As mentioned iteration is often a good way to work through circularities. In educational technology for instance, hardware, training and management must be tackled in a seemingly simultaneous manner. In real life, this tends to be impossible. There are good reasons why any one of the three items should come first. The reality is if any one item gets too far ahead of the other two, there are problems. Training, management and hardware don't have to progress at identical rates, but as soon as one gets too far out of sync with the others, people notice limitations. The answer is to keep cycling from one component to another.
For some time, management needs to be seen as the solution. Some time later, hardware, then training, etc. The difficulty is this shifting tends to burn out people in organizations. Human resources are generally designed to implement static solutions. They can handle cycling, but the frequency has to be carefully managed. The general way to handle this is to put some sensors into the process that light up as soon as people start sensing limitations. However such feedback loops are easier said than implemented. In fact, they tend to grow to require what John Ralston Saul calls heroic leadership.
A good philosophical base from which to approach circularity issues is Charles Sanders Peirce. Clark has a very good philosophy / religious blog based around his ideas. As a pragmatist contemporary with Dewey and William James his ideas fit well with education. Dewey has been popular with the education crowd for a number of decades, but since the rise of post-modernism, I think Peirce's perspectives are much more timely.