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)

26:15I 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 I'm I'm a sucker for that kind of thing but I'm like well if 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 I don't want to act like I think this is the best.

26:52It's easy to be clear but in the like the grand scheme of things like I wish that the people who have this pure love 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 and in other industries and so people would naturally gravitate toward that. And I know you know I totally got it until you get paid better like no real judgment for me.

27:32I just I wish I saw more but 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. Okay I'm glad you showed 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. It almost help people think the way you think and see the way you think so that they can operate at a higher level.

28:09Talk about that but that looks like and why that's important. 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's thing. And it makes things super inefficient. I think people often say like oh it's a process problem. It's not a process problem.

28:48It's not an approval process problem. It's a transparency and it's 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 strategy document. Great 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.

29:28And so if you're your the way that you understand what's going on at the company 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 what 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 of my company think. And I want my team to understand how I think. And when I feel confident that people on my team understand how I think like I don't need to read their emails.

30:07I 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 I don't have confidence that these people understand how I think or I don't have confidence that they understand. And how this 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 the company. So I'm constantly hearing the things that they're saying and paying attention to sort of a note behind the note. Why do I think they're saying this?

30:46What do I 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 and most important conversations with 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 and here's 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.

31:21And these aren't long and sometimes if I don't have time I'll just like in a team meeting I'll literally just go through my notes from the week and sort of voice over stuff and editorialize it as I go. And over time I think my my team has like a pretty good sense of what people are saying and 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 like how what the CEO thinks matters. What level of like risk tolerance the company has things like that.

31:58Then 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 so that it's like the way you put it almost is when they're emailing them are asking for some they 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 may you keep it anonymous just to make this little real of the kind of mental model you might want to build around someone.

32:29So our CEO will is somebody who obsesses over pixels in a way that is you know challenging to get things through a 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. And he doesn't compromise and I think this can sometimes get in this construed 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 this doesn't feel like the future and everything that we're building needs to feel like the future.

33:24A lot of people hear that and they're kind of like oh gosh like you know we're never going to get this thing done time like we can't make any sort of sacrifice is 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 heart feeds and we're pulling it 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 a VO2 max which is the you know a measure of your cardiovascular health.

34:07You 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 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 this feels like the future this feels like I'm very conscious of the fact that this product knows so much about me and is able to sort of sort of sort out the signal from the noise on that in these really small and elegant ways.

34:56And so for something like that like I would get that feedback and design review or I'd hear that in a design review and maybe one of my PM to 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 like I've noticed that recently we are consistently getting this type of feedback. 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 a I 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.

35:47And really try to make that magical so I'm connecting with dots for my team right I'm saying you weren't in all these meetings but I saw 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 like here are some things that I think we can do in across our products going forward. Essentially these are principles values or tenants per person of what matters to them exactly for Nick it's this needs to feel like we're living in the future you can just be like another heartbeat tracking out. This is so cool and there's so much trickle down benefit 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's like I don't know what's happening.

36:29So there's so much of his ability to all the secretive stuff happening in the meetings. I don't know what people are deciding my fate's in 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 even if I don't agree with the feedback 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. And although 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.

37:04But 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 when I hear the people the people who are like I don't know what's going on this company like I think they do the opposite 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.

37:46But 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 on to something that you're not on to and it's amazing how much you can like learn and to 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. And I think that's a great thing. Oftentimes you will find that x y and z is happening. I'm glad you went there when it's actually fall this thread which is kind of a different direction but I think a lot of people are always struggling with this as a leader when your leader disagree it does say something that you completely disagree with.

38:21But 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 said so you know because you lose power as leader. You have any just there's 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 teams 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 as open -ended question like why are we doing this. 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 so the 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 that's not just like this kind of arbitrary feeling.

39:14But whatever it is like I really try to get to the bottom of let me let me really make sure that I have done my best to understand this person's point of view 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 can't it in a way where like it's still respectful like I think what you want to avoid is a situation where as a manager you're like. This you know I have no control of the 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 you do hear that you do see that happening.

39:54And so I think what I try to do in the situations is separate out like my opinion from it from the like well what is the insight that makes it makes sense of this person and explain the 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 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.

