Top 10 technical questions you should be asking before upgrading your customer to SharePoint 2010

Before doing anything else i mean upgrade, you need to ask your customer a few simple questions just to make sure you understand the situation (customer installed WSS 3.0 alone) so that you can make the right assessment. Please note: these are just general questions, in a full-scoped project you need to ask many more…

Questions

• 1) Have you installed Windows SharePoint Services 3.0 Service Pack 2?
  If you are not sure go to Central Admin > Operations > Services and SharePoint Version will be displayed.
  • Why am I asking this question? You can only upgrade to SharePoint 2010 (any edition) if you have installed Windows SharePoint Services 3.0 / SharePoint 2007 Service Pack 2. You customer might not have this information so you will probably get only version number (e.g. 12.0.0.6219). You can „convert“ the version to actual service pack via this table.
• 2) Are you planning to do in-place upgrade or there is another (new) server ready for SharePoint 2010?
  (in this case we are not doing Core Infrastructure so there will be different company installing OS)
  • Why am I asking this question? In case customer is planning to do in-place upgrade you need to make sure operating system is supported and bunch of other things like downtime, some other system that might be problem etc…
• 3) Are you aware of SharePoint 2010 operating system requirements? You need Windows 2008, 64bit architecture and 8GB of RAM.
  • Why am I asking this question? Customers and other non-SharePoint Microsoft partners do not know about SharePoint requirements and they do not care. That’s okey! You need to double check these 3 things: Windows 2008, 64bit architecture and RAM amount! You can check the full list of SharePoint 2010 requirements here. Depending on company size they might need more than one server, check TechNet for more details…
• 4) Can you install Windows 2008 R2?
  • Why am I asking this question? Although both Release1 (Windows 2008) and Release2 (Windows 2008 R2) are from same product family, R2 comes with number of improvements and it is much easier to install and maintain SharePoint installation on top of R2. If possible ask customer/partner to install R2. People are not always aware that R2 exists. In case you will be using Windows 2008 make sure it is fully patched.
• 5) Did you install any 3rd party solutions, or some custom code?
  • Why am I asking this question? Well, if you are not doing in-place upgrade you will have to install these again and you need to make sure you have proper WSP packages to install.
• 6) Did you use any of the Fabulous 40 templates?
  • Why am I asking this question? When upgrading these templates you also need to make sure these are installed. AFAIK there are no Fab40 version for 2010 at this time, and some of these might not work. I already had problems with Bug Tracking template, and chances are some other templates might not work correctly at this time…
• 7) Do you use any non-English language packs?
  • Why am I asking this question? Well Microsoft didn’t release all the language packs for SharePoint 2010 at this time (e.g. Croatian language pack is still not available, and probably a number of “smaller language” packs are yet to be released). Make sure you have all the language packs you need.
• 8 )  Are you using SQL Server or Windows Internal Database as backend?
  • Why am I asking this question? SharePoint 2010 now ships with SQL Express 2008(?) as default database (embedded) backend. SQL 2008 Express has 4GB per database limit, SQL Express 2008 R2 has 10GB per database limit while Windows Internal database (shipped as embedded with SharePoint 2007) didn’t have this limit. Your customer might have e.g. 100GB of data in a Windows internal database and you will not be able to upgrade database this big to SQL 2008/2010 Express.
• 9) Can we use SQL Server?
  • Why am I asking this question? I always prefer to install on top of full-blown SQL (Check previous question too). Express is nice but some management tools like Maintenance plans, backup scheduling and some other stuff are only available in full SQL so always install on top of SQL if possible. If you plan to use SQL Server 2005 or SQL Server 2008 (not R1) make sure it is fully patched before installing.
• 10) Do you have SharePoint licenses?
  • Why am I asking this question? You need to double check this! They might say they have but then they cannot find the proper key. Make sure they have the key ready before you start installing… You should also always use their image, not the one available on the Microsoft download site. Some Microsoft keys like VLK (Volume Licensing Keys) for some products cannot be activated on top of incompatible images. Always use keys provided by your customer and their installation images!

I hope this will help you run your upgrade engagement. For full list of SharePoint 2010 upgrade resources check this post by Joel.