Lenny's Podcast: Product | Career | Growth - How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

Starting point is 00:00:00 Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive. You spent a lot of time thinking about how to help your team learn to take a punch. If they come to me and they're upset, I try to focus them less around how you litigate another person's impression of you and more on what is the action that you can take. To counterprogram the narrative that you are afraid that this other person has of you. What are you going to do next to demonstrate that you are the person that you know yourself to be? You have specific tactics that you teach your team to deal with hardship.

Starting point is 00:00:31 I would really love it if more people were like, screw it. I'm going to do something that's probably going to fail. It's important and it's worth doing and I'm going to do it well. Is there something you've learned about when your leader tells you to do something you disagree with? People think that the game is all about influencing the CEO, influencing the people around them. You come up thinking like you're the protagonist. But in the story of work, you are probably not the protagonist. You're not special.

Starting point is 00:00:52 Today, my guest is Hillary Gridley. Hillary is head of core product at Woop. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox. Even more importantly, she wrote what is now the sixth most popular post of all time in my newsletter, How to Become a Super Manager with AI. She's also the first ever crossover guest between this podcast and her sister podcast, How I AI with Claire Vow. And not just that, her episode with Claire is on track to be the most popular episode of the podcast.

Starting point is 00:01:22 So all that to say, Hillary is incredible and I'm so excited to continue learning from her. this conversation is packed with advice that will make you a better product leader, builder, and also just a better human. If you know it's good for you, you don't want to miss this episode. A big thank you to Sam Propis, Danielle Raynall and Kelvin Wong for sharing suggestions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including superhuman, notion, linear, perplexity, and granola. Check it out at Lenny's newsletter.com and click bundle.

Starting point is 00:02:00 With that, I bring you Hilary Gridley. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point your customers will start asking for enterprise features, like Samo authentication and skim provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand,

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Starting point is 00:04:18 Whether you're a startup or an enterprise business, Persona has a plan for you. Learn more at With, persona.com slash Lenny. Again, that's with P-E-R-S-O-N-A dot com slash Lenny. Hillary, thank you so much for being here and welcome to the podcast. Thank you, Lenny. I'm so excited to be here. I talk to a bunch of people that I work with you about about what we should talk about and what you're amazing at. First of all, every one of them loves working with you so much. One of them's like, I joined Woop just to work with Hillary. And of that, there's kind of this theme that emerged that I think is a good kind of overarching

Starting point is 00:04:57 theme for our conversation. And it's something that you spent a lot of time thinking about. And it's how to help your team and how to help people within your company learn to take a punch, essentially how to help them deal with hard stuff and do hard stuff and build hard things. So I guess just broadly, does that ring a bell? Does that resonate? Yeah, absolutely. It's something I care a lot about. I've been, I think, pretty lucky in my career. I've been very drawn to working on hard product problems, regulated areas. areas, really hard business models, things with pretty high emotional stakes for the users of the products. You're really likely to run into a lot of setbacks along the way. And I think this is

Starting point is 00:05:40 really relevant today because I look out and I talk to a lot of people and I hear fear and I hear uncertainty. And I think it comes from a few places. I think obviously I'm really excited about AI and how it's transforming the way we work. And I think a lot of people are. but I think a lot of people are scared too. And they're embracing these tools. They're learning these tools. But a lot of them have a question in the back of their mind. Like, what does this mean for the future of my job?

Starting point is 00:06:07 And in many cases, what does this mean for my identity, right? Like, I think it makes people question even just how we provide value as humans in society. And I also think, you know, people, especially young people today haven't even necessarily been in a career environment where there wasn't always kind of a threat of layoffs or things like that. And I think that's taken a real psychic toll on a lot of people. And so I think all managers now really need to be able to lead their teams through uncertainty, through fear, through hard things. And I love the concept of taking a punch. I've got a couple other tools that I like to use. But I think it can teach people how to thrive in these environments.

Starting point is 00:06:46 And it's really important to me because I would love if more people took on hard things. I think there's so many really hard, challenging problems out there to solve. and the more people are kind of fearful about the future of their careers or the future of work, I think the more they gravitate toward things that they feel like they're likely to succeed at. And I think that's wonderful. We need that too. But I would really love it if more people were like, screw it. I'm going to do something that's probably going to fail.

Starting point is 00:07:12 And it's important and it's worth doing and I'm going to do it well. There's so many kind of end diagrams of why this skill is so important, especially today. One is it feels like the easy stuff is done. Like the stuff left to build is hard. Like it feels like hardware, deep tech is where things are heading. Also just like machine learning, AI skills, just like stuff that's really hard. And then the other is just AI is just changing so much. It's just such a stressful time and hard time for a lot of people.

Starting point is 00:07:39 Let's actually walk through some of the things that you have learned about how to help people get good at these things, about how to learn, how to help people learn to take a punch, aka do hard things, deal with struggle. the first is you actually actively teach them. You have specific tactics that you teach your team to deal with hardship and to take a punch. So what are some of those things? What are some of the things that you teach your team and help them develop the skill? So at its core, when I say take a punch, what I mean is you're going to run into situations where something has gone wrong. Maybe you have misstepped.

Starting point is 00:08:14 Maybe you are just hearing someone speak critically about your work, whatever it might be. you're going to feel like you have taken a punch. Like it's a very physical feeling. And I think as managers, you spend a lot of time teaching your team how to be successful, right? You want to prepare them to maximize the chances of a good outcome. But if you don't also prepare them for what happens when that outcome isn't as good, you're going to run into some problems. And so when I think about how to take a punch, what I say to my team is,

Starting point is 00:08:45 if they come to me and they're upset because, something has happened. Maybe they said something in a meeting that wasn't received well, or again, they're hearing somebody else talk about them in some way, whatever it is. I try to focus them less around whatever happened and how you litigate another person's impression of you based on something that has already happened. And more on what is the action that you can take next? To counterprogram the narrative that you are afraid that this other person has of you. And I think the counter program piece is really important because Because whenever we feel our ego is injured, I think it's very natural for all of us to say,

Starting point is 00:09:24 like, well, that's not fair. I want to correct the record. When you do that, I think more than often, more often than not, you come off as just looking defensive. And you kind of start obsessing over things that you don't actually have control over, which is what another person thinks of you. And you don't even necessarily have that information. And so I always ask myself in these moments, what is one thing that I can do, small,

Starting point is 00:09:45 that will demonstrate the opposite of what I'm afraid this person thinks of me. And so I'll give you an example of this. I was in a meeting a while ago, and we were talking about different things that we wanted to start tracking in the WOOC journal. And our chief technology officer suggested ketamine tracking. And I thought she was making a joke, and I laughed. And she looked at me very seriously and was like, this isn't funny, Hillary.

Starting point is 00:10:13 Like, this is a serious issue for life. lot of people. And it's, it's an emerging, uh, problem in some cases. And I think we should take it seriously. I think there's a lot of value we could provide here. And I was completely humiliated. Um, humiliated because I actually take this stuff really seriously. Like I take addiction really seriously. I have a ton of empathy for, for people who struggle with it. And I also think of myself as somebody who embraces new ideas and wants to be on the forefront and would never laugh off something that kind of seems like a fringe issue that's, I think, becoming actually more and more

Starting point is 00:10:48 a big part of what's happening today. And so I realized that in that moment, I was having that reaction because of the feeling that it gave me about who I am as a person. And I became so worried that this other person had the wrong impression of me. And I wanted to follow up with her after

Starting point is 00:11:08 and say, like, let me explain myself. Like, let me explain why I didn't mean that or whatever it is. But I just, as I said, I think, I think usually that you're fighting a losing battle when you're trying to do that. And it draws attention to the thing that you kind of did poorly. You don't really want to draw more attention to it, right? You want to move on, take action, move forward. And so I thought about, well, what am I afraid that she thinks of me?

Starting point is 00:11:31 I'm afraid that she thinks that maybe I don't take some of these health issues seriously. I'm afraid she thinks that maybe I'm somebody who kind of like laughs off emerging trends. And so I thought about what's something that I could do to demonstrate the opposite of that. And I did some research very, very quickly on, you know, what are some like emerging public health concerns that people really aren't talking about that would be interesting to track. And I found some interesting research about sports betting and especially young people in sports betting. And it's sort of becoming this thing that a lot of public health experts are very worried about.

Starting point is 00:12:08 And so I very quickly just sent her a note that said, wanted to be able to be a bit. build on this idea you had today. I really liked that idea, by the way. I, you know, I saw this article, I saw this research about this other emerging thing, sports betting. And I think it'd be really interesting for us to start tracking that because we could maybe draw some correlations between people's stress. We have stress monitor and whoop. We can track your stress. We could draw interesting correlations between betting behaviors and stress levels. And so that's all I did. It took me five, ten minutes total. But I think it's a great example of showing this idea of like counterprogrammed that narrative, don't fight about the narrative. And so when I teach this to my

Starting point is 00:12:48 team, I'm always doing the same thing. They come to me, they seem kind of agitated about something. And I say to them, like, it seems like this is really bothering you. What's going on in your head? What are you afraid of? What are you worried about? And often it will emerge. You know, I'm worried that this other person thinks I'm bad at my job. I'm worried that this person thinks I'm an idiot, whatever it is. And I challenge that. I think this is really important for managers, too, to kind of challenge this negative thinking when you see it happen and not just sort of validated and allow them to go down these negative spirals, I challenge it and I say, first of all, I don't, I don't think there's evidence for that. Is there evidence for that? And, you know, even if there is,

Starting point is 00:13:25 it doesn't really matter, what's, what's something that you could do to show them that's not true? Because you know it's not true. And I think giving people that power to focus on the next step they can take and the action that they can take that helps them feel more secure in their identity in who they are because their action demonstrates that. It just gets them out of that negative thinking and it gets them through that trough of despair that comes after you feel like you took a punch. So the idea here is when you're afraid somebody that matters in your career thinks ill of you of something that you did, of you're not good at something or you think something that they're not happy about. Like this is a version of getting punched basically.

Starting point is 00:14:07 is you just feeling like someone thinks you're not doing a great job. And so the tactic here is how to change their mind almost about you and give you something tangible to do. Yeah, okay. Okay. And so the question to ask, and I wrote this down as you were talking, is this is what you ask of your reports. What is the one thing that you can do that demonstrates the opposite of what you think this person thinks about you? Exactly. This comes up all the time.

Starting point is 00:14:31 Like, there will be narratives that emerge. Some are good, some are bad, about you and your. career. And I think especially when people get to a place where they're putting themselves out there more, right? They're talking in more presentations. They're talking in more meetings. It's very natural for them to become concerned with the perception of themselves. And it is scary because it feels like something, as I said, you don't have control over. And so exactly, if instead of focusing people around, what do these people think of me? You focus them around, well, what are you going to do next to demonstrate that you are the person that you know yourself to be?

Starting point is 00:15:07 I think that can just be incredibly effective at giving people more of a sense of agency. I guess talk about the balance of I'm just going to prove everyone wrong against what they think versus here's who I am and I know this is me. And this person is mistaken. And instead of debating them, I'm going to show them who I am. Just like not overstressing about everyone thinking things about you in different ways. There is some value, I think, in having a little bit of a chip on your shoulder. I think that that's definitely been you see that people who are really. successful. They do have a little bit of like, I'm going to prove them wrong. And so I don't want to

Starting point is 00:15:41 say that like you shouldn't think about it at all or you shouldn't care. Like of course it's natural to care and of course it's fine to care. But I do want to just sort of help my team build this habit of doing the things that you know to be right and having conviction in that and, you know, being open to learning along the way and sort of calibrating as you go. But not not becoming overly concerned with your fears of what other people are going to think of you because I think, especially for otherwise really thoughtful, you know, really kind of the people who are kind of hard on themselves, I think that that just holds them back from being the person that they can be. So a key part of this is this is going to help you stop just spiraling on thinking about what

Starting point is 00:16:27 they think about you and gives you something to do that will change that. And then the other key point here is don't try to convince them otherwise. you're not going to go to your manager like, oh, I really think ketamine therapy and addiction is really important. And I'm, I didn't mean to say it this way and that kind of thing. You know, I'm not interested in litigating the things that happened already when we can move forward. And I'm certainly not interested in litigating what another person thinks about a thing that happened. I just, I feel like I've spent so much time talking to people in meetings, whatever it is, where it's just this kind of like ruminating on something that has already happened.

