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Expecting project teams to resolve issues and challenges without any education is wishful thinking. Establishing effective project management training programs is one of the greatest challenges facing training directors because project management involves numerous complex and interrelated skills. In the early days of project management, project managers learned from their own mistakes rather than from the experiences of others. This chapter discusses the importance of determining the right balance between quantitative skills and behavioral skills. Project management skills based on trust, teamwork, cooperation, and communication can solve the worst problems. Selecting the people to be trained is critical. Executive-level education in project management can significantly improve working relationships with customers and resolve issues in a manner that satisfies all parties. The growth in computer technology helped expand project management applications to almost all industries. The chapter presents detailed case studies drawn from diverse industries and global organizations that provide a breadth of practical insights.