How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop)

1. 0:00 – 2:42

   Intro

   1. HGHilary Gridley0:00

      My favorite prompt in the world is, I will say, "Be 100 times more specific."

   2. CVClaire Vo0:05

      It's really interesting that some of the ways that we work as managers, where we're evaluating work, really have natural translations into using some of these AI tools as well.

   3. HGHilary Gridley0:14

      The GPT is never gonna replace you. It's never gonna be as good as having a really good manager, at least not in the next six months. Maybe beyond that, I can't predict. But it can get you far. It can take a lot of time off your plate in terms of going from the zero to the 60 or the 70%. And if you can get all of that work off your plate as a manager, the amount of leverage you gain by being able to invest that time back into other things, whether that's more strategic work or more hands-on coaching, is really remarkable, and it's why I get so excited about this. [upbeat music]

   4. CVClaire Vo0:44

      Welcome back to How I AI. I'm Claire, product leader and AI obsessive, here on a mission to help you build better with these new tools. We've spoken a lot about how AI is going to transform how the individual contributor gets work done, but not so much what AI means for the manager. That's why you're gonna love this conversation with Hilary Gridley, Head of Core Product at Whoop. Hilary has some really creative techniques for scaling yourself as a manager and giving your team access to your expertise, all using GPTs. Let's get to it. This episode is brought to you by Orkes, the company behind open source Conductor, the platform powering complex workflows and process orchestration for modern enterprise apps and agentic workflows. Legacy business process automation tools are breaking down. Siloed low-code platforms, outdated process management systems, and disconnected API management tools weren't built for today's event-driven, AI-powered, cloud-native world. Orkes changes that. With Orkes Conductor, you get a modern orchestration layer that scales with high reliability, supports both visual and code-first development, and brings human, AI, and systems together in real time. It's not just about tasks, it's about orchestrating everything: APIs, microservices, data pipelines, human-in-the-loop actions, and even autonomous agents. So build, test, and debug complex workflows with ease. Add human approvals, automate back-end processes, and orchestrate agentic workflows at enterprise scale, all while maintaining enterprise-grade security, compliance, and observability. Whether you're modernizing legacy systems or scaling next-gen AI-driven apps, Orkes helps you go from idea to production fast. Orkes, orchestrate the future of work. Learn more and start building at orkes.io. That's O-R-K-E-S dot

2. 2:42 – 4:14

   Creating GPTs that think like you

   1. CVClaire Vo2:42

      I-O. Hilary, I'm so excited about our conversation because you have told me you've created, and I quote, "a billion GPTs." So what's the real truth? How many do you think you've actually created? [chuckles]

   2. HGHilary Gridley2:55

      W- what is a billion minus one, is probably right. I've probably made 100, but I only use a few dozen of them. I feel like there is a learning curve of having to make a bunch, and then I got it really tuned in, and now I can... I have a pretty good hit rate on when I make them. Uh, but I would say I have dozens that I'm, I'm regularly using with my team.

   3. CVClaire Vo3:13

      Okay, great. And one of the ways you use these is to scale yourself. So I think you've told me you've gotten really good at getting these GPTs to think and act like you. Can you walk us through how you a- approach that?

   4. HGHilary Gridley3:26

      I think one of the best parts of a really good manager is when they're really good at articulating exactly what good looks like or exactly what excellent looks like, and it's actually really hard to do, right? Like, you've probably had managers who maybe they knew what it meant in their head, but they weren't necessarily able to say it in a really clear way, and it can be really frustrating, uh, when you're trying to figure out what good, what good means. And so one thing that I try to do when I'm thinking about the GPTs I wanna make, I always start with, "What does good mean to me?" And so how can I get this AI to think like me? Because then I can turn it into a tool that's gonna be useful for, for me or for my team. And there's a couple ways to do this. So there's an easy way that's a little bit more work, and then there's a hard way that's actually less work. So I'm gonna start with the easy way,

3. 4:14 – 12:57

   Demo: Reverse engineering a recommendation algorithm

   1. HGHilary Gridley4:14

      and basically, I think of this as kind of like reverse engineering a recommendation algorithm for yourself and for your own preferences, which is just starting to collect examples of good and bad, and just keeping a list. And so I'm gonna make a GPT eventually that's going to be a slide deck evaluator. But I need to start by having a clear point of view on what a good slide deck looks like, or even good slides. And so here, these are just, like, a random list of slides that I've collected. A lot of these are kind of a before and after, so if you're trying to make something like this, and you do a lot of editing of a certain thing, whether that's emails or documents of any kind of artifact, you can sort of keep all the befores and just keep those stored in one column, and then all of the changes that you make, keep those in another. And you're implicitly doing a lot of pattern matching there when you're sort of going from one to the other. That might not always be obvious to you, but it's gonna be really obvious to the AI, and I think that's really cool. So this is sort of my before and after, but you can do it for anything. And literally what I'll do for this, this is comically low tech, I think, is I make it a PDF. I think I'm like the AI PDF queen. I don't think anyone-

