How to get your whole team excited about AI (and actually using it) | Brian Greenbaum (product designer at Pendo)

0:00Brian Greenbaum:I had tried Cursor for the first time and what I was able to create just blew me away. I sent a message to my manager, my manager's manager, the CPO, and then a few other folks that I knew were really interested in AI. And I was like, listen, I had this really profound experience and I think we really need to uplevel the skill of our entire product organization, not just designers, but also PMs. We need to become more familiar with this technology. We need to understand how we can use it. This is actually the message that I sent while I was on paternity leave that definitely got my leaders really fired up.

0:26Brian Greenbaum:I didn't know exactly how this was going to go. All I knew was that I needed to get more folks paying attention to this AI stuff. If you were the first to raise your hand that says, you know what? I want to figure out how our team can use AI. I'm going to lead this organization. It's such a unique leadership opportunity to show cross-functional broad impact on teams.

0:48Welcome back to How I AI. I'm Clara Vo, product leader and AI obsessive, here on a mission to help you build better with these new tools. Today, I have Brian Greenbaum at Pando, and he's going to show us not only how he uses AI in his own product work, but a step-by-step plan for getting your product and design teams adopting AI as well. Let's get to it. This podcast is supported by Google. Hey, everyone. Shrestha here from Google DeepMind. The Gemini 2.5 family of models is now generally available. 2.5 Pro, our most advanced model, is great for reasoning over complex tasks. 2.5 Flash finds the sweet spot between performance and price.

1:31And 2.5 Flash Lite is ideal for low-latency, high-volume tasks. Start building in Google AI Studio at ai.dev. Brian, thanks for joining us on How I AI. Happy to have you.

1:44Brian Greenbaum:Yeah, so excited to be here. Well, what I am excited about in our conversation is in a lot of our How I AI episodes, we've shown specific ways that you can use specific tools to build or do things with AI. And you're going to help us take a step back and say, you know, let's say you have all these tools and you want to start using them. How do you get a full team or a full organization, a full company actually adopting AI? And so this is a how I get everybody else to use AI episodes. So I would love to start with what I call the inception phase, which we all have gone through or are all in the process of trying to get our team to go through, which is when you get people excited and sort of jumpstart the energy around AI.

2:34And I think you approach this in a really interesting way. So I'd love you to walk us through what you did at Pendo.

2:40Brian Greenbaum:Yeah, absolutely. So to take you back, it's the end of last year. So last July, I had my daughter, Maya. My daughter, Maya, was born. You can kind of see the nursery in my background. This is sort of a shared office nursery. And I was on paternity leave at the end of last year. And I'm sort of like a tech geek. I've been following AI for a while. My day job is a designer at Pendo, but I've always sort of been into tech. And so I've been following AI very closely. I've also had some experience building side projects and things like that. And I think it was back in November, Cursor came out. Maybe it was a little bit earlier than that.

3:15Brian Greenbaum:But Cursor, I tried Cursor for the first time. and what I was able to create just blew me away so I had like a side project idea this hobby app in my mind about a music player where I can play albums by scanning a QR code on sort of like a piece of paper I was very jealous of people who had record players I don't have space for a record player in New York and they get to choose music by sort of flipping through through albums and I like having you know unlimited access to music via Spotify but I sort of missed that sort of like tactile experience so it's like well what if I create these sort of like laminated cards and I have this way of just being able to play the albums that are on that so I had this idea of like what if I can create sort of a mobile app where I can scan like a QR code or I could recognize the album cover and I can print these album covers out and just be limited in that way and I had no idea how to do that like on my own like I'm not an active developer I can't sit down and write that application and I pulled up cursor and like within a couple hours I had a working prototype and like that just blew me away.

