I look at the organisation and its impact on your systems - remember that systems are not just what you build or have built for you, it's also the people. Conway's Law and continuous learning can help us make sense of digital transformation.
Understand that your business needs are met not as a whole, but by individuals and departments. Those individuals and departments shape the systems they use - they create them all the time. Your IT systems and your IT systems change process had better recognise this.
I quote Melvin Conway: "Any organization that designs a system (defined broadly) will produce a design whose structure is a copy of the organization's communication structure."
"the most important thing you can do before taking on a new software or IT project as an organisation is to zoom out" RB