Starting point is 00:17:03 You know, it's a very anxious thinking pattern, I think. And people can just get stuck in it. And so, you know, let them do it. Like, I often think about, it's like when you get bad feedback, right, or critical feedback. And you kind of naturally have this reaction of, oh, well, you know, that's not fair because they don't understand. I actually have numbers I have to deliver on.

Starting point is 00:17:28 Or, like, I only had 10 minutes to do this. So, like, of course it wasn't perfect. Like you naturally come up with these reasons why you're actually not wrong. And that's fine. Like it's, I don't want to say like you should feel bad for doing that. Like let yourself have the pity party. Let yourself feel those things. But then, but then you've got to move on as quickly as possible because those feelings,

Starting point is 00:17:51 they actually do tend to spiral and get worse if you're not actively working against them. Oftentimes these sorts of lessons come from the person. experiencing this themselves? Is this something that you dealt with when you were starting your career or even now? Oh, absolutely. 100%. And I think it is more than just my career, but just my general mental health and my life. A lot of where this comes from is a concept in cognitive behavioral therapy called behavioral activation. And in my former job, I was working for a company called Big Health. And we make digital therapeutics. So those are mobile apps. that have been clinically validated to treat behavioral conditions like insomnia, depression, anxiety.

Starting point is 00:18:38 And I was working on a new depression therapeutic. And so I went very deep on this and was working with a really wonderful clinical team full of clinical psychologists who helped me understand the techniques that therapists use when they are working with people who have depression. And so much of depression is characterized by these negative thinking patterns and this like this feeling that I feel bad. and I just need to wait until I feel better, and then I will start doing the things that are good for me, right? I don't feel like responding to this text, so I'm just not going to do it, but I'll respond when I feel better. I don't feel like working out, so I'm not going to do it,

Starting point is 00:19:17 but I'll do it when I feel better. And the truth is that doesn't go away on its own, especially if you have depression. And it's something that, again, the idea of behavioral activation, is you have to identify these actions that you can take that will reverse that negative spiral and will improve your mood. And so the sort of misconception is I'll feel better and then I'll act. And the thing that therapists try to teach people, they're working with them in therapy, is I will act and then I will feel better. But acting is hard if you are in the throes of depression.

Starting point is 00:19:56 And so easier said than done. And a lot of the work is in how you help people, identify specific actions that they can take that will reliably lift their mood. And I mean, I have a list of myself. I've had a list on my phone of my behavioral activations. And it's things that I know I can do if I start feeling like the walls are closing around me. If I if I like feel myself kind of getting sucked into like very low mood or negative thinking or whatever it is. And you can you can see how effective that is. It's just getting you out of there versus the instinct to just sort of like go in line bed and feel bad for yourself, which I understand very well. And so that understanding that concept, which is that, you know, at its core, a therapeutic

Starting point is 00:20:39 concept used in cognitive behavioral therapy. But it kind of, it kind of changed how I see the entire world and how I see, especially as a manager, the ways that people in my team think and behave and how easy it is to get stuck in some of these like downward spirals that you really need to actively push back on. And as a manager, I want to help them do that. I want to help them, A, see that, like see the ways they are in some ways sabotaging themselves, getting in their own ways with whatever is going on in their head. And then I want to help them counterprogram it in themselves. And also, you know, as I said, counterprogram the things that you are worried about out there as well. So interesting. So the core of this technique is what's an action? And you said this. It could be

Starting point is 00:21:27 very small. Very small. You can take that in this case shows someone else you're not, they're not, you're not who they think you are. Like, you're worried they think, think about you in a certain way and you want to take an action that helps them see you're not that. So that, yes, that's the taking the punch concept. The behavioral activation could be anything, right? It can be, it can be picking up a piece of laundry off of the chair and putting it away. And that's just sort of enough to get you out of the downward thing you're in. So behavioral activation just conceptually is, you know, how are you taking action to reverse the downward feeling, the negative feeling that you're feeling? And then the take a punch concept is kind of that applied in the context of I'm in a working environment.

Starting point is 00:22:09 I am very conscious of how I'm being perceived by other people. That's causing me a great deal of stress. I think especially for product people who are, you know, so much of their self-identity is wrapped up in having the answers, being competent, getting things done. and so many of them have been people who have been really good at that for most of their careers, which is how they got into these jobs in the first place. I think that can be an extremely stressful thing for them, that in many cases can be like the driver of burnout and the driver of like, I can't really handle the stress of this job anymore.

Starting point is 00:22:44 And so I think of the take a punch concept is more just applied to that sort of specific problem of, I'm struggling at work and I'm struggling largely because of my perception. of other people. And I want to feel more agency in that situation. This is so cool. Okay. On the idea of the specific take-a-punch concept, what kind of impact have you seen this have on people's mood and careers? Is this, like, how big a deal is this specific tactic? Well, I think it's a big deal, like, on two levels. One, it's a big deal because it can help you in a crisis or a minor crisis. But I actually think it's a bigger deal because I see so many people who don't put themselves out there because they're afraid of how it's going to go.

Starting point is 00:23:30 And so I think of the classic example of, I'm often trying to encourage people to like speak up in meetings more. To practice the skill of how you move a conversation forward in a way that contributes value, both because doing so I think is important because nobody wants to be in bad meetings, but also because it will help with your career, right? like this is how you kind of get on people's radar as somebody who's like, oh, that person's got great ideas, thinks about things the right way, whatever it is. I think it's just, it's one of these things that I talk to people about it and that, you know, they are interested in coming to the meeting and hearing about these big decisions are getting

Starting point is 00:24:08 made, but they just kind of want to sit there and observe. And I'm like, first of all, like every additional person in a meeting has a cost because every additional person in a meeting makes the people in that meeting less candid than they would have been if there were fewer people in that meeting. And so one key piece of a meeting is like, you usually have a problem you're trying to solve collectively as a group. And it's really hard to do that if people are being overly cautious about what they're saying because there's like too many people in there. So when I tell people this, I'm like, you know, it's really important that you earn your place in this meeting. And let's work on like how to do that. And the core piece

Starting point is 00:24:47 of that is like you've got to say stuff that's valuable. And people always come up with all these excuses for why they can't do it. And one thing I've learned is that I think people are really good at coming up with very rational sounding reasons to not do things that just make them uncomfortable. But in their head, they're like, oh, no, you know, like, I'm too junior. Like nobody wants to hear what I have to say or everyone was already thinking it or, you know, I like to process things internally and by the time I say them, the conversation moved on, whatever it is. Um, And so so much of like that skill, it's like a communication skill at its core, it's just how to express yourself verbally. But so much of the blocker of that is, I think, fear.

Starting point is 00:25:28 Fear of saying their own thing. Fear of looking stupid. Fear of just the discomfort of everyone in a room turning and looking at you, right, as you're kind of like trying to formulate a half-baked thought. And so if you can help people be less afraid of that, that's like 90% of the challenge of actually improving some of these skills. And so I think when you give people the skills of taking a punch, you are helping them feel less afraid of getting the punch in the first place. And that's why I think it's so important. That's profound. The second order effect of the skill.

Starting point is 00:26:01 There's something you mentioned when we were chatting earlier that stuck with me with this idea, but too many PMs and too many people are playing on easy mode and not trying hard things. Uh-oh, we're getting ourselves in trouble here. Okay. Let's say more. Oh, I think this is my hot take. Like, you know, you hear people talking about craft and taste and product management, and it's all very wonderful. And I'm like totally on board. Like, I love it.

Starting point is 00:26:26 I'm a photographer, that kind of thing. But I'm like, well, if you are like really in it just for pure love of the game, like, you just love product management, like, why are you building products for people exactly like you who have all your exact same problems at a company that sells to other companies? that doesn't worry about pricing. Like, there's no real bear. I mean, there's, I don't want to act like, I think this is easy to be clear. But in the grand scheme of things, like, I wish that the people who have this pure love

Starting point is 00:27:02 of product management and have this pure love of building things, that you would see more of that applied to building for low-income people, building for, you know, social services, things like that, that really, really need that kind of work. And I think there's a level of prestige, obviously, associated with working in certain companies, and you know, you get less of that in other industries. And so people would naturally gravitate toward that. And, you know, I totally get paid better. Like, no real judgment for me.

Starting point is 00:27:32 I just, I wish I saw more of it. I wish you would see more people. And I'll say this. I know there's a lot of you out there. I know there's a ton of people out there doing really, really important work in really, really hard spaces. And I see you. And I appreciate it and shout out to you. Awesome.

Starting point is 00:27:47 Okay. I'm glad you should have that. Thank you. I think this will resonate with a lot of people. I want to move on to another trait slash habits slash skill that you are good at and help people learn, which is being very transparent in what's happening within the organization, within your thinking. You almost help people think the way you think and see the way you think so that they can operate at a higher level. Talk about that, what that looks like and why that's important.

Starting point is 00:28:12 It's interesting. I think another thing I hear a lot of people complain about in organizations is like the, why do 10 people have to sign off on this email before I send it kind of problem? And I think the answer to that is like, because those 10 people all have different information, different context, and in many cases, completely different, like working models for how the CEO of the company and other strategic leaders in the company think. and it makes things super inefficient. I think people will often say, like, oh, it's a process problem.

Starting point is 00:28:47 It's not a process problem. It's not an approval problem. I think it's a transparency and it's a communication problem, like downward communication, outward communication. And what I mean by that is when I think about like artifact-based communication, so reading a strategy document, for example, everyone at the company reads a strategy document. Great.

Starting point is 00:29:07 Everyone is working from the same idea of what the strategy is. but then things change, right? Like, especially if you're working in a really dynamic space, new competitive threats emerge, new opportunities emerge all the time. This is especially true now with AI. Obviously, everyone is lighting their strategies on fire and trying to figure out the best way to sort of transform their organization. And so if you're, the way that you understand what's going on at the company

Starting point is 00:29:32 is from reading a document that was written six months ago, you're going to be working from outdated information and you're not going to be able to, like, think and respond to new things that happen. And so what is much more helpful than understanding what your CEO thinks is, I think, understanding how your CEO thinks. And that goes for all sorts of levels of the company. I want to understand how all the strategic leaders that my company think, and I want my team to understand how I think.

Starting point is 00:30:01 And when I feel confident that people on my team understand how I think, like, I don't need to read their emails. I don't need to approve things. The times where I feel like I need to do that is because I'm working with people where I'm like, I don't have confidence that these people understand how I think. Or I don't have confidence that they understand how this email or whatever it is is going to be received by this important person. And so I try to teach that to my team. And the way that is a few ways. First, I'm in meetings with people, like important people at the company. So I'm constantly hearing the things that they're saying and paying attention to sort of the note behind the note.

Starting point is 00:30:44 Why do I think they're saying this? What insight do they have that they're bringing to this conversation that might not be obvious? And I try to make an effort every week. I don't always do it when I try to send my team just a quick rundown and slack of here are the most important conversations or the most interesting conversations I had this week. here's what that person said verbatim. Again, I write a lot of notes, so I've got it. If you've got a transcriber, maybe that'll help you.

