Do you know if your on-premise and ASP hosted applications are good candidates to migrate to cloud hosting services?
It's probably one of your first questions...whether your business has five applications in a single application portfolio or five thousand applications across a few hundred application portfolios.
Which cloud hosting pattern (IaaS, PaaS, SaaS) would that an on-premise application use if it were migrated to cloud?
Which applications should be replaced with the supplier's SaaS offering (and when will that be ready)?
Of the most costly, value generating, and/or business differentiating applications, which ones could be redesigned to incorporate the cloud-native capabilities (and cost benefits) of multi-tenancy and/or elasticity?
Will a Lift-and-Shift of an application onto cloud IaaS services result in significantly lower hosting costs...or are there other benefits that could justify the migration effort?
These are the kinds of questions you should be able to answer and formulate into a viable strategy before attempting to implement any major cloud transformation effort.