Medicine presents a particular problem for creating artificial intelligence (AI), because the issues and tasks involved are surprisingly subjective. Valid and useful AI requires not only reliable, unbiased, and extensive data, but also objective definitions and intentions. Assistance is most needed in day-to-day complex decision-making that requires data synthesis and integration, tasks we now approach with clinical intuition. This process is generally accepted as representing the ‘art’ of medicine despite being riddled with cognitive biases and often based on large information gaps. Resolving the subjectivity of medicine with the objectivity required for digitization—and the secondary creation of AI—first involves resolution of a number of questions: What do we want to do? What do we need to do? What can we do?