By far the biggest problem recorded by organization attempting to become more agile is the problem of changing the culture from a traditional “waterfall” oriented shop to one focused on an agile approach. This is because, more than anything else, a move to agile represents a different way of thinking about how to be successful with software development projects. More information can be found at:

• What Are The Changes in Culture That Need To Happen with Agile?

As you do more and more of this work, you see a number of anti-patterns / smells / problems that organizations have when trying to change how they work. More information on this can be found at:

• What Kinds of Problems Do you Typically See As The Organization Transforms to Agile / Lean?