How I AIMastering ChatGPT: Advanced techniques for workplace communication and productivity | Hiten Shah
EVERY SPOKEN WORD
45 min read · 8,558 words- 0:00 – 2:55
Introduction to Hiten
- CVClaire Vo
I wanna learn how to use ChatGPT the right way. So you gave us one tip, which was, "Be thoughtful about its memories." But what else? What are your tips?
- HSHiten Shah
I usually won't start anything without a ton of context or with the intention of giving it context over time. Just show it what great looks like. It's like a human. If a human doesn't know what great looks like, they're not gonna know what great looks like.
- CVClaire Vo
You do have an example of something that you think is great, which is your boss's operating manual.
- HSHiten Shah
My boss's name is Morgan, so it's What Would Morgan Do? So I'm gonna create the project, and then I'm gonna add these files here. I wanna pitch Morgan the craziest product idea I can think of. What is the best way to pitch it to him so we can go after it? [laughing] Now it's like, this is what you want Morgan to say. Yeah, that sounds like him.
- CVClaire Vo
This is a tip for all the ICs out there: Go and replicate your boss, and prep for conversations with them. [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 a great conversation with Hiten Shah, who's been building B2B SaaS for over 20 years. Not only is he a great founder and product thinker, but he is, by my estimation, a total ChatGPT power user. He's figured out how to load up ChatGPT Projects with information about yourself and about your boss to figure out the best way to communicate with each other and get work done. Let's get to it. This episode is brought to you by Paragon, the integration infrastructure for AI SaaS companies. Are AI features on your 2025 product roadmap? Whether you need to ingest data for RAG from your users' external apps, like Google Drive files, Gong transcripts, or Jira tickets, or build AI agents that automate work across your users' various tools, integrations are key to building useful AI features. However, building every one of these integrations costs months of engineering, time you simply can't afford, given the rapid pace of AI advancement. Paragon is an all-in-one embedded integration platform for AI products. Industry leaders like AI21, you.com, and Copy.ai use Paragon to connect over 100 of their users' SaaS applications to ingest data for RAG and provide their AI agents with thousands of integration actions. They've accelerated their integration development velocity by up to 50X, allowing their engineering teams to focus on core product features. Want to fast-track your integration roadmap this year? Visit useparagon.com/howiai to learn how. That's useparagon, P-A-R-A-G-O-N, .com/howiai.
- 2:55 – 4:12
Why Hiten primarily uses ChatGPT
- CVClaire Vo
Thanks for being here! I am excited to talk about everybody's favorite friend, ChatGPT. Today is all about ChatGPT, right?
- HSHiten Shah
Yep.
- CVClaire Vo
How did you get to ChatGPT being your, your favorite?
- HSHiten Shah
You know, it's, it's really funny. I, I obviously started using ChatGPT first. Uh, it existed first. There's a bunch of experiments I did with the API and all that prior to ChatGPT itself, so with OpenAI's APIs, and then when, when, when it came out, started playing around with it. It really wasn't doing what I wanted in terms of my output that I was looking for. I think it was still helpful in a bunch of areas that we'll talk about today, but it wasn't quite getting there. So then I started using Claude when it came out, and I was... In the initial days of using this stuff, I was actually way more Claude-heavy by, like, more than 50%. Even though ChatGPT came out first, I had access, I upgraded and all that. And I think the turning point for me, which I can't prove because I don't know the dates, was when memories started working, and that made it so that... And, and I'm a very, like, um... I don't try to talk to ChatGPT about everything, and if I'm gonna talk to it about things that are, like, a little random, I'll actually start
- 4:12 – 7:58
The importance of context and memory management
- HSHiten Shah
a temporary session.
- CVClaire Vo
I wanna learn how to use ChatGPT the right way. So you gave us one tip, which was, "Be thoughtful about its memories." But what else? What are your tips? Uh, I'd love to see them.
- HSHiten Shah
One of the biggest things here, we talked about memories, but temporary for things that you don't care for it to remember is really important, and then I'll archive chats 'cause they don't, they don't count, so to speak, in the memories from last I checked. You can also unarchive them. At one point, I actually archived all my chats, and then I started pulling out the ones I liked. It was definitely a pain for a number of reasons, 'cause I have a lot of chats. I have, like, thousands and thousands. That's why we're not going into [chuckles] my ChatGPT today. I have a blank one with the $200-a-month plan or whatever, which was also a game-changer. Once ChatGPT introduced that plan, it definitely changed a lot of things for me in terms of my usage. I still get limits with Claude. I barely get limits with ChatGPT, although I use Projects a lot, so I definitely hit decent amount of limits. But Claude's limits were also another very, like, brutal thing for, for when you're trying to use it and trying to get something out of it, especially when you need it now. I think my next point is something everybody knows, and that's that context is everything. So, for example, um, um, I don't have it shared here, but I have a project to make projects. I have a project to make deep research prompts.
