The Harvard Business Review published "Leading Digital Transformation Is Like Urban Planning" - in which they argue that the right analogy for digital transformation is urban planning... See if you agree (emphasis added):
Most companies want?their businesses to keep pace with digital startups, but end up bogged down by the need to?fix the daily challenges that their decades-old IT systems create. How do you redesign and rebuild major infrastructure while keeping the day-to-day work going? This kind of challenge is often referred to as ?repairing the airplane while you?re flying it.? But a?more instructive analogy might be the redesign?of a major city?s?infrastructure.
Specifically, there are three urban planning?strategies, commonly followed by major metropolises, that leaders can use for inspiration in the race to keep up with digital competition. They include building glistening landmarks that anchor their digital strategy (as Dubai has done), removing roadblocks and bottlenecks to improve their underlying speed and agility (Boston), or changing course altogether to construct an entirely new city (Shanghai).