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Leadership is all about planning and establishing courses of action that contribute to the attainment of desirable outcomes. Despite Winston Churchill displaying great personal courage as Britain’s Prime Minister and Leader during the war, he had a poor planning weakness. Winston Churchill can be linked with various poor planning circumstances. For example, Churchill authorized the invasion of Norway during World War II, which ended in defeat (D’este % Werner, 2009). The poor planning of the invasion by the leader contributed to heavy losses to the British forces. Thus, this poor planning trait by Winston Churchill was one of his weaknesses.