How I Work Quick Win: The AI experiment that made a CEO obsolete
Oct 26, 2025
Georgie Holt, co-founder of Flight Story, embarked on a transformative 60-day AI experiment to make herself obsolete as a CEO. She created Scout, a custom AI assistant that automated hiring tasks, saving her 20 to 25 hours weekly. The discussion dives into the question that sparked this initiative, the importance of mapping out pain points, and the shift from efficiency to presence in leadership. Georgie highlights how this newfound time allowed her to concentrate on people and long-term vision, elevating her role beyond operations.
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60-Day CEO Obsolescence Experiment
- Georgie set a 60-day experiment to hand over the operational side of her CEO role to AI.
- The experiment aimed to free her from admin so she could focus on leadership and purpose.
Scout: A GPT-Built Hiring Assistant
- Georgie built 'Scout' inside a GPT by conversing with the model rather than coding.
- The tool saved her roughly 20–25 hours per week by automating hiring admin.
Build Assistants By Mapping Pain Points
- Map your process end-to-end and explain pain points to the GPT before building an assistant.
- Iterate through conversation with the model until it builds the workflow you want.