Starting point is 00:31:13 And here's what I interpret that as. Here's why I think they say that. Here's where I think that's coming from. And here's what I'm going to do differently as a result. And these aren't long. And sometimes if I don't have time, I'll just, like, in a teen meeting, I'll literally just go through my notes from the week and sort of voiceover stuff and editorialize it as I go.

Starting point is 00:31:31 And over time, I think my team has, like, a pretty good sense. of what people are saying and how to think about the thinking behind it and how this person thinks, how this person thinks, and how I think. And I think when you get an entire organization working that way where everyone's working from the same models of what the CEO thinks matters, what level of like risk tolerance the company has, things like that, then you can actually start to move much, much faster and communication becomes much, much, much less painful. So the tactic here is to help your teams kind of build a mental model of everyone in the company that matters

Starting point is 00:32:10 so that it's like the way you put it almost is when they're emailing them or asking for something. They already know how they're going to respond. Is there an example you could share something like this of just like something, a person at whoop of how they think? I don't know, maybe you can keep it anonymous just to make this little real of the kind of mental model you might want to build around someone. So our CEO will is somebody who obsesses over pixels in a way that is challenging to get things through design review. But I think results in a product that is a thousand times better than it would be if he were accepting of, you know, small excuses here and there for, oh, well, this, you know, we had to cut scope here. We couldn't quite do what they wanted here. Like he sets a high bar and he holds it.

Starting point is 00:32:59 And he doesn't compromise. And I think this can sometimes get misconstrued. And I think a lot of people might think that he just wants like maximal scope on everything. And I think that is a misunderstanding of what he cares about. We often get feedback from him that's like, you know, this doesn't feel like the future. And everything that we're building needs to feel like the future. A lot of people hear that and they're kind of. And I'm like, oh, gosh, like, you know, we're never going to get this thing done on time.

Starting point is 00:33:31 Like, we can't make any sort of sacrifices to scope or anything like that. But when I hear that, like, what I hear is more that we have this AI coach in the product. We have all this amazing data in the product. You know, we're tracking every single one of your heartbeats and we're pulling all this other data. And we have every, like, every screen is a moment to show that to people in a way that feels like something. that has never existed before. And there are small ways to do that, right? It's like how you pull in, if you're explaining a concept like V-O-2 Max,

Starting point is 00:34:05 which is a measure of your cardiovascular health, you can explain that to people with static content, or you can explain that to people by bringing their data into, you know, the method of explanation that you're using. You can make it really conversational because you're using this AI coach. You can make it feel more like you're talking to a person. And a person who, by the way, has all the data, about you, which doesn't exist today.

Starting point is 00:34:29 Like, your doctor doesn't have that. Your coach doesn't have that. And that's not like, oh, gosh, we've got to blow up the scope on this thing and make it 100x as big. But it's finding these, like, little touches to say, like, wow, that was really magical. That was really thoughtful. And this feels like the future. This feels like I'm very conscious of the fact that this product knows so much about

Starting point is 00:34:49 me and is able to sort of sort out the signal from the noise on that in these really small and elegant ways. And so for something like that, like, I would get that feedback in design review or I'd hear that in a design review. And maybe one of my PMs would be in that design review. And so I bring that to the team. And I hear things like that in a few different design reviews. So I bring those back to the team. And I'm like, I've noticed that recently we are consistently getting this type of feedback.

Starting point is 00:35:15 Here's why I think it's really important to Will because I think he's really focused on building, you know, the health company of the future. And I don't want you all to think that this just means, like we have to just throw AI at everything and we have to just throw like maximum scope at everything. I think the key is understanding like on the matrix of cost and effort for impact. Like what are those high impact but low cost ways that we can just find and sprinkle through the experience? And really try to make that magical. So I'm connecting the dots for my team, right? I'm saying you weren't in all these meetings, but I saw it.

Starting point is 00:35:53 Here's what I heard. here's my interpretation of what I heard and here's how I'm thinking about how this other person thinks about it and so as a result here are some things that I think we can do across our product going forward essentially these are principles

Starting point is 00:36:08 or values or tenets per person of what matters to them so for Nick it's this needs to feel like we're living in the future you can't just be like another heartbeat tracking out this is so cool and there's so many trickle-down benefit

Starting point is 00:36:21 to this one is people feel like they're aware what's happening. That's one of the most common. I think piece of feedback people have a big company is like, I don't know what's happening. So there's so much of visibility, all the secretive stuff happening in the meetings. I don't know what people are deciding my fates and all these discussions. So I think just even knowing that you're sharing all this is so powerful. Well, and on that note, like, when I approach these conversations, I always try to think of them as, um, even if I don't agree with the feedback, if I don't agree with the decision, like, what is the insight that I'm missing? like how am I wrong about this in ways like what would be true for this other person to be right?

Starting point is 00:36:57 And I'll go through that thought exercise and I might not get to the other side and agree with it. I might still, you know, think I'm right or whatever. But oftentimes it forcing myself to think that way forces me to think about how this other person thinks it. And if I do that enough, I will be like, oh, this makes sense. I think this makes sense if. I think this makes sense if and oh, maybe this other thing is true. And I think when I hear the people, the people who are like, I don't know what's going out of this company. like I think they do the opposite.

Starting point is 00:37:23 Like I think they look for reasons to disagree and they look for holes to poke in, well, this decision doesn't make any sense because I came up with something that might be wrong about it. And I think that's another thing, by the way, in terms of just sort of like helping your team have the emotional maturity to exist and thrive in an organization is helping them think that way. Like helping them understand you have a point of view. Your point of view is important. But on some level, like, you do kind of have to have respect for these other points of view. and have the humility to think that, like, maybe they're onto something that you're not onto. And it's amazing how much you can, like, learn into it without having to have all the facts just by doing that. If you're like, well, this person's behavior makes sense in a situation where X, Y, and Z is happening, oftentimes you will find that X, Y, and Z is happening.

Starting point is 00:38:09 I'm glad you went there. I wanted to actually follow this thread, which is kind of a different direction, but I think a lot of people are always struggling with us as a leader. when your leader disagree, it does say something that you completely disagree with, but you still need to represent that as like, here's the thing we're doing. But you don't want to be like, oh, just because Nick sets so, you know, because you lose power as the leader. Do you have any just, is there like something you've learned about how to do that well when your leader tells you to do something you disagree with and you still need to get your team to do it? First, I do try to go through like the, the what if I'm wrong exercise. I think a lot of people just sort of like expect that if you ask somebody an open-ended question, like, why are we doing this?

Starting point is 00:38:52 You're going to get a straightforward answer. And oftentimes the answer is not straightforward for various reasons. Like maybe there's confidentiality reasons. Maybe there's just like, you know, somebody is acting on a hunch. But that hunch is informed by years or decades of reps of developing judgment. And like they're probably really on to something. And it's not just like this kind of arbitrary gut feeling. But whatever it is, like, I really try to get to the bottom of, let me really make sure that I have done my best to understand this person's point of view.

Starting point is 00:39:23 And I have some sort of tools for doing that, which I can also talk about. But if I've done that and I still disagree, I'm, like, relatively candid about that. But candid in a way where, like, it's still respectful. Like, I think what you want to avoid as a situation where as a manager, you're like, ah, this, you know, I have no control. This sucks. this decision is so stupid, but like, that's a job, so we have to do it. Like, obviously, that's not going to, you know, set your team up for success or make anybody happy about it, but you do hear that.

Starting point is 00:39:53 You do see that happening. And so I think what I try to do in those situations is separate out, like, my opinion from it from the, like, well, what is the insight that makes it make sense to this person? And explain their rationale, even if I'm comfortable saying, like, you know, I don't necessarily think, like, this isn't how I would do it, or I don't even really agree with how they're thinking about it. But from their point of view, from their perspective, their professional experience, whatever it is, I could see how this makes sense. And like, they might be right. I don't think they're right, but they might be. Let's find out. Like, we're not going to find out

Starting point is 00:40:28 if we are all squabbling about whether this is a good idea the whole time. Like, the only way we're going to find out is if we give it the best shot that we have and try to do it. And if we're wrong, like that happens sometimes and we try again. I like that this comes back. I like that this comes back to your mental model orientation of here's their mental model. Here's what their experience has been like. Here's how they see the world, the trends. And then this is why they think, the way they think. And so instead of encouraging your team or yourself even to be like, no, no, you're wrong here. It's more, okay, here's their data set. Let's try this. And this will inform that data set. It may be changed their mind. Yeah. Because I think in product, like I like to joke, there's no right

Starting point is 00:41:05 answers, right? There's only wrong answers. And you're just trying to execute well on like the least wrong answer that's available to you. And so I think it is like, you know, the sort of reasonable people can disagree about this of it all of, you know, like this is what I think and this is how I'd approach it. I think this is what they think. And I think this is why they would approach it this way. And again, like, the only chance we have of succeeding is not being torn apart on that. And so at the end of the day, like if it's not like a obviously terrible answer, and sometimes

Starting point is 00:41:38 even if it is an obviously terrible answer, you're still more likely to succeed if you just sort of like, sort of reorient yourself around a world where it's not a terrible answer and then just try to will that into existence. You said that you have some tools to help you understand someone's point of view.

Starting point is 00:41:53 I can't help but ask more about that. I talk about what I like to call magic questions. But the thing about magic questions is they're not actually questions, they're statements. And the end with, do you agree or is that right?

Starting point is 00:42:06 And so I have found this like the most helpful way for kind of trying to understand a person's mental model is to just like put facts in front of them and see when they say no to and what they say yes to. And then if you can get them to explain great. And if they're good communicators, they often can. But if they're not, like you don't have to let that stop you. And so, I mean, I'll do this even just as an example in a non-leadership context with if I'm working with like legal teams or compliance teams or things like that,

Starting point is 00:42:35 they're often working from a literal set of rules, right? There are laws. There are regulations. And you are trying to understand, like, what, you know, if we were to take this path, would that be okay? Would that not be okay? And sometimes that's not straightforward. Sometimes, like, there's regulatory areas that are, you know, up to interpretation.

Starting point is 00:43:01 And so when I first started working in, like, a regulated space, I would find this kind of frustrating and confusing because I would say, can you just like, can you just like give me the rule so I can understand what's right and what's left of it? And they'd be like, oh, well, it depends. It depends. And so I learned that if I kind of flipped that and approach that like, well, you know, what if we did X, Y, and Z?

Starting point is 00:43:22 Like, what if this is what it looked like? What if this is what the copy said? Would that be okay? No? Yes. If no, why? If yes, why? And so I'm sort of teasing out the mental model rather than asking them to explain it

Starting point is 00:43:33 to me. And this is what I tell my team all the time to do this to me. Like when they come to me and they say, well, what do you think I should do? Or, you know, what could I have done differently? I'll say, like, rephrase that as tell me what you think you could have done differently. And then ask me if I agree. And when I do this, I think it has a few benefits. One, it helps them kind of calibrate their judgment over time.

