The art of asking open-ended questions, has always found a place in the world that has evolved thus far, notwithstanding the complexities, frailties and diversities of what human species, have confronted. From time immemorial, all forms of transformations and progress can be traced to a variety of educational inputs, cultural practices, economic impetus, political pressures and societal changes. Brainstorming, thinking out of the box, perspective generation and innovative pursuits invariably emanate out of deep reflections, prompted by stimulating questions, that goads travel beyond the current standards of excellence. Given the context of human evolution, corporate world bears no exception. Pioneering alternatives and new found strategies to combat rapidly changing business scenarios are handled better, when managers and leaders are skillful in asking open-ended questions, to themselves and those whom they lead. This process unleashes abundant responses, ideas and answers, which reside within individuals and teams and also enables commitments and resolutions to be owned and anchored by individuals and teams.