How I AI

How AI got me 3 promotions: the ultimate guide for EAs (w/ Zapier’s EA)

Cortney Hickey is the executive assistant to the CEO at Zapier, where she’s leveraging AI to transform traditional EA responsibilities into scalable, organization-wide systems. In this episode, she demonstrates how she’s built AI workflows that automate meeting preparation, reinforce company culture through automated feedback, and democratize strategic knowledge across the organization. Her approach shows how EAs can use AI not to replace their roles but to elevate them—working on higher-impact initiatives while creating systems that benefit the entire company. *What you’ll learn:* 1. How to build an automated meeting prep system that researches participants, checks CRM data, and delivers actionable insights before important meetings 2. A framework for creating AI-powered culture reinforcement through automated meeting feedback aligned with company values and operating principles 3. How to develop an AI-powered document review system that helps teams align with executive expectations before formal reviews 4. A strategy for creating a centralized knowledge base that makes company strategy accessible and interactive for all employees 5. Why “progress over perfection” is the key mindset for building effective AI workflows that evolve over time 6. How EAs can use AI automation to work themselves out of repetitive tasks and into higher-impact strategic roles *Brought to you by:* WorkOS—Make your app enterprise-ready today: https://workos.com?utm_source=lennys_howiai&utm_medium=podcast&utm_campaign=q22025 Brex—The intelligent finance platform built for founders: https://brex.com/howiai *In this episode, we cover:* (00:00) Introduction to Cortney (02:48) Overview of meeting prep automation with Zapier Agents (04:43) How the meeting prep agent works (10:21) An example of the meeting prep agent in practice (12:16) Creating a culture reinforcement system through meeting feedback (15:45) EAs’ unique position to leverage these tools (18:12) Building an automated meeting coach (24:03) Developing an executive document review system (33:15) Creating a centralized strategy companion in NotebookLM (36:18) How AI is transforming the EA role, not replacing it (40:00) Lightning round and final thoughts *Tools referenced:* • Zapier: https://zapier.com/ • Zapier Agents: https://zapier.com/agents • Todoist: https://todoist.com/ • Slack: https://slack.com/ • HubSpot: https://www.hubspot.com/ • ChatGPT: https://chat.openai.com/ • Google NotebookLM: https://notebooklm.google/ *Where to find Cortney Hickey:* LinkedIn: https://www.linkedin.com/in/cortneyhickey/ *Where to find Claire Vo:* ChatPRD: https://www.chatprd.ai/ Website: https://clairevo.com/ LinkedIn: https://www.linkedin.com/in/clairevo/ X: https://x.com/clairevo _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email jordan@penname.co._

CHCortney HickeyguestCVClaire Vohost

Dec 15, 2025·44m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Why EAs should embrace AI: from repetitive work to higher-leverage impact

   Claire introduces Cortney Hickey (EA to Zapier’s CEO) and frames the episode as a hands-on guide to using AI for real admin and ops leverage. Cortney explains her motivation: eliminate repetitive work, stay ahead of the curve, and reshape the EA role into more strategic, creative, relationship-driven work.

2. 2

   Building a weekly meeting-prep agent in Zapier Agents (what it automates)

   Cortney walks through her flagship workflow: a scheduled weekly meeting prep agent that scans the upcoming calendar and prepares research and context. The agent replaces a multi-hour Friday routine of prep and information gathering across tools.

3. 3

   The agent’s “second brain” workflow: calendar + CRM + email + Slack context

   The meeting prep agent mimics what an EA would do manually: check attendee background, CRM history, and internal communications to assemble a single briefing. Cortney emphasizes this reduces scattered searching and prevents critical context from living only in her memory.

4. 4

   Outputs that drive action: Todoist tasks + Slack weekly digest with insights

   Cortney explains the two core outputs that make the automation actionable: prep tasks created in Todoist and a structured Slack digest. Beyond summarizing facts, the agent generates recommendations on what to prioritize for the week.

5. 5

   Improving agent quality over time: traceability, feedback, and “progress over perfection”

   Cortney shows how she inspects the agent’s step-by-step reasoning and iteratively upgrades it (e.g., adding LinkedIn links). The emphasis is on starting simple, then refining based on real usage and observing where the agent fails or misses context.

6. 6

   How to think about agents: narrate your process and train an “intern”

   Claire and Cortney discuss why agents are approachable: you can simply describe the steps you would take. Cortney likens agents to interns—initially imperfect, but trainable to learn your systems and eventually operate reliably with minimal supervision.

7. 7

   Beyond prep: calendar optimization and personal-professional constraints

   Claire adds an extension to the workflow: use agents to find calendar issues and protect time (including personal constraints). The chapter highlights that meeting support isn’t just research—it can also improve schedule health and sustainability.

8. 8

   Culture reinforcement via automated meeting feedback (from Fathom experiments to org rollout)

   Cortney shares how she began prompting meeting transcript tools to generate coaching feedback tied to team effectiveness frameworks. Over time, this became an automated system that normalizes feedback and reinforces Zapier’s operating principles.

9. 9

   Designing the automated meeting coach: tone calibration, guardrails, and delivery

   The team refines the coach to balance being “demanding and supportive,” including making feedback more direct when needed. Cortney outlines guardrails (meeting length, participant type, sufficient context) and automated delivery to each participant via Slack mapping.

10. 10

    Stress-testing strategy docs with an “exec prep” GPT (scaling Wade-style feedback)

    To prevent herself becoming a bottleneck for strategic docs, Cortney builds a ChatGPT-based reviewer that critiques and strengthens decision documents before they reach execs. The GPT helps writers clarify purpose, surface trade-offs, and tighten recommendations—sometimes eliminating the need for a meeting.

11. 11

    What powers the exec-review GPT: internal knowledge, examples, and adoption proof

    Cortney explains the knowledge base behind the GPT: strategy memos, norms, good examples, and “managing up” guidance. She highlights why building it in ChatGPT encourages psychological safety and shows adoption metrics as evidence of org-wide enablement.

12. 12

    NotebookLM as a centralized “strategy companion” (interactive strategy + AI-generated podcast)

    Cortney describes a company-wide NotebookLM workspace that aggregates dozens of strategic sources (docs, all-hands, transcripts, org action plans). Employees can query it for personalized guidance and even consume strategy via auto-generated audio summaries.

13. 13

    Lightning round: AI won’t replace EAs—it promotes them; limits of “AI exec clones”; prompting style

    In closing, Cortney argues AI elevates EAs by removing time constraints and enabling deeper, broader organizational impact—citing three promotions as proof. She notes partial executive replication is possible (writing style, norms), but keeping up with a fast-evolving leader’s thinking is difficult; her prompting style is direct, detailed, and iterative.