This week on How I AI: How Zapier’s EA built an army of AI interns
Your weekly listen from How I AI, part of the Lenny’s Podcast Network
Here’s a weekly recap of new episodes across Lenny’s Podcast Network:
Every Monday, host Claire Vo shares a 30- to 45-minute episode with a new guest demoing a practical, impactful way they’ve learned to use AI in their work or life. No pontificating—just specific and actionable advice.
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Cortney Hickey, executive assistant to the CEO of Zapier, shows what happens when you stop using AI as a sidekick and start using it as infrastructure. Instead of manually prepping meetings, chasing context, or giving ad hoc feedback, Cortney built AI agents that do the repetitive work automatically, freeing her up to operate at a much higher level. The big idea: AI doesn’t replace EAs but turns them into force multipliers who scale executive thinking, culture, and strategy across the company.
Biggest takeaways:
If you’re doing a repeated task every week, spend that time automating it instead. Rather than manually prepping for meetings each Friday, invest that time in building an agent that can handle the process going forward. The initial investment pays dividends every week thereafter.
Create an AI version of your executive to help teams stress-test their communications. Cortney built a GPT that thinks like her CEO, allowing anyone to get feedback on strategic documents before formal review meetings. This improves document quality, saves executives time, and increases team confidence.
Start with “progress over perfection” when building AI workflows. Cortney emphasizes starting with basic functionality and iteratively improving: “I started this one with just a quick digest, and then over time I was like, oh, here’s something else that might be helpful.” This approach prevents perfectionism from blocking automation progress.
Make company strategy accessible and interactive with AI knowledge bases. Cortney built a strategy companion in NotebookLM that ingests all strategy documents and allows employees to query it conversationally, take quizzes, and even listen to AI-generated podcasts about the strategy—making static documents dynamic and engaging.
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More shows coming soon. . . 👀
If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.
Catch you next week,
Lenny
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