The article which I posted above was a knee-jerk reaction by the reporter to a memo circulating out of the mayor's office. Now, months later, it seems like the reporter got everything right. The mayor has become extremely adamant about this, and demanded that the switch be finalized before the end of the year. I happened to talk about this incident last night with a high-ranking IT official with the city of Seattle, who shall remain nameless. I'll refer to him as F (not his real initial), and all you need to know about this man is that he is in a position to know the truth.
First, F says that the primary impetus behind the mayor's desire to switch from Groupwise to Exchange was mostly one of convenience. Mayor Nickels probably had a friend at some other city tell him how Exchange eliminated some minor inconvenience somewhere (which may or may not have been true), and Nickels jumped on it like a dog on a mailman. It goes without saying that the mayor doesn't know enough about IT to know the difference between one email system and another. It also goes without saying that the mayor doesn't realize how big a job the switch is.
Another thing F pointed out is that the mayor is up for re-election next year. Whether that means he's got some secret deal with Microsoft, we'll never know. But F believes that the mayor is interested in some sort of personal legacy - something he can point to as a technological progress he alone was responsible for. Which is probably why the mayor is taking a particular interest in the email project - normally, the mayor would have better things to do.
F also mentioned that one of the problems with the whole affair is that is has way too much to do with Seattle's relationship with Microsoft. Apparently (I didn't press for details), Seattle has done Microsoft favors in the past, and Microsoft has implied that it would repay the favors. This kind of mutual back-scratching goes on in municipal government all the time, and is nothing new. But when the city went to Microsoft and asked whether some sort of discount or deal could be worked out, Microsoft refused. Which made the city IT department so angry that they tried to kill the whole project. At that point the mayor stepped in and told the IT department to basically "get it done or find a new job".
So the switch from Groupwise to Exchange is going to happen, and the initial planning stages have already begun. The mayor has insisted that it be done before the end of 2009, which will be just in time for February special elections. Believe it or not, having a year to complete the project might not be enough time. The amount of interim hardware that has to be put into place in order to ensure that email service is uninterrupted during the switch is staggering, and the amount of extra security that will have to be built in is also monumental. Because of the way Seattle is set up, it's not just municipal employees either - Seattle owns its own water, electrical, and garbage utilities, so the replacement of servers and the seamless introduction of new email software extends all the way to dams in British Columbia and windfarms in Oregon. Not to mention the extra support that a major change like this involves.
Because of how complex the situation is, F says it's going to cost a lot more than anyone ever imagined. But the project department has built in a number of what project managers call "kill points". These are specified intervals at which the project is reevaluated to a certain scope/cost/schedule standard. For example, they may identify ahead of time that if costs exceed $10 million by March 1, it is time to abandon the project and cut losses. Since the city had an IT project about 5 years ago that exceeded $100 million before it was finally scrapped, this sort of kill point evaluation will be taken quite seriously. The mayor won't be happy, but he can't fight that kind of fail.
In regards to the future of Groupwise, F calls that a self-fulfilling prophecy. If someone gets nervous about future support and ditches, it makes worrying about future support more realistic, and a lot more companies will ditch. Eventually, because so many customers have ditched, Groupwise will actually curtail support for the product, forcing the original prophecy to become true.
Back to the original discussion trend of the thread, there's not any obvious evidence that there is some kind of conspiracy between Seattle and Microsoft. It is pretty clear that Microsoft's actions have complicated the issue, though, but that shouldn't be a surprise to anyone here.