40:37And if we're wrong like that happens sometimes and we try again. And 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 this is why they think they way they think and so instead of encouraging your team or yourself even to be like then you're wrong here it's more. Okay here's their data set let's try this and this will inform the data set and maybe change their mind. Yeah because I think in product like I like to joke there's no right answers right you're just there's only wrong answers and you're just trying to execute well unlike the least wrong answer that's available to you.

41:13And so I think it is like you know the sort of reasonable people can disagree about this of at all of you know like this is what I think and this is how I 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 even if it isn't 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 a trick systems.

41:49You said that you have some tools to help you understand someone's point of view I can't help but ask more about that I talk about what I like to call the magic questions. But the thing about magic questions is they're not actually questions they're statements and they end with do you agree or is that right. And so I have found this is 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 what they say yes to and then if you can get them to explain great and if they're good communicators they often can.

42:23But if they're not like you don't have to let that stop you and so I mean I 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 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 that's not straightforward sometimes like there's regulatory areas that are you know up to interpretation. 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 it depends depends.

43:15And so I learned that if I kind of flip that and approach that like well you know what if we did x y and z 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 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 what would you think I should do or you know what could I have done differently I'll say like rephrase that at the end of the day. And so that's because tell me what you think you could have done differently and then ask me if I agree.

43:51And when I do this I think it has a few benefits one it helps them kind of calibrate their judgment over time so they're 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 me for answering these questions I think that's kind of a trap so 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 somebody's on your own.

44:29So again I think like the magic questions to me is that right do you agree and 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 is 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 sounds like it could 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 times and you need someone almost interview you in a really effective way to get out all this knowledge.

45:07And this is just a really simple way of getting that idea. 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 got to go and peer apart like you've got to go in. So 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 here's what I think like you agree you agree like of course you're okay. That's where you are or you might get the answer you might get a yes if your goal is to get to yes. That's not what I that's not what I'm talking about if your goal is to understand and you are coming from like a help me understand how I'm wrong.

45:41I'll be understanding 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 it 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 two and a half times talk about today.

46:08I wanted to come back to you said this interesting insight about your CEO that he wanted to build something that was felt like the future. I would just want it to share there's a story that is always stuck with me at Airbnb. There is a big launch coming up and there is a designer sitting at late in the office trying to read update the website to include this new product. There was a launch of Airbnb neighborhoods like 10 years ago and he's and she was just like hey Joe and this is Joe Gebio 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 which are we try to and it was going to launch in two days he's like build something the internet has never seen before.

46:49And now this makes like it's interesting because when I always think about that story until 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 world view why why is that the way he saw the world and why we needed to build a site like that which I can start thinking about that that's a really interesting way to just like handle things that sound absurd and out of the way. I agree so much I proud former English major and so I'm a huge proponent of reading fiction and reading in general and I I feel like that's where so much of this comes from for me is just like a curiosity for like in what world does this make sense for this person.

47:38And it's so easy to look at in other persons behaviors none other persons 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 word context like when you approach it with that like what what is the world of this person where the thing that they're saying makes sense and I like 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 I've had to learn over time because when I come home from work and I'm just like this person said this and it didn't make any sense and this person's told the out to lunch and leadership doesn't know what's going on like all I was doing was making 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 beautiful insight.

48:34And all these other people have no unique beautiful perfect concise just wrong opinions and so I feel like it'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 I think a lot of it comes from a really fiction. I love that we're just unpacking the onion of the power of this very specific habit of just helping you learn the mental model of the people and round you and I just make it like a crazy person. No there's so much power to this like it's 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 they just asking all these ridiculous things keeping the barway 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 you should this is true I should like I don't know your competitor and this is how they see it maybe it's not let's let's look into that little deeper.

49:53Yeah it's really interesting I am I last company when I started reporting to the CEO they found various coaches for me to work with and one of them was the former chief product officer at coinbase who's gone to found bridge which is just that a part by stripe for a ton of money and one thing that he said to me that really stuck with me is when you're reporting to the CEO and like if as a chief product officer the big mistake that people make is they think that the game is not going to be a big deal. 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 role 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.

50:53So that's the definition of it in the form of product 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 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 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. 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 like people aren't people don't see it my way 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 things and it's not like that.

51:53So I think it's like a lot 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 like it becomes extremely inefficient and it becomes extremely painful because you're just everyone's just fighting all the time. And so in some ways like it feels like you're kind of like it sounds almost defeat us like I'm always worried about the sounding like I'm just like yeah just do whatever the boss says.