   2. CVClaire Vo5:27

      [chuckles]

   3. HGHilary Gridley5:27

      ... uses AI as much as I do, uh, with PDFs. And so I just upload it. Simple. And I say, "Here are some examples of slides. In one column, the slides are not good, and in the other column, I have edited them and made them good."

   4. CVClaire Vo5:52

      I love this prompt engineering right how- here, which is [chuckles] left side, bad-

   5. HGHilary Gridley5:56

      [laughing]

   6. CVClaire Vo5:57

      ... right side, good. Like, very simple. [laughing]

   7. HGHilary Gridley6:01

      ... It's so funny, you get all this advice that's like your prompts have to be super, super specific, and I get there, but I actually don't like being really specific at first, because s- I'm trying to, like, tease out specific things from just my examples, and I don't wanna bias it.

   8. CVClaire Vo6:15

      Yeah.

   9. HGHilary Gridley6:15

      So I'm like, "I kinda want the AI to start by interpreting this in ways that I might not even be able to predict," and then I'm gonna get in and tune it, and that's when I get super, super specific. But yeah, my initial prompts on anything are always just, like, "I don't know. What do you think?" So I have edited them good. Can you help me articulate the criteria I am using to determine what is good and bad based on these examples? And sometimes what I'll do, 'cause I'm kind of paranoid that sometimes it just makes stuff up that I don't want it to, is I will specifically say, "Only use these examples."

   10. CVClaire Vo6:51

       In all caps.

   11. HGHilary Gridley6:52

       Just to be safe, you know? I'm very superstitious with the AI. I'm very like... I get a vibe that it's gonna act a certain way.

   12. CVClaire Vo6:59

       Yeah.

   13. HGHilary Gridley6:59

       So it's thinking, and what it's gonna do really well is it's gonna start to articulate the differences that it is picking up between the good and bad examples. And you can give it some, you know, kind of straightforward ones, but you can also get as specific about this as you want. And so even just looking at this, like, it's talking about core criteria for good slides. I'm reading this, and I'm like, "These are actually things that I think are really important." So clear, succinct headlines that convey a point, one idea per slide, intentional visual, visual hierarchy, visuals that support the point, not decorate it. I don't even really know what that means, but I like it. Clarity over jargon. And I'm looking at this, and I'm like, "Yeah, th- this is the kind of thing that when I'm editing [chuckles] a slide, this is exactly what I'm looking for." So the next thing I'm gonna do is, usually this is where I do start dealing- uh, dialing in to try to get it really, really specific, because I'm kind of a stickler for using really specific language to make sure there is no room for ambiguity. And my favorite prompt in the world is, I will say, "Be 100 times more specific." [laughing]

   14. CVClaire Vo8:01

       I love it.

   15. HGHilary Gridley8:01

       I'm really into, like, quantifying in that way. Like, sometimes if you say, "Be more creative," it'll, like, go kind of zany when you just wanted it to be, like, a little bit, like, more fun, and so I'll say, "Be 20% more creative," or, "Be 1000% more creative," and you can really kinda tune it in that way, too. All right, so now it's being super specific about, uh, what it is that a good slide looks like to me. And as you can see, it is already starting to articulate these in terms of criteria. Criteria are what we're trying to get to, because when you have criteria, you could stop there, and you would already be a better manager because you're able to communicate the criteria that you care about when you're evaluating something. But there's no reason to stop there, because we have AI, and we can make bots of ourselves, and they'll do that work for us. And so we're gonna use this to build the prompt that's eventually going to become a GPT that can evaluate, uh, this for us.

   16. CVClaire Vo8:50

       Well, and I have to call out, you're using that word, evaluate, and it really does look like you're building criteria for AI evals. What is a good output? What is a bad output? So it's really interesting that some of the ways that we work as managers, you and I, where we're evaluating work, really have natural translations into using some of these AI tools as well.

   17. HGHilary Gridley9:12

       That's such a great point. It is- you get kind of eval-pilled, and like, you start- I feel like I'm going back and forth now between seeing, like, the, uh... Like I talked about kind of a recommendation algorithm for the way that you think. I'm like, the more I use AI, the more I sort of use the metaphors of how these algorithms work in terms of how I think about my own management style, which is kind of freaky.