- CVClaire Vo
Well, this is, this is some of the feedback that we've consistently gotten from guests, which is, you can try to improve your output, or you can try to improve your input, and everybody says, "Improve your input, and the output will come." And so they, they really recommend, which I think you're gonna show us, is how do you front-load the time to make sure your prompts make sense, that your projects are set up accurately, that your GPTs are well-structured? If you can do that, then you're gonna get that consistent, high-quality outcome. So what are those-... kind of go-to practices that you think everybody should do as they're building these things?
- HSHiten Shah
Yeah. You know, if you don't love frameworks, then you need to start loving frameworks. Um, I love frameworks, and I don't mean that in the, oh, seeking wisdom, Warren Buffett's mental models and frameworks, although I kinda do, but those are more like a bunch of tools. I think the strategy is, if I'm trying to get something done, can I find something that's good enough or great that already works for other people and that someone's already shared? Oftentimes, the models already know the framework, so now you're just trying to, like, tease them into the right spot or give them the framework itself, and then it sort of gets even more contextual about it. And I've just noticed this over and over again. So I usually won't start anything without a ton of context or with the intention of giving it context over time. 'Cause I don't wanna say that, like, I won't just do a one-sentence prompt. Yeah, I'm, I'm- I do that all the time, but I don't expect that one-sentence prompt to just magically work. I actually will even oftentimes be like: "What context do you need? This is what, what my goal is." Or... And another one that, like, I don't see enough people doing is taking great outputs, whether it's from AI or not from AI, and using that to help AI codify that kind of output, and it lets you build more outputs like that. That's probably one of the magical ones that I've found, which is just show it what great looks like. It's like a human. If a human doesn't know what great looks like, they don't have to know what great looks like. So then you're just get in, in, in some ways, feedback hell, so to speak, of going back and forth until they get it or until you've put something together. But typically, as a, as a human, if you give them an example and say, "Hey, this is what the thing I'd like from you," they can do a pretty good job of filling in the blanks, so to speak.
- 7:58 – 13:30
Demo: Creating “What Would Morgan Do” project
- HSHiten Shah
I think AI can do a better job. [chuckles]
- CVClaire Vo
So you do have an example of something that you think is great, which is your boss's operating manual.
- HSHiten Shah
Yes.
- CVClaire Vo
So could we use that as an example to get into-
- HSHiten Shah
Yeah
- CVClaire Vo
... exactly how you might do this?
- HSHiten Shah
Yeah. Uh, we'll, we'll create the whole thing. So I would first create a project, and my boss's name is Morgan, so it's What Would Morgan Do?
- CVClaire Vo
[chuckles]
- HSHiten Shah
Or What Would Morgan Say? So it's WWMD. So I'm gonna create the project, and then I'm gonna add these files here. And so he has an operating manual. Really great human being, built this out, sent it over, uh, when he first joined the company and became my boss, and then I've been sending this to everyone. And now, everyone's already seen it, [chuckles] and new people that join, 'cause someone else is sending it to them. Great. So that's his manual, and for anyone that doesn't know, these are things that oftentimes, you know, it used to be a bigger thing back in the day, I think, where people would create their operating manual, so you knew how to work with them. Now, there's some other tactics and stuff that are actually part of other projects that we can talk about. Then he also tends to share a few different sort of docum- uh, not documents, but, like, articles he likes, and so there's one he shared called Job Is Communication. I'm sure it's out there somewhere in the world. Uh, if it's not, whatever. So I would put those two things in, and that's the project files, right? Then I would add instructions. So I'm gonna open a new chat and be like... I, I actually would do exactly this. I would add this, add these two in here. So this is a chat. I'm gonna keep stick to what I, what I know, which is 4o.
- CVClaire Vo
4o!
- HSHiten Shah
Yeah, yeah, yeah.
- CVClaire Vo
Classic.
- HSHiten Shah
Yeah, yeah. I'm a, I'm very classic on that.
- CVClaire Vo
Mm.
- HSHiten Shah
So I'll do that. I'll pick 4o. I really like 4o, b- but all of them tend to work. 4o is just faster and, and gets me what I want quicker. And so here I'll say, "I'm, I'm creating project, uh, with these documents, and I want to be able to converse with it, with the project, and simulate type of feedback or advice that my boss would give me. Can you create the instructions for that project, knowing that I'll be using these files in the project?"
- CVClaire Vo
I love that you corrected your typo because I just roll right through it.
- HSHiten Shah
Yeah.