Starting point is 00:43:57 So they're actually forcing themselves to make this assertion. And then they're kind of calibrating how close that was. to like how I would think about it, which will get you much faster, much further than just asking open-ended questions and getting the answer. And then the second part of it is they don't become reliant on meat for answering these questions. I think that's kind of a trap that a lot of managers fall into is you people come to you with questions. You want to help them. You answer the question. And then you find that they come to you with all their questions. And you're kind of like, yeah, you got to solve some of these on your own. So again, I think like the magic questions to me,

Starting point is 00:44:31 is that right? Do you agree? And it. anytime you find yourself, like, tempted to ask an open-ended question to somebody whose brain you're trying to understand, stop yourself and say, like, let me just say that. Somebody say as a statement, what I think, and then try to calibrate based on their reaction. And, like, I think that's the fastest way to understand how another person thinks. It makes me think about a lot of people, like, it can come across as it's like a weird, manipulative way of asking someone stuff. But it turns out, like, we're not good at really knowing what we think or know a lot of

Starting point is 00:45:03 times and you need someone almost to interview you in a really effective way to get out all this knowledge. And this is just a really simple way of getting that out of your head. You know, it's funny because I like, when I talk about this, I get that reaction a lot where people are like, well, doesn't it feel coercive? And I'm like, well, you've got to go in pure of heart. Like, you've got to go in. So, so, see. Open to being wrong and even expected to be wrong. And you have to make that clear to them, right? Like, if you're coming in and you're like, oh, here's what I think. Like, you agree? You agree. Like, of course you're not going to answer you want. Or I mean, you might get the answer you will. I might get a yes. If your goal is

Starting point is 00:45:33 get to yes, that's not what I'm, that's not what I'm talking about. If your goal is to understand and you are coming from like, help me understand how I'm wrong, help me understand what I'm getting wrong here, and approach it with that sort of like curiosity and humility and make sure that you're like carrying yourself and presenting yourself to this person in a way that, that shows that, that you're not coming in like hostile or forceful or something. Yeah, because there are absolutely circumstances where you're doing that and you're going to get bad intel because you're making the person uncomfortable, so they're going to lie to you. But that's like a, I think, a whole set of interpersonal skills that we probably don't have

Starting point is 00:46:07 time to talk about today. I wanted to come back to you said this interesting insight about your CEO that he wanted to build something that felt like the future. I just wanted to share there's a story that has always stuck with me at Airbnb. There was a big launch coming up and there was a designer sitting at late in the office trying to read, update the website to include this new product. It was a launch of Airbnb neighborhoods like, I don't know, 10 years ago. And she was just like, hey, Joe, and this is Joe Gebby.

Starting point is 00:46:37 It was walking around the office. And she's like, hey, Joe, what do you think I should? What do you want the website to be? What do you want it to look like? What should we try to? And it was going to launch in two days. He's like, built something the internet has never seen before. And now this makes me, like, it's interesting because when I always think about that

Starting point is 00:46:54 story and tell that story, it's like, this is a crazy ask. And now as you share an approach for how to handle something like, that. It really changes my perspective to like, okay, what's Joe's worldview? Why is that the way he saw the world and why we needed to build a site like that? Which I could start thinking about, but that's a really interesting way to just like handle things that sound absurd and out of nowhere. I agree so much. I'm a proud former English major and so I'm a huge proponent of reading fiction and reading in general. And I feel like that's where so much of this. comes from for me. It's just like a curiosity for like, in what world does this make sense for this

Starting point is 00:47:36 person? And it's so easy to look at another person's behaviors and other person's actions and what they say and just be like, that doesn't make any sense. And I just, I find that, I don't know, like your relationships become so much richer, even just in a work context. Like when you approach it with that, like, what is the world of this person where the thing that they're saying makes sense. And I feel like in my life, honestly, like a lot of my frustration has come from being frustrated with other people. And so this is something that I've had to learn over time because when I come home from work and I'm just like, oh, this person said this and it didn't make any sense and this person's totally out to lunch and leadership doesn't know what's going on. Like all I was doing was making

Starting point is 00:48:19 myself miserable. And actually worse than that, I was making myself miserable and I was making myself pretty useless to the company. And so I would get frustrated because I was like, you know, now nobody appreciates my perfect, unique, unique, unique, unique, unique, beautiful, perfect concise, just wrong opinions. And so I feel like that's been like a big area of growth for me, honestly, is like learning to approach people that way. It's not just like, oh, this is a nice thing to do, but I think it, like, genuinely makes me a happier person. And yeah, I think a lot of it comes from reading fiction. I love that we're just unpacking the onion of the power of this very specific habit of

Starting point is 00:48:59 just helping you learn the mental model of the people around you. This is just making me sound like a crazy person. No, there's so much power to this. Like, as you talk, I'm like, wow, there's so much value here. Because not only is it, you talk about how this is the source of a lot of burnout for a lot of people where they're just so frustrated. The CEO or the chief product officer designers just like, I hate this. Where are they just asking all these ridiculous things?

Starting point is 00:49:23 keeping the bar way too high. It's just nothing's ever good enough. But not only does it help you feel better about their asks because you can understand where they're coming from. It also helps to be more effective in helping them change their mind potentially and see a different perspective because now you see the data that informs their perspective and you could help adjust that or or kind of poke at it. Like, hey, are you sure this is true? Are you sure like, I don't know, your competitor and this is how they see it? Maybe it's not. Let's look into that little Yeah, it's really interesting. I, at my last company, when I started reporting to the CEO, they found various coaches for me to work with.

Starting point is 00:50:04 And one of them was the former chief product officer at Coinbase, who's gone to Found Bridge, which is just that apart by Stripe for a ton of money. And one thing that he's said to me that really stuck with me is when you're reporting to the CEO and like, as a chief product officer, the big mistake that people make is they think that the game, is all about getting what is inside their head and like influencing the CEO, influencing the people around them to make it so. And if you go into the rule trying to do that, you're going to fail because actually, like what your job is to do is to understand what the CEO's vision is and like what they care about again, sort of how they think about things and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of product.

Starting point is 00:50:56 And that was just such a radically different way from what I ever thought my job was. Again, to go back to sort of the fiction example, like, you know, you kind of come up thinking, like, you're the protagonist. And you can be the protagonist in your life. You can be the protagonist in the story of your family. But in the story of your work, like of a company, like, you are probably not the protagonist. And as much as it can feel kind of weird to say that, I genuinely think, like, some of the best advice I've got in my life in terms of things that have just not only transformed how I see the world and how I act in it, but just like my own sense of happiness is like you're not special. And it's like, I used to spend so much time and energy just being like, oh, like, people aren't, people don't see it my way.

Starting point is 00:51:46 And I have to convince them. And when you're in an organization, like, it's an ecosystem, right? Like, it's an organization full of people who are all trying to work together to get a thing done. And if every single one of those people is operating from their own, like, protagonist viewpoint of this is how I actually see the world. This is what I think we're here to do. And I need to convince everyone around me at all times. It becomes extremely inefficient. It becomes extremely painful because you're just, everyone's just fighting all the time.

Starting point is 00:52:15 And so in some ways, like it feels like you're kind of. Like, if it sounds almost defeatist, like, I'm always worried about this sounding. Like, I'm just like, yeah, just do whatever the boss says. And that's not how I feel at all. Like, I think it's incredibly important to bring your skills and your talents and your perspective to the job you have and really your taste and your craft and all of these things. But I do think this idea of, like, understanding how to build a shared mental model of everyone together that definitionally cannot be defined by your own narrow perspective

Starting point is 00:52:44 actually just makes work a lot better for everybody. So then a lot of people, like you said, I love that you went there. It's just like if you're, because it could sound like, okay, your job is just to execute what the CEO tells you. There's no value to your insights and perspectives and you're just get out of the way. You're just get everyone to do the thing they see it wants. Where do you, I guess in your experience or just advice on where's the fulfillment for you then as a CPO or example or direct your product where, you know, it's not that fun just to be there executing a CEO. vision and not have any input. Well, and I think, like, there's, there's so many decisions all the way down.

Starting point is 00:53:23 And there's so many, like, micro places where you can, you can zig where others would have zagged. And I think I personally, like, a lot of where my fulfillment comes from is from feeling, like, if somebody else were in this job, it would be done differently. And, like, something about the product is different because I was the one who worked on it, because I was in the job. And that comes from, like, my unique perspective, my unique point of view, the experiences I've had in the past, like my various influences.

Starting point is 00:53:52 And I think it's trying to like figure out the right level for it so that you're not, you're not pushing against an immovable force. You know, it's almost like if you're playing Jenga and you're sort of trying to feel around to find like, okay, well, where are the pieces that can move? And when you know how somebody else thinks, A, like you can find that there are immovable forces. Those are not the battles worth fighting. but there are also areas where maybe they don't know as much. And there's also areas where maybe like they're actually kind of scared because they don't

Starting point is 00:54:24 know as much. And maybe that's an area where you have an interesting point of view. And so you can step into that role and be tremendously valuable and being tremendously influential. But you can only do that if you have a good like frame for kind of what your, what the, model is. And where are the things where it's like, okay, we are operating on a person's insight here that is, it is itself extremely unique and extremely valuable,

Starting point is 00:54:49 and it is the reason this company even exists in the first place. But that, I mean, there's millions of decisions have to get made, you know what I mean? And there's millions of different places that you can put yourself. And so I think it's just like kind of constantly feeling out for like, where are the places that I'm really spiky, where are the things that I think I do really well, where are the gaps? And again, you can only find those if you're engaging really good faith. and engaging earnestly and like really understanding out what are people think.

Starting point is 00:55:19 There's two really interesting thoughts that I have as you're talking that I think will even further crystallize what you're saying. One is that you're just saying this is the way the world works. It makes me think about Jeffrey Feffer. He was a guest on this podcast. He teaches this class at Stanford Business School about how to gain power in the world. It's like in the rules of power. And it talks about, you know, it's like it's like all these ways to influence and win and achieve and gain

Starting point is 00:55:44 status and all these things. And he's like, you know, this part doesn't sound fun and great, but I talk about here's the way the world works and is not the way you wish it would be. And what you're describing is the way a company works is the CEO is in charge. And your job is to, you know, they're the boss. And the sooner you understand their vision trumps your vision, the easier everything gets. Like you're not there to tell the CEO, here's what we should be building. Right. Their job is,

Starting point is 00:56:13 to own the vision of the business and the company. Yeah, I think that's true. And if you disagree with it, you probably shouldn't be working on that company. Yeah. The other pieces, it's just the vision. Like, here's the vision of the future of where we are heading. If we win, here's what will be true and the world will look like.

Starting point is 00:56:31 But there's so much more that you need to figure out that is to achieve that vision. And that's basically the role of this of the CPO and director products, all those sorts of folks. And everyone at your level. And everyone at the company. How you said it there is so right on because it is like the vision is in many ways. I mean, in some ways it's execution based, but in many ways it's a vision of what the world is going to look like in five years, in 10 years. And so in some ways, I would say like your job is if you can understand that and you can understand here's what this person thinks the world is going to look like, assuming all that is true, what are the things that I can do to.

Starting point is 00:57:13 maximize the chances of that and becoming the actual future. And then also what does that mean for a product? Like what does that mean for if it has to be true that like, you know, take whoop, for example, if there's a vision of the future where you have all of your health data in one place and we're able to detect health issues before you even know you have them and we're able to do really hyper-personalized coaching to help you understand like how you, your behaviors today are impacting how healthy are going to be in decades. What does that mean for what WOOP needs to be today?

Starting point is 00:57:51 And what does that mean for how it needs to evolve in the next couple of years in order to both make that a reality, but also like win in that world? And I do think that's exactly where the like the people in the rank and file can be tremendously influential. It's that level of like, I'm going to fight with you about how the world's going to work in five years where I think you're just fighting a losing battle. And if you don't like the vision, you could leave, right? It's like, or try to change it.

Starting point is 00:58:17 Like, those are two options. And I think to your point about pushing back, because you asked about this, like, I, again, I never wanted to sound like I'm just like defeat us, like, just accept it. Like, I'm a very opinionated person. Like, I go to the math for things that I think are true. And so I, you know, I teach my team, like, you have to be really good at forming arguments. And that can be, that can show up in different ways. Like, some people are really good at doing that with data.

