Most technology projects fail on people, not technology. These articles cover change management as the actual hard part of any transformation: getting an organization to work differently, which no software can do for you.
TL;DR Do digital transformation in this order: people, process, technology. People first, always, which means asking what happens to each person. Do they get retrained? Retired? Where do they go?
TL;DR Most digital transformations fail for an unglamorous reason: poor testing. Everyone tests whether the system works normally. Almost nobody tests what happens under real load, or what happens when
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