Whiteboards, while invaluable for initial brainstorming and collaborative ideation, fall short as a tool for documenting complex, evolving distributed systems due to their static nature and lack of context. As systems change, whiteboards quickly become obsolete and require constant manual updates, leading to inaccuracies and misunderstandings. Instead of relying on whiteboards, engineering teams should consider leveraging tools like Multiplayer that automatically generate and update system visualizations using telemetry data, thus providing real-time insights into system architecture without the need for manual maintenance. This approach retains the creative value of whiteboarding sessions for ideation while addressing the need for accurate, dynamic documentation in modern software development environments.