"How do you know this idea is going to work?" This question tumbles even the most seasoned designers. Businesses are recognizing the importance of design and the competitive advantage that a design-led approach offers. Designers are moving up the corporate ranks and we're now beginning to see titles like "Design Strategist," "Chief Creative Officer" and "Chief Design Officer" take hold within organizations. As designers, the decisions that we are now making carry much more weight and inherently, more risk, to the companies we serve. This presentation proposes 3 questions that designers can ask to identify measurement of success early in the creative processes. It will explore methods to develop measurements that will enable designers to make faster decisions, create better alignment with businesses, and have more courage to push creative boundaries in our work.