- CVClaire Vo
That was very polite of you.
- HSHiten Shah
Yeah. I, I... It's funny, like, the way I type is always correcting anyway.
- CVClaire Vo
Mm-hmm.
- HSHiten Shah
So [chuckles] it wasn't for ChatGPT's sake, uh, 'cause, you know. Uh, yeah. So yeah, but that's great. So okay, so here it already gives me the objective, fine. Boss is Morgan, great. Uh, system configuration, personal. Okay, okay, interesting. It has not given me the actual instructions, right?
- CVClaire Vo
Yep.
- HSHiten Shah
So I'm like: "Okay, where are the actual instructions?" So I'm gonna go, and this, this is, like, in another doc in there, which I call AI Shaping, 'cause you're basically trying to shape it to get it what you want. So this is a classic example of, I could paste all this crap in there, so to speak, but... And it says project setup, but it doesn't feel right, so it's like, "Can you give me the specific instructions that I can use in the project so I can just paste those in there?"
- CVClaire Vo
So I find this a useful kind of, like, prompt, which is just tell it where it's gonna go, [chuckles] and maybe it'll give you a little bit better... Oh, now we got some... Oh, well, there's some instructions.
- HSHiten Shah
Yeah, so usually what I've already done is, uh-- and, and this is another trick. I've done this in, in several chats. So when I find one where it actually did what I wanted, which, eh, we can argue. We'll, we'll probably just try this one, or I can copy one over if this doesn't work from where I have it. But this is what I find most useful. If I can get a good output, I will always try to get it to codify the output, especially if it's one where I'm gonna have to do this over and over again. So in this case, I said, "Hey, give me the instructions." I think just for shits and giggles, so to speak, I'm gonna use these, um, 'cause I think they might be good enough. Um, and I'm not trying to review it, and I also don't really care too much about this, as long as it looks good enough, because I can always iterate, uh, and do things. And I also use the word simulate. I don't always use the word. In this case, I felt like, okay, let's try it like this. So there's just a lot of, like, "Okay, we'll do it like that." But if this were really, really good, and I'm like, "Oh, crap, this is impressive," I'd make it codify it, and I'd turn it into... I could turn it into a project or something. So one thing I would do if I love this is, "Hey, can you help me create a project so I can create these type of instructions in the future?"... and that's what's got me a very good system of projects helping me use-
- CVClaire Vo
Project for projects.
- HSHiten Shah
Project for projects, yeah, whatever. I know it's-
- CVClaire Vo
So you're gonna add the instructions right here?
- HSHiten Shah
Yep, right here. So they're all in here, cool. Let's say... And then now I'm just going after it. I wanna pitch, wanna pitch Morgan the craziest product idea I can think of, of for us. What is the best way to, to pitch it to him so we can go after it? [laughs] Now it's like, "This is what you want Morgan to say."
- CVClaire Vo
Oh, yeah!
- 13:30 – 16:20
Using personality types to improve AI coaching
- CVClaire Vo
man. So we've had a lot of people on the pod, or a couple people, who have explained how, as a manager, you can replicate yourself, but this is a tip for all the ICs out there. Go and replicate your boss, and prep for conversations with them. And, you know, it's funny, I, I read this, and I was thinking, "Oh, is this just kind of generic?" And I was like, "Some of that would work on me, some of it wouldn't," but I bet people that work with me could pluck a couple artifacts and, um, make a, make a project or a GPT that really does... Uh-oh, find out everything about me in a professional sense. There you go. So you're doing it.
- HSHiten Shah
So what I would do if y-
- CVClaire Vo
Yeah
- HSHiten Shah
... you were my boss-
- CVClaire Vo
Yeah
- HSHiten Shah
... is I would literally do this, 'cause I know there's enough-
- CVClaire Vo
Mm
- HSHiten Shah
... about you out there.
- CVClaire Vo
Yeah.
- HSHiten Shah
Now, in another kind of example we can give, or it'll be in the doc, I, I do the same for myself. I call it, like, a personal OS, and it has my personality type, any of the personality tests, Myers-Briggs and everything, and then it helps me a lot. But if I know that about you... So M- Morgan is actually an Enneagram 5. I'm an Enneagram 9. What I would actually do is feed that into the instructions in that as well, if I wanna make it specific to me and our relationship. Because these personality tests help you... Well, Enneagram in particular, helps you with relationships and how to sort of, uh, meet in the middle around communications and stuff like that.
