How Zapier’s EA built an army of AI interns to automate meeting prep, strengthen team culture, and scale internal alignment | Cortney Hickey

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: How to build an automated meeting prep system that researches participants, checks CRM data, and delivers actionable insights before important meetingsA framework for creating AI-powered culture reinforcement through automated meeting feedback aligned with company values and operating principlesHow to develop an AI-powered document review system that helps teams align with executive expectations before formal reviewsA strategy for creating a centralized knowledge base that makes company strategy accessible and interactive for all employeesWhy “progress over perfection” is the key mindset for building effective AI workflows that evolve over timeHow EAs can use AI automation to work themselves out of repetitive tasks and into higher-impact strategic roles— Brought to you by: WorkOS https://workos.com/?utm_source=lennys_howiai&utm_medium=podcast&utm_campaign=q22025—Make your app enterprise-ready today Brex https://brex.com/howiai—The intelligent finance platform built for founders — 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 [email protected].

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I think from EA's I hear like, oh, AI doesn't think the way I do. I'm like, it can though. It can, as long as you can figure out the system behind why you're doing things and be able to articulate that. 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 this kind of second brain for me where, yes, I have all this and part of my superpower as an EA is remembering all 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 context, rather than diving through the CRM, my email, Slack, and looking at all these things separately.

• 0:43Speaker 00

  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.

• 1:04Claire Vo?

  Welcome back to How I AI. I'm Clara Voe, product leader and AI obsessive here on a mission to help you build better with these new tools. Today, we have Courtney 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 going to 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.

• 1:45Claire Vo?

  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

• 2:27Claire Vo?

  features so your app can become enterprise-ready and scale up market 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.

• 2:49Speaker 00

  Courtney, 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? Yeah, so I work for Zapier, which is an automation and AI orchestration company. So of course, it's part of our company ethos, but I am just personally super passionate

• 3:34Speaker 00

  about using AI because I think it can help work myself out of the boring, repetitive manual parts of my role so I can do more interesting work. And so I truly believe that it's not a if you have to use AI in this type of role, it's a when. So I like to be ahead of the curve. I like to learn by doing. And so I've spent as much time as I can over the past couple of years really diving into this and seeing how I can change the shape of my role with this new tech. And what I like is we're going to start off on a workflow and use case that I think everyone can relate to, which is meetings stink.

• 4:14Speaker 00

  Or not meetings stink, but meetings could be better used in most organizations. They're expensive, you have a lot of people in them, and I think like prep and follow-up are so valuable and aren't really done well by organizations. So I'd love for you to walk us through a couple of your meeting-related Workflows. Totally, yeah. I mean, as an EA, the, my life runs off of the calendar, so that was naturally one of the first places I dove into with AI. And so, let's jump into one of my favorite workflows that I've built, and this is within Zapier Agents. So, our agent's product, uh, it, within Zapier, we have a bunch of different products, all the way

• 4:56Speaker 00

  from super deterministic automations that run the same way every time with little creativity, to these agents that can do tasks that involve more reasoning and, uh, have a lot more freedom to operate. So, you could build this in a Zap, but I wanted to like, paint the, you know, change the color of the sky with this agent for myself. So, this is an example of one I use personally, but you can replicate this for anyone you work with. But, this is essentially my weekly meeting prep agent, which on Fridays, I used to have maybe, let's say, two hours blocked, 30 minutes to like, do a retro on that week and anything I need to change, but then like, spending an hour or so,

• 5:39Speaker 00

  really diving into the next week and what I need to be prepared for. So, the way this agent works, and it's kind of developed over time, but it, it has a few steps it goes through. And the key thing is, this is scheduled to trigger every week. I have it do it at Friday, 8:00 AM, so you can have it whenever. And basically, it goes through my calendar for the upcoming week. It identifies all meetings that require prep, so personally, I don't need to prep much for routine 101s, a team stand-ups, or recurring internal meetings, but I do have more and more external meetings on my calendar now that I'm doing more out in the world with, with AI and automation and teaching folks how to do the same. So, basically, I have it be a bit of a research buddy at first. So, first, it just pulls my calendar, then it goes and does all of the research for me. So, this, uh, takes

• 6:24Speaker 00

  anyone without a Zapier email and does a web search, basically. It researches their current role, their industry experience, anything, um, anything noteworthy that I might want to know about them. And then, it does this cool thing, which also goes and checks in our CRM, which we use HubSpot at Zapier, but you can, you can put in any, uh, you know- Of our 8,000 integrations here and use your CRM. But for each external participant, it goes and then looks at what their relationship is with Zapier. So it looks at email address first, then by company name, figures out what if they're in a deal, if there's any recent sales team notes, if there's any interaction I should know of. And then it also goes and searches internal comms history.