4:13Brian Greenbaum:I was creating QR codes. I was creating PDS. I was like doing all this like really, really, really cool stuff. And, you know, like I said, my day job is a product designer. And I immediately understood that like, okay, this is really cool as a sort of side project. It's really fun, but I could use this to build interactive prototypes. I consider myself pretty proficient with Figma, especially when it comes to prototyping, but I understand the limitations of using Figma for prototyping. A lot of what I do at Pendo is sort of working on features that are analytics-based. And so when you're creating mock-ups and prototypes that are data-driven, it's really hard to communicate how these things are actually going to work with real data.

4:53Brian Greenbaum:So having a prototype that is code-based, that is working with even just fake data and interacting sort of in a more dynamic way is really useful. So I was like, wow, I think we can really use this at Pendo. So I had the, you know, even though I am on paternity leave, you know, I had this idea And I was like, I couldn't contain myself. You know, I wasn't going to come back to work until the beginning of January. So in December, I wrote a whole bunch of folks at Pendo. I still had access to my Slack. And so I wrote, you know, I sent a message to my manager, my manager's manager, the CPO, and then a few other folks that I knew were really, really interested in AI.

5:27Brian Greenbaum:And I was like, listen, I had this like really profound experience. And I think, you know, we really need to uplevel the skill of our entire product organization, not just designers, but also PMs. We need to become more familiar with this technology. We need to understand how we can use it. I had already understood that there's no playbook for how to learn this stuff. There's no class you can take. There's no book you can read. And the technology is evolving so fast that the only way to really know how to apply it is to become very familiar with how it works, to kind of stay current with all the latest technologies and the tools, and just sort of see a bunch of examples.

6:01Brian Greenbaum:And like selfishly, like I wanted to spend more of my time at work doing these things. But I also wanted to help my colleagues and my company just be more successful because I saw a clear path to that. And just getting more of my peers, more of my colleagues, like doing the same thing and sharing their experiences, I know would help me learn. And I think it would just sort of like, you know, rise all the boats. And so this is sort of an example here. Not an example. This is actually the message. I pulled it up that I sent while I was on paternity leave. Just to kind of give you an example. of what something like this looks like.

6:34Brian Greenbaum:And I wrote this pretty long message. I mean, for folks that are not watching this, I just kind of said TLDR in a similar fashion to, there was an engineering-focused sort of group that had been around for at least a year, but nothing really focused on PMs and designers. I was like, I'd like to lead a group like that before a cross-functional product team with designers, PMs, and et cetera with two goals. um pendo's product team can leverage the cutting edge of ai tools to get more done in fewer hours less resources improve decision making and communicate and validate ideas more effectively and then two because pendo is also sort of servicing a lot of product organizations that are going through similar transformation um to help position pendo as a thought leader in the space because i knew it was going to be really important and then i went through like a longer version of sort of like my my experience of like building this app and um and why i thought it was important.

7:29Brian Greenbaum:And, you know, I'm really fortunate to be part of an organization that supports sort of initiatives like this. And so, you know, that definitely got my leaders like really fired up. In fact, the CPO was like, hey, can you come to like All Hands next Monday and talk about this concept? And I was like, I'm on paternity, I can't do that yet. But I will start as soon as I come back. And so that's sort of what happened. So that was a catalyst for this idea. And I got to say, like I'm the kind of person that, you know, sometimes I can be like type A and like really like think things through. But I also know that sort of committing to something or just like forcing myself to like throw myself into a situation without knowing like how it's going to work out can also result in something really interesting.

8:16Brian Greenbaum:So I didn't know exactly how this was going to go. All I knew was that I need to get more folks paying attention to this AI stuff. And I also need to create time in people's calendar where everyone can just like focus on it and play or maybe like hear a presentation on something new. So I have to call it a couple things here that I think are really important. One, for anybody trying to, you know, give a justification if you need it for investing extra time, resources and energy into this AI transformation in your organization. I love that you call up actually the two things that really matter.

8:53They're very similar things to how I called out the value of AI transformation at LaunchDarkly, which was one, our team's got to know how to use this stuff. Like we've just got to know how to use these tools, get more done, be more efficient, just use the best of the best. The second one, though, I think is really interesting. And there's still a lot of opportunity here. You know, you're on this podcast, which is there's this opportunity for leading organizations to position themselves as thought leaders in how you get stuff done with AI in your vertical. And so for us, it was like, we have to be great AI engineers because we need to, you know, be great engineers.

