In their 1973 essay Dilemmas in general theory of Planning-Rittell and Webber distinguished between “tame” and “wicked” issues i.e. between issues for which a known methodology to tackle exists and those whose complexity or newness means the solutions have yet to be devised. Addressing the former (tame) while they may be complicated requires administration of known management procedures and addressing the later (wicked) requires innovation new ideas and courage to take people in unknown direction in other words- Leadership. The scale and standard of skill challenges faced by India are unprecedented. No one can claim to know the proven management techniques will deliver skilled India; getting their will involve entirely new solutions and approaches that draw on but not replicate what happened elsewhere in the world. Skilling India is without doubt a “wicked issue” one that needs diverse leadership to deal with it. Leadership means compelling vision for people of India. A vision of a country that offer all its citizen whatever their talent, interest and aptitudes a route towards fulfilling career, stable and dignified livelihood. A vision of a country that recognises learning achievements. A vision well articulated by Swami Vivekanand “ Pleasure is not the goal of a man but learning and knowledge as pleasure and happiness come to an end but learning and knowledge builds karmayog and character.”