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The company I work for is currently in the planning stages of a MOSS to 2010 migration (we have a business critical environment with >500 users to port). With this in mind I was wondering what are some of the less known problems you have found or tricks you know for making this transition go easier?

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I will allow this question, as it is relevant even though it is very broad. All answers will be community wiki –  Anders Rask Feb 7 '12 at 19:52
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What we've done in some cases is to put up a SharePoint 2010 site somewhere (separate from the actual new environment) and put up a survey or discussion board there.

Survey can be pretty much anything, but if you can figure a good survey that is related to MOSS or SP2010, maybe asking "what could be improved in the current environment", etc. Then you just sit and wait for the people to say certain unpleasant things of the current environment and try to turn those around how SP2010 will improve those. Another benefit of that is that people will use SP2010 to fill in that survey.

Regarding discussions, it can be again anything, but can be related to the survey, or some company event. Idea is just to get people into SP2010 and familiarize with it without even realizing it.

You can think of similar things with other SP2010 functionalities.

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Had similar experience. My 5 cents:

  1. Delegation. You need "SharePoint Champions" for each department (i.e. tax, legal). This should be a person who has communication skills, willing to learn and the most important willing to help others and answer their questions. This person must be from this department because he knows the business process inside it. He should be a Proxy between IT staff and end users. This approach will simplify the incoming threshold for business. Users usually don't like changes and don't like to learn especially if its complicated. The Champs will help to solve this have more influence in this situation than IT staff.
  2. You need to "sell" some features of SharePoint. If the straightforward s solution doesn't work - be creative. In my situation people didn't like to use theirs photos in the User Profile. We figure out that some of the are fond of photography. We make a contest for the best personal photo and asked them to do this.
  3. You need to train end users to fulfil the company's document management approach. Otherwise in 2 weeks your documents will be in very messy state.
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Familiarity - make sure you have a plan to give users time to adjust to the new look, behaviour (eg. ribbon) and layout.

Plan training sessions to allow users to translate their existing skills from 2007 to 2010 (e.g. changing list views).

Use SharePoint 2010 functionality to keep the existing visual styles to help manage the changeover.

From a technical standpoint, review and test customisations before the deployment, and check for any content dependencies on customisations too. Even if you don't plan to port a customisation over, how will that effect existing lists?

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In your experience how have you found general user reception to 2010? We've had Office 2007 deployed to everybody for some time so I feel that they'll adopt the ribbon somewhat better then they would otherwise but I can't say for sure –  ElvisLikeBear Feb 6 '12 at 23:53
    
At first users can be wary - it is new and different and they can't do their job as quickly at first. It has a significant change, especially UI-wise, which can make users uncomfortable. Emphasise the similarity with Office, and that it is trying to have a fimiliar feel across services. –  Russell Feb 7 '12 at 1:45
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