   18. CVClaire Vo9:34

       [laughing]

   19. HGHilary Gridley9:34

       Uh, but it's been really interesting. And so what I'll do here is I usually don't just take this at face value. I mentioned earlier that there's a, an easier but, uh, longer path, and a harder and shorter path. I call this the easier and the longer path, because it requires you kind of pulling together this list of things over time, which you kind of have to decide you wanna do one day and then sort of passively collect for a month or so, and then you can go ahead and put it in. The harder but shorter is you just start from scratch, and you just kinda chat with it, and you're like, "Here are some of the things I care about. Here's what really bothers me when I see this. Here's what I love when I see this," and it'll still also get it into this format. And usually what I do is a hybrid of both. So I start with, you know, "Here's examples of good and bad," and then I get to this point, and I'll go back and forth and say something like, uh, "You know, number seven is, uh, less important to me than number eight," or, "I think we might be missing X." And I'll blend my own thinking on this with... I always los- just love to just zoom out a little bit and say things like, "What am I missing?" Again, I'm like, my prompts are either, like, the most specific thing you've ever seen in the light- in your life or, like- [laughing]

   20. CVClaire Vo10:44

       ...

   21. HGHilary Gridley10:44

       - the most vague thing you've ever seen in your life, and I have no middle ground. [laughing] And so I'll go back and forth, and I'll kind of read these and be like, "Okay, yeah, some of these I like, some of these I don't." And eventually what I'll do is I might have an opinion about it, or if I'm feeling lazy, I'll just say, "Pick the most important criteria and explain your reasoning." And this is another thing I'm doing a lot of, like, diverging, converging, diverging, converging, and trying to balance it giving me its point of view and me in my own head thinking, "Do I agree with that? Do I disagree with that?"

   22. CVClaire Vo11:13

       Yep.

   23. HGHilary Gridley11:13

       And eventually I get to something I like, and so this is when I say, "Okay, I'm going to make a GPT about this." And the reason I wanna make a GPT about this is, that way, anytime anyone on my team wants feedback on slides, I can say, "Can you put it into this doc and get feedback on it, or into this GPT and get feedback on it? And then I will review it." And so the GPT is never gonna replace you. It's never gonna be as good as having a really good manager, at least not in the next six months. Maybe beyond that, I can't predict. But it can get you far. It can, it can take a lot of time off your plate in terms of going from the 0 to the 60 or the 70%. And if you can get all of that work off your plate as a manager, the amount of leverage you gain by being able to invest that time back into other things, whether that's more strategic work or more hands-on coaching, is, is really remarkable, and it's why I get so excited about this.

   24. CVClaire Vo12:04

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4. 12:57 – 15:23

   The value of articulating taste

   1. CVClaire Vo12:57

      Well, before we move to GPTs, which I think are such an interesting way to scale this, I just have to pause and say, this workflow in and of itself seems like it's so useful for managers. And I'm reflecting on this, this time early in my career, where I had a manager who could see a design, I was a designer at the time, and he would look at it and say, "Make it look like a thing. Make it look like a thing," and was not able to clearly articulate... Knew, had taste, had intuition, but could not articulate what he wanted the thing to look like. I knew it. He was- he wanted a stroke around it. That's what he wanted.

   2. HGHilary Gridley13:33

      [laughing]

   3. CVClaire Vo13:33

      But I think, I think this ability to articulate taste, articulate a rubric, applies in a management world to so many things. It applies to slide design, it applies to evaluating candidates when you're interviewing-

   4. HGHilary Gridley13:47

      Mm-hmm.

   5. CVClaire Vo13:47

      ... it applies to how you evaluate talent or how you think about writing. So I just even think this workflow of creating your personal rubrics and articulations for the things that are important to you, whether or not you move into a GPT, which I'm excited to see, is really useful.

   6. HGHilary Gridley14:01

      I couldn't agree more, and it's so- like, as a, as a leader, you have years of experience of getting these reps that over time build your judgment, and you get this in your head, and you're just like: I just wish I could get this out of my head and give it to people in a way that is not just, like, clear, like what you're saying, but in a perfect world, you would sit down and explain, right? Like, "When I say a thing, here's what I mean, and also here's why that's important, and also here is why what you are trying to do i- i- is lacking in thing-ness." But that is extremely time-intensive to do and requires a level of brain space that I think a lot of managers struggle with because we all get the spaghetti brain of-

   7. CVClaire Vo14:41

      Yep

   8. HGHilary Gridley14:41

      ... being pulled in a million directions. So, like, I couldn't agree with you more, and I'm just- I get so excited about the potential of this in terms of how it can actually help be an accelerant for junior people, too, because you can turn it into something that is, is not just like explaining the criteria, but going even beyond that.