52:24And 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 actually just makes work a lot better for everybody. So then a lot of people like you said I love that you went there is just like if you're because it could sound like okay your job is just execute with 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.

53:03Let's get everyone to do the thing to see what's 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's vision and not have any input. Well, and I think like there's there's so many decisions all the way down and there's so many like micro places where you can you can dig where others would have zacked. 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.

53:43And that that comes from like my unique perspective my unique point of view the experiences I've had in the past like my various influences. 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 in movable 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 have somebody else thinks a like you can find that there are a movable 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 know as much.

54:25And 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. Like frame for kind of what you're 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 you it's self extremely unique and extremely valuable 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 you can put yourself.

55:01And 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 you can only find those if you're engaging really good faith and engaging earnestly and like really understanding out our people thick. 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 good. He's a guest on this podcast he teaches this class at Stanford Business School about how to how to gain power in the world it's like in the rules of power and he talks about you know it's like it and it's like all these ways to to influence and win and achieve and gain status and all these things and he's like you know this part doesn't doesn't sound fun and and great but I talk about here's the way the world works and is not the way you wish it would be.

55:54And 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 there job is to own the vision of the business in the company. Yeah I think that's true and if you don't if you disagree with it like you probably shouldn't be working on that company. Yeah the other pieces it's just a vision like here's the vision of the future of where we are heading if we win here's what will be true in the world will look like 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 direct your products all those.

56:40And at the level and everyone at the company how you said it there is so is so right on because it is like the vision is is in many ways I mean in some ways it's a huge space 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 in some ways I would say like your 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 maximize the chances of that and like becoming the actual future and then also what is that mean for product like what does that mean for if it has to be true that like you know take who for example if 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 code.

57:41So this is my suggestion. So, I'm just gonna share some of the things that I think is really interesting to help you understand how your behaviors today are impacting how healthy are going to be in decades. What does that mean for what will needs to be today and what does that mean for how it needs to evolve in the next couple 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 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 the losing battle.

58:12And if you don't like the vision, you could leave, right? It's like, or change, try to change it. Like those are two options. And I think it's 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. Some people are really good at doing that with, you know, sort of the quality and the quant and moving it together.

58:47But 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 seeing 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, you don't start from like, well, I got nothing to say here. So I think it's, you know, no more you are on that journey. It's important too. This reminds me there's a PM leader at Airbnb who ended up leading a new initiative and ended up doing a bunch of stupid stuff.

59:26And 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, I was stupid. And you, like, you will see that idea is that 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.

59:57And it is important to get really good at knowing the difference and knowing where you go from there. This episode is brought to you by Atio, the AI Native CRM. Atio is built to scale with your business from day one. Connect your email and calendar and Atio instantly builds a CRM that matches your business model. With all of your companies, contacts, and interactions enriched with actionable insights, sync in your products usage, billing info, or any other data sources. And Atio's flexible data model will handle it all without any rigid templates or workarounds. With Atio, AI isn't just a feature.

1:00:33It's the foundation. You can do things like instantly prospect and route leads with research agents, get real -time insights from AI using customer conversations, and build powerful AI automations for your most complex workflows. Industry leaders like Flatfile, Replicate, and Model are already experiencing what's next for CRM. Go to atio .com slashlennie to get 15 % off your first year. That's atio .com slashlennie. I want to move on to another skill you really get at. But first of all, something I noted that I wanted to touch on real quick. You mentioned that Moop now does Vyotumax and that's not a promotion for Moop.

1:01:11But that's so cool. That's a huge thing to track. This is 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 as your Vyotumax. It's like your blood oxygen level. I'm going to exactly push this. But that's cool. Then you want to do that. There's so much cool stuff for doing Moop right now. I don't know if I want to get into it all right now, but I can. We'll get back to it. We'll get back to it. Let's get back to it. Okay, cool. 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, it's just building habits, helping your team build good habits and coming back to the CBT stuff, just like behavior loops and things like that.

1:01:53Talk 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 in all of these things. 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 an education model where it's like, you teach the thing, you assess the thing, and then there's some accountability around the thing. I think if you think about it more in the context of behavioral psychology, it actually works a lot better.