9:34Generally, this is the next phase of how software engineering is going to get done. We need to be thought leaders in the space. And very similarly for you on the product side, I think it's just really important that you can create platforms for your company to be experts in the space if you lean in early into these technologies. You know, the other thing I want to call out is, you know, I try to tell people this all the time. This is like promo making work. And what I mean is like, this is the kind of initiative that doesn't come around that often as an opportunity. And if you were the first to raise your hand, like if you were the first designer that says, you know what, I want to figure out how our team can use AI.

10:17I'm going to lead this organization. It's such a unique leadership opportunity to show cross-functional broad impact on teams. And like there's only going to be one or two of you that get to be the leader of it. So I'm like really encouraging people to be like you. Raise your hand early to take on the initiative for the organization. One, because I think it's the right thing to do for the team. But two, it's really great from a personal career perspective.

10:41Brian Greenbaum:Absolutely. And like, yeah, I wasn't I wasn't going to focus on that. But I will. But like what you're saying is absolutely 100 percent true. So like this this sort of initiative has opened so many doors. We'll get into it in a moment, but it's opened so many doors internally within the organization. Like I'm speaking with you. There's no way I think I would be speaking on such a high profile podcast if I didn't start working on this. and sort of build up sort of the body of work that I have over the last nine months. I get to work on some really cool AI projects. I have folks throughout the organization that are not even in product and design, folks I didn't even know reaching out to me and sort of like looking to me as a thought leader.

11:21Brian Greenbaum:And that wasn't my intent, but it's absolutely true. It's like there are opportunities across all organizations right now, regardless of your level. I mean, I'm a senior staff, but I'm an IC. I mean, I'm just a product designer. Like I'm having an influence way beyond my scope. And I think regardless of where you are, like if you have the initiative and the energy, and it does take a little bit of time, like there is some nights and weekends that like I kind of put into it. But I also love this stuff. Like I was kind of doing it anyway. And so absolutely, it is a career builder. Yeah. And then, you know, maybe my last reflection is, do you know how many people I know that have gone on parental leave and in between rocking their newborn have been shipping stuff with like cursor?

12:04Every single parent I know, this just might be my peer cohort. Everyone I know has been texting me from parental leave being like, Claire, I've been vibe coding with my baby and I am so into it. So if you have somebody on parental leave right now, it's very likely they're going to come back AI pilled for sure, because that is what I have seen consistently with some of my friends. Okay, so let's actually get into this message, kick things off. But then you actually have to functionally make this happen. And you sort of had like a two pronged approach to two things that were really effective in getting this going in your organization.

12:39So what were those two things?

12:41Brian Greenbaum:Yeah. Yeah. So the two things. So I'm just kind of bringing up here in case it's helpful. So this was sort of the first announcement I made within the organization. I had come back in January. This is sort of like our private shuttle of the entire product organization. So within Pendale product, the product team are PMs, designers, writers and a few other folks. And so I was like, hey, I'm starting this initiative. And in my mind, I was thinking that there's sort of a two prong approach. There's an asynchronous and asynchronous. One thing that I was very familiar with, like just in my own life, but also talking to other people, is that you'll typically hear something like, yeah, that AI stuff, like I know it's important, but I just don't have the time.

13:24Brian Greenbaum:Like I don't have the time to like watch all the videos and, you know, vibe code and lovable or whatever it is. Right. And the crazy thing is like if you don't make the time for it, you're never going to learn it. And at some point you're going to get behind. Right. And so it was really important for not just there to be a place within Slack and encourage people to share on Slack asynchronously to do it at their own pace, but also to create time in people's calendars so that they can come and focus on like whatever the topic is. And also within that session, it's not just about a presentation.

