Matt and Bill join Paul for a conversation about a counterintuitive question at the heart of how we work with AI: does giving AI more information and instructions actually make it better? They begin with standard operating procedures, or SOPs, and the tension between consistency and autonomy. They explore why SOPs and checklists can be essential in environments like aviation, healthcare, and the military, while also considering whether applying the same thinking to AI could unnecessarily constrain what these systems are capable of finding. The conversation then turns to what Paul calls the “flip” side of design fixation: not only can AI influence the way humans think, but the context humans give AI can constrain its thinking as well. Through examples involving chess, StarCraft, and AI-assisted debugging, they explore what happens when AI is given an outcome rather than a prescribed process, and whether removing context can sometimes lead to better or more unexpected solutions. Paul, Matt, and Bill also dig into AI and creativity, questioning what it actually means for AI to be creative when human creativity itself is shaped by conventions, trends, biases, and limitations. They explore experiments with Suno, the difference between highly prescriptive and minimal prompts, and why giving AI only a few words can sometimes produce something more compelling than a carefully engineered set of instructions. The conversation examines the role of imperfection in human creativity through examples from music, including John Bonham and Wichita Lineman. They consider whether the imperfections, mistakes, and unexpected decisions that make human-created work memorable might be precisely what AI struggles to reproduce, while also asking whether AI could eventually create something genuinely remarkable by being given enough freedom to surprise us. They ultimately return to the question of when humans should constrain AI and when they should deliberately step back. Paul challenges the assumption that more context always produces better results and proposes an experiment: give AI the same outcome twice, once with minimal information and once with everything available, and see what emerges. The episode ultimately asks whether the future of working with AI may depend as much on knowing what not to tell it as knowing what to tell it. Resources Mentioned: The Dot and the Swarm by Ethan Mollick Article: Read here! The Checklist Manifesto: How to Get Things Right by Atul Gawande Amazon: Get the book here! Team of Teams: New Rules of Engagement for a Complex World by General Stanley McChrystal, Tantum Collins, David Silverman, and Chris Fussell Amazon: Get the book here! Humanity Working is a podcast focused on helping individuals, teams and organizations be ready for the future of work by maximizing their human potential. For more information, and access to our weekly newsletter, visit us at humanityworking.net.