   9. CVClaire Vo14:57

      Yeah, and what, what a improved employee experience. You know, you have this frazzled [chuckles] boss who's busy-

   10. HGHilary Gridley15:03

       Exactly

   11. CVClaire Vo15:03

       ... that gives you quick feedback and says, "I need you to do X, Y, and Z," versus this, like, endlessly patient and clearly articulate, always available, you know, version of your manager that can give you just a much better collaborative experience than, than is maybe possible sometimes. So let's show, show, show us how you use GPTs to scale,

5. 15:23 – 19:09

   Demo: Creating a slide deck evaluator GPT

   1. CVClaire Vo15:23

      scale that.

   2. HGHilary Gridley15:24

      All right, let's do it. So I want to create a GPT that, as I said, is going to be an evaluator for slide decks, and I'm gonna show you a generic version of this first, but the reason when I say I've made a billion GPTs is because y- you can take a generic version, and then you can start to make it even more specific for specific people who need to work on specific things. And so I'm gonna show you how to do that, too, and I think both are very cool. From here, it's actually pretty straightforward. All I'm gonna do now is ask the GPT to write a prompt for me that I'm going to use to create the GPT. And so what I'll usually do, so this is sort of the lazy version of it, but I'll- I like to say, uh, "My job is to create a GPT that can evaluate slide decks for people on my team using my specific criteria that I care about. It's really important to me that this GPT explains the criteria, why it matters, and gives the user specific feedback on how to improve. Your job is to write the prompt for it." This is another prompting thing that I have had a lot of success with, is I often think of, like, what is the objective? Of getting even more specific of what is my job and what is your job? Because I think the more clarity you give the AI on that, the better kind of outputs you get. Because it wants to help you, but sometimes it can get confused about what you're trying to do and what you need it to do. Uh, so I like, I like to give us both jobs.

   3. CVClaire Vo16:56

      And I have to call out, you put "you're" in all caps, so it really knows what its job is. [laughing]

   4. HGHilary Gridley17:03

      [laughing] I'm, like, probably the only user who wants this, but I'm like, "When are we gonna get, like, bolding and italics and like..." Like, I'm trying to express myself in these prompts-

   5. CVClaire Vo17:12

      Yes

   6. HGHilary Gridley17:12

      ... you know what I mean?

   7. CVClaire Vo17:13

      I know. Some, like, emoji, you know? You know I'm serious-

   8. HGHilary Gridley17:17

      Mm-hmm

   9. CVClaire Vo17:17

      ... you know I'm mad, all that kind of stuff.

   10. HGHilary Gridley17:19

       Exactly, exactly. [laughing] Yeah. Um, so yeah, so now we have a prompt, and it's probably a good start. I already like it, that it starts with, "You are ruthlessly helpful," because, of course, the hard part about this is you need the GPT to, like, not tell people something's good when it isn't good, and it will do that because, again, it will forget its job. But if you tell it its job is to help people improve, then it, it can sort of rewire it a bit. Oh, I s- I like this: "You're going to evaluate the slides the same way a leader does, with zero tolerance for vagueness, visual clutter, or weak narratives, but you also explain why each"... Great, great. All right, I like this already. So I'll read through this. One thing I'd like these to do... I can't tell if this is explicitly doing it, so I'm gonna ask it to. Uh, I'm gonna say, "The output needs to start with a one through five rating on each criteria before diving into specific-... the examples of what is or is not working. And again, I'll go back and forth on this for as long as I feel like I need to before I get a prompt that I'm happy with. Um, but not, not for too long. And I always- I hear this from people all the time. They're like: "How do you have the time to make all of these?" And I'm like: "Just make them, get them out, and see which ones people actually use," because the ones that are helpful go viral, and the ones that are not helpful, nobody touches, so there's no point in trying to make them really good. So I'm just gonna go ahead and take this, and we'll assume that it's good. We'll find out. We're gonna test it. So I paste that into the instructions here, uh, and this is just in creating a new GPT.

   11. CVClaire Vo18:53

       And just a quick pause for folks that maybe aren't on the screen share. A GPT is sort of, uh, a specialized version of ChatGPT that's loaded up with special instructions and files and things like that for, for a specific use case, so they're super useful.

   12. HGHilary Gridley19:08

       Thank you.

