When organic students are asked to design a total synthesis of a molecule, they are often overwhelmed by the multitude of possible transformations. A decision tree is a useful tool to break complex problems up into simpler steps and scaffold the thinking process that many seasoned chemists take for granted. While many comprehensive resources present the logic and reaction strategies of retrosynthetic analysis, students still require scaffolded training in analyzing the functional group patterns of a molecule to arrive at the most prudent reaction. This work presents a 1-page flowchart that is readily implemented by undergraduates, organizes content, and ultimately helps students gain an appreciation for the more systematic aspects of retrosynthesis and organic synthesis more broadly.