This research aims to support sustainability practitioners at the beginning of a change initiative towards sustainability to increase the success of the change. Moving towards sustainability is a complex journey and requires radical and structural transformational change in companies. Mutual understanding of the company and the practitioner is required to design a suitable change process. Existing tools related to sustainability, change management, corporate analysis and assessment were analyzed. In addition, practitioners in organizational change and sustainability were interviewed. Identified were eight Areas of Inquiry for the practitioner to focus on at the initial stage of an engagement: Vision; Purpose and Commitment; Urgency, Importance and Business Case; Level of Integration of Sustainability; Business Goals and Strategy; Culture and Capacities; Communication and Stakeholder Engagement; Measurement and Reporting. These areas form a platform for dialogue to guide sustainability practitioners in gaining understanding of the organizational change capacities and sustainability within the company and, in doing so, contributes to addressing the sustainability challenge at large.