- CVClaire Vo
Yeah, that's actually a really great idea, because I do all this. When I start as a new leader on a team, I do the work of gathering, you know, has anybody done DISC or Enneagram or any, you know, um, Myers-Briggs? We kind of do that. We also have this questionnaire, which I'm happy to share in the show notes, which is 10 questions about me. What am I motivated by? How do I like to receive feedback? How do I work? All this stuff, and I actually do... I have this repository in a Google Drive file of everything I know about the team that they've been told or that they've told us themselves, and I haven't yet put it in a GPT, and that's so smart. 'Cause then I could say, you know, and, and sorry, sorry, Zach and Amanda, I can say, "You know, Zach and Amanda are not seeing eye to eye on project X. What would be an effective way, given what you know about them, to come, to come together?" So it's a really interesting idea. Uh-oh, psychological warfare in the workplace, all for the greater, [chuckles] all for the greater good, empowered by OpenAI.
- HSHiten Shah
So we'll, we'll, we'll let it do its thing. It's... What I'm doing is I'm doing research on you, and I said to get stuff in the professional sense or whatever. Sometimes I'll even include, "Hey, she's blah, blah, blah at this place." That way it doesn't get the wrong person. So it might, but we'll see. I don't think there's too many Claire Voes, but maybe there are. So we should be good. Uh, and then, yeah, so we'll see what happens there. We can continue with whatever
- 16:20 – 20:55
Building a personal operating system in ChatGPT
- HSHiten Shah
else.
- CVClaire Vo
Great, so I, I love... You know, you, you showed this about someone else, and you're, [chuckles] you're doing deep research on me, which, you know, is always gonna be thrilling to watch on the other side. But I wanna go back to this thing that you said about your personal OS-
- HSHiten Shah
Yeah
- CVClaire Vo
... this self-aware, you know, addition. How did you build that? Why did you build that? Um, you know, who uses it? How are you adding to it? I'm so curious about this specific use case.
- HSHiten Shah
So I, I have a bunch of these links. This one is the personal OS. So I used my project creator to create this, um, and it's basically a project description, what to use it for, and then these are the actual instructions, right? So what I would do is basically take this or take the instructions here and put them into a project. So we'll just go do that so that we can show, not tell, right? And then it even says things like files to upload, and then even has, like, a kickoff prompt if you wanna play around or whatever. So I will go here, make a new project. I don't need to put any files in there, but I'll probably do that too. But what you'll notice is up here, it's like, what are these things, right? So this is 9. This is 1/3. If you don't know Human Design, you should know Human Design, but I'm not gonna get into that-
- CVClaire Vo
You know, this is the-
- HSHiten Shah
... 'cause it's on the woo-woo side. Yeah.
- CVClaire Vo
This is the third time Human Design has come up. I live in San Francisco. I don't know if this is an SF meme that's happening right now. It has come up in the last week. So yes, it is quite woo-woo. They'll send you a PDF for free, but why not?
- HSHiten Shah
Yeah, I highly recommend. Um, okay, so I also have a voice and tone guide that was made for me a long time ago, 'cause I used to write a lot more. And so, uh, I'll just put that in there, just for shits and giggles, so to speak, although it probably isn't as relevant. So here, here we are with this. Let's, let's play some games. So I'm gonna take Morgan's manual and basically talk to it as if I just got this boss, 'cause this is kind of what I did. So this manual is from my boss, Morgan. Uh, I'm newly reporting to him and would love any and all advice on how best to work with him, considering my own personality, et cetera.... By the way, he's an Enneagram type five. So already, it's like I didn't have to do the work, and it's already giving me the contrast. Here, I would have to do a bunch of Google searches to be like, type, "Enneagram type 5 and type 9 relationship," and then I gotta wait, right? But this is kind of what's interesting, where it started mixing in the 1.3 from Human Design, which I love, and that's why I love giving it that context. Then there's like, "Here's our working style alignments," right? All this is true. Like, I, I've done this before. I know, I know that this is all very accurate, and then this is where things start getting interesting, 'cause it starts coming up with shit. Then that's why, like, the one-sentence ones are great, 'cause it's like, wait, a check-in format? Huh. So this is how I could give him a weekly update on whatever, or this is how I could put our one-on-one doc in ManageUp, and he's gonna love it, 'cause this is how he thinks, right?
- CVClaire Vo
The- is this how, how you- what, what you would like? Do you think it's accurate?
- HSHiten Shah
Yeah, I've read his manual.
- CVClaire Vo
Yeah, yeah.
- HSHiten Shah
And it's... I h- I know it by heart.
