This report explores the impact of corporate culture and leadership to an organization’s workforce. This analysis involved the case study of Josh Martin, an administrator at the Centre Street Settlement House, and the president of the organization’s for profit construction company. This report takes note of the bureaucratic culture and authoritative leadership and the stifling effects it has on creativity creating employment dissatisfaction especially of the modern liberal workforce. The organization’s motivation strategies, which this report also assesses does not satisfy the important human needs in spite of its fiscal advantages. The report establishes that they are accompanied by increased irrational expectations, which ultimately hamper productivity. In addition, the analysis identifies the top management’s communication as uncivilised and unappreciative of commitment, and able to inspire a negative attitude throughout the work environment. Recommendations include need for participative leadership which is accompanied by democratic culture as a plausible alternative for a more receptive environment.