The redesign of the Gatsby CLI was initiated to enhance user experience, as it serves as the main interface for interacting with Gatsby. Through usability tests, it was discovered that the current error messages often lack clarity and sometimes do not comply with best practices, prompting a need for improvements. By evaluating other CLI tools and style guides, the team identified several areas for enhancement, including optimizing error messages and creating a comprehensive CLI style guide. Future steps involve utilizing telemetry data to identify common errors, improving the most frequent error messages, and implementing changes based on user feedback and RFCs. The goal is to streamline the CLI's usability, making tasks less time-consuming and frustrating, with efforts supported by the Gatsby community through collaborative input and ongoing development work.