- CVClaire Vo
Yeah. [chuckles]
- HSHiten Shah
And this is, this is, like, exactly it. And one of the big ones for him-- And again, everyone will know this if they know how to lead, but that's a different story. But y- if you're a good manager, my opinion is that, and so is Morgan's, is that you're just unblocking all day. And, and he said that in the manual: "My job is to unblock you so we can get shit done." Not, not in those words, those are my words. So yeah, this is perfect. This is exactly what he'd want. Because if there's a blocker, I know he's the first person I should hit up. If I can't solve it any other way, he will just solve it. Um, and so that's cool. There's some really interesting things around conversations. He does ask you to defend things, but he never makes you feel, uh, like you're offended when he asks you to defend things. So he's always got a good way of doing it, so that's an interesting point there. This is kinda interesting. This is interesting, right? So this is in his doc.
- CVClaire Vo
So it's quo- it's quoting directly from the manual.
- HSHiten Shah
Yeah, and that's why I make these projects, so-
- CVClaire Vo
Got it
- HSHiten Shah
... If I didn't make it a project, which I've done before, and done the same thing, I don't get this level of cont- context coming back to me.
- CVClaire Vo
Got it.
- HSHiten Shah
I get more of like, "Oh, you put this in. I'm gonna go fill in the blanks, or I'm gonna do something like that." Here, I get these kind of references and all that kind of stuff that I just... It's just much harder to get that in a chat. 'Cause I used to try this with a chat, maybe before they had projects. I know they had... And custom GPT is a whole 'nother mess I don't
- 20:55 – 23:20
Mixing structured frameworks and personal context
- HSHiten Shah
like getting into. But yeah.
- CVClaire Vo
So one of the things that, that I notice here that I wanna call out is, you said you like frameworks. And so what I saw in some of this, this prompting, and is here are personality-type frameworks or, you know, guides that-
- HSHiten Shah
Yeah
- CVClaire Vo
... have been well-established or well-documented, the LLMs probably know, probably know about.
- HSHiten Shah
Yeah.
- CVClaire Vo
You also listed a set of interpersonal dynamic or workplace dynamic frameworks for conversations in that list, and then loaded that up with an individual's context. And then you're able to, in a pretty structured way, address common workplace things, whether, "I'm gonna have a hard conversation," "I'm gonna pitch something," "I'm in conflict with someone." And I think that idea of mixing structured frameworks and personal context is really useful. And one of the things that I'm really empathetic towards new leaders are... I get lots of new leaders in, in my organization. They're in the biggest job of their career, and they always ask, "Can I get coaching?" And I don't know if you've... The coaches out there are really- you're really making money out there. Coaches are expensive. Good coaches are expensive, but a lot of times they're doing this work. They're doing 360s to gather information about you. They're applying frameworks to help you understand yourself and someone else, and then they're helping you get out of, you know, mental patterns or, or giving you other ways to look at, um, problems in a structured way that allows you to move forward. And I think you just basically built, like, both a kind of coach for you to work with your boss, but I can imagine just a coach for yourself. So if you loaded this up with your own personality [chuckles]
- HSHiten Shah
So this works.
- CVClaire Vo
Yeah, yeah.
- HSHiten Shah
Like, this is a coach for me, right? Like, like, I'm really mad right now about someone... Let's, let's come up with a scenario. Uh, let me make one up. Someone trying to get control over one of the projects I'm working on because they are trying to lick the cookie, as, uh, as I've been told happens. So I just did that without even giving it a bigger problem, and then this is where it gets interesting. This reaction makes perfect sense. Okay, fine, ChatGPT, you wanna be positive? Cool. But then it tells me why, right? It threatens my control. Not just my control, my integrity of what I'm building, and this is accurate. Like, when someone says, "Oh, I'm threatening your control," I'm like, "Yeah, I'm a control freak, but that's not the problem here." But then it said the
- 23:20 – 30:00
Demo: Winning by Design sales framework implementation
- HSHiten Shah
integrity. There you go.
- CVClaire Vo
Okay, so you've done deep research on me. I'm gonna give you my Enneagram and my Myers-Briggs, and because we're fun in my team, I'm a Sagittarius, so we're gonna toss that into the mix. And I, I just wanna test, I wanna test if this passes my brand Nira to it sniff test.
- HSHiten Shah
Okay.
- CVClaire Vo
Well, while we're waiting for that to happen, let's switch over to one more use case, which is your sales use case, which I think is super interesting.
