Every leader who has lived through a major system replacement carries the same scar: the cutover weekend that turned into a cutover month, the “go-live” that quietly went back to the old system, the migration that technically succeeded while the organization ground to a halt. These failures are why so many organizations keep running systems they know are obsolete. The legacy platform is painful, but it’s a known pain—and the fear of replacement feels worse than the cost of staying.
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