Having worked for a company that has a massive B2B platform, I can say we definitely experienced the pain of trying to go against this advice.
When we first launched our shiny new platform, the feedback was amazing. We had a lot of people excited about switching over, so we decided that we would just force the remaining stragglers to switch… (what could go wrong?!) … and yeah that did not go well. All of these tiny little features (which honestly in some cases were worse for our customers) became critical to them.
Since then we got a lot better at it. Every time we would launch one of our products on the new platform, we would keep the old one around in case they wanted to keep using it. Then we would just continue to add more features and continue to refine the new product until it basically became irresistible for our customers. If they wanted those new enhances or time-saving workflows they had to switch. (Scheduling webinars to train the remaining folks was also quite effective.)
Thanks for a great article Marko!