Digital transformation and agile are all the rage these days. However, for companies that have existing businesses and services, every change is hard and in some cases (mine) really hard. I wrote this article primarily for self-reflection and to remind myself what challenges we have to face with change. Eight years back, I was involved in a large transformation initiative for a large bank (institutional securities trading) that was meant to resolve the fragmented business and system landscape that the company had acquired through purchases of broker/dealers over the years. The idea was simple: create new systems with a uniform messaging and business logic layer so that it’s possible to normalize the data with the goal to retire the legacy processing platforms. I have taken away several key themes from that undertaking: People Your initiative is D.O.A. if you’re not capable to bring the people on board. I’ve seen this play out in many scenarios but all ended badly if you do not have the...