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I think that we (cloud users) are all experiencing a similar challenge.
On our Jive-N community, which was upgraded last weekend, similar to your scenario, I had several hard-coded URLs to “ask a question” for specific spaces that I had to update with the new question URL. I had to schedule time in the middle of the night to make these updates while we had minimal users in the system. I don’t have a good answer besides setting aside a lot of time the weekend of the upgrade (or when you plan to enable a given feature).
The other thing we do is that we communicate to our users a longer window of when the system will be down (i.e. through Sunday) and include a disclaimer that although the overall community may be available, some functionality may be impaired while we configure the final stages of the upgrade. So they know that between Friday and Sunday things will not be optimal, even if they can get into the system.
We put this notice in the header so that it is visible to anyone no matter where they are in the Community.
It’s not ideal, but it has minimized calls to our helpdesk during that timeframe. We still encourage anyone to post issues to a particular space, just in case it is truly an issue, but in most cases our response back to them is that their issue was specifically related to an in-progress configuration.
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I'll roll up some resources and suggestions I've heard from other customers. And will you be at JiveWorld in March by chance?
- As part of your subscription you have access to a shared Cloud preview where you can view and test out all coming features in advance - just wanted to make sure you're aware of that and following updates in Customer Hub so you don't have to wait until they are in your own environment to test out. That's also a good place to provide feedback! The release schedule is: @Jive Release Schedule
- We also now offer the option of a (paid) private Preview instance for some of our customers who want to do extensive testing or have a dev environment - more info here: The Best Way to Test Our New Features in Cloud Releases and Cloud Private Preview & Cloud Public Preview comparison
- Within your live site many customers will set up one or more private or secret "test" places to test out place-specific features or preview those to certain stakeholders and advocates, although I think your question is more about global features. For global features the best best is probably the private preview or the weekend as Kara suggested.
- I also know Kim England has thought a lot about this in her organization - and blogged about aspects Four months in the Cloud, what is it really like transitioning to Activity + Pages? - and will be speaking on related topics at JiveWorld.
I hope that helps and please come back and share updates and lessons learned as you go forward!