech support to a local non profit. We are in the position to obtain a grant to update almost all of our computers (many of them 5 to 7 year old machines running XP), provide laptops for users that need them, etc.
We are considering switching our users from PC (WinXP) to Macs. The technical aspects of switching will not be an issue for the team. We are in the process of planning data conversions, machine setup, server changes, etc regardless of whether we switch to Macs or much newer PCs.
About 1/4 of the staff uses or has access to a Mac at home, these users already understand the basics of using the equipment. We have another set of (generally younger) users that are technically savvy and while slightly inconvenienced and slowed for a few days should be able to switch over quickly. Finally, several members of the staff are older and have many issues using there computers today. We think in the long run switching to Macs may provide a better user experience, fewer IT headaches, and more effective use of computers.
The questions we have is what resources and training (webpages, Books, online training materials or online courses) do you recommend that we provide to users to enable the switchover to happen smoothly. Especially, with a focus on providing different levels of training and support to users with different skill levels.
If you have done this in your own organization, what steps were successful, what areas were less successful?
I think you can plan this up the wazoo and it won't work the way you want it to.
You have to tailor the approach to each user. You can talk about benefits (far fewer viruses, lower overall cost over time, machines that don't go out of date quite so fast, etc.) and they won't care. For the most part those things are justification after the fact; they just want to get their work done, and they need to be assured that they will be able to get their work done.
You may need to dedicate plenty of initial time just holding hands while showing them how to get the initial bumps worked over. They won't want training or reference tools unless they absolutely must (granted you may have some people that will use a Dummies guide or any other quick switcher's books available on Amazon or B&N) in a pinch, but really, the ones that will refer to other things for help will probably already know how to use Google or they'll call you up.
You may even need to arrange for remote access to their systems so you can help in a pinch remotely until they're happy.
The best tool is enthusiasm. Sell the idea to a few people who are already somewhat familiar with the Mac and have them evangelize it internally. Let others see how they get their work done with it. Most employees in our organization prefer getting immediate help from a neighbor, if possible, rather than stopping and contacting us, where there's usually a wait involved and they just want to get their tasks completed. Getting a keyboard combo or a "how do I..." from someone at the next desk will make them happier.
You can spend days making mini-movies, providing links, making charts...and you'll still get calls about something you JUST showed them.
In my experience, seeding enthusiasm and positive experiences will go a long long way for gaining acceptance of the new product. Make sure everything they need to do, from special software to favorite websites, works on their Mac. Find out and test that their workflow is uninhibited. Don't do a mass-rollover. A couple people at a time, and address their concerns as soon as possible, because otherwise one bad person in the bunch will quickly spread word about how the evil IT department is making everything ten times harder, and then even a minor glitch is suddenly the end of the world and you'll get the brunt of their complaints about something that should be a minor hiccup.
We haven't converted everyone, but we did make a significant dent in getting Macs into the workplace. I won't get into details here, but many people ended up liking them more, and more people didn't care one way or the other. They just want to watch a movie, or type a letter, or get on YouTube. The platform isn't the key. It's allowing users to get their work done with minimal hassle.
After you get warm fuzzies from positive acceptance, then bring up things like lack of malware and ease of use. These are things that help after the fact. Otherwise, just be there for them, and be prepared to get them into the groove of things. They're going to panic because it doesn't look like it used to or work in quite the same way. Videos, posters and books aren't going to blunt that!
I would start with Apple's "Switch 101" site.
You should also consider talking to a local Apple store if you're located near one, or Apple's Enterprise or Small Business sales group if you're not. The store would probably be happy to have your users come in for a switching seminar & some basic training & the other groups may be able to arrange something if you're buying a lot of gear. Hands-on training is really the best way to adjust your users to the transition.
It's in Apple's interest to have "switchers" be satisfied with the transition and the new platform, and the store staff would probably be familiar with all the usual challenges & have canned explanations that will make sense for most of your users.
To the second part of your question, having made the transition at my current job things went seamlessly. We're an exception however: Everyone was either using Macs at home or had experience with them, so we didn't really have a learning curve to deal with. Stuff that caused us issues was mostly software that has no Mac version (VMWare management software), or that has Mac/PC incompatibilities (Quickbooks, MS Word).
For the most part we purchased new licenses for Mac versions & worked through the occasional glitch/incompatibility, but some people (including me) have VirtualBox on their workstations to run a copy of Windows with mission-critical software that's PC-Only, which has worked out to be a decent compromise.