Starting point is 00:58:41 some people are really good at doing that with, you know, sort of the qual and the quant and moving it together. But you have to be able to advocate for what you think is true in the most compelling way possible. And you have an obligation to do it. And if you have done it and you've done it well and it didn't work, that's when it's time to say, well, maybe there's something here that, you know, that I wasn't seen previously. And that's where I think, you know, it's time to have some humility around it. But this, you know, it's a journey. You don't start from like, well, I got nothing to say here. So I think it's, you know, knowing where you are on that journey is important to.

Starting point is 00:59:18 This reminds me there's a PM leader at Airbnb who ended up leading a new initiative. And they ended up doing a bunch of stupid stuff. And he's like, I just, I'm realizing that it's me that needs to be pushing back on stuff now that I'm in charge of this product team. I'm the person that needs to convince the CEO. This is a bad idea. And I'm just realizing that after. doing a bunch of stuff that was stupid. And you do, like, you will see that ideas

Starting point is 00:59:44 and you do have an obligation to try to convince them that it's a bad idea. And you're going to be right sometimes and you're not going to be right every time. And I think that, like, that's why it's so hard to talk about these things in absolutes, because like, sometimes you're right and sometimes you're not right. And it is important to get really good at knowing the difference and knowing where

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Starting point is 01:01:03 I want to move on to another skill you really good up. But first of all, something I noted that I want to have to touch on real quick. You mentioned that we've now. does VOTOMX and this is not a promotion for Wu. But that's so cool. That's like a huge thing to track that this is like the thing that Peter T and all these guys are always saying this is the thing you want to track to understand your health and progress is your VO2 max.

Starting point is 01:01:22 It's like your blood oxygen level. I don't know exactly what it is. But that's cool. Then you let's you do that. There's so much cool stuff we're doing a hoop right now. I'm like, I don't know if I want to get into it all right now, but I can. We'll get back to it. All right.

Starting point is 01:01:34 Let's get back to it. Okay, cool. Yeah. Okay. So another habit slash skill that you are really good at that I've heard from folks is, and you've mentioned this a couple of times, is just building habits, helping your team build good habits and coming back to the CBT stuff, just like behavior loops and things like that. Talk about just what that is, why that's important, what you help your team learn there. Yeah. I'm kind of obsessed with habit formation and reward loops and behavior change and all of these things.

Starting point is 01:02:04 And when I think about trying to change behavior on your team or just trying to encourage your team to do more of the behaviors that you believe are associated with success, I think a lot of people think about it more of like an education model where it's like, you know, you teach the thing, you assess the thing and then there's like some accountability around the thing. And I think if you think about it more in the context of behavioral psychology, It actually works a lot better. And so I'll give you an example. I, like many leaders, have been trying to think about how to drive AI adoption, AI upskilling on my team and what that can look like. And when I talk to people about this outside of the company, I'm always surprised because they're like, well, how, you know, how do you measure it and how do you enforce it? And I don't really think about any of that stuff. Like, I'm thinking about, like, how am I creating habits around using this?

Starting point is 01:03:05 And for me, there's a couple things there. So it's consistency. How are you getting someone doing something every single day? And to do that, like, it has to start small. It has to start super easy. You have to give them things that take no more than a minute or two to do. And I actually, I have like 30 days of GPT, I call it, of like a list of 30 things to do one every single day that I don't know anyone who has gone. through this and not come out the other side feeling a hundred times more confident in their

Starting point is 01:03:33 skills and actually using it every day as a habit. Because it's built like as a habit formation tool and not an education tool. This is using a specific GPT built or building their own GPT or what's the habit there? The habit is using chat TBT or Claude or any of the people. Okay, got it. Got it. Got it. In just sort of like a kind of generic get work done way. And so I have this little tool. If you sign up for my newsletter, I'll send it to you. What's the URL the newsletter? Well, as you mentioned then.

Starting point is 01:04:03 Thanks for asking. It is hills.substack.com, hils, s, that subsdack.com. Sweet. But basically, it's one little thing you can do every single day. And the key with this is, again, consistency. So you need to get people doing this thing every day. Reducing friction. I think a mistake a lot of people make when they start thinking about how to drive adoption.

Starting point is 01:04:23 is they're like, oh, we have to show people how to do their work with these tools. But I'm like, well, work is hard. And if you are on a deadline for something, you've got to get something done. The last thing that you ever want is more friction associated with getting it done. Like, it is so annoying when you're trying to get a thing done and like your tools are being changed on you. And you don't know how the thing works. And like, you know, the hot keys are all different or whatever. And so I actually think, like, using it in, like, situations that have nothing to do with your work are way easier because you're removing all of that friction of, like, oh, wait, I got to go think about, all right, what's a project that I'm working on?

Starting point is 01:05:05 Oh, I put this into chat, GPT, and I, like, didn't really get a good answer. And now I'm frustrated because the thing's taking longer than I needed to take or whatever. And so, you know, I start with things that are just, like, fun, simple use cases. like, you know, it might be coming up with times to take a vacation or place it on vacation, or it might be, like, uploading your calendar into chat, GPT, and asking it for ideas, for talking points for the meetings or, like, things where the person doesn't have to think, because it's all just spelled out, and things where, like, there's no, there's no, like, external work pressure that you have to apply this to that's going to make it, like, an unpleasant

Starting point is 01:05:42 experience. So, consistency, reduce friction, and then most importantly, designing reward loops. And this is something that when I'm talking to people about designing for behavior change, the number one thing I always tell them is you are not thinking enough about the reward loop. And the reward loop needs to be powerful. It needs to be immediate and it needs to be emotional. So that when this person does the thing that you want them to do, they feel like a million bucks. And so when I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about is like, how can I make sure that when a person does this? they feel really great. And part of why I like custom GPTs as a tool for helping people learn to use LLMs,

Starting point is 01:06:24 and I talk about this on the podcast I did with Claire on how I AI, is because if you put in the prompt, you as the person building the custom GPT, you write the prompt, you put it in, you design it such that somebody can upload a specific document, and then they can get a specific output, like feedback on that document, or maybe something more fun than feedback. an improved written version of that document, they get the joy of like, oh, this helps me.

Starting point is 01:06:53 This was cool without any of the like despair of, oh, I'm not very good at prompting and this didn't really work and I'm frustrated. And so I just always think about that in general. Like if I'm trying to build any kind of habit on my team, it's less about like the accountability of like how I'm forcing this and more about like how I make it so rewarding for people to do it that they do it naturally. I wrote down notes as you were talking. So kind of the four parts of habits.

Starting point is 01:07:19 And I'm going to ask you for an example to help people see how this actually works in real life. But basically to help people build an actual habit, the three steps are consistent. The three things you want to focus on, consistency, friction, and reward loop. And within a reward loop, you want it to be powerful, immediate, and emotional. What is an example of this? Yeah, I can give some actually examples of like how we do this in product, if that would be interesting. interesting. Absolutely. Because I think there's something whoop is really good at. So I think one of the most interesting kind of anti-reward loops on whoop is around alcohol. Um, Woop has this recovery

Starting point is 01:07:56 system. Uh, you get a recovery score every morning. It's red, yellow, green, and it's basically like, how recovered you are and how ready you are to take on the day. And if you drink and you're on Woop, you will very quickly learn that if you, anytime you drink, you get a red recovery. And it's so interesting because it's not like people who were drinking weren't getting hangovers before. Like they weren't like they knew that it was disrupting their sleep. Like none of this is news for people. But there's something about seeing that like red score that just feels like it just feels bad. It has like this really profound emotional impact on people.

Starting point is 01:08:38 And when you see the green score, it feels great. It's like, oh, I'm like, I'm doing something well. Like I'm taking care of myself. I'm a healthy person. And I hear this when I talk to members all the time, and I hear people say, I've been, you know, I've had problems with drinking for years, and it wasn't until I got on whoop

Starting point is 01:08:54 that I was really able to get a handle on my drinking. And I'm always, again, kind of, like, amazed by this because I'm like, you had all the information you needed before. But there's something about, though, like, you wake up and you get that red score that's just, like, it manages to override, like, whatever was driving people to do it in the first. place. And then I think continuing to like have that data where you can look back at your data

Starting point is 01:09:17 and see, oh, that was the red day. That was the day that I did this thing. And it's something that we've actually been trying to, you know, find ways to do this in a longer term way. Because when you have these short reward loops, it's easier where it's like, I did a thing and I immediately either got a reward green recovery or got an anti-reward, red recovery, and that is changing my behavior as a result. And we have this new feature health span that we just launched with our new hardware. And basically what it's trying to do is help you have this reward loop between your behaviors and activities that you're doing today and what that means for how healthy you're going to be in, you know, 20, 30, 40 years. And so we have something similar where we have this, we call it the amoeba. It has your wub age in it.

Starting point is 01:10:04 It's like it has colors and sort of kind of moves around. And that changes based on how your behaviors and your activities change every single day. and the colors change when you're doing better and when you're doing worse. And you can kind of see it all broken down how you sleep, your VO2 max, the consistency of your sleep, how much time you're spending in different heart rate zones, how much time you're spending strength training, things like that. And we found that, again, it's just this incredibly powerful reward loop because we're taking something that historically has been really, really hard, which is like when I make healthy changes today, not only do I not see the results of those for decades,

Starting point is 01:10:39 but the short-term reward loop of those often feels pretty bad because change is hard and it feels bad before it feels good. And trying to build that reward loop that is more rewarding for people to see those numbers change and to see those colors change so that they're actually able to make those changes and see that progress and feel really good about it. I love that you're using all these habit-building tactics that folks have been using historically

Starting point is 01:11:04 to get you to check your Instagram likes and your Facebook posts for actual good, for helping people live longer and happier. That makes me very happy. Is there an example of doing this sort of thing with your team of helping them build? And you talk about AI, like learning to use, you know, cloud chat, GPT. Yeah, I think that's really, I think a lot of it is just shouting people out, right? Like, when somebody is doing the, like, using AI to solve a problem that they wouldn't have used AI before, like, give them a shout out in the team meeting, let them demo that. like again make them feel like a million bucks for doing the thing and people respond to that like

Starting point is 01:11:40 people will see I mean maybe it's because I work at whoop and we're all obsessed with reward loops so we're all like award looping each other here's here's your reward no exactly but no like like people see that and people respond to it um I think you know another example is like something that I think about a lot and is relevant to our conversation about um just like how you build teams that can do hard things is how you encourage people to take care of themselves outside of work. And it's something that, like, I'm always trying to model for my team and make it really visible the ways that I'm doing this, and sort of, like, having my hobbies and my other various things.

Starting point is 01:12:17 And as a result, I also try to reward, like, have these reward loops when I see people on my team doing the same thing. Because I think people, bosses often inadvertently create reward loops for, like, oh, this person, you know, they had to stay up until 2 o'clock to get it done, but they got it done. And when you create those reward loops, that's the behavior that people start mimicking. And so, you know, I try to do the opposite. Like, I try to find ways that I really am impressed with my team and the ways that they take care of themselves outside of work.

Starting point is 01:12:47 Because I think that makes them better at their jobs, frankly, and just happier humans. And so, like, there's a PM on my team, Emily, who teaches at Handelbar. She's a fitness instructor in her spare time. And so whenever we have, like, a long meeting, I'll be like, oh, Emily, why don't you, like, lead stretches to get, like, the energy level in the room up, just like, you know, nothing serious just for a minute before we start the meeting. And it's kind of fun. Everyone has a laugh about it. Like, Emily's doing her thing.