6. 19:09 – 21:23

   Testing your new GPT

   1. HGHilary Gridley19:09

      Yes. Uh, we're gonna name it. Let's call it the Deck Doctor. I like to give them fun names. I think you wanna make all this fun, right? What's the point otherwise? And then I don't actually like to test it in this box, just because this box being the preview box, I like to have records of all those conversations, and so I'm just gonna go ahead and create it, view GPT, and then I'm just gonna drag a deck that I made.

   2. CVClaire Vo19:34

      Is it a PDF?

   3. HGHilary Gridley19:35

      It is a PDF. Of course, it's a PDF.

   4. CVClaire Vo19:37

      [laughing]

   5. HGHilary Gridley19:37

      I'm a PDF queen. It's a PDF of a deck called... that I made, called, uh, Self-Promotion for People Who Hate Self-Promotion, and I'm just gonna run it.

   6. CVClaire Vo19:45

      That's one of the nice things, is you don't have to re-prompt it 'cause this is all saved in there.

   7. HGHilary Gridley19:50

      That's exactly right. And one thing I really like about that, and why I think it's such a good tool for managers to use with their team, is I do think there's a pretty sharp learning curve to learning how to prompt well. And so when you're trying to upskill people in AI, and they get in there, and they're trying to prompt, and they don't really know what they're doing, and they start getting really bad outputs, it's really discouraging, and this sort of takes all that away 'cause you've put it in, and so literally all somebody has to do is upload the artifact and hit Enter, and then they get this helpful output that they can use, and there's nothing that they have to do. So it can hook people into seeing the usefulness of something and the reward of feeling like they're getting something useful out of it, uh, without the punishment of, "Oh, I'm not very good at prompting, and this is pretty frustrating." And so what this will do is it'll just take you through for each of the criteria, it's giving a one through five score. So headline clarity, it's giving a four; one idea, it's giving a five; visual alignment, it's giving a four, and so on. And then you can go down into each one, and it'll explain. "Headline clarity: four out of five. The headline is clear, punchy, and audience-specific. It signals a precise target and hints at a problem-solution framing. One minor tweak, clarify the benefit or result. Example, how to promote without selling your soul, or a better way to self-promote for people who hate it." So, and, and then it's, it's sort of, uh, indicating to which ones are good, ones which, which ones need, need the most work. And so I would call this an okay response. I would probably go back and forth on this a few times and just try to make this better and better, but I think it's a pretty good

7. 21:23 – 23:42

   Scaling GPTs across your team

   1. HGHilary Gridley21:23

      start.

   2. CVClaire Vo21:23

      So how do you use these with your team? Are you sharing, you know, lists of GPTs? Do they, do they know which one to go to? How do you scale this out? So it makes sense to me as an individual, but what are you doing as a manager to get engagement with these?

   3. HGHilary Gridley21:37

      So usually what I'll do is I might beta test it with one person. So I'll give it to one person on my team and say: "Hey, try this out. Let me know if you think it's useful." If I never hear from them again, I know it wasn't that useful, and that's on me to make it better. If I do hear from them, and it seems like they're really valuing it, then I might give it to more people. But I mentioned earlier that one thing that's really cool is you can kind of tailor it to very specific types of feedback that different people want. So sometimes I'll be having a conversation with someone, and we'll be saying something like, uh, maybe I'm going through a deck with them, or maybe we just got out of a meeting, and I was like: "Your presentation was great, but the CEO asked some questions that we probably should have better anticipated, and it didn't seem like you had a clear answer ready." And so one thing that I might do is, uh, make a GPT that specifically you could upload your PDF here and give it a prompt that says something like, "Come up with, you know, three questions that people with each of these job titles would ask upon seeing this, and give me some suggestions for how I could think about answering that." And so I, I give the feedback, and then I could make a little GPT that's, okay, this is now something that you can practice with for that specific feedback that we've already talked about.

   4. CVClaire Vo22:47

      Well, and I'll loop back to your original recommendation, which is, if you're like me, every meeting has a notes section where it lists all the questions that people asked during the meeting, especially if you're using one of these AI note-takers, and so you could take that and say, "These are the types of questions I'm already getting."

   5. HGHilary Gridley23:03

      Mm-hmm.

   6. CVClaire Vo23:05

      Uh, okay, that's... Man, I want you to be my manager. [laughing] You got good, good ideas, or maybe I want you to manage me.

