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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.

Cortney HickeyguestClaire Vohost
Dec 14, 202544mWatch on YouTube

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not 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

Read the available transcript
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.

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