• 7:04Speaker 00

  So within my Gmail to see our prior relationship, if any, within Slack to see if there's any callouts to their company. And so it's doing all these things that I would do manually. And then it's delivering me two outputs in the end. So one of them is tasks for my actual prep with all this in it. So I like it to create a task in To Do List, which is my To Do List app with the, within a certain project of meeting prep. It pulls in all of this information with this intelligence from the agent and tells me to prep for it. It puts it on my calendar for two hours before the meeting start time. So you can see what that looks like in real life, you know, here. Here's a couple of meetings I have next week and they're automatically queued in my To Do List.

• 7:49Speaker 00

  But the second thing it does is delivers this weekly digest to Slack. So this is, and you could do this day by day too, if you have a ton of meetings. But again, I'm mostly internal. So I have it create a structured digest, which includes all of the meetings and intelligence. Any error handling I might need to know, like if the agent couldn't find someone or if there's anywhere I should do a manual follow up. And then it does this like pulls its own, uses its own creativity to create these insights for me about what I should pay most attention to for this upcoming week. So I can pull up a real example here.

• 8:31Speaker 00

  So I just ran this this morning, just for this example, but it's going, looking at the next week. It's pulling all of the key meetings that require prep preparation. It's saying, okay, so we have a team onboarding with Fellow. We're changing our AI note taking app. And so it did some intelligence on who we're meeting with for this. It's confirming that this is a new vendor relationship. Relationship. We've previously purchased this meeting management. They're our implementation specialist. And then, you know, here's, here's more context on this. So it's like, it's, it's serving in this kind of second brain for me where I, yes, I have all this and part of my superpower as an EA is, is remembering all these things about people.

• 9:13Speaker 00

  But this is making sure that I don't, it's not all in my head and, and I can really refresh my memory quickly on all the context rather than diving through the CRM, my email, Slack and looking at all these things separately. So one place is, is key. And then it pulls in this like key prep recommendations at the end, which is where the agent gets a little bit creative here. So it's saying, I should review my previous carve session. This is a EA automation session I do every once in a while. Tells me to prepare some new demos, tell me to familiarize myself with fellow before the onboarding session and check with our head of marketing for PR priorities before the agency call.

• 9:51Speaker 00

  So I love that it, you know, does exactly what I need to do, like, you know, gives me all these preps in my to do list and it does those actions. But it also kind of serves as like a double check. Maybe there's something I haven't thought of. Maybe I didn't think I needed to update my deck and it gives me something new. So I think what's great about this agent is it does everything you want and then more. And, and over time you can make it more intelligent. So as you, as you learn how this works and so. I'll give you an example of how this actually works in reality. So this is the test that I pulled right before this call, just to give us a clean Slack output. And it walks you through step by step what this agent was thinking. It's like, okay, I'm testing this.

• 10:34Speaker 00

  I'm going to go look at the calendar. I'm going to go research all these participants. You can click in and see even more information about what it was thinking. You can see that it went in HubSpot, couldn't find someone for there, couldn't find someone, we probably didn't have a relationship with them. Oh, great. It found someone. And then it tells you everything it did. So over time, if, if something's not performing as you intended, or you want to update it. You can really look at how this agent works on the backend and give it some feedback. And we have this great co-pilot where you can go in and say, you could say like, you could go into co-pilot and be like, oh, I actually would love to have a hyperlink to their LinkedIn.

• 11:17Speaker 00

  Page included in my to do list things. You can say for each participant.

• 11:24Speaker 00

  And you also add a LinkedIn hyperlink within the Slack digest. So you can kind of, I always tell people when they're starting with an agent like this is progress over perfection. Like I started this one with just a quick digest. It didn't, it didn't have our CRM connected. It didn't have that. And then over time, I was like, oh, here's something else that might be helpful. And so like, build something basic, see how it works, learn, and then, you know, make time to improve it over time so that you make sure it's really being impactful for you and doing all of the things it can. And you know, these tools are getting smarter every day. So also keep on top of, you know, the new, new capabilities.

