Skip to content
How I AIHow 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._

Cortney HickeyguestClaire Vohost
Dec 14, 202544mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Zapier’s EA shows AI workflows for meetings, culture, strategy scaling.

  1. Cortney Hickey explains how she uses Zapier Agents, ChatGPT custom GPTs, and NotebookLM to offload repetitive EA work and increase organizational leverage.
  2. A flagship “weekly meeting prep” agent scans the calendar, researches external attendees, pulls CRM/email/Slack context, and outputs both Todoist prep tasks and a Slack digest with recommendations.
  3. She also built an automated meeting-coaching system that turns transcripts into culture- and values-aligned feedback delivered to participants, normalizing continuous improvement while reducing interpersonal friction.
  4. Finally, she shares tools that ‘scale exec thinking’: a GPT that reviews strategic docs in the CEO’s preferred style and a NotebookLM ‘strategy companion’ that makes company strategy queryable and consumable (even as an auto-generated podcast).

IDEAS WORTH REMEMBERING

5 ideas

Automate the weekly grind first to buy back time immediately.

Cortney targets Friday meeting-prep as a predictable, high-frequency task; once automated, she gets hours back while improving prep quality and consistency.

Great agents mirror your real workflow—describe it in natural language.

Both hosts emphasize that agent-building becomes easier when you narrate your steps (“check calendar → research people → scan Slack/CRM → summarize → create tasks”).

Combine multiple context sources to create ‘second brain’ meeting readiness.

The prep agent triangulates web research, HubSpot relationship history, and internal comms (Gmail/Slack), eliminating manual searching and reducing missed context.

Design outputs that land where work actually happens.

Cortney delivers actionable artifacts: Todoist tasks timed before meetings and a structured Slack digest, plus error handling when data can’t be found.

Iterate agents like training an intern: start simple, then refine.

She recommends “progress over perfection,” using execution traces and copilot edits (e.g., adding LinkedIn links) to incrementally improve reliability and usefulness.

WORDS WORTH SAVING

5 quotes

If you are doing a repeated task every week, spend time that week automating that task.

— Claire Vo

It’s serving as this kind of second brain for me… making sure that it’s not all in my head.

— Cortney Hickey

I always tell people… progress over perfection.

— Cortney Hickey

Are we who we say we are?

— Cortney Hickey

I’ve gotten three promotions… and been able to work myself out of multiple roles.

— Cortney Hickey

Weekly meeting prep automation (Zapier Agents)Calendar research: web + CRM + email + Slack contextOperational outputs: Todoist tasks + Slack digestAgent iteration: copilot feedback, progress over perfectionAutomated meeting coaching from transcriptsCulture/values reinforcement (Five Dysfunctions, operating norms)Executive/strategy scaling: doc review GPT + NotebookLM strategy companion

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome