Rachel Wolan, the Chief Product Officer at Webflow, has created an AI chief of staff to streamline her workweek. This AI assistant handles calendar management, meeting preparation, email triage, and even provides candid feedback. In a conversation with Claire Vo on the podcast "How I AI," Rachel emphasizes the importance of building personal AI tools for executives. She finds that hands-on experience with AI, which she describes as "getting blue-pilled," can shift perceptions about what AI can achieve. Rachel's approach to personal software is unique. She designs tools specifically for her needs, allowing for tailored solutions that can be discarded when no longer useful. This flexibility makes software feel as accessible as documents. She maintains a knowledge base using markdown files, which supports both her AI applications and her personal organization. This setup helps her create a personal knowledge graph, enhancing her interactions with AI. In terms of organizational culture, Rachel highlights the need for both top-down directives and grassroots enthusiasm to drive AI adoption. She sets clear expectations with her team by requiring prototypes for meetings, while also encouraging participation and recognition through initiatives like Builder Days. One of the notable features of her AI chief of staff is its ability to analyze her calendar, suggesting which meetings can be skipped or delegated, thus freeing up time for more impactful work.