Podcast Summary: How I AI

Episode: How Zapier’s EA built an army of AI interns to automate meeting prep, strengthen team culture, and scale internal alignment
Host: Claire Vo
Guest: Courtney Hickey, Executive Assistant to the CEO at Zapier
Date: December 15, 2025

Episode Overview

In this practical and insightful episode, Claire Vo interviews Courtney Hickey, Zapier's EA to the CEO, about how she's leveraged AI—specifically Zapier agents and AI-powered tools—to revolutionize the executive assistant role. They explore automating meeting preparation, scaling culture and feedback, and democratizing strategy alignment across a rapidly growing, remote-first tech organization. Courtney shares actionable workflows and tips anyone can deploy, regardless of role, to save time, reduce stress, and increase impact through AI "interns".

Key Discussion Points

1. Why Automate? The Case for AI in EA Roles

• Courtney's Perspective:
  • Working at Zapier, automation is part of the ethos, but Courtney is personally passionate about using AI to eliminate repetitive work and focus on higher-value tasks.
  • "It’s not if you have to use AI in this type of role, it’s a when. I like to be ahead of the curve." (03:21, Courtney)
• AI as an Enabler:
  • AI lets EAs (and similar professionals) “work themselves out of the boring, repetitive manual parts” for more creative, strategic projects.

2. Automating Meeting Preparation: The Weekly Meeting Prep Agent

• Courtney’s Workflow:
  • Built using Zapier agents.
  • Every Friday at 8AM:
    • Pulls upcoming week’s meetings from the calendar.
    • Identifies meetings needing prep (excludes basics like 1:1s or routine standups).
    • Researches external participants (via web search and CRM).
    • Checks relationship history (HubSpot, Gmail, Slack).
    • Compiles prep tasks and insights.
    • Pushes outputs: tasks in Todoist and a structured Slack digest (with error handling, creative recommendations, context).
• Key Benefits:
  • Context “second brain”—centralizes information otherwise scattered across systems.
  • Creative suggestions for prep.
  • Easily customizable and improvable based on feedback.
• Notable Quotes:
  • "This agent does everything you want and then more and over time you can make it more intelligent. It’s certainly serving as this second brain for me." (00:20, Courtney)
  • "Progress over perfection... build something basic, see how it works, learn, and then improve it." (11:28, Courtney)
• Timestamps:
  • Description of full workflow: [04:34 – 12:16]
• Practical Takeaway:
  • If you're doing a repeated task weekly, spend that week automating it!
    "I highly recommend people just say, this week I’m going to spend that hour automating this into an agent and see if I can replace that flow." (12:16, Claire)

3. Thinking in AI “Interns” and Systematizing Leverage

• Courtney’s Approach:
  • Treat agents as trainable interns—start simple, articulate your workflow, iteratively improve.
• Empower the Organization:
  • EAs can systematize their leverage and share templates for broader organizational use.
  • "Teach people how to fish—and teach these interns your way of thinking, these agents. Over time, you’ll be surprised by how much you can do." (14:01, Courtney)
• Cultural Mindset:
  • The more process you codify, the more scalable your impact (for yourself and others).

4. Calendar Optimization and Personalization with AI Agents

• Mixing Professional and Personal:
  • Example: Using agents to block time for walking kids to school, flag days without lunch, or identify back-to-back meetings.
• Idea:
  • Use agents for both productivity and life balance, and automate identifying time sinks or combining redundant meetings.
• Memorable Moment:
  • "If you really want hyper efficiency, you just make an agent that says, find all my meetings. Cancel all of them. Give me my take." (17:51, Claire)
  • "The Ron Swanson agent...Schedule all my meetings for March 31st." (17:59, Courtney)

5. Scaling and Normalizing Feedback: Automated Meeting Coaching

• The Use Case:
  • After executive meetings, Courtney used to prompt Fathom for team coaching insights (e.g., “How did we perform against the five dysfunctions of a team?”).
  • Built a workflow to automate team feedback, emphasizing growth feedback as a value, not just action items.
  • Process includes extracting meeting transcripts, using organizational values/norms for personalized, real-time feedback.
• Impact:
  • Normalizes feedback: removes stigma, makes it routine, and reinforces culture and operating principles.
  • Provides both supportive and demanding feedback, per leadership philosophy.
• Memorable Quotes:
  • “When feedback is expected after a meeting...then folks learn to expect it and it becomes part of their behavior...You can build this meeting coaching across the org.” (18:25, Courtney)
• Example Output:
  • Personalized, actionable feedback sent directly to participants with links to company values and growth insights.
• Timestamps:
  • Meeting feedback system: [18:13 – 27:10]

