One of the biggest hurdles in getting to Continuous Delivery and truly being Agile does not lie within the development team itself. Change requires a mindset that all people (managers and executives too) must adopt. Just as it takes a village to raise a child, it also takes a (corporate) village to raise a new culture. The movement away from Waterfall to Agile and Continuous cannot be handled just by one person.
Does the following situation sound familiar? Someone asks you for an estimate for the Level of Effort (LOE) of a feature. Not just a t-shirt size, but in days — something to be delivered sometime that year. You don’t have much time to really dive into it (it could even be during the same meeting that you first hear about the new feature), but you have to know all the details up front. So you give a number that you aren’t supposed to be held to because of all sorts of caveats you listed. But, someone remembers that number. And since someone said you are Agile (and Continuous Delivery), now you have to not only meet that estimate you gave up front, you are now tied to an Agile sprint with no room for error. This goes against everything you say you are!