- HSHiten Shah
Yeah, this one's really fun. Um, I find myself over, over time getting really excited about frameworks that I have applied in work, and also that the people who built them applied them, and I can prove it. So whether that's Lean Startup from Eric Ries or I guess they call it the Sean Ellis score now. It's, it's al- it was always called the Product-Market Fit score in my world, but that and a bunch of these other frameworks. So when I landed on this Winning by Design framework, I was, like, over the moon. And so I did what a lot of people would do if you were really curious about it. So I did a site: their website filetype pdf in Google, and this is before deep research and all that, of course. So I found all their PDFs, which was before AI, too. So I was like, "Okay, great, now I can use these and, and do what I'm about to show you." It took hours to do this kind of stuff, and now I can do it in seconds, literally. So basically-... I have, I have this entire kind of, uh, context put in. So this one's already set up. I can obviously set it up again, but the deal is, there's a bunch of these documents, and these documents are all about the framework and the various processes. These are all publicly available. They also have a bunch of private ones you can get if you go through their courses. Then I, I use my instructions project, you got it, to basically build this, and it's pretty simple and straightforward. It's not really crazy, 'cause a lot of the context is in the files. So, and again, this is easy to tweak anytime.
- CVClaire Vo
This will be familiar to anybody that's in a revenue organization. All leaders come in, and they have their favorite sales framework, enable the field on it. You get a bunch of PDFs, but then I'm, I'm hoping you're gonna show us how to apply this-
- HSHiten Shah
Hundred percent
- CVClaire Vo
... consistently over time. Okay, great.
- HSHiten Shah
So I actually did this already. So I actually asked it, "What can you help me with?" So I didn't even wanna, like... Again, I do a lot of that sometimes with these projects, just 'cause I want it to tell me what it thinks it can help me with. Just like a human, right? Like, "What can you do for me?" Or, "What, what, what's your best skill?" Whatever. So it's like, I can create and refine, create or refine sales processes. Wow, okay, so I can build a discovery script, call script. Cool. Perfect discovery call playbook, draft that. Cool. Design customer-centric stories, messaging, run impact meetings, coach your GTM team. Cool. Cool. Okay, great. Where do I start? Okay, can you create a SPICE discovery guide? And I did it for your product, and it didn't know much about your product 'cause it didn't, I didn't go do a web search. I solved that problem, too, as you probably can guess. But... And then it's basically like, okay, VP of product, director of product management. Cool, this is a problem space. So now I know that if I give it this context myself, it will probably tweak things. So already I think I'm winning, 'cause I can-- I have now learned something of how to use this thing, which is another piece I go into. And then now it goes into situation, 'cause the whole premise of this framework is there are questions you should be asking on sales calls, so you're only demoing, like, five or ten minutes of a twenty or thirty-minute call. Not even five or ten, five minutes. So what you're trying to do is diagnose pain. So we imagine these are like d- those discovery calls. So these are a set of calls, uh, or a set of questions, which is like how many PMs are on your team, whatever. Great. I, I literally, every time I do this, I'm surprised by at least one or two questions in there, which would've been super challenging for me to think of on my own. So that's where I find a lot of the value. Otherwise, you can look at it and be like, "Yeah, yeah, yeah, this is obvious." Yeah, a lot of it is, but that's not the point. The point is that if you're gonna go get on a call and you wanna use this sales process, you wanna do a really good job, hopefully. These questions help you figure out how to do that.
- CVClaire Vo
Yeah, this question under pain, I don't ask, but I should, which is, where do things typically break down? I'm not good at, at pain discovery, so this is already giving me, giving me some ideas.
- HSHiten Shah
Yeah, exactly. And so, like, and pain is like, uh, you know, as you know, one of the most important things when you're trying to actually do sales, and then the impact questions are always valuable. But again, this is part of the value of the framework. So I think the key thing to highlight is, I love that you like that. It makes perfect sense. It's the framework producing it. It's not ChatGPT. I mean, it is, but it's that framework that taught ChatGPT how to answer these questions very precisely, 'cause it has, like, twenty PDFs from these people, you know? Um, and then, uh, critical event is a big one. So if you're into sales, you know that you need to figure out if there is a date tied to the init- and there's an initiative tied to it, so this is great. So yeah, I, I had it do it, right? So then, to your point, oh, maybe it doesn't have context, maybe it doesn't know enough. Great. You can imagine what I did. I did a, a, deep research prompt. I asked for a deep research prompt on it. I did it in the sales Winning by Design project on purpose. Even though the project is not meant for that, of course it can do whatever the heck I try to get it to do. But I purposely did that because I wanted to improve the Winning by Design outputs. So already did this yesterday. It's right here. So I did some kind of analysis. It got me all kinds of things about your product company, whatever's going on. I... You know, same prompt it gave me, did all the corrections. So now all I do, and this is how dummy I am about it, because it usually works, I'll just copy it.
- CVClaire Vo
Hit the copy button. [chuckles]
- HSHiten Shah
Just don't even need to read it. I don't care. It's all good. Don't worry about that. Okay, now here is context on ChatPRD in terms of the history, et cetera, of the product and research, uh, related to it. Fine, whatever, it could say whatever. Then I would probably go in and say, "Please improve the deliverable above using this con- this new context, this updated context."
