"Wow! I wish I'd written that question..." Many instructors struggle to write Peer Instruction questions that can drive the intellectually engaging discussions necessary to fully develop learners' discipline fluency. Does your question bank contain the questions you need? How would you go about evaluating this and even if you did, how would you know what you're missing? We present a framework for uncovering the variety in the discipline representations, intellectual tasks, and difficulty levels employed in hundreds of multiple-choice questions produced by faculty in our workshops over the years. We then exploit this framework to generate new questions using underutilized representations and tasks. Through this work, we illustrate a process for creating fluency-inspiring questions. Learning environments that make use of fluency-inspiring questions afford learners more robust opportunities to unpack complex concepts, practice critical discernment, and develop discipline fluency.