The 21st century has been termed as an era of uncertainty by leaders like Joseph Ackermann, Carlos Ghosn and Ellen Kullman who once led some of the most vibrant and largest organizations of the world like Deutsche Bank, Nissan and DuPont. And in this new age of globalization, hyper-connectivity, evolving demography and innovative technology leaders are facing challenges which are more complex and dynamic than ever before. The terrorist attacks on September 11, 2001 brought about a new challenge for the world, the threats of terrorism. It has one of the greatest implications for the militaries and security industry, and the people leading and managing them in this century. The global war on terror shifted the focus and scope of the states towards fighting terrorist groups which created strategic and tactical challenges for the governments . For functioning efficiently and effectively leaders and managers who are fighting these wars require to have new skills in this volatile environment. The real-time problem-solving and quick decision-making ability in a crisis situation are must have qualities for leaders, both in the unpredictable war zones and globalized economic market of this century. To substantially influence the followers to execute any plan, to coordinate the actions within the organization, to provoke the subordinates to take risks and to persuade the superiors to support their policies and agendas, the required leadership and management skills and qualities are not always available among the leaders. However with right attitudes, training and education these attributes, which are essential in this knowledge driven market, can be achieved by those who are not natural leaders. Leading and managing multi-national forces which have become common since the first gulf war requires strong communication and motivational ability to encourage the troops to enhance their performance and successfully realize the objectives . The coalition forces fighting in Iraq, Afghanistan, Syria and other places as UN peacekeepers are comprised of not only armies from various countries but also private military contractors and security companies. To manage such a huge group a leader needs patience, dedication and passion . Leaders need to have sound knowledge about the changing nature of the battlefields, the advanced technologies and the newer threats which have direct implications for the entire force. The leadership style and personality of a military commander have huge impact on the followers. So one has to develop and adapt their leadership approaches to implement a command effectively. The military commanders usually follow the servant leadership style which is based on following the top-level order, dedication to the nation and sense of service to the community. What differentiates such commanders from skillful leaders is the willful following of command in the harshest environment by the soldiers. To have such dedication of the subordinates, leaders in the 21st century need to have transactional and transformational leadership qualities too. These qualities would help them to adapt to the requirements of the situation and thrive for an outcome that is mutually satisfying . Leaders will have to empower the followers mentally and keep their moral high in the bewildering situations of the war field. To manage a group and have the desired result out of them, a leader need to inspire the subordinates about comradeship and bond, hold them accountable, take responsibilities and portray a character that is full of vigor, knowledge and intellect . Thus a leader can earn the trust and respect of the soldiers which can be further strengthened by engaging and working with them side by side, sharing their burden, showing empathy, and instilling a sense of value and pride among them. To effectively manage and lead the growing, dynamic and innovative security industry of 21st century, the leaders and managers face the challenge of technological revolution, and the outpouring of information and knowledge in the field of security. Leader will have to be conversant about the updates, intentions and strategies of the competitors in this field and critically formulate policies, principles operational plans and set objectives that will keep their organizations leading in the market. Leaders are expected to be competent and capable having persistence and determination to lead the company in the right direction, to design and plan appropriate measures, intervening with intelligence when problems arise. Be it in the battlefield or the planning table, leaders need to have insights and awareness for evading for troubles. A smart leader will be a good listener of the suggestions and complains from the subordinates. Leaders will have to take necessary steps to avoid any internal feud within the organization and among the subordinates and manage any volatile situation by prudent and careful judgment pacifying all the parties leaving no chance for future repercussion . Discipline is mandatory for any organization and the troops which is often violated. According to Hunt & Philips (1996), to subdue any such situation and to set an example for other possible miscreants, leaders often will have to strict and implement severe punishments. And at the same time, a good leader will reward any success, welcome any achievement and congratulate any accomplishment. People in this era thrive for freedom and personal liberty. So leaders would have to take calculated steps while exercising power and never misuse it being tyrannical . For managing the large coalition armies smoothly, leaders need to be culturally tolerant, learn to accept the differences, act above any ego and prejudice, and show complete impartial behavior. And in these scenarios leaders need to have the power to have preponderant influence on the actions of the soldiers who are from different regions having different mindset . For managing the social and economic structure within the diverse security industry and also the military, coordination and participation are required . Leaders, in the inconvenient environment of the 21st century, through coordinated actions with knowledge based intelligence and managerial skills, will have to minimize the diversity and bring out the maximum potential to reach the desired goals.