- CVClaire Vo
I am a dash caret, uh, dash, you know, arrow little instructor as well.
- HSHiten Shah
[chuckles] All the time.
- CVClaire Vo
This arrow-
- HSHiten Shah
It just feels like it splits it up-
- CVClaire Vo
Yeah
- HSHiten Shah
... but it probably doesn't matter, but I just wanna do that. I love it.
- CVClaire Vo
I completely agree.
- HSHiten Shah
So this is, this is my point about the memory, right?
- CVClaire Vo
Yes.
- HSHiten Shah
It'll tell you when it does that.
- CVClaire Vo
Yeah.
- HSHiten Shah
So oftentimes I'll sit there and just start pruning it.
- CVClaire Vo
Yep.
- HSHiten Shah
And so that's what I like about it, is like, just makes it really easy to go cut that out of the memory-
- CVClaire Vo
Yeah
- HSHiten Shah
... if I want to.
- CVClaire Vo
I don't need that. Yep.
- 30:00 – 31:44
Creating discovery call scripts
- HSHiten Shah
that's, that's the way I would do this stuff. And I'd probably prompt it a little differently and be like, okay, and I'll probably say this: "Can you give, give me a demo script for the most relevant, uh, ICP/persona," whatever, in case it doesn't get it, "that the research identified?" And I don't even know if the research identified this, but ChatGPT tends to-
- CVClaire Vo
'Cause you just, you just clicked the Copy button.
- HSHiten Shah
Yes. Uh, savvy sales and... Oh, interesting! Huh.
- CVClaire Vo
Well, so I think what it did, if I read above-
- HSHiten Shah
Yeah
- CVClaire Vo
... you didn't prompt it very well.
- HSHiten Shah
No, not at all.
- CVClaire Vo
Uh, which is-
- HSHiten Shah
Yeah
- CVClaire Vo
... it, it tried to integrate the framework into my product-
- HSHiten Shah
Yeah, and that was the-
- CVClaire Vo
... I was supposed to integrate the framework into the kit.
- HSHiten Shah
So let's do it again.
- CVClaire Vo
Yeah, but I, this is one of the things I love about AI is-... you know, imagine I told some research analyst, "Go do this for me," and they came back three days later, and I was like, "No, no, sweet child, totally wrong." So expensive! You get this wrong, whatever, it's 90 seconds we just lost, and we can just give it another go.
- HSHiten Shah
Yep, exactly.
- CVClaire Vo
And I think this goes back to what you said at the beginning, which was, who cares if you have to re-prompt it? It's so cheap, it's so fast. Like, who cares if we have to do this again? It totally just works.
- HSHiten Shah
Yeah, and I'll keep doing that. I don't care, like, it takes nothing, right? And, and I think that's great. Like, I, I kinda love the mistakes it makes, actually. Sometimes I learn all kinds of weird shit from the mistakes it makes. Yeah, it keeps saying rev ops and product persona, which is interesting.
- CVClaire Vo
[laughs]
- HSHiten Shah
I know ...
- CVClaire Vo
Well-
- HSHiten Shah
I should...
- CVClaire Vo
I think this gives us, whether or not it gives us-
- HSHiten Shah
Yeah
- CVClaire Vo
... a good output-
- HSHiten Shah
Yeah
- CVClaire Vo
... it gives us some good ideas. Let's see if our research, um, your deep research on Claire is done. I don't
- 31:44 – 36:30
Using ChatGPT’s deep research feature to understand Claire’s leadership style
- CVClaire Vo
think there's actually that much, um-
- HSHiten Shah
Yeah
- CVClaire Vo
... interesting about me on the internet, but let's, let's see.
- HSHiten Shah
Oh, we're about to find out.
- CVClaire Vo
Yeah.
- HSHiten Shah
Okay. Let's see.
- CVClaire Vo
Oh, we got it. Okay, so you got a novel-
- HSHiten Shah
Yeah, that was the point
- CVClaire Vo
... on Claire.
- HSHiten Shah
Yeah.
- CVClaire Vo
I do have board roles, so...
- HSHiten Shah
Oh, you do? Okay.
- CVClaire Vo
I do. Look at me.
- HSHiten Shah
Okay. Okay.
- CVClaire Vo
Okay.
- HSHiten Shah
Okay, I just wanted to check.
- CVClaire Vo
Move along.
- HSHiten Shah
Okay. Yeah. No, I, I'm never surprised at how much it gives me these days, 'cause it tends to give me a lot when I do these kind of prompts.
- CVClaire Vo
Yeah.
- HSHiten Shah
I do these kind a lot. Okay-
- CVClaire Vo
Okay, so you're copying it.