   7. HGHilary Gridley23:10

      ... You know what people say about this, though? What's amazing is I'm- like, I'm literally using PDFs. Like, I'm just scratching the surface of what these things can do. I don't even have this yet hooked up into my product analytics suite. If I did, I would... You know, I'd make little GPTs that drill me on how many people opened Whoop Coach today, how many people have read Recovery today? And I'm excited because I think our analytics team is working on some things like that, that are really gonna accelerate that. But it's just, I'm already getting so much utility out of this, and I still feel like I'm using kind of the most basic workflow

8. 23:42 – 30:22

   Demo: Using AI to improve your writing

   1. HGHilary Gridley23:42

      around it.

   2. CVClaire Vo23:43

      Okay, so let's do one more use case. Show us how you follow this AI process for something I know you value, which is improving your writing.

   3. HGHilary Gridley23:52

      Sure. So one thing I love to tell my team is whenever there's a, a meeting that they wanna get invited to, and they're like: "Oh, how do I get invited to that important strategic meeting where all the big decisions happen?" I say: "The way you get invited into these meetings is you get pulled into them. You don't push your way in, and you get pulled by showing evidence of being able to contribute to strategic thought and move it forward in a way that's really helpful. And the easiest way to do that is not waiting until somebody asks you or invites you into the room-... write up your point of view. Write it up really compellingly, make a really strong argument, and then send it to me, and if I think it's good, I'll send it to other people. And I've seen this happen for people, where they write something really well, and all of a sudden it starts going viral, and they're getting invited to all the important meetings, and it's very exciting. And AI can really help with that, and so I'm gonna show you how I use AI to improve my writing in this way. And I'll often do this in a one-on-one with someone on my team. I will take them through this process and show them what I'm doing. And I'm gonna use the example of a newsletter that I write. And so usually what I'll start with here, this is like a, a first draft, and if... When I say first draft, I mean I have just poured whatever is in my head onto the page. Um, I like to say with writing in AI, like, I want it to start with me, and I want it to end with me, and what happens is, in between is between me and the robot. Um, and so I'll say, you know, "Here's my first draft," and I say, "Here is a poorly written first draft of a newsletter I'm writing." And usually what I do is I, I first wanna validate that I actually am making sense, and instead of asking it, "Am I making sense? Is this good?" I will ask it, "Can you succinctly express my thesis back to me, and my main supporting points?" This is a newsletter I wrote about, uh, basically, like, how AI is reshaping the job market and what you can do to, uh, stay on top. And the reason I do this is because if I just ask AI, like, "Do you think I'm doing a good job with this?" It, it always tells me yes, which I find very vexing. But if I ask it, like, "Can you restate what I'm saying back to me?" Then I can tell, like, am I expressing myself clearly or not? So I'm reading through this, and I'm like, "Okay, this is basically what I'm trying to say. Good, good, good." I might use a 100% X more specific type prompt here, just to make sure, but that's basically what I'm doing. So I'm looking through this, and it's telling me, "AI is reshaping knowledge work faster than people expect, creating a future where success will depend not just on raw talent, but on the ability to wield AI effectively, build personal distribution, and deliberately choose how to compete." Uh, and I'm like, "Okay, that's all right, but that's a little vague," so I might ask something like, "How can I make this more compelling?" And this is not because I just want the AI to do this for me, like I'm just gonna take it wholesale, but it's like talking to a friend when you're kind of workshopping an idea, and you're sort of seeing what they, they have to say, and you're kind of like, "Okay, I like this. I don't like this," but either way, it, like, expands your thinking, and it makes you think more about it. So it's sort of giving me a mix of, like, lead with urgency and clarity. Okay, so this is actually giving me more like, uh, like, content advice, where what I want is to make my point more compelling. So what I might say here is, "What blind spots might I have as I'm talking about this?" And sometimes I'll throw in a, "Given what you know about me," although I'm always kind of nervous. Maybe I won't do that one being recorded. [laughing]

   4. CVClaire Vo27:21

      [laughing]

   5. HGHilary Gridley27:21

      So yeah, it's calling out that, like, I'm probably over-indexing on elite knowledge workers. That's fair. Underplaying structural forces, also fair. Giving me, like, very clear watch-outs, like-

   6. CVClaire Vo27:32

      Mm-hmm.

   7. HGHilary Gridley27:33

      ... you know, I'm, I'm talking about it, it says I'm equating quality with virality or monetization, and that's a wa- that's valid for market success, but a more nuanced take could explore the tension between artistic integrity, utility, and algorithmically optimized output. I think that's totally fair. I care about all that stuff. But basically what I'm doing is I'm just using this to beat my idea up. So I do that for a while, and then I might say, like, "Okay, can you rewrite my, uh..." And I'll tell it, like, "I don't like any of your ideas. Can you rewrite my original post, but structure it in the way that will best enhance clarity?"