1:02:36I'll give you an example. Many leaders have been trying to think about how to drive AI adoption, AI upscaling on my team and what that can look like. When I talk to people about this outside of the company, I'm a hoist surprise because they're like, how do you measure it and how do you enforce it? I don't really think about any of that stuff. I'm thinking about how am I creating habits around using this? There's a couple things there. It's consistency. How are you getting someone doing something every single day? To do that, 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.

1:03:21I have a 30 days of GPP, I call it, of a list of 30 things to do when every single day, that I don't know anyone who has gone through this and not come out the other side, feeling 100 times more confident in their skills and actually using it every day as a habit because it's built as a habit formation tool and not an education tool. This is using a specific GPP built or building their own GPP or what's the habit there? The habit is using chat to BT or cloud or any of these. Okay, I got it. Palm tools together work done. In just a 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.

1:04:01What's the URL of the newsletter? Well, as you mentioned that. Thanks for asking. It is hills .substack .com, hils .substack .com. 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 I'm going to stake a lot of people make when they start thinking about how to drive adoption. Is there 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.

1:04:34The 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? Oh, I put this into chat, you be tea. And I like didn't really get a good answer.

1:05:08And now I'm frustrated because this thing's taken 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 plays a demomication or it might be like uploading your calendar into chat, CBT 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 experience.

1:05:43So consistency, reduced 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 and 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.

1:06:19And part of why I like custom GPs as a tool for helping people learn to use LLMs and I talk about this on the podcast I did with Claire on how I AI is because it 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 and improved written version of that document. They get the like the joy of like, oh, this helps me. This was cool without any of the like despair of, oh, I'm not very good at prompting and this didn't really work on frustrated.

1:07:00And 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're talking. So kind of the four parts of habits and I want to 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.

1:07:33And within reward loop, you want it to be powerful and 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. Absolutely. Because I think this is something loop is really good at. So I think one of the most interesting kind of anti -reward loops on whoop is around alcohol. whoop has this recovery system. 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 whoop, you will very quickly learn that if you any time you drink, you get a red recovery.

1:08:14And 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. 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 you 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 rent drinking for years.

1:08:53And it wasn't until I got on whoop 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 the 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 day and 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.

1:09:28Because when you have the 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.

1:10:02It has your woob agent it. It's like it has colors and sort of kind of moves around. And that change is 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 a 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, but the short -term reward loop of those often feels pretty bad because change is hard and it feels bad before it feels good.

1:10:46And trying to like 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 to get you to check your Instagram likes and your Facebook posts for actual good for helping people to 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 any talk about AI like learning to use you know, ClodChat, CBT?

1:11:21Yeah, I think a lot of it's 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 responded that, like people will see, I mean maybe it's because I work at Wooten Robstance with reward loops, so we're all like, you're using that. Here's your reward. No exactly, but no, like people see that and people respond to it. I think you know another example is like something that I think about a lot and is relevant to our conversation about just like how you build teams that can do hard things is how you encourage people to take care of themselves outside of work.

1:12:09And 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. Then sort of like having my hobbies and my other various things. 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 two 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 I, you know, I tried to do the opposite.

1:12:39Like I tried to find ways that I really am impressed with my team and the ways that they take care of themselves outside of work. 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 handlebars, 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, I think serious just for a minute. Before we start the meeting, and it's kind of fun, everyone has a laugh about it.

1:13:13Like Emily's doing her thing and I'll be like, you know, everyone, everyone come check out Emily at handlebars and Charles down this Saturday at 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 out to Emily. But it seems like that. Like it's just, 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 bucks for doing something that in many cases they might think like, oh, am I allowed to have this other job outside work?

1:13:46Like, is this okay? And so yeah, you got to, you had to like proactively build those reward loops. I love the reward loop of Emily getting this shout out right now. This is so meta. 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 is like focus on things you want to encourage more less. So hey, they worked 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.

1:14:19So it's more like shift your reward announcements to things you actually intentionally want to create. Yeah. And just just be really, really thoughtful about it. Okay. So let's come back to the taking care of yourself because it'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 you create space for creativity. And I think to a lot of people, a lot of PMs, especially is just like, I have no time for anything. I just have meetings back to back all day.

1:14:51I 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 fine. I'm glad to hear people think I'm going to do this because I'm like, I'm terrible at like organizing events. 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.