6. Making Strategy Interactive: AI-Powered Knowledge Bases

• The Problem:
  • People struggle to connect day-to-day work with high-level strategy and to find relevant information.
• NotebookLM Workflow:
  • Centralize all strategy docs, meeting transcripts, and plans into an AI-powered searchable “strategy companion.”
  • Employees can ask questions (“How can I contribute to the 2026 strategy?”) and get tailored, source-linked answers.
  • Produces multimodal outputs, like a fully-AI-generated internal podcast summarizing strategy themes.
• Key Insight:
  • This helps every employee align their work more closely with evolving company goals, at scale.
• Timestamps:
  • Strategy AI tool description: [33:34 – 36:19]

7. Scaling EA and Exec Insights Through AI “Clones”

• Replicating Executive Thought Process:
  • Courtney built a ChatGPT-based “Exec Prop GPT” that reviews strategy docs (“tee ups”) using the CEO’s and her own feedback style and standards.
  • Provides writers with actionable feedback before documents reach execs, freeing up Courtney and reducing bottlenecks.
  • “Sometimes the tee up is so clear now that we can skip the meeting entirely, which is great as well.” (27:54, Courtney)
• Limitation:
  • Models can mimic writing and decision patterns, but struggle to keep pace with an evolving executive’s thinking.
  • “The pace at which leaders learn—how do you replicate that? That’s something models can’t yet fully match.” (40:29, Courtney)
• Timestamps:
  • Executive “clone”/GPT workflows: [27:54 – 32:43]

8. AI’s Impact on the EA Profession

• AI Won’t Replace EAs—It Multiplies Their Value:
  • Courtney asserts AI will never replicate the breadth, strategic depth, and relational aspects of top EAs. Instead, it enables them to be more creative and impactful.
  • “Think about the scope of what we do... now you can be wide, have more depth, and have more time for projects and special things for your team.” (39:01, Courtney)

Notable Quotes & Moments

• On Iterative AI Building:
  • "Progress over perfection...build something basic, see how it works, learn, and then improve it." (11:28, Courtney)
• On Agents as Interns:
  • "If you can teach the intern your system...over time your intern gets smart enough to run and do things on their own." (14:01, Courtney)
• On Feedback Normalization:
  • "If everybody in the meeting is getting feedback, and it’s coming from a neutral evaluation place, then you might be more open to hearing and adjusting your behaviors." (25:56, Claire)
• On Replicating Executives:
  • "How can you grow at the pace of someone’s brain? Their thought process does change over time... That’s something models can’t yet fully match." (40:29, Courtney)
• On Prompting AI:
  • "I'm a ramble...I don’t understand why you’re doing it this way—show me your reasoning. Just give it top of mind, pretend it’s someone with no feelings, and be demanding." (42:28, Courtney)

Important Timestamps

• Introduction to Courtney & Automating the EA Role: 02:49 – 04:04
• Detailed Meeting Prep Agent Workflow: 04:34 – 12:16
• Designing and Growing Agents as Interns: 14:01 – 15:48
• Calendar Optimization & Personalization: 16:45 – 17:59
• Automated Meeting Feedback for Team Growth: 18:25 – 27:10
• Scaling Executive “Thought Partnership” (Exec GPT): 27:54 – 32:43
• Interactive Strategy Knowledge Base: 33:34 – 36:19
• The Future of EAs & AI: 38:23 – 40:29
• Prompting Techniques for AI: 42:23 – 43:10

Actionable Tips & Takeaways

• Automate Repetitive Tasks:
  If you find yourself doing the same prep or admin work every week, invest the time to automate it—a one-time investment pays dividends.
• Start Simple, Iterate Often:
  Don’t wait for perfection. Launch basic agents, observe results, and improve them via feedback (from both humans and the AI outputs).
• Normalize Feedback:
  Use AI to deliver routine, constructive feedback in line with company values, lowering the emotional barrier and reinforcing culture.
• Democratize Knowledge:
  Make strategy and operations accessible: AI-powered companions or knowledge bases let anyone, anywhere, ask questions and learn.
• Elevate, Don’t Replace:
  AI’s true power is in automating the mundane, freeing you up for higher-leverage, human-centric, creative, and strategic work.

Resources & Follow-Up

• Connect with Courtney: LinkedIn
• EA Exec Ops AI Playbook: Courtney recently published a playbook with replicable automations for EAs and ops professionals.
• Replicable Workflows: Many of these agents and prompts can be shared and adapted via Zapier, ChatGPT, and Google’s NotebookLM.
• Podcast Links: Find more episodes and resources at howiaipod.com