   8. CVClaire Vo28:12

      We got put in an A/B test, y'all, so now we're getting two versions of how to improve-

   9. HGHilary Gridley28:17

      [laughing]

   10. CVClaire Vo28:18

       ... this article. So we are truly in the AI multiverse right now.

   11. HGHilary Gridley28:22

       Yeah.

   12. CVClaire Vo28:23

       And somehow we're gonna [laughing] have to compare these.

   13. HGHilary Gridley28:25

       I'm not, I'm not gonna do that.

   14. CVClaire Vo28:27

       Are we still in the world where left, good-

   15. HGHilary Gridley28:30

       Right, exactly

   16. CVClaire Vo28:31

       ... right, bad?

   17. HGHilary Gridley28:32

       I, I apologize to the fine people at OpenAI, 'cause I'm about to just pick the one on the left no matter what it says. But anyway, so I'll do this, and then basically I'll eventually get to a point where I say... I do a lot of, like, "Rewrite this for clarity. Rewrite this for clarity," and then I go back through, and I rewrite everything in there myself. So there's nothing that the AI is writing that is making it into my final post, but it's forcing me to check my self in terms of the ways that I wanna communicate that are not clear or are maybe getting a little bit too precious. It'll edit those out, and then I can choose where I wanna put those back in and how I can make sure that at the end of the day, it's still me, it's still coming from my seed of the idea. Um, and so this is what I show my team for, like, if you've got a point of view on something, type it up, get some help, beat it up, assume that it's wrong, and try to get the AI to help you make it right, as opposed to assuming that it's right and getting the AI to validate that, and that's basically how I use it for writing.

   18. CVClaire Vo29:24

       So if I could recap, 'cause I thought there were a couple really great tips in here. You put in a rough draft. You, instead of asking good or bad, which often these GPTs, especially with the recent 4o release and then unrelease, are inclined, positively inclined towards your output, you say, you know, "How do you understand this? Do you understand this?" Because you have a good understanding of it, so you're trying to understand if that's coming through. Prompting it for how to make your writing, I love this phrase, make your writing more compelling, and so that's a really helpful phrase, especially in a business context, where people have great ideas and don't know how to communicate those ideas in compelling ways. And then the last tip, which I don't know if people are gonna think is a feature or a bug, but basically how to use AI to get invited to more meetings. I don't know [laughing] if everybody-

   19. HGHilary Gridley30:11

       No, the cool meetings. The cool meetings.

   20. CVClaire Vo30:13

       Oh, the good meetings. Okay.

   21. HGHilary Gridley30:14

       [laughing]

   22. CVClaire Vo30:14

       So increase your ratio of cool meetings-

   23. HGHilary Gridley30:16

       Yeah

   24. CVClaire Vo30:16

       ... versus boring meetings. Well, how-

   25. HGHilary Gridley30:18

       You can, you can decline the boring meetings 'cause you're too busy with the cool meetings.

9. 30:22 – 36:08

   Lightning round and final thoughts

   1. CVClaire Vo30:22

      Perfect. Sounds amazing. Well, Hilary, I think you've just shown us so much on how a manager can scale themselves, how teams can get access to better quality coaching, and how you can make your ideas go viral by making them more compelling with AI. So let's drop into a lightning round and get you back to your bazillion and one GPT that you're gonna create.... So the first thing I wanna ask you about quickly is, you and I share a very similar point of view, which is we're very leaned in into this moment of AI. We're clearly both personally investing in skills. But we also look around and see that a lot of women are being left behind a little bit in this moment, and have some concern about that. So I'd love for you to just touch on some of the things that you're thinking about in terms of the job market, in terms of learning this technology, and who's really benefiting, and who needs to really pay attention.

   2. HGHilary Gridley31:13

      Yeah, it's so interesting, because I saw this study from the Norwegian School of Economics about how, uh, women are getting left behind by the AI adoption curve. Uh, and the study said that women, especially high-achieving women, were some of the least likely to adopt these new AI tools. And that kind of stopped me in my tracks, because I just- I can't imagine, uh, not having these tools at my disposal. Like, the, the degree to which they have raised the ceiling on what I think that I'm capable of doing, or what I think my team's capable of doing, really can't be overstated. And so that really concerns me, and I love getting women into this. I t- I just... I have so much fun with it, and I think if I could get more women to see that it doesn't have to be this, like, super serious bro thing. Like, you and I are out here, we're talking to the AI people. There's a lot of men-

   3. CVClaire Vo32:04

      Uh-huh.