13:56Brian Greenbaum:It's also like it's really important for that presentation or that session to be interactive. So let me give you an example of that. So this was a kickoff as well as an exercise about building apps. Just to sort of give you an insight into how I started this off, I was like, hey, AI is getting better. It's getting faster. And it's evolving how software is planned, designed, and built. And this was really meant to speak to not just us as builders, but also sort of the product that Pendo is building. And right around that time, Andrew Ng had a really, I thought, thoughtful blog post about how he was thinking about how PMs need to position themselves sort of in the AI, in this AI future.

14:37Brian Greenbaum:And AI is typically sort of in the space of sort of engineering and technical stuff. And, you know, he was positioning AIs as perhaps being, or at least engineers being better positioned to sort of like take advantage of all this stuff because they are technical. But he was saying it was really important for PMs. And I would also put designers in that camp as well to become proficient. And so these were the sort of five things that he was, he really wanted to focus on technical proficiency, just iterating on the development, like using AI in a sort of iterative capacity, being very proficient with data, skill and managing ambiguity and his ongoing learning.

15:11Brian Greenbaum:So like that was really sort of the emphasis I wanted to drive. and so again the structure of sort of like or at least the goals sorry the goals of the the product AI was around to up level and modernize the skill set of our of our product people to improve our comprehension and literacy and then because our customers are also builders to empathize and assist with them as well and I wasn't sure if this technique again was going to work but this was how I was thinking about approaching it just being more hands-on getting our hands dirty radical many-to-many sharing, being intentional, creating the space, and then identifying the patterns that worked, and then sort of turn those into reusable patterns.

15:48Brian Greenbaum:So in this opening session, like I was saying, it's really important to have an interactive session. And I'm not going to go through the slides of how I talked about code building tools and the various types and some things that I had built. But there was a section that was at least, I think, 10, 15 minutes where I was like, all right, everyone, go to Bolt.new. That was the app that we chose to use at the time. And create an account if you haven't created an account. And then everyone go to Bolt and copy and paste this. So this was just a prompt that I had created. It wasn't hyper-optimized. It was about creating a to-do list, the most basic like little mini SaaS app that you could possibly build.

16:22Brian Greenbaum:And I had everyone type this in. And then there was like a little enhanced prompt thing that I wanted everyone to use just to sort of see how like this app could sort of take a very basic thing and turn it into a more sophisticated thing and then let it rip. There you go. And I would say I wasn't expecting this when I did this the first time. But the thing that really stood out, because it was sort of like obvious to me that this is what would happen. But some of the feedback I got was like, wow, like we all typed in the same thing. We all clicked on the enhance prompt button and we all got different results.

16:53Brian Greenbaum:So like this was just sort of an example of like these were all the to-do list applications that the app created after running that query. And I think in the third of the cases, like Bolt just came back and said, nope, like error or whatever. And then like, so we immediately got into sort of the whole thing. Oh, okay. Don't worry. Like if you get in there, just download the fix it, blah, blah, blah. And everyone sort of like got through it after two or three rounds. So that is like, it was great to experience that as a team and not only just to like do it and see how it worked, but also just see the diversity of like how like these applications are built and how Gen AI is being used.

17:27Brian Greenbaum:And then the other thing I had people do in the last like 10, 15 minutes is experiment on their own. And I told people just to do crazy stuff. Like we're not doing this for any, like we're not really building a to-do list. And the AI will do its best to do as you say. So you can give it like the most wacky instructions, right? Like, you know, make it, you know, add a retro 8-bit pixel art theme, you know, introduce a dark mode toggle, make it look like MySpace from 2007. And so that was sort of like an interesting thing too. So like people sort of like went nuts, they shared some things. Like I think there's a few examples here of like people saying, oh, you know, I tried, yeah here this is what UI will look like in 22 ,200 here's my tumblr style you know to-do list and like this was intentional to sort of like make it fun these are designers but there's also PMs and like we all know sort of like the there's a line between sort of like professional stuff and personal stuff but like what I really wanted people to experience is that this can be fun and just think like to broaden their minds about how they can apply this technology.

