Given the popularity of the cloud, CIO wanted to build a business case/RFP for migrating all of the IT portfolio to the cloud. They called for a few month consulting engagement where we would do initial data collection, build business case for migration to cloud based on IT cost estimates and prepare and RFP for large GSIs/vendors to execute the migration over a multi-year period.

Was called in to specifically collect all the IT/cost data based on existing applications & infrastructure so that we can build a TCO and business case. Seeing the portfolio data and technical debt, it was obvious to me that there is no business case here and the cost of migration would be very high.

So, turned around after few days and proposed that we scrap the program and re-purpose the consulting money towards modernizing one or two key applications and build that business excitement instead of building a fake business case and waiting for board approvals to do anything. So, we ended up modernizing/using cloud/new architecture to dramatically change 2 applications improving the stability and end-consumer perception of the business.

Based on the initial success of the applications, customer changed directions to a more agile, modernize applications as part of regular projects than a big-boil-the-ocean outsourcing program. They are 2 years into the initiative now, and ~40% of the applications now use the cloud in a modern way and almost all of their development/testing efforts use the cloud enabling them to be really agile.