1:15:22I think there's the creativity, which for me is like probably more outside of work. And for me, it's creativity.

1:15:32But back to the point of behavioral activation, like understanding what the things are that a person needs to be happy to be the 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, all 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, I try to always tell people, like, here, here's how I'm doing these things.

1:16:14Like 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'm needing someday. But like, that's a little bit self -inflicted, I think. 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'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. And then I say, maybe I don't need to require this anymore.

1:16:50But like, like, ways to just make it really visible, 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, 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 are we going to do about that? And like, what do you do even know what those things are? 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.

1:17:21Like, 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 all a lot of times, like, people don't even know. And then, and then you kind of behavior 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 what seemed to 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.

1:17:48I'm so busy. I've been 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, to start to take back our life. I could see why people love working for you. Being asked in your one and one, or if you've done anything today that brings you joy. And if you happen, that's a problem. Wow. That's important, you know? That's like, it'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 will do better work.

1:18:20I think that's like, tell them correctly if I'm wrong, but it feels like that's an element of this. Well, and it, you know, 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'm 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 world, there's so much more or just acceptance of, uh, how did I even want to say limits, but just like, you have to take the time to do the things you need to be your best.

1:19:08And 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. Um, but we just come up with excuses to like, not give it to ourselves. I think it's, it's kind of self -sabentages at a certain point. I definitely come up with excuses not to do that and work all the time. So I could use this advice myself.

1:19:42That'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 follow part. 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.

1:20:14The walls are, are going to start closing in around me. And I'm not, I'm not like 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 don't 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. Yeah. Okay. As maybe a final area, but I have a few more questions after this.

1:20:50So 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 how I AI to talk through some of this stuff. But when we were talking earlier, you said that you think people still are completely under valuing the power AI could have on their ability to learn and improve themselves. And I know you spent a lot of time on this with all these GPDs you've built. Just talk about this sense of how much you think people still underappreciate, how much power there is in AI and helping them become better.

1:21:25Yeah. 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 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 fields too. I hear this like from ever I certainly feel this way.

1:22:05Like 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 camera. I forget actually it was like crazy.

1:22:47Like I forget what the original was. I think it was 140. Okay, 140. It was it was sort. 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 in half third, like whatever it needs to fill the space. Like I can admit that in my sleep because I got all these wraps very early in my career. 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.

1:23:23And so the fear that I hear at least is, um, where if you're not getting those reps early in your career, like maybe it's not contributing that so much value to the company at that moment, but it's how you learn to be great later on. And so there was a fear that in five, 10 years, like we're just not going to have that 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. 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.

1:24:02But like, why does that have to take two years? And why does that model of like you, you grind over this thing, you wait for feedback, eventually you get that feedback. Maybe that feedback's good. Maybe it's not, um, you go back, you try to get like it, it actually is really inefficient when you think about it. 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 would be giving them.

1:24:43But 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 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 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, deciding like what to edit, what to cut, what to, you know, put into the trailer or whatever it is you're making.

1:25:25That'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. And so I just, yeah, I think that that's sort of my hot take is, yes, it is, like 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.

1:26:04It's such a powerful point. And we're already seeing this. I imagine you've seen these studies. I think it's a 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, they think, like we're already seeing it. And it's hard to just 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 or what do you do? Oh, airs, bubble.

1:26:34Yeah. Air start all, okay. Now we're going to add with that air. Staddle, 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 else that like this, the test that you take to get into law school, that is what that tests.

1:27:13And 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 for anything or you can just do generic, you know, however you want to do it.

1:27:49And it's actually like, it's kind of fun because it gives you the scenario. And it's like, you know, you or 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 retained better. Like it just sort of gives you these little things. And it's like follow that logic, which is the, which is the logically best path from this. And it gives you a little multiple choice answer use select one of that explains why you're right, Ron.

1:28:29And so I think that's just like another example of, you know, you can't, 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. But it's 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 interests, relevant to the things they care about. I think there's a ton of real interesting potential there too. So we're going to link to this GPT that you're talking about that people can tread out.

1:28:59And what's you see like holy shit, I should just be doing this all the time because you just get so many reps as a as a product builder. And that's, you know, we were talking about a similar one with like understanding engineering benchmarks. 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?

1:29:38And you can say, oh, you know, this sounds small or whatever. 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 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. 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 weak.