18:32One thing I want to call out as a meta benefit to this slide that you showed, and maybe we could go back to it of like now go wild or optimize it, is I think as designers and product managers in companies, and you can tell me if you have a different experience, but we have just gotten beaten by the scope creep stick so frequently that we have actually lost our muscle for like asking for the magic thing. We always start with the MVP. We always start with like, what is the bare minimum thing I can ship to meet the user requirements that I know engineering can do? And like, we've lost this ability to imagine like, what if it did this?

19:13And what if it did that? And it could be interactive or there could be voice. and what I like about AI is one it makes those magic things a lot easier to build you know more efficient to build but two like it's gonna let designers and product managers return to the craft of building the awesome product as opposed to like the viable product which is so like if you reflect on it it's so sad that we have put on a pedestal like minimum viability as just like such a low bar. And now our bar can just be so much higher for what we build. But you have to reignite this muscle of how to even think about what those things could be.

19:58So I love the idea that you put these iterations in categories like visual iterations, interactive iterations, entertaining or gamification iterations. And then media, again, is something that's really interesting that you can do with AI. I know as a designer, like how many times have you been like, oh, an illustration would be amazing here, but no one wants to spend the time to like draw a custom icon or a photo would be here, but like we don't have any stock photo budget for this project. So I'm just going to like erase that and put white space. And so I just think like that piece is so underrated for AI is like getting out of getting us out of MVP mode.

20:38Yeah.

20:39Brian Greenbaum:And I got actually a really cool example of that as well so like you know that was the sessions right but then there's also the channel and so um you know there's people are constantly sharing things links to articles experiments that they've tried i mean that was the whole intent of it right it's just to sort of have a space where people can share things and i think there's an example in here where ah yes here it is so mark you know he's a he's a product designer and i think this is right around the time that mid-journey um launched the ability to do animations or video and he was like wouldn't it be cool to have you know sort of in this intro screen these little animated characters that sit there and just like wave at you right and it's so cute exactly right and that it wasn't that hard i mean like i think you know he iterated on a couple of prompts like this this is not in the product it's not in the product yet but i mean he was able to create an asset that not that hard to drop in if you have the right spot for it um and like like you said before it was oh man like really cool to have an illustration or an animation, but I got to go talk to a professional or I got to go spend like nights and weekends working on it.

21:38Brian Greenbaum:It's like not worth the effort. And now we can bring a little more life into our applications. And that life, of course, turns into like what I just did, which is like, oh my God, I love it, which is just like customer connection to your brand, to your product. A little bit of sense of like this team actually really cares about the craft and is going to continue to invest in this product experience, all that, all the great stuff. And then And I just want to call out for folks that maybe missed this in part of the transition. So the two kind of major pieces you put in were these sessions, these product and AI sessions.

22:09And you showed us the kickoff deck of what that looked like, both the why and then like, let's actually get into it. Let's do it together. And then the second piece, that's a sync piece. And you do those weekly, right? We do them biweekly.

22:23Brian Greenbaum:I mean, we could probably do them weekly, but we've done them biweekly. Yeah, I put in a similar thing. We called them like AI power hours on Friday. And it was like every week we would do that. And then the second thing is the async channel, which like if you do not have it, you should definitely have it where folks are just sharing. sharing. I like this bullet point that you had in your slide that was like radical peer-to-peer share. I forget what it said, but it was such a good phrase. Yeah, radical many-to-many sharing. And so one of the things that I think organizations often suffer from during this AI transformation is information hoarding and like secret AI.

23:03And I think it happens for two reasons. Secret AI can happen because people aren't sure what they can use. And we're going to talk about that in a minute. And so they like kind of pretend they're not using AI or they use their like Gmail account, Gmail, ChatGPT account because they don't want to get in trouble, but they're going to use it anyway. And so there's like secrecy because people don't know the golden path of using AI. And then there's like information and skills hoarding right now, which is like the dark side of being an AI agent or an AI change agent, which is people are like, well, I'm the only one that knows how to do this.