Two ideas to help your company move to the cloud
1. Portfolio Assessment
2. Application Assessment and TOC Analysis
The idea: classify your portfolio of applications into three categories based on migration effort.
Category 1: Small Effort
It mostly just requires re-packaging for Azure—a fairly straight forward migration.
Examples: ASP.NET Apps, WCF Services, Web Services, Simple SQL Server deployments, etc.
Category 2: Medium Effort
Fairly easy but requires some to moderate code changes.
Examples: moderate use of file system, dependency on SQL features such as SSIS, SSRS, etc.
Category 3: Large Effort
Probably would require a re-write anyway. Installed as Administrator, uses unmanaged code; extensive use of registry, etc.
Examples: Legacy ASP, C++ app, extensive use of file system and registry.
Once the applications are classified, then applications from category 1 and 2 can be further analyzed and eventually migrated. The cost of moving a category 1 application will usually fall within a small range of effort. Category 2 apps will need to be estimated on a case-by-case basis.
To analyze a portfolio of applications, you need a simple set of assessment questions to handle the higher volume.
Application (or System) Assessment
The idea: use a much deeper set of questions and total cost of ownership analysis. It will help you understand the effort involved in the migration. A TOC analysis can help you understand the amount of money that you will save for a particular application—usually over a 3-5 year period. It can be significant. It is difficult to compete with the economies of scale that cloud providers such as Microsoft can provider, because Microsoft is buying 1 out of 4 servers in the US and 1 out of 3 in the world.
Best of luck azure getting into the cloud and let me know if I can help make recommendation.
Ultimately, you will need to get your feet wet by doing an application assessment and migration.