Our first we tried to push and she had the most problems making the complete transition. The next three we would just keep asking when they're ready and they eventually would just tell us they were ready.
Once they were at that point we had very few issues with a complete conversion. And usually we were surprised, with a couple of them it seemed they would be comfortable going to college in diapers. But one day we would ask and all the sudden it all fell into place. Maybe we were just lucky but it worked great for us.