The concept of feasibility is a central, but often underappreciated, part of the planning processes and resulting senior leader dialogues that allow civil and military leaders to make difficult choices. Identification of flexible military options demands that political, strategic and operational echelons coordinate to maintain the means-ways-ends balance. Discussions and synchronization of means allows military leaders to know what is within the realm of the possible and enables a discussion of ways with civilian leadership. The narrative of this paper seeks to explain some of the more salient points that allow senior leaders to accomplish good feasibility assessments. The selected historic examples illuminate where many of these points either aligned to provide the civilian-military leadership team with the flexibility to meet the final desired end state, or where non-adherence to feasibility assessments resulted in a less savory end.