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

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

How I AIDec 15, 202544m

Cortney Hickey (guest), Claire Vo (host), Claire Vo (host)

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

In this episode of How I AI, featuring Cortney Hickey and Claire Vo, How AI got me 3 promotions: the ultimate guide for EAs (w/ Zapier’s EA) explores zapier’s EA shows AI workflows for meetings, culture, strategy scaling. Cortney Hickey explains how she uses Zapier Agents, ChatGPT custom GPTs, and NotebookLM to offload repetitive EA work and increase organizational leverage.

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

Cortney Hickey explains how she uses Zapier Agents, ChatGPT custom GPTs, and NotebookLM to offload repetitive EA work and increase organizational leverage.

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.

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.

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).

Key Takeaways

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.

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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”).

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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.

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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.

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

She recommends “progress over perfection,” using execution traces and copilot edits (e. ...

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AI can systematically reinforce culture—not just productivity.

The meeting-coach automation maps transcript feedback to company values and frameworks, making norms visible and routine between quarterly culture interventions.

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Scale executive judgment with doc-review tools to reduce bottlenecks.

Her exec-prep GPT helps teams stress-test strategy docs against norms/strategy and the CEO’s expectations, improving async quality and sometimes removing the need for meetings.

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Notable 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

Questions Answered in This Episode

What exact criteria does your meeting-prep agent use to decide which meetings ‘require prep’ (and how do you prevent it from over-prepping recurring meetings)?

Cortney Hickey explains how she uses Zapier Agents, ChatGPT custom GPTs, and NotebookLM to offload repetitive EA work and increase organizational leverage.

Get the full analysis with uListen AI

How do you handle privacy/security when the agent searches email/Slack and pulls CRM data—what are your guardrails and red lines?

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.

Get the full analysis with uListen AI

For the meeting-coaching system, how do you calibrate ‘demanding and supportive’ so feedback is helpful without creating fear or performative behavior?

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.

Get the full analysis with uListen AI

What prompt components (values, norms, frameworks like Five Dysfunctions) had the biggest impact on feedback quality—and which ones added noise?

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).

Get the full analysis with uListen AI

How do you measure whether the culture-feedback automation actually improves meeting quality (e.g., decision speed, inclusion, conflict health) rather than just generating messages?

Get the full analysis with uListen AI

Transcript Preview

Cortney Hickey

I think from EAs I hear like, "Oh, AI doesn't think the way I do." I'm like, "It can, though. It can," [chuckles] as long as you can figure out the system behind why you're doing things and be able to articulate that.

Claire Vo

I think this is going to be one of the most practical, time-saving, and stress-saving episodes of How I AI we have ever had. This agent does everything you want and then more, and over time you can make it more intelligent. It's serving as this kind of second brain for me, where, yes, I have all this, and part of my superpower as an EA is remembering all of these things about people, but this is making sure that it's not all in my head, and I can really refresh my memory quickly on all the contexts, rather than diving through the CRM, my email, Slack, and looking at all these things separately. If you are doing a repeated task every week, spend time that week automating that task. I definitely am a believer that AI can only enable us in this role. I think it's a when, not an if. We will have to be folks that adopt these tools. [upbeat music] Welcome back to How I AI. I'm Claire Vo, product leader and AI obsessive, here on a mission to help you build better with these new tools. Today we have Cortney Hickey, EA to the CEO at Zapier, and yes, of course, she uses AI to automate all of the admin tasks related to meetings, and document preps, and feedback, but she's also gonna show us some unique ways that you can use AI to reinforce your cultural values and operating principles. This is a really great one for anybody thinking about organization at scale, operations at scale, and culture at scale. Let's get to it. This episode is brought to you by WorkOS. AI has already changed how we work. Tools are helping teams write better code, analyze customer data, and even handle support tickets automatically. But there's a catch: these tools only work well when they have deep access to company systems. Your copilot needs to see your entire code base. Your chatbot needs to search across internal docs, and for enterprise buyers, that raises serious security concerns. That's why these apps face intense IT scrutiny from day one. To pass, they need secure authentication, access controls, audit logs, the whole suite of enterprise features. Building all that from scratch, it's a massive lift. That's where WorkOS comes in. WorkOS gives you drop-in APIs for enterprise features, so your app can become enterprise-ready and scale upmarket faster. Think of it like Stripe for enterprise features. OpenAI, Perplexity, and Cursor are already using WorkOS to move faster and meet enterprise demands. Join them and hundreds of other industry leaders at WorkOS.com. Start building today. Cortney, welcome to How I AI. I am really excited about this episode because I think this is going to be one of the most practical, time-saving, and stress-saving episodes of How I AI we have ever had. So I'm just pumped to have you on. Can you just tell us a little bit about why you've chosen to dive headfirst into using AI in your role, aside from the place that you work?

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