1:30:10Maybe, 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. 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.

1:30:44So this is a new segment. I'm trying out. I'm going to call it pivot pivotal corner. And here's the question. What's the most pivotal moment in your career? I mean, I think it was at my at my former company. I'm at big health when I my former boss left the company and I started reporting into the CEO. And again, I think it was my first time just having like up close, like working with the 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 ranking file of like a big tech company earlier in my career.

1:31:27You get in the room and you talk to these people and you're like, Oh, this like this actually makes sense. Like I understand why this person has come to these conclusions. 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 the things that they are.

1:32:03And 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 for more. I'm sitting. So therefore it must not make any sense. It's so cool that this connects back to your habit of doing this, having seen it and being like, Oh, I see. This is why I guess 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 in like how I felt about everything.

1:32:34And 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 possibility that maybe I'm missing something. So I actually asked your boss, Kelvin, which is an awesome name, by the way, Kelvin about this moment when asked him what to ask you and he brought this up actually. And here's the way he described it. 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.

1:33:07She was an incredible first principles thinker, quick to tune the framing of problems that she learned more context. It's a great example of luck is what happens when preparation meets opportunity. Thanks, Yolanda. That's her last. He also said, I wonder if she remembers how terrified she was now because she absolutely knocked it out of the park. And I felt 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, a failure of like, I am not doing a good job.

1:33:50This is not going well. I don't know what I'm doing. You know, I'm what was that time. Kelvin actually gave me some great advice that was, but this is maybe kind of scary advice. But when I asked him when his advice for me what the time was and he said, product leadership is a the type of role where if you are not in control of 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 and everyone is looking to you to make the right decisions.

1:34:31And 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, you, 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 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.

1:35:12Well, and to the point of like when you 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? 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 it is understanding those types of things to allow you to understand how for some things. I wonder if you could ask Jatshipyt to build or claw out to build these mental models.

1:35:44Like here's their LinkedIn, here's their bio, here's a few things. What's how do they see the world? I will admit that I have tried this. And I think I think I think it's a great 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 he did say things like you could upload a you know, doc or whatever and be like, what are the three 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.

1:36:21And that's great. In this hypothetical example, what do you what do you context you share with with this model to help it be good? Great question. Hypothetically, I told you that I take all these notes on here's what this person said and here's how I interpret it. And LLM's 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 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.

1:37:04More 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 how all these meeting notes and you could just feed it. Here's all the things Hillary said and what is she what is she probably going to say about this? 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's 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?

1:37:44I mean, I think the one that probably looms largest in my mind is, I mentioned this 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 would 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 like I look at it and I'm like this was a great product that we put so much heart and soul into it and I think the like the lesson that I like from that is I think there's there's always a shot clock right when you're working especially now as you're at a 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 it we like we got to take the time to figure this out and get it right and that's what's most important but the 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 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 I worked a drop off for all I saw this happen all the time where we would like 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 installed 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 arms race and everyone's trying to really quickly of like yeah there's there's always a shot clock and you might not be aware of it but it's there and you got to you got to build your heart out and you don't ship and you got to get things out because at any time like that clock might run out.

1:39:49Speaking of shot clock not necessarily but I want to spend a little time on whoop the you guys just launch something that feels like a really big deal I'm excited that's the reason I got it there's always really cool new features I think you call whoop 5 .0 what should people know what's the newest coolest thing that's happening with who yeah I'm really excited you got it I know I know you tried it before and that's right that's right well who have tried who've been the past maybe felt like it was like very focused on like elite athletes and that is exactly what I felt. And I think what we've what we've done with our new experience is we've really built something that can help everyone be healthier and live better.

1:40:31I think we're I would say we're no longer for 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 mission or history we've updated our mission so we're now saying that we've exist 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 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 old age and I think that as I mentioned earlier I think it's really rewarding we've also have a lot of personalized coaching for AI in terms of actions that you can take to improve your bookage to improve your sleep to feel better and it's all part of our broader aim to make health more actionable and accessible.

1:41:39I think one thing I'm really excited about is we have a bunch of new women's health features so we have hormonal insights with improved menstrual cycle tracking I'm actually pregnant and I know that. Well, I've been announced me. Wow, congratulations Hillary, that's so exciting. But I actually I part of how I