Starting point is 01:13:14 And I'll be like, you know, everyone, everyone come check out Emily at Handelbar in Charlestown this Saturday, 10 a.m. And by the way, like, you all out there in the podcast world should should do that if you're in the Boston area. She's great. Shout to Emily. But it's things like that. Like, it's just finding these small ways to, like, because people are already. laughing, people are already smiling, we're doing this silly thing. Everyone's in a good mood. And I'm like, boom, perfect time to give someone a shout out and make them feel like a million

Starting point is 01:13:40 bucks for doing something that in many cases, they might think like, oh, am I allowed to have this other job outside work? Like, is this okay? And so yeah, you got to, you have to like proactively build those reward loops. I love the reward loop of Emily getting this shout out right now. That's so meta. She's going to have a full class coming up in Boston. Is there anything else along those lines because that was really interesting. And also people like, you know, I know managers already kind of do this just like, you know, promoting. But so I think the core lesson here

Starting point is 01:14:07 is like focus on things you want to encourage more, less so hey, they work the weekend, they got it done. So awesome. Thank you for doing that. You know, you're saying that's almost an anti-pattern because you don't necessarily want that as a habit. So it's more like shift your reward announcements to things

Starting point is 01:14:23 you actually intentionally want to create a team. Yeah, and just be really, really thoughtful about it. Okay. So let's come back to the taking care of yourself because there's something else they came up. Almost everyone mentioned this. So you're doing a good job with this of finding time to take care of yourself and modeling that for other people. Specifically, a lot of people commented on how you create space for creativity. And I think to a lot of people, a lot of PM especially is just like I have no time for anything.

Starting point is 01:14:48 I just have meetings back to back all day. I barely have time to go to the bathroom or eat. And I'm curious to hear just how you do this. How do you create space in your day for creative work and deep work? and thinking outside of the meeting. Yeah, it's funny. I'm glad to hear people think I'm going to do this, because I'm like, I'm terrible at, like, organizing events.

Starting point is 01:15:06 Like, my team's always like, oh, we should do, like, a fun event. I'm like, yeah, that's a great idea. And then I don't organize it. So I like to think I do this in other ways. And I do think one of them is just, like, in modeling how to carve out space for things. And a couple of things. I think there's the creativity, which for me is, like,

Starting point is 01:15:25 probably more outside of work. And for me, it's creativity. But again, it's like a big part. of me as a manager, what I think I can help people with is back to the point of behavioral activation, like, understanding what the things are that a person needs to be happy, to be their best self, to be a high functioning person. And that is, that depends on their values. It depends on a lot of things about them. So, you know, for Emily, it's fitness. It's teaching. It's these things. For me, it's having like my, my crafts that I do, my illustration, my writing, my reading,

Starting point is 01:15:56 all of these sorts of things. I think that that's the first step is just as a leader, like understanding what those are for people on your team. And then, as I said, modeling it. Like, I try to always tell people,

Starting point is 01:16:11 like, here's how I'm doing these things. Like, I talk about them so it's really normalized because I think, I mean, a lot of PMs are like, oh my gosh, I'm so busy. I have no time. I mean meetings all day. But, like, that's a little bit self-inflicted, I think.

Starting point is 01:16:23 Like, at some point, like, you have to be the one responsible for getting yourself out of the weeds. And it's hard to do, but it is, it's doable. And so I think just like showing people that it's possible, like showing people that you can do these things. And I talk about them. I bring them to lessons. I have like a book club that I sometimes require at work.

Starting point is 01:16:46 And then I say, maybe I don't need to require this anymore. But like, like ways to just make it really visible make people, make sure people know that I'm doing it. and then ask them about it. And, you know, if I, in my one on one, and I'm checking in with people, I'm asking them, like, what do you do for joy? Like, are you doing something every single day that's bringing you joy in your life? And if they say, no, I'm like, that's a problem. Like, how, what are we going to do about that? And, like, do we even know what those things are?

Starting point is 01:17:13 Because I think a lot of people don't. And, like, a lot of people, it's great. Like, they're like, oh, I need to be getting X number of hours of exercise, X hours of sleep. Like, I know I need to eat lunch right at 12 or else I turn. into a pumpkin. And if it's somebody who like knows what all those things are and you're just there to kind of help them carve out time, that's one thing. But I think it a lot of times, like, people don't even know. And then and then you kind of behavioral activation them where you're like, all right, well, why don't you try some things and get back to me and like let me know what seemed to

Starting point is 01:17:41 work, what seemed to make a difference. But I do think so much of it is like a permission structure because people feel the pressure to be like, oh, I'm so busy. I'm so busy. I'm in meetings all day. I can't, I can't decline these meetings. I can't not do these things. And so in many ways. I think just modeling it gives them the permission structure to start to take back their life. I could see why people love working for you. Being asked in your one-on-one

Starting point is 01:18:03 or have you done anything today that brings you joy and if you haven't, that's a problem. Wow. It's important. You know, that's what life's all about. Like, why are we here if it's just to toil and be miserable? And also, like, you know, they will be better people at work and they

Starting point is 01:18:19 will do better at work. I think that's, like, correct me if I'm wrong, but it feels like that's an element of this. Well, and it's so funny because so much of this stuff, it's like obvious when you apply it to an athletic context. And obviously, you know, I talked about the like recovery score. This concept of like athletes need to recover is very obvious. Like no one, I think, would argue with that. If you're just pushing yourself at 100% of your physical capacity all the time, like not only are you going to burn out, but like you're literally going to suffer performance decline. And, you know, in the same way, like I think in the athletic,

Starting point is 01:18:53 world, there's so much more just acceptance of, I don't even want to say limits, but just like, you have to take the time to do the things you need to be your best. And that's not just running into the wall all day. And I think we forget that at work, but I think, I mean, the analog is 100% there. I also think about this with, um, in terms of being able to have creative breakthroughs of any kind, it's, just so important to have active rest. It's so important to have heads down time. Like, this stuff is all very well documented. We know it all. But we just come up with excuses to, like, not give it to ourselves. I think it's kind of self-sabotage at a certain point.

Starting point is 01:19:36 I definitely come up with excuses not to do that and work all the time. So I could use this advice myself. And that's why. Here's the thing. Here's the thing. Like, the reason I'm so regimented about this is because, like, if I'm not, I will fall apart. Like, there's this quote. I can't remember where I saw this, but I love it. It's like, you know, I have exercised the demons from my head, but they are outside and they are doing push-ups. Like, the threat of the demons coming back is always there. And so, like, I take this stuff really seriously because I know, like, I, if I'm not, if I let myself start to slide into, like, I'm not doing the things I need to do to take care of myself, like, I'm going to have a bad time. The walls are going to start closing in

Starting point is 01:20:16 around me. And I'm not, I'm not shy about that. And so to me, there's no point in torturing myself and like just working so, so, so hard and having no room for joy and having no room for creativity, even just from a practical standpoint, like, it's not, I'm not, I'm just not going to succeed. So this comes back to your point about, I think it was called behavioral activation of like doing the thing instead of waiting for you to feel a certain feeling, do the thing that will make you feel that way. Yep.

Starting point is 01:20:45 Okay. As may be a final area, but I have a few more questions after this. So maybe not the final area is AI. I'm happy that we waited this long to get deep into AI. We're not going to spend a lot of time here. You wrote a whole guest post about this. You did Hawaii AI to talk through some of this stuff. But when we were talking earlier, you said that you think people still are completely undervaluing the power AI can have on their ability to learn and improve themselves.

Starting point is 01:21:13 And I know you spent a lot of time on this with all these GPTs you've built. Just talk about the sense of how much you think people still underappreciate how much power they're. there is an AI in helping them become better. Yeah, I think we are not being nearly creative enough when it comes to how to think about learning with AI. And I think, you know, you hear people worry about entry-level jobs. And when you think about an entry-level job, it is sort of inefficient by design because you have like taken to analyst sort of a classic entry-level role. They're doing grunt work. They're doing really tedious work. But they're getting a lot of reps in because that's exactly how you learn the judgment to do higher level jobs well. And I hear this in creative

Starting point is 01:22:02 fields too. I hear this like from every, I certainly feel this way. Like the work that I did in the beginning of my career, it didn't feel like it was all that important in terms of the impact it was having. But it did feel like it was transformative in terms of my own judgment and my own taste and how I think about like just making like very quick judgment calls now. I just wouldn't have been able to do that if I didn't spend years learning like, you know, I used to do social media. Like the skill of having to condense something that I want to say into like 120 characters or whatever it used to be on old Twitter, 240. I can't remember. I forget, actually.

Starting point is 01:22:46 It was like crazy. Like, I forget what the original was. I think it was 140. Okay, 140 characters. It was short. And you got, if you had to get a link in there, like, good luck to you. But, oh, my gosh, my ability to just like look at something written today and just cut it that text and half third, like, whatever it needs to fill the space. Like, I can, I can do that in my sleep because I got all these reps very early in my career.

Starting point is 01:23:08 And so I think people see the way that, you know, there's a threat of companies not wanting to hire. as much entry-level talent because, you know, it's like, oh, this is the kind of work that AI can do. And so the fear that I hear, at least, is if you're not getting those reps early in your career, like maybe it's not contributing so much value to the company at that moment, but it's how you learn to be great later on. And so there's a fear that in five, ten years, like, we're just not going to have that class of people who have learned to do the jobs well and who have built judgment in that way. But what I think that misses is it assumes that, you know, you go and you do this analyst job for two years.

Starting point is 01:23:55 And at the end of it, you have a person who knows how to make models really well, knows how to do a few things really well. But like, why does that have to take two years? And why does that model of like you grind over this thing, you wait for feedback, eventually you get that feedback. Maybe that feedback's good. Maybe it's not. You go back, you try, like it actually is really inefficient when you think about it.

Starting point is 01:24:22 And the sort of learning applications around AI that I get really excited about are how do you shrink that loop? So in my podcast with Claire, I showed her how, like, I build these GPs that kind of think like me. And the purpose of that is so that my team can get feedback that is at least 80% close to the feedback that I have. would be giving them. But instead of having to wait until I get to their message or until our one-on-one, they can get that on-demand as many times as they want, you know, forever. And I think there's a lot of

Starting point is 01:24:55 things like this of like ways that things that require other people just naturally slow things down, require getting feedback from other people just naturally slow things down. We can build AI tools that like, you know, in my view, there's no reason why the amount of reps that you you get at whatever task you're doing. Like you can be a you can be a film editor just like sitting there pouring over the film, uh, deciding like what to edit, what to cut, what to, you know, put into the trailer or whatever is you're making. That's an incredibly tedious job that takes forever. And I think there's no reason we can't like make that way more efficient with AI in way is that make the learning like more fun. Um, and so I just, yeah, I think that that's sort of my hot take

Starting point is 01:25:42 is yes, there is this threat of a lot of these jobs that are things that seem like you can just automate them away that might happen. But like we absolutely still need to be investing in people's skills. I just don't think we need to be investing in them historically in the way that we always have. And I think in the future we'll find that those ways actually seem quite inefficient compared to what's possible today. It's such a powerful point. And we're already seeing this. I imagine you've seen these studies. I think it's in Nigeria where they give students AI tutors and they just like zoom to the next, they accelerate so quickly in their progression of just like reading and math, I think.

Starting point is 01:26:21 Like we're already seeing it. And it's harder to measure in PM and product and all these things. But like in school, it's a lot easier to measure and we're already seeing results there. Yeah, 100%. And to make this very real for people, you have this specific GPT, I think it's called Socrates. Oh, Aristotle, yeah. Aristotle, okay. Oh, no, we're going to edit that out.

