Warhead to Forehead is a collection of essays on matters military and have been curated in two key silos of warfighting and leadership, the warhead defines the paradoxes of modern warfare and their linkages to history. As Carl Sagan once famously put it “You have to know the past to understand the present.” But the past too is complex hence drawing inspiration from Thucydides, Clausewitz and Jomini, an attempt has been made to link the past and the present for a better understanding of future of war and warfare. Clausewitz had famously noted that ‘“War is a human endeavor—a fundamental clash of human will” and hence the forehead section focuses on the challenge of human leadership in the complex battle space of today and tomorrow. Paraphrasing Clausewitz, nature of leadership remains constant but the character of leadership is evolving with time and hence the future leadership should remain rooted to the fact that wars are not won by machines but the men who use them. The aim of the book is not to find answers but to provide questions for military leaders to grapple with. Leadership as a skill cannot be overlooked and managerial jargon cannot usurp the basic mantra; leaders engineer change, managers just manage it. This book is an honest attempt to provide a practitioner’s perspective tempered with academic rigor. The need for each leader to be an autodidact is the key.