- HSHiten Shah
What is the best way we should do this? Should we make a project?
- CVClaire Vo
Yeah, make a project.
- HSHiten Shah
Okay.
- CVClaire Vo
Claire.
- HSHiten Shah
Claire. Okay.
- CVClaire Vo
Claire. [chuckles] It's just Claire.
- HSHiten Shah
Yeah. Okay, download that. Let me put that in here.
- CVClaire Vo
Okay.
- HSHiten Shah
Okay.
- 36:30 – 42:53
Lightning round and final thoughts
- CVClaire Vo
always on GPTs or models. Um, so this is y- it's been all about ChatGPT, but it's been super useful. Uh, we're gonna do a couple lightning round questions, and then I'm gonna, I'm gonna get you out of here. So question number one, you've said that most of your AI usage is ChatGPT. You mentioned, um-... Claude a little bit. What else is in your stack?
- HSHiten Shah
I use AI three to six hours a day, is what I'm clocking in at.
- CVClaire Vo
Mm-hmm.
- HSHiten Shah
It's always three at the minimum.
- CVClaire Vo
Yep.
- HSHiten Shah
It used to be about two, and the specific tools are ChatGPT and Claude. The most useful tool I use is not public, so I can't talk about it or the name. It's actually a desktop app. Um, and, and that's outside of ChatGPT. Uh, outside of that, I try probably 10 to 20 new tools a week. I, I guess here's what I'll say.
- CVClaire Vo
Yep.
- HSHiten Shah
Uh, I think the tools are fine.
- CVClaire Vo
Yeah.
- HSHiten Shah
But when I go back to AI tools, nothing beats a blank canvas for me from ChatGPT today, and there's a f- bunch of reasons why, but the one that I keep coming back to, that I see people making a big mistake of, which we kind of did here, too, to demonstrate it, which is y- so many people try to go to automation when I need to l- understand what's the prompting that's gonna work, and how do I get this thing to spit out reliable prompts? Again, we call it evals and stuff in the product world, which I have lots of opinions on, but the bare metal, the chat, messing with that... Like right now, in five minutes, I could fix that sales winning by design thing so it actually gives the output we want. It's probably the instructions. It probably doesn't understand that when I give it context, it needs to use the context and nothing else, right? Simple thing, I could fix it. If I tried to automate that and say, "I wanna do automated sales scripts," where I just toss it in and do it and use one of these automated tools ... I know there's all these fancy, awesome ones, even Zapier, et cetera. I'm probably gonna be stuck with all the outputs suck. Okay, and then I'm done. But I don't wanna be done. I wanna go build the plan on how to build the automation, and the only way to build the plan is to manually do it repeatedly. Then there's the which model and all that, which is a whole 'nother can of worms, uh, 'cause, like, you use the API for obvious reasons with the product you're building. You have a specific model that you know every time you throw the prompts at it, that you like to throw at it, it gives you the output that the customers like. So I think people are racing to automation, and that's a mistake.
- CVClaire Vo
Yeah, and I'll, I'll just call out my friend Pete Koomen at YC did this article basically begging, begging a- AI product people to let users manage the prompts a little bit better, so.
- HSHiten Shah
Yeah, I, I have so many opinions on that, a- and, and... Yes and no. I think the big one that I would point people to if they need actual, true, good inspiration on that-
- CVClaire Vo
Yeah
- HSHiten Shah
... is a product called Lex, lex.page-
- CVClaire Vo
Mm-hmm, yep
- HSHiten Shah
... L-E-X. They've instrumented the whole product so you can tear up all the prompting-
- CVClaire Vo
Yeah
- HSHiten Shah
... make it your own, et cetera, in a very impressive way. So the yes and no is, like, some products, it makes sense. I think others, it will lead you in a bad direction, and I haven't told Pete this yet, but I've read his whole thing, and I have similar thoughts in general. Some of the products we're building, the Lex model makes sense, and I call it-
- CVClaire Vo
Yep
- HSHiten Shah
... the Lex model because Nathan's one of the best product people out there.
- CVClaire Vo
Yep.
- HSHiten Shah
Don't tell him I said that, although he's gonna hear it.
- CVClaire Vo
Yeah, well, we love him-
- HSHiten Shah
Um, and that's Nathan from Lex
- CVClaire Vo
... we love Lex.
- HSHiten Shah
Yeah.
- CVClaire Vo
Yeah.
- HSHiten Shah
So, so but the way he thinks about this is very much aligned with what Pete was saying. I would just advise people that some products don't make sense to make the user see all that or do all that kind of work.
- CVClaire Vo
Yep. Okay.
- HSHiten Shah
So then all this is back on us product people, so.
Episode duration: 42:53
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