Starting point is 01:26:37 Aristotle, Aristotle, where it gives you scenarios in a product scenario, like, or like give an example just to give people a sense of what this can do. Yeah. So this came from, I was talking earlier about learning how to make a really strong logical argument or just like a strong argument for your point of view in general. And the sort of fundamental skill for that in my view is logical thinking, logical reasoning. And when I think about like the best way we have to test that today, at least like the best is maybe not the right word, but the standard way we have to test that. The LSAT, like the test that you take to get into law school, that is what that test.

Starting point is 01:27:12 And it sort of gives you these different scenarios. And we'll try to say, like, you know, if A is true, then which of the following is true is not true? Like, sort of testing some of these different, like, logical relationships. And so what I did was I made a GPT that I basically told it, like create LSAT style questions to test logical reasoning, but put them in the scenarios of things that a PM would encounter. And I have like a version of this that's very specific to whoop and working in consumer health. But you could do it for anything or you can just do generic, you know, however you want to do it. And it's actually like, it's kind of fun because it gives you this scenario.

Starting point is 01:27:52 And it's like, you know, the sales team is telling you that we need to invest in feature A. And the, I don't know, the engineering team is telling you that we only have time to do feature B. and the metrics are telling you that, you know, people who get this feature retain better. Like, it just sort of gives you these little things. And it's like, follow that logic, which is the logically best path from this? And it gives you a little multiple choice answer. You select one and that explains why you're right and wrong. And so I think that's just like another example of, you know, you can't create those like hyper-personalized learnings where I can make one that is like literally so specific to you and your life.

Starting point is 01:28:40 But it is like testing and sort of like training you on this like broader skill set. And I think you can, you know, you can make things more fun that way. Even just like the school context in terms of doing that in a way that's just relevant to a person's interest, relevant to the things they care about. I think there's a ton of really interesting potential there too. So we're going to link to this GPT that you're talking about that people can tread out. And once you see it, like, holy shit, I should just be doing this all time because you just get so many reps as a product builder. And that's, you know, we were talking about a similar one with. like understanding engineering benchmarks.

Starting point is 01:29:12 I don't have an engineering background. So this was really hard for me, like when I was moving into product, is just getting an instinct for what types of things tend to be easier or harder for engineering teams. And so we can have one similar that's saying, you know, like, here's the scope that's being proposed. If you had to t-shirt size this, like, which one would you choose and why? and you can say, oh, you know, this sounds small or whatever.

Starting point is 01:29:41 And it'll say, oh, actually, like, these types of integrations tend to be complex for this reasons. So it's probably going to end up being more like a large. And, you know, it doesn't have enough context to, like, really, like, inform you in the way that, you know, your tech stack at your company is, although I guess you could build it and give it that information. And then it would. That would be cool.

Starting point is 01:30:01 You should do that. But again, it's like you do that, like, as a PM, you might get a chance to do that I don't know, a couple times week, maybe, maybe less often than that. And when you have this little tool, you can do it infinity times. You can do it, you know, you can spend an afternoon doing it. And so again, like, both the speed of those loops and the, like, the number of those loops that you're able to get is just, like, radically different with AI compared to just, like, when they come up in the course of your job. I think this is extremely cool. We're going to link to it.

Starting point is 01:30:33 People should definitely play with this. Okay, I'm going to take us to two corners, recurring segments of the podcast, and then I want to talk about whoop before we get to a very exciting lightning round. So this is a new segment I'm trying out. I'm going to call it pivotal corner. And here's the question. What's the most pivotal moment in your career? I mean, I think it was at my former company at Big Health when my former boss left the company

Starting point is 01:31:02 and I started reporting into the CEO. And again, I think it was my first time just having like up close, like working with a CEO so closely. And it just like definitely trial by fire. But it made me understand so many things that seemed like they didn't make sense to me before when I was just like in the rank and file of like a big tech company earlier in my career. You get in the room and you talk to these people and you're like, oh, this like this actually makes sense. I understand why this person has come to these conclusions.

Starting point is 01:31:36 And some of it's like understanding the pressure they're under. Some of it's understanding, again, like the way they view the world. But I think that was, you know, to get to our earlier point around like the humility of understanding that like maybe this person is right about something that I don't see. And maybe I can start by, if I start by giving them the benefit of the doubt, it is not only like a nice thing to do. But it is also like it will get me, it will help me understand why they're doing this. things that they are. And I think I would have been so much less frustrated earlier in my career if I understood that instead of just being like, oh, this doesn't make any sense from where I'm sitting. So therefore, it must not make any sense. It's so cool that this connects back to your

Starting point is 01:32:15 habit of doing this, having seen it, and being like, oh, I see. This is why. Maybe I'm wrong. Maybe I could be wrong. Well, that's, I mean, that's what it is. Like, I feel like I've had so many of those times where like, I don't know, when I was growing up, I was just so like, I felt so confident and like how I felt about everything. And then you get and you get out there and you're just like, oh, I was, I was missing some things. And after a while, you're kind of like, okay, maybe I should, maybe I just approach these situations a little differently with the, with the possibility that maybe I'm missing something. So I actually asked your boss, Calvin, which is an awesome name, by the way, Kelvin, about this moment. When I asked them what to ask you and he brought this up, actually, and here's the way he described it.

Starting point is 01:32:58 She may describe it as being thrown into the deep end or baptism by fire. but the reality is that she had the core skills, and this was simply an opportunity for her to let those shine even more. She was an incredible first principles thinker, quick to tune the framing of problems as she learned more context. It's a great example of luck is what happens when preparation meets opportunity. Thanks, Kalma. That's where that. He also said, I wonder if she remembers how terrified she was now

Starting point is 01:33:23 because she absolutely knocked it out of the park. And it felt like it was an inflection point that grew her confidence significantly. Oh, I was terrified. Yeah, big time terrified. And then, I mean, this is also like what I was saying about why it's so important to like be regimented about having these things outside of work that allow you to continue to thrive even in the face of just like utter feelings of failure of like I am not doing a good job. This is not going well. I don't know what I'm doing. You know, a lot of it was at time.

Starting point is 01:33:55 Kelman actually gave me some great advice that was, that this is maybe kind of scary advice. but when I asked him, when his advice for me at the time was, and he said, product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive. And, you know, I think it's right. Like, as I said, it is so often this, like, feeling like there is not a clear right answer and not even necessarily a good answer. And everyone is looking to you for clarity.

Starting point is 01:34:28 and everyone is looking to you to make the right decisions. And everyone sees the errors, or at least like everyone can spot the flaws in whatever decision you make or whatever recommendation you make. And, you know, as I said, like every path forward has flaws that can be poked in it. And so understanding that like the existence of potential ways

Starting point is 01:34:51 to be criticized about something does not, does not warrant criticism in a way that like, can, I think, often result in a lot of negative self-talk for people. So, yeah, I mean, it had a tremendous impact on me. It's interesting how so much of these habits and skills you've built seem to, like, it's clear where they come from, from all these experiences that you had. Well, and to the point of, like, when you start talking to people and you start trying to build this mental model of how they think, like, that's exactly what you learn, right?

Starting point is 01:35:19 Is, well, I can see how this person kind of, you know, worked at this company this time. And I can see how this person had this kind of relationship with this other person. And like all of these things shape the way that we approach problems and the way that we try to, you know, just move through the world. And it is like it is understanding those types of things that allow you to understand how a person thinks. I wonder if you could ask JatsyPT to build or Claude to build these mental models. Like here's their LinkedIn, here's their bio, here's a few things. How do they see the world? I will admit that I have tried this.

Starting point is 01:35:52 And I think it, I think it's a great thing. idea. I think it does help. I have not gotten to a point where I'm like comfortable sharing it with other people, nor have I told anyone that I have tried to do this for them, but I've certainly done it for myself. And I think it would be helpful because you could say things like you could upload a, you know, doc or whatever and be like, what are the free questions that this person's going to ask me about it? And then you could be prepared for the questions that that person's going to ask you. And that's great. In this hypothetical example, what do you, What context do you share with this model to help it be good?

Starting point is 01:36:30 Great question. Hypothetically, you know, I told you that I take all these notes on here's what this person said and here's how I interpret it. And LLMs are really good at pattern matching and sort of spotting the like, you could feed all of those in and just say, you know, come up with the like 10 criteria that this person is most likely to use to assess a possible recommendation or path forward. or give me like the top 10 ways that this person is like likely to pick apart an argument or object to something and you're going to get a good answer. More reason to build this habit of taking notes and sharing with your team. On the other hand, this might also be a good use case for granola or something like that where you have all these meeting notes and you could just feed it. Here's all the things Hillary said and oh, what is she, what is she probably going to say about this? Totally.

Starting point is 01:37:19 Wow. So cool. Okay. next corner I'm going to take us to fail corner and in fail corner the idea here is people come on this podcast they share all these wins and success everything's up into the right and amazing but in reality things don't always go that smoothly so the question is just is there a story you could share of failure in your career where things didn't go the way you hoped and what you learned from that experience I mean I think the one that probably looms largest in my mind is I'm you know I mentioned this

Starting point is 01:37:50 depression therapeutic that I spent about a year working on. And ultimately, the company ended up acquiring a different depression therapeutic. And we kind of ended up like merging the two of them. And a lot of the stuff that we had initially built that I have really loved about this product we were working on didn't really ever end up seeing the light of day beyond the kind of testing that we had done around it. And it was heartbreaking because like, I still, I wish this product existed.

Starting point is 01:38:23 Like, I look at it and I'm like, this was a great product. And we put so much heart and soul into it. And I think the lesson that I learned from that is, I think there's always a shot clock, right? When you're working, especially on zero to one product, I think it can be very easy to feel like you have the luxury of time of just like, you know, we got to take the time to figure this out and get it right. And that's what's most important.

Starting point is 01:38:46 but the sort of build versus buy question is always live and it's always fair and whether you want to admit it if you're the one working on it and you probably don't I didn't want to admit this um there is a point at which like it makes more sense for the company like if it is taking too long to develop something and there is a solution out there that works like it is the right decision to acquire that and I mean I've worked a Dropbox where I saw this happen all the time, where we would acquire products that other teams internally have been working on. And it's just like, it's kind of heartbreaking when it happens. But I think there's like an urgency that that has instilled in me that I think is actually really good and healthy, especially again, like working in this era where there is kind of this AI

Starting point is 01:39:35 arms race and everyone's trying to do it really quickly of like, yeah, there's always a shot clock. And you might not be aware of it, but it's there. And you got to build your heart out and you got shipped and you got to get things out because at any time like that clock might run out. Speaking of shock clock, not necessarily, but I want to spend a little time on whoop. You guys just launched something that feels like a really big deal. I'm excited. That's the reason I got it. There's all these really cool new features.

Starting point is 01:40:01 I think you call Whoop 5.0. What should people know? What's the newest, coolest thing that's happening with Whoop? Yeah, I'm really excited you got it. I know you tried it before. That's right. That's right. People who have tried who've in the past maybe felt like it was very focused on like elite

Starting point is 01:40:17 athletes. And that is the way we love to the company. And I think what we've done with our new experience is we've really built something that can help everyone be healthier and live better. I think we're, I would say we're no longer just for elite athletes. Like we're really now like a health and performance companion for anybody who wants to feel their best. For the first time in our company's history, we've updated our mission. So we're now saying that WOOF exists to unlock human performance and health span. And health span, I think, is, I mentioned earlier, this feature I'm really excited about because I do think it's, it is kind of the most powerful version of like a longevity type feature I have seen because it is so focused on your behaviors

Starting point is 01:41:04 and your habits today. And we built it to be super, super actionable. So rather than just like giving you a score that you're kind of like, okay, that's nice. If you, start sleeping even like 20 minutes more, 30 minutes more tonight, like you're going to see how that changes your pace of aging. You're going to see how that changes your whoop age. And I think that, as I mentioned earlier, I think is really rewarding. We've also have a lot of personalized coaching to our AI in terms of actions that you can take to improve your whoop age, to improve your sleep, to feel better. And it's all part of our broader aim to make health more actionable and accessible. I think one thing I'm really excited about is we have a bunch of

Starting point is 01:41:41 new women's health features. So we have hormonal insights with improved menstrual cycle tracking. I'm actually pregnant. And I... What? I didn't know that. Well, I have a big announcement. Wow.

