[johncessna]

The argument I always got while trying to argue against delaying features for large customers was that it causes a training headache. If you have large enough customers, redesigning a UI triggers a training initiative for the 100s, if not 1000s of customers that use your software.

[cweagans]

That's a fair concern. There are other ways to address it though. For instance, release the new UI as a "preview" that users can switch to if they want to. If they hate it or can't understand it, they can switch back. Even better: redesign the UI in smaller parts and roll it out slowly over time.