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This week on How I AI: How Zapier’s EA built an army of AI interns

12/15/25
Source: Lenny’s Newsletter by Lenny Rachitsky. Read the original article

TL;DR Summary of How Cortney Hickey Transformed Executive Assistance with AI Automation

Cortney Hickey leverages AI agents to automate repetitive executive assistant tasks, freeing time for higher-level work. She created a GPT model that mimics her CEO’s thinking to improve team communications and document quality. Starting small with AI workflows and iterating leads to effective automation without perfectionism. Additionally, AI-powered knowledge bases make company strategy interactive and accessible for employees.

Optimixed’s Overview: Revolutionizing Executive Support and Strategy with AI-Driven Automation

Introduction

In a recent episode from Lenny’s Podcast Network, Cortney Hickey, executive assistant to Zapier’s CEO, shared insightful strategies for integrating AI deeply into the executive assistant role. Instead of using AI as a mere assistant tool, she treats it as core infrastructure that multiplies impact across organizational functions.

Key Innovations in AI Usage

  • Automating Repetitive Tasks: Cortney invests initial time building AI agents to handle recurring weekly duties like meeting prep, resulting in significant time savings over time.
  • AI Executive Simulation: By creating a GPT-based model that replicates her CEO’s mindset, Cortney enables teams to receive strategic feedback on documents before official reviews, enhancing quality and efficiency.
  • Iterative AI Workflow Development: Embracing a “progress over perfection” mindset helps launch useful AI tools quickly and refine them gradually, avoiding delays caused by perfectionism.
  • Interactive AI Knowledge Bases: Transforming static strategy documents into dynamic resources using NotebookLM allows employees to engage through conversational queries, quizzes, and AI-generated podcasts, boosting strategic alignment.

Impact and Takeaways

Cortney’s approach demonstrates how AI can serve as a force multiplier for executive assistants, empowering them to scale executive thinking, company culture, and strategy more effectively. Her methods encourage organizations to rethink traditional workflows and invest in AI-driven automation that delivers compounding benefits.

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