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I recently got a requirement to build a list of questionnaire which a DBA should have answer prior to work on any SQL Server Upgrade projcet. Here are few notes

1. What is the requirement for upgrade?
2. What are current bottlenecks?
3. What are expectations from upgrade?
4. Know Infrastructure environment
5. Know the application environment
6. Expected downtime which is acceptable to business during upgrade?
7. Is this In-place upgrade or new Hardware will be used for upgrade?
8. Know the SQL Server Inventory which includes
   1. Windows environment where SQL Server is hosted
   2. Hardware
   3. Software Inventory should cover all SQL Components like
      1. Database Engine Components
      2. Analysis Services
      3. Reporting Services etc

For Example, here are few points which should be considered for Database Engine Inventory

1. Database information
2. Security Information, Authentication mechanism, Security Policies etc
3. All other components and dependencies
   1. iv.      Service Broker etc
   2. v.      SOAP
   3. vi.      Linked Servers
   4. vii.      MSDTC
   5. viii.      DTS
   6. DR / High availability strategy which are currently deployed
      1. ix.      Clustering
      2. x.      Replication
      3. xi.      Mirroring
      4. xii.      Log shipping
      5. xiii.      Snapshots
      6. xiv.      SAN replication etc
   7. SQL Server Utilization / Load
   8. Scheduled Tasks
   9. Administrative Contacts etc..