Starting point is 01:41:57 Congratulations, Hillary. That's so exciting. But I actually, part of how I found out I was pregnant was in seeing my WOOP data. What? What? Which is pretty remarkable. And the way that we have this cycle tracking now, You can see the way that your different, you know, your HRV, your resting heart rate,

Starting point is 01:42:16 things like that, that's your heart rate variability in your resting heart rate, fluctuates throughout different times of your cycle. And even in like the time leading up to that, like I had a not straightforward pregnancy journey. And having these tools to like really understand what was going on in my body was tremendously helpful and tremendously like empowering for me. And honestly really has changed my life. So I'm really excited about that. We have a lot of great new heart health.

Starting point is 01:42:41 health features. We have a heart health screener with blood pressure insights and ECG. That's really cool. We got a lot of great stuff cooking. So even if you tried to move in the past and thought it wasn't for you, I think the new experience is a real upgrade. And it's something that I'm deeply proud of having worked on and really excited to have out in the world. I am generally very excited about this. Like you could do, you said blood pressure and VL2 Max. And I know the battery is even longer to you. There's just like so much stuff. Oh, we got a 14-day battery life. I didn't even say it. We have these beautiful new leather vans. Oh, wow. Okay. 14-day battery's life is insane. Like, I'm going on vacation tomorrow and I'm like, I don't even need to bring a charger. Like,

Starting point is 01:43:23 this is fantastic. Oh, man. This sounds like a Wup ad, but I'm like very excited about this. I'll say one more thing, which is we also have, um, we've opened a wait list for advanced labs. And so pretty soon you're going to be able to have like comprehensive lab work, uh, in the, in the app. And I think, you know, talk about the feature of health of having, like, control of all of your health data in one place, and then being able to, like, not just sort of find the signal in it and sort of understand, like, you know, how your sleep is impacting your metabolic health or things like that. But again, get really actionable coaching on actions that you can take to feel better and be your healthiest.

Starting point is 01:44:00 And, yeah, just pushing the limits of all the data that we're pulling into the loop ecosystem. So really excited about that, too. I'm hoping the whoop can actually take my blood and labs. Is that, was that where this is going? Because that would be so convenient. Okay. That'd be, like, it'd be weird, but also awesome. I don't have to go anywhere to do that.

Starting point is 01:44:19 Hey, Larry, we covered so much ground. Okay, before we get to a very exciting lightning round, is there anything else that you wanted to touch on, anything else that we haven't covered that you think? Or less nugget you wanted to leave listeners with? I don't think so. I feel like we covered everything. We did.

Starting point is 01:44:31 We covered so much in the best way possible. With that, we've reached our very exciting lightning round. Are you ready? I'm ready. What are two or three books that you find yourself recommending most to other people? Bunny, you can't call something a lightning round and then ask me about books. That's like, we could go for a whole other podcast. That's, we create a time box for it.

Starting point is 01:44:55 Yeah, exactly. Like in the ground. Okay. I'm going to hear what I'm going to say. I'm like, I'm going to go full fiction on this. I'm going to say, if you're going to read a book, like, you don't bother reading a business book. Like, even the business books I love the most that like shaped how I think. I'm like, I kind of got the gist of them partway through.

Starting point is 01:45:12 But fiction, I'm like, everybody should read East of Eden by John Steinbeck. And everybody should read The Sun Also Rises by Ernest Hemingway, which is like my comfort book. I think I, like, what I love about fiction is it just, it teaches you how to sit inside tension, right? I think so much of working in product is, as I said, like, you're in this fog and you just have to provide clarity. And you have to be really good at, like, providing structure to ambiguous things and finding the way for. forward. And to succeed at the job, you have to be able to do that. But I also think to succeed as a human in the job, you have to be able to sit in the mess and sit in the ambiguity. John Keith, the poet, talks about this concept of negative capability, which is the ability

Starting point is 01:45:55 to remain in uncertainties, mysteries, doubts without any irritable reaching after fact and reason. And I love that. That sounds like a perfect quote for all PMs to... Exactly. And it's like, you got to be built, right? Again, fiction. of dualities. There's a lot of dualities in fiction, a lot of like warring forces within people that is like, you know, can be so driving for people but can also be the source of so much anguish. I think it's, it is important to live in both in the, I'm going to break down this problem. I'm going to structure it. I'm going to get out. But also like, I'm going to sit here and I'm going to accept that there is no right answer and there is no perfect answer. And I,

Starting point is 01:46:35 that's life. So, you know, you don't learn that from, to the, to the extent that you learned that from a book at all, which maybe you don't. But I think you can, I think you can learn it in fiction. I don't know how you feel about this book. I think you'll be proud of me. I'm reading Anna Karen Anna right now. Oh, I was, I literally, I literally, that's the book that I'm bringing on vacation with me tomorrow. Wow. You've never read it. I've never read it. Cool. Me neither. Okay. We'll exchange some notes. It's very long. I'm realizing, because I'm reading on the Kind of 10%. Okay. Now, now I really have to read. I was like kind of way right. I was like, is this really what I'm going to want to read when I'm like sitting by the pool?

Starting point is 01:47:11 But I've committed to- do it. Another guest recommended it. And I saw it on some lists recently and I'm like, oh, I should read that. So yeah. Okay, great. Next question. Do you have a favorite recent movie or TV show that you've really enjoyed? Oh, um, I've been watching the rehearsal with Nathan Fielder. Have you seen this show? I saw the first season. I've been a huge fan of Nathan Fielder for so long. I don't know if he saw his previous thing that he did. Oh yeah. It's called. Okay. He's so hilarious and such a genius. Nathan for you. Oh my God. I haven't seen any season now.

Starting point is 01:47:40 The man is a freaky genius. Like, I, just when I thought that I had like a good sense of all the human emotions that exist out there, like, I watch the show and I feel things that I'm like, I have no, I feel like 10 different things that I'm like, I have no words for any of the things that I'm feeling right now.

Starting point is 01:47:59 It's weird. It's weird stuff. But I'm enjoying it. I got to watch it. Do you have a favorite product you've recently discovered that you really enjoyed other other than the whoop? I love my Zwift. Swift, it's like a program that you can hook up a smart trainer to, like for an indoor cycling situation.

Starting point is 01:48:16 And you kind of bike around like you're in Mario Kart and you're sort of in these virtual worlds biking with other people. It's, I think for very serious cyclists, I am not a very serious cyclist. For me, it's been amazing as somebody who actually really like struggles to find time to exercise. I, like, they have sphere reward loops. They have one of the most amazing reward loops, which is you're biking along and you, You get into this, like, track and a ghost of your previous self breaks out from you and starts racing alongside you at, like, your personal best for that track. And you have to beat your personal self, or you have to beat this ghost version of yourself.

Starting point is 01:48:53 And like, nothing has ever motivated me more in my life than, like, past Hillary being, like, I'm coming for you. And I'm like, I don't get that competitive with other people, but like past Hillary comes for me. And I'm like, this I can't let happen. So I think it's a great product. I'm thinking about how to use that mode for other use cases, like the ghost version of something to motivate you. I've been so many product meetings where I'm like, can we make like a ghost version of yourself?

Starting point is 01:49:20 Yeah, okay. Like shut up about the ghost. Okay, amazing. Okay, two more questions. Do you have a life motto that you often come back to find useful in work or in life? I've obviously one that's been top of mind for me recently because I was talking about the highbrow fiction. I also have to go lowbrow. I saw this clip of Beavis and Butthead online recently

Starting point is 01:49:42 where they were watching a music video for Creep by Radiohead. And it starts off really slow. And one of them, I think maybe Butthead is like, oh, this sucks. And then the chorus comes and it starts getting like all hyped. And they're like, oh, this rocks. And then I'm not going to do by Beavis and Butthead impression. So then it gets back to the slow part. And they're like, oh, wait, this is.

Starting point is 01:50:07 sucks again. And then Butthead is like, why don't they just play the cool part the entire time? And Beavis is like, because if they didn't have the part of the song that sucked, the cool part wouldn't be as cool. And I was like, that is so profound. Like, that is what life is all about. It's just like, if it didn't have the parts that sucked, the cool parts wouldn't be as cool. And we're always chasing the cool parts. We wanted all to be the cool parts, but it can't. So thank you, Beavis and Budhead. people and put it. Okay, final question. I love that you're talking about fiction books, because this is where my question was going to go. What's a fiction book that most impacted your product building approach or career or the way you think about product? Can I give a poem?

Starting point is 01:50:54 Absolutely. Even better. Poem, extra credit. There's a poem by Derek Walcott about, it's called Sea Grapes, and it's about Odysseus. And he talks about Odysseus being driven by the ancient war between obsession and responsibility. And I read that line when I was like 18 years old and it has always stuck with me. And I, you know, I sort of mentioned earlier, I think about these like dualities that that drive us. And I think as a product person, I always feel like I'm like living between these two. like the obsession and the responsibility. Like I just, I want to like, I want to go so deep on this.

Starting point is 01:51:41 And I want to, I want to spend like as much time as I possibly can just like sorting every little piece out. But like we live in a society. We exist in a business. I am trying to create value for shareholders. And trying to like bring these two things together. I feel like A has been like a, you know, the kind of defining struggle of my career. I think of many people's careers is like how you have. something that you feel like you can really obsess over and have that flow over,

Starting point is 01:52:10 or have that flow when you're working on. But then, like, it's got to kind of, like, work in this broader system as well. And I think that that's sort of been, like, the thing that I think of as the guiding post for, like, what I want to do with my career and with my life. So I think it's got to be Derek Walcott. What a beautiful way to end it. Hilary, two final questions. Where can folks find you online if they want to reach out, maybe find out?

Starting point is 01:52:36 follow up on stuff that you talked about, and how can listeners be useful to you? Great. Thank you. So as I mentioned, I have a newsletter. It's hills.substack.com. That's h-i-l-s dot substack.com. I'm also teaching a maven class on being a super manager with AI. So if you were listening to all this and you were like, oh, Hillary, that sounds so great. But like, I don't have time for any of that. How do you have time for all that? Like, honestly, hyper-leveraging myself with AI has been a big part of how I find time. to do any of this stuff. And so I share a bunch about how I do that, how I use AI as a manager, building on a lot of

Starting point is 01:53:14 the stuff that I shared on Claire's podcast as well, how I AI. So you can find me on Maven there. We've got a couple cohorts coming up. And then, yeah, I encourage everyone to try out Whoop. You can get a free month on me at join.com. Join.com. That's Hillary with OneL. and you can post at me or tweet at me on X and let me know what you think of it.

Starting point is 01:53:41 And I would love everyone's feedback because we're really excited about it. As you were talking, I looked up your course just for make sure people can find it. So you go to maven.com, you just search for Hillary Gridley and you'll find it. Yep. You can also, I realize that if you Google Super Manager, you will find me. So that is my new claim to fame. Oh, my God. That's so great.

Starting point is 01:53:58 4.9 stars. Holy moly, there we go. Okay, Hillary, thank you so much. This was incredible. covered everything I was hoping to. This was everything I wanted it to be. Thank you so much for being here. Thank you. Thank you for having me. This was so fun. So fun. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review

Starting point is 01:54:25 as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast.com. See you in the next episode. Thank you.

Lenny's Podcast: Product | Career | Growth - How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

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