• 12:07Speaker 00

  So you can start building those into agents and automations and things that you've built in the past. So that's a quick overview of the agent. Something I want to, I want to call out for folks is I think this workflow highlights a couple of strategies that I think people really need to think about. One is I tell people, if you're doing a repeated task every week, spend time that week automating that task. And so I, when I had fancy jobs, had an EA as well. We had a very similar process where on Fridays, we would actually do a retro of the past week, prep for the next week, find out like all the stuff we needed to prep, make sure that I knew everything that needed to happen.

• 12:52Speaker 00

  And instead of spending that hour doing that prep on a Friday, I highly recommend people just say, this, this week, I'm going to spend an hour automating this agent and see if I can replace that flow. And so I think that's a really useful mindset to bring into what and when you can automate. Yeah.

• 13:14Claire Vo?

  The second thing I would say is I love agents, in particular, this sort of like natural language format of describing agents, because you can literally just narrate what you would do. You would be like, first, I would go to Google and I would look at all the meetings for the next week and I would decide which ones I need to prep for. Then I would go look at my email and see what the heck we're actually meeting about. Then I would dig through Slack. I would probably go look at HubSpot. And then I would, if I was doing a great job, organize it in this way, send it to myself in Slack as a reminder and create a bunch of to-dos.

• 13:50Speaker 00

  Yeah.

• 13:50Claire Vo?

  You can actually use that natural language to describe an agent structure. And so I think it's a really natural way for people to get started designing some of these workflows.

• 14:01Speaker 00

  Yeah, I agree. Like, I think of agents, when I first started using them, I kind of started thinking of them as interns almost. So they're not going to operate and do something completely independently from the start. But if you can teach the intern your system and how you think and give it the tools it needs, then over time, your intern gets smart enough to run and do things on their own. And so, you know, this is something that now I rarely touch this agent because it works as I planned consistently. You know, right now, that was a good little ad that I just did for the LinkedIn profile, so I can quickly add them. But, you know, there's not much else I have to do here. And now I've given

• 14:41Speaker 00

  myself that time back. And even bigger, I can showcase this to everyone at Zapier, enable them with this template, which you can share. And then everyone can have this meeting prep agent. They can, you know, they can add different things if this isn't their exact workflow. Like, not everyone uses Todoist, or, you know, not everyone wants XYZ, but they can customize it for their own. And so I think it's like, yeah, teach people how to fish and teach these interns your way of thinking, these agents. And over time, you'll be surprised of how much you can do. I think from EAs, I hear like, oh, you know, AI doesn't think the way I do. I'm like, it can though. It can. As long as you can figure out this.

• 15:24Speaker 00

  System behind why you're doing things and be able to articulate that. But yeah, I love the like, um, the dictate to co-pilot too, because I do that. I'm like, okay, so usually I talk to it just like that, like as if I'm on a walk with a friend and see what it comes back with. And so, yeah, this is, this is like one of those things that's just a no brainer to spend a little bit of time on. And then you just runs in the background.

• 15:48Claire Vo?

  Yeah. And I think, you know, EAs in particular are so well positioned to make some of these tools for the broader organization. Because, you know, you're a point of leverage in a team. And if you can systematize that leverage, I think two things happen. One, you can do a higher level job, supporting your exec or your team. Two, everybody else gets a little bit of a boost that you wouldn't be able to personally give them. And so, I think, you know, everybody should think like, oh my gosh, I could have my own little mini, you know, assistant. Or I could have my own little army of interns if I can just describe what I need them to do. And I think that's really interesting.

• 16:33Claire Vo?

  The last thing I will say is I have a very almost exact workflow in Zapier Agents. It's called my Sunday scaries prep. I do it on Sundays when I start to feel lots of anxiety.

• 16:45Speaker 00

  Yeah.

• 16:46Claire Vo?

  Now, um, what I'm planning for the next week, and the one add that I put in here is you can actually mix professional and personal stuff. So I put in there, if my mornings allow me to walk my kids to school, block off, you know, this hour to this hour. Because I know I can like walk the kids to school and by Sundays, you haven't booked me on an early morning, you don't get me. And so, like add these little, you know, call out days that I don't have time scheduled for lunch. Like call out days where I have six hours of back to backs with no break. Like, give me an opportunity to improve my calendar. So I do think in addition to prep, you can do a little like calendar optimization too, which is really nice.

