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To produce better information systems, products, and services, we need a deeper understanding of how and why prototyping practices affect design results. My research empirically examines the creative process and design outcomes. I will describe experiments on iteration and comparison, two key principles for discovering contextual design variables and their interrelationships. We found that, even under tight time constraints when the common intuition is to stop iterating and start refining, iterative prototyping helps designers learn. Our results also indicate that creating and receiving feedback on multiple prototypes in parallel—as opposed to serially—leads to more divergent ideation, more explicit comparison, less investment in a single concept, and better overall design performance. Moreover, we found that groups who produce and share multiple prototypes report a greater increase in rapport, exchange more verbal information, share more features, and reach a better consensus.