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Jesse -- we upgraded just before I came on board as ECM, but what my predecessor did was create a new "help" space with all new documentation. Once we had upgraded, she then made that space live and removed all permissions from the "old" help space so us admins can always see the information / move it back when applicable, but users won't find the information and get confused about what's what.
There have been a handful of questions that require that I go into our "old" space and move over the documentation, but for the most part everything has worked out quite well. (I should note that I wasn't the one who had to rewrite any of the documentation, though -- obviously that takes a lot of time and needs to be a consideration in your upgrade strategy.)
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We started on version 4.0 & are about to upgrade to 6.0. After asking our advocates & power users we decided not to delete the old historical information. We didn't really want it in search for most people, but we wanted to be able to look back at old issues/questions we had faced. In the end we made a secret group to archive everything in it. Any advocate / power-user was free to ask to be a part of it since we publically discussed the decision to archive. Each member of the archive group is an owner too in case they want to move something back to the main Help area again.
We started with 5.0 and then upgraded to our current version 6.01. Our 5.0 training included documents and videos that Jive provided as part of the training package. As questions were raised that Jive's training didn't address, I would create something to cover it. I wasn't always great at keeping the information organized so I had some redundancy depending on the spin that the question and my response had.
When we planned our upgrade to 6.01, I decided to take the opportunity to clean/organize our existing training and provide a common look and feel, plus consistent naming and tagging conventions for all of them and screenshots. I know, I "should" have started out that way - oh well, "shoulda, coulda, woulda"
I went through all of them (about 150) and captured the number of bookmarks, comments and views that they had. I wanted to understand how disruptive it would be to just pull them out and the possible impact on user points. I finally decided that too many people probably referenced them in their own pages or were using them for their own training so I created a matrix cross-reference that had the "old" training document name listed with a link and the "new" training document listed with a link. In cases where the feature was no longer available, or it was a new feature, I added a line and commented on that as well. I left the old training documents, the matrix and the new ones up for about 2 months with a blog post in our training site that explained what I did and when I planned on moving the documents offline, to give people some idea of how long they had to update their own information.
I still have the documents in a private space, mostly because my memory isn't what it used to be and if something comes up, I want to be able to refer back to them. I probably eventually get rid of them.
As far as the discussions go, I left those up and probably will for the next version as well. Even though the feature might have changed and the discussion is no longer relevant, I like the type of activity they represent.
I don't know what individual community members did with the documents they might have created for their own teams.