• 17:29Speaker 00

  Totally. I agree. Like, yeah, which meetings might be able to combine, uh, or get rid of that look duplicative. You know, give it, give me some recommendations for optimizing my focus time. Like totally the sky's the limit with, with these things. And yeah, you can totally combine personal and professional calendars into this to make it a jack of all trades and do everything. But this one, yeah, this one for me is focus on work.

• 17:51Claire Vo?

  You know, if you really want hyper efficiency, you just make an agent that says, "Find all my meetings, cancel all of them, give me my date."

• 17:59Speaker 00

  Yeah, the Ron Swanson agent, I don't know if you watch Parks and Recreation, but April Ludgate scheduled all of his meetings for like March 31st one year because she didn't think that existed.

• 18:09Claire Vo?

  Yeah, exactly.

• 18:10Speaker 00

  Perfect. "Get all my meetings for March 31st."

• 18:13Claire Vo?

  You know, you have one other meeting-related workflow, which I think is really interesting, which is making sure that the meetings that you do really are high value.

• 18:21Speaker 00

  Yeah.

• 18:21Claire Vo?

  So I'd love for you to walk us through what you do there.

• 18:25Speaker 00

  Totally. So there's a few things on the other side of meetings that I do. So one of them is, you know, this is Wade, the CEO of Zapier. So I was basically, the way this workflow came up, was we use Fathom for our meeting note-taking. So I was manually going into Fathom after each executive meeting and giving it a prompt, like, "How did we perform against the five dispositions of a team?" Which is a framework we use from the Table Group. Or, "Who in this meeting could have spoke up more?" And I was giving it prompts to see how Fathom did with more reasoning and more of a loose, like, feedback, creative prompt versus what were the action items, which of course it does excellently.

• 19:09Speaker 00

  And over time, I was like, "This is pretty useful." And so I was manually doing that in Fathom, sending it to the exec team. And Wade sent me this message, he's like, "I feel like we need to turn this meeting coaching on across the org. It's a pretty useful accountability mechanism." I think the other thing here is when feedback is maybe automated, growth feedback is one of our values, so it's part of how the company runs. But when feedback is expected after a meeting and becomes a part of routine and coaching, then folks learn to expect it and it's part of their behavior. It doesn't make their like, you know, that nervousness spike up when they get feedback come in. So I think the more feedback folks can get, the better. But- I think the other thing this does is take some spit off the ball.

• 19:53Speaker 00

  So, so, you know, after meetings, I've worked at this team, this exec team for five years. So no one would be offended if I said, like, you know, Brandon, you really like should have spoken up on that topic. I can call them out because they've given me the permission to do that. But for folks who are newer to organization or don't have that comfort level with the team, you can build this meeting coaching across the org to and automate it based on any meeting transcript. So, you know, I started working with him with, you know, with Fellow, because we're moving over to Fellow for AI note taking and was testing an agent. You know, I was giving Wade, you know, here's an example of the feedback it generated.

• 20:35Speaker 00

  It gave him speaking time. It gave him, you know, what went well. It gave him opportunities to amplify impact. And then he's like, this coaching is too soft, like this, this is still what went well. Let's have it be tougher. So then I gave it, you know, I fixed the agent instructions to give it a better balance of being demanding and supportive, which is a term we use a lot here at Zapier of like, you have to be a demanding leader, but you also have to be supportive. So I gave him this one, which, which did, uh, did give some more growth opportunities, like address misalignment more directly, you know, challenge the decision-making speed. It seems like you have some fear of conflict. And so we worked at that, gave it a more concise version, thought it was good enough to ship.

• 21:16Speaker 00

  And then, so now we've, we've shipped this kind of meeting feedback automation system through, through Fellow. But this basically takes all of the transcript content, meeting metadata, make sure there's some, you know, some parameters, like if a meeting is only 10 minutes, probably not worth the feedback. And, and make sure it's only Zapier employees, make sure there's, you know, only sufficient context to offer valuable, specific feedback. And then for each participant, it can look up their Slack, match their email address to Slack, and then send them some, you know, some, some feedback. And I gave it context on our company values, you know, some of our meeting norms, you know, how we think about decision-making. And then these are impact behaviors for like what we expect from folks at Zapier. And then I gave it the five.