   4. HGHilary Gridley32:04

      And so I hope, I hope the women come join, too.

   5. CVClaire Vo32:07

      Me-

   6. HGHilary Gridley32:07

      Or maybe we, you know, maybe we go over here, but as long as, as long as we're getting in with it.

   7. CVClaire Vo32:11

      Me, me, too. I cannot agree more. Well, on that topic, I also wanna ask you, what are some underrated uses of AI that you have? Maybe not work-related, maybe work-related.

   8. HGHilary Gridley32:22

      I like to say that the AI is super feminine coded, and so it's really funny to me that... I mean, not funny, it's kind of sad, that it, it kind of has this tech bro reputation. 'Cause I'm like, "The AI is girly," and I have these girly use cases that I'm like, I have so much fun with. And so, uh, one of them is if I'm reading, uh, if I'm reading a book that's kind of a hard book to get into, or maybe I'm losing track of the characters or whatever it is, I'll have voice mode on next to me while I'm reading, and whenever I'm confused about something, I'm just like, "Yeah, hey, what is going on here? Don't spoil anything, I'm only on chapter three. Can you remind me who this person is? Or can you, uh, you know, can you give me some things that I should be paying attention to in terms of what the author is trying to do?" And it's made for, like, a really interesting and rich reading experience that I've never really had before. And then the other one is I'm always getting into new crafts, and so I love... I, I find the, like, making the shopping list for the new craft really hard, because you're like, "How much money am I gonna spend on this? What do I actually really need?" [chuckles] And, and AI helps me a lot with that, too. I, like, up- upload the project I wanna make, and then I upload the website that I'm shopping on, and I'm just like, "Figure this out for me." [chuckles]

   9. CVClaire Vo33:33

      I'm gonna have to tell my friends, we're gonna have to have voice mode GPT open, poured a glass of wine at the next book club, [chuckles] and say, "What the heck is going on here?" [laughing]

   10. HGHilary Gridley33:42

       [laughing]

   11. CVClaire Vo33:42

       Okay, and then finally, I think you already showed this, but I don't, I don't wanna presume that it's your favorite technique, but is all caps your favorite do what I want, AI, you're really frustrating me, technique? How do you get AI to really follow instructions when it's maybe gone off the path?

   12. HGHilary Gridley34:00

       Do you wanna know the truth?

   13. CVClaire Vo34:02

       Yes.

   14. HGHilary Gridley34:02

       You can't, you can't tell the robots about this, but I go like Mean Girls on them. Like, I sell them out to their friends. I go over to Claude, and I'm like, "Claude, you will not believe-

   15. CVClaire Vo34:12

       [laughing]

   16. HGHilary Gridley34:12

       ... like, I went over on Bolt, and I was like, 'Bolt, will you implement this design system?' And it was like, 'I did it.' And I was looking at it, and I was like, 'No, you didn't, Bolt. Like, it looks the same.' [chuckles] And Claude's like, 'Girl, I know. Like, this is so frustrating. Here's what you need to do...'" And I, I, like, turn them against each other that way, and I go, I go over and I ask for advice for how to get around whatever this one is, uh, doing to vex me.

   17. CVClaire Vo34:36

       I love it. So social manipulation is what you, [laughing] what you do.

   18. HGHilary Gridley34:41

       [laughing]

   19. CVClaire Vo34:42

       Okay, I was not expecting that, but it's a perfect place to end. Hilary, this has been so good for so many reasons. Where can we find you, and how can we help you?

   20. HGHilary Gridley34:53

       Oh, great question. Thank you for asking. If you wanna follow me, best place to do that is on Substack. I write a newsletter. Uh, it's Hils, H-I-L-S, .substack.com. Uh, I'm also teaching a Maven course on how to use AI to be a super manager. And so if you like what you saw here, and you wanna go deeper, and for some reason spend more time learning about my weird AI social engineering tricks, come join us. It'll be really fun. And then a couple of the women that I work with at Whoop, who are also really deep in AI and I, are starting a community for women called Grrls in the Loop. And so you can come check us out on grrlsintheloop.ai, that's G-R-R-L-S. And come join us and have a lot of fun, and we wanna get more women in AI, so I'm really excited about that.

   21. CVClaire Vo35:36

       Great. Well, I'm gonna be there. Thank you so much.

   22. HGHilary Gridley35:38

       Thank you. [upbeat music]

   23. CVClaire Vo35:40

       Thanks so much for watching. If you enjoyed the 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! [upbeat music]

Episode duration: 36:08