New technologies like artificial intelligence force us to rethink our prototyping strategies. Although we have access to more and more tools and techniques, building the right prototype at the right time can be hard. While we need to evaluate the viability of new ideas fast, we also need a certain degree of fidelity for a prototype to feel intelligent and real. But was does fidelity mean in this context anyway? Based on my experience developing AI-driven products in healthcare, I will discuss the following questions: How can we build and test prototypes for emerging technologies both effectively and efficiently? How can we foster meaningful conversations about humanlike behavior? How do we answer questions about transparency and the personality of intelligent systems? How can we combine multiple prototypes to tell a coherent story? I will introduce a holistic approach to prototyping, discuss current challenges for UX and IA professionals and show examples of applied prototyping strategies.