• 22:00Speaker 00

  Just function of a team. And so I really worked on this prompt over time to help it generate this direct constructive feedback on all these dimensions. And then, you know, you can see what the outcome is going to be. And this is, you know, clarifies it's AI generated, it's coming from a bot, gives, you know, very quick feedback after a meeting of one to two specific growth opportunities and one to two things they can do next time. So this is something that I think can, over time, really just change the way that a team works together and change the usefulness of a meeting. So this is a, maybe not something that was a huge part of my job. And I don't

• 22:41Speaker 00

  calculate this as like a big time-saving agent for myself, kind of like the meeting prep was. But this is something that's like really reinforcing the company culture and making folks better at their jobs. So I think this is, it's cool to build stuff like this. That's more, that's more just enablement and accountability for folks, especially among the exec team. So you make sure that they're being like the best displayers of company values and norms over time. So this is a fun one that I had a good time creating with Wade.

• 23:13Claire Vo?

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• 23:54Claire Vo?

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• 24:04Claire Vo?

  So Courtney, what I think is great about this is people really think that culture is hard to systematically reinforce. You really think that culture has to be something that individuals or leaders have to carry through sort of soft interactions with the organization. But what you're showing here is more than, hey, can I give you, you know, skills coaching on closing a customer, or I give you communication coaching on managing stakeholders. This is, are we embracing our operating principles, our cultural norms? Are we keeping an eye out for issues in interpersonal conflict or communication that we know teams are biased

• 24:48Claire Vo?

  towards? And are we creating sort of a ego protective system in order to continually check and keep ourselves accountable to that system? And so I think like, take the meeting part of this aside, the ability to kind of consistently check interactions and projects and initiatives inside your organization with alignment on your stated cultural norms is a really powerful thing. And, you know, you mentioned Table Group, I've worked with them before. And like, you get, you get them like, once a quarter.

• 25:25Speaker 00

  Yeah.

• 25:26Claire Vo?

  All this great work for your leaders. And you're like, yeah, we're gonna like, be the best team. We're totally aligned.

• 25:32Speaker 00

  Yeah.

• 25:32Claire Vo?

  Giving everybody feedback, but they're not whispering in your ear during the executive me, I mean, I'm sure they would for a price, but during executive meetings, you know, they're not listening into your company, you know, town halls or AMAs. And so I think this is just such a nice way to observe your organization from a third party, kind of like vantage point.

• 25:55Speaker 00

  Yeah.

• 25:56Claire Vo?

  And then, as you said, like, just normalize feedback. This is very stressful feedback for people to receive, maybe from their boss.

• 26:03Speaker 00

  Yeah.

• 26:04Claire Vo?

  Like, hey, you didn't do this, or you didn't do that. But if you know, everybody in the meeting is getting feedback. It's coming from sort of a neutral evaluation place, then you might be more open to hearing and kind of adjusting your behaviors based on that feedback.

• 26:21Speaker 00

  Yeah, totally. I think you hit the nail on the head with a few of the main reasons why I like this. I think it's, are we who we say we are? You know, are you who you say, are we what we say our culture is? And are we keeping that top of mind in between things like, you know, we're a fully remote company. We do only meet with Table Group once a quarter, once a half. And so we need to keep these behaviors top of mind consistently. And folks have a hard time keeping anything top of mind for that long. And so making sure this is repetitive and continuing to reinforce those things is valuable. But yeah, I mean, we've got the other type of agent for, you know, sales reps, for example, that gives them after gone calls, what they could have done. That's more like, okay, you should have brought up this ROI or this metric,

• 27:05Speaker 00

  or you know, more specific sales coaching, but I love the culture stuff.

• 27:10Claire Vo?

  Okay, this is great. So we have schedule prep. We have culture checkpoints, which I think are awesome. But let's answer the question with AI that I'm not saying every IC manager and leader in the organization thinks about a lot, but they might, which is, will this fly with CEO? Or will this fly with Executive A? Or how do I know I'm not walking into a tough meeting? So you've done some work to sort of stress test what your CEO might want or participate in without having to bother him. So I'd love to see your sort of exec replicate workflows.

• 27:54Speaker 00

  Totally. So yeah, again, on the meeting side, but this is a GPT I built within OpenAI's ChatGPT. And we have this public feed in Slack, which is Feed TFS, which are basically any strategic doc that need review across the company. We've kind of centralized this in a feed for transparency, accountability, and make sure folks know why we're making certain decisions. And so the Folks were often coming to me for thought partnership of like, hey, here's my doc. Do you have any feedback on it before I share this with exec? You know, you know how Wade thinks. You've worked with him for five years. Well, what do you think about this? And I love doing that thought partnership stuff and I don't want to replace it. But again, it's not scalable and I don't want to be a bottleneck for someone to get their doc out into the world.

• 28:39Speaker 00

  And so I built a GPT that kind of thinks like, like I do and has some of the same materials of like, company values and, and norms, but it helps people sharpen these T-ups. And so sometimes it makes sure that, you know, folks come into a meeting with more confidence and their opinions are stress tested and the right data is included and make sure we make the most of those meetings that we're in. But sometimes the T-up is so clear, uh, now that we can skip the meeting entirely, which is great as well. So you can see here, like, you know, Wade said he, he tried it out, caught several things that would strengthen the work. We've got, you know, Lindsay saying, I was worried it would just tear my doc apart, but it suggested really great, simple tweaks. And so we gave it a bunch of knowledge.

• 29:24Speaker 00

  So I'll dive into that right now. So, um, this is the exec prompt GPT. I gave it a prompt here to say, give feedback on a T-up doc, which was one of the main prompts considered. And I created a fake doc, which is a very, very poor T-up, just to give an example for this. So this was a T-up that basically I just had created a really bad EA T-up doc. So this, this is like, you know, gives a really loose purpose, uh, you know, doesn't have an approver. It's like, just something we've been thinking about, doesn't have much background. So it's, it's a bad doc. So it's not, but it's not going to give you the, the most exciting feedback.

• 30:03Speaker 00

  But it goes in and again, like takes the spit off the ball of feedback and helps people, uh, you know, get more confident, but. This is saying, you know, this reads more like a jam session than a T up. You will get better feedback if you clarify these things. Let's tighten it up. And so it gives a quick read of what you have, gives feedback on how to strengthen it, to service trade offs out of recommendation. And then, you know, it gives an example rewrite even in this case because the doc was so loose on details. But it gives, you know, a couple of top fixes before the bullpen and then, which is what we call these kind of T up meetings. And then one bold coaching question. So I, I love that it does this and even gives you a suggested next step.

• 30:48Speaker 00

  Like let's, let's give a tight Wade style, one page rewrite of this T up. So it's bullpen ready. So I love that. And this, uh, this GPT is built off of the back of, I'll dive into it really quick. But it's built off the back of, uh, you know, again, our team norms, our revenue roadmap, our strategy memo, good examples of T ups, you know, Wade feedback tuning and managing up to Wade doc. So it gives like all of this context on the backend that can help simulate people's feedback. Again, to make sure they're sharper, clearer and better at unlocking decisions. So I love this one because it's again, just helps enable everyone that's happier.

• 31:32Speaker 00

  I love when the things that I build don't only help me, but then can have these kind of ripple effects within the organization. I think that's how you can become really an AI champion and transform your org is by starting with your own wins. You know, start with your own meeting prep or whatever, but then be like, okay, how can I enable the next set of folks on this? How can we make this like org wide? And so I love that. I love that this is really something anybody can use. You know, on the, I created in chat to BT for many reasons, but one of them being that I don't have context to the conversation. So folks can really feel comfortable putting all of their information in there and making sure that, you know, no one's on the backend like reviewing it. I think we can see the, I think we can see some analytics here on, you know,

• 32:17Speaker 00

  278 people have, have used this to sharpen a strategy doc. So again, it feeds back into things like my impact reviews and showing that I'm enabling the whole org. So I, I love this one as well for just making sure our meetings are more efficient, making sure I'm not a bottleneck. And then I can still provide my coaching where it makes sense and I can still have those people where I'm thought partnering on with their docs, but this helps me scale me basically and scale the execs before it gets to a meeting.

• 32:43Claire Vo?

  Yeah, and what I would say is people also love when you come to an exact meeting or a feedback session where you say, I've already checked it against our strategy or I've already tried to do a loop of this with this GPT, like just that extra effort to go through an independent loop before taking synchronous time to get feedback is both probably improving the quality of your work, but also just saving people's time and people really appreciate it. So I think that sort of initiative is also useful. And what I want to go to for our last use case is really you've extended strategic thinking through the organization

• 33:24Claire Vo?

  with another tool. So I'd love to see kind of our last strategic alignment tool that you've built using AI because I think it's a really neat one.

• 33:34Speaker 00

  Yeah, so one thing we just launched about a month ago is in Notebook LM. So this is enabled through Google and this is like the announcement we made in Slack to give you a high view of why we did this and what it is. But it's basically a strategy companion, which we know that folks have a hard time looking at this big picture strategy work sometimes and then saying, okay, how does that impact me? And sometimes it's just hard to find the answers you're looking for within all these different strategy docs, all hands, meetings. And so we gave folks this basically knowledge base. Here's a screenshot of it

• 34:18Speaker 00

  of what these look like in reality. I just cleared out the summary of our strategy to make sure I'm not like totally revealing everything here. But what's great is that we can continue to add sources over time. So you can see we've got a few dozen sources in here, which are everything from the top level strategy doc to all hands we've had to transcripts from other meetings we've had around strategy to every org's strategic action plan. And so folks can go and interact with these, but they can also interact with this in a chat capacity and ask it anything they want. So here's an example of it in real life. So I'm saying, I just gave it a Simple prompt of as an executive assistant,

• 35:02Speaker 00

  how can I contribute to Zapier's 2026 strategy? And it's saying, oh, that's a great question. We, I think you can help with champion clarity, focus and speed. Make sure we're spending time on the right priorities. You know, make sure that you're driving internal AI transformation. And so I love that it gives me, you know, some of that and connects back to the sources. But there's also fun things here like this. It auto generates a podcast. So I don't know if I'm fully sharing my computer sound here, but I'll play it for a couple of seconds. This is fully AI generated just based off of the back of these sources. So it talks like this.

• 35:38Speaker 02

  Welcome to the deep dive. Today, we're really giving you the essential shortcut here. Absolute alignment on the strategy. We're pulling the core ideas straight from the Zapier 2026.

• 35:49Speaker 00

  And all this is AI generated of things you can create. So it really helps make the strategy interactive instead of a static doc and static thing. And helps folks get their questions answered again before going to their leader or going to someone in their org. And so I love this for just enabling folks to be able to connect their work and be able to query this over time. And it's something that we can keep updated and, and make sure that it has the most recent information. So everyone can, can get value out of it.

• 36:19Claire Vo?

  So Courtney, I love these use cases. What I keep reflecting on is people are like, oh, EA's, EA's are going to go in this age of AI. And I'm like, have you worked with a fabulous EA? Because the second they automate one task, they figure out 10 more that are so high leverage for the organization. Culture carrying behaviors, strategic like communication, operational efficiency. Like you are just demonstrating that this can happen at a next level. And so zooming back out, what we saw today was everything from helping yourself dig, dig out of a busy calendar with meeting prep to enforcing your cultural goals and leadership norms through always on feedback.

• 37:06Claire Vo?

  Checking feedback ahead of asynchronous meetings. You can make sure it's aligned with both how executives want to receive it, but also kind of the important business initiatives and goals of the company. And then finally, how you can take all this content that's always jet. I mean, I just don't know an organization that is not consistently writing strategy documents. Just one strategy document to the next, big strategy document, little strategy document, strategy update, strategy goals. And so just creating a purpose-built repository for that information that can then be accessed in a multimodal way for people to learn, align their work, be educated, all that kind of stuff, I think is super awesome.

• 37:50Claire Vo?

  So these are really, really great workflows. We're going to do a quick lightning round and then we will get you out of here. I think the first thing is kind of this thing I said, which is a lot of people think your role is going away or they're afraid of AI taking over this role. And I think you're showing actually you're just becoming so much higher leveraged. You don't have to be having so much more fun. So tell me, how do you respond to that feedback around AI? And in particular, the kind of EA role?

• 38:23Speaker 00

  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. There is simply too much to do. I think there's the, one of the biggest problems that EA's have is we always have more work that we want to do than we have time for. And so that's what it's consist, I'm consistently hearing, I don't have enough time. I don't have enough time. Like this is how we can do that. And I, I mean, to, I don't like talking about myself very much, but to humble brag and tie this back to real impact, I've, I've gotten three promotions since I've been here last year and been able to work myself out of multiple roles.

• 39:05Speaker 00

  And, you know, I think that this is how you can do that. You can be this really great AI partner for your company and make sure that you're at the forefront and take all that busy, manual, repetitive work off your plates. You can be, do the human stuff, the fun stuff, the stuff you like to do, the stuff that's creative and, and relationship driven and those things that we wish we had time for. And so I think that it's just. It's such an exciting thing for our role and I don't think it's going to take our jobs. There may be, you know, certain admin things it does take eventually, but it's not going to take the whole thing.

• 39:45Speaker 00

  Think about this couple, what we do, our whole job is to be, you know, all wide across the org and a little bit of depth in each area. But now you can be wide across the org, have more depth and have more time for, for projects and special things that you can do for your team.

• 40:00Claire Vo?

  Okay. So speaking of special things, you have been one of the people I think is closest to answering this question, which is how close do you think we are to replicating executives? How happy is Wade with your AI versions of him? And do you think we're actually working towards a world where those get quite high fidelity relative to individuals, preferences, feedback, thought process, communication process?

• 40:30Speaker 00

  Yeah, it's a great question. I think there are certain parts where we're getting kind of close on. So over time, you know, I used to think of myself as a clone of Wade in certain instances. I could write columns like him. I could run his schedule. I could do things like him. And now we've, we've got a clone of AI tools that are helping me do things like him too. So there's certain parts of, of what he thinks and does that we're pretty close to replicating with these AI tools. What I'm not sure of is Wade or any exec, but speaking just for Wade here, he's a constant learner. He is, he is ingesting so much information, learning new things, trying new things, building every day, like hands on keyboard.

• 41:15Speaker 00

  Like the amount he can grow and learn, like the pace of that is so high that I wonder how you could keep these models up to date with that because like, I, you know, I know they, they update fast, but like, how can you, how can you grow at, at the pace of, of someone's brain and how? Your evolving does change, your thought process does change over time. So there's things, old things in Zapier history where someone's like, "Oh, I heard Wade said we'll never do XYZ." And he's like, "That was an old decision, that was an old decision." Like, I have so much new context that's changing the way I think. And so for a leader who's constantly adapting, changing the way they think, and using new information to help them make smarter decisions,

• 41:59Speaker 00

  how do you replicate that part of it? I don't know. There's things, but the consistent side, like how he writes internal memos, or, you know, how he writes certain things are, we're pretty close to replicating.

• 42:12Claire Vo?

  Okay, and then final question. When AI Wade is not replying to you the way you want, or you're not getting what you need out of a specific prompt, what is your prompting technique? Do you, are you an all caps girl? What do you do here?

• 42:28Speaker 00

  Oof, I'm not an all caps girl. I'm a ramble. So I love the dictate feature and I love to talk to it. And I give it feedback very, very direct. I'm just very direct as a person and demanding. And so I do that. I'm like, "I don't understand why you're doing it this way. Show me a reasoning of why you did it that way, because I told you to do this and this is what I'd like to see. And here's the feedback I have." And I just ramble and give it, you know, everything I'm thinking. I think folks like sometimes don't know where to start and try to give it this very specific feedback and write it. No, just like, give it top of mind, pretend it's someone with no feelings, and be demanding. So I don't know, hopefully the AI robots don't come for me. I do say please and thank you sometimes, so.

• 43:10Claire Vo?

  Good. Good. AI, AI, we know you have feelings. I don't know. It's 10 years. Yeah. Okay, Courtney, this has been so great. Where can we find you and how can we be helpful?

• 43:27Speaker 00

  Yeah, so feel free to connect with me on LinkedIn. I love posting about additional use cases, things I'm building, workshops we're having. But I'd love for y'all to check out this EA Exec Ops AI Playbook I just made recently, which has like, you know, six different categories of things that the EA's do consistently. And in different ways, we've automated that and ways that folks can replicate it and give me feedback on it. I'd love to hear what we're missing, what we can build out more. I'm looking for new things to build all the time. So I love, I love getting feedback from the community on what would be helpful.

• 44:00Claire Vo?

  Awesome. Well, thank you for joining us.

• 44:02Speaker 00

  Yeah, thank you, Claire.

• 44:04Claire Vo?

  Thanks so much for watching. If you enjoyed this show, please like and subscribe here on YouTube, or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at howiaipod.com. See you next time.