Abstract: An enquiry engine for systematically developing business questions for an organization is provided. The engine includes a problem definition module to analyze at least one business problem and develop a plurality of hypothesis based on a current state, a desired state and one or more business gaps between the current and desired states, a business transformation module to determine outcomes for the business problem, a complexity representation module to represent organizational complexity and interconnections between problem areas, a progress monitoring module to monitor progress of solutions implemented by different types of stakeholders to achieve the desired state, and a questions design module to integrate information from the problem definition module, the business transformation module, the complexity representation module, and the progress monitoring module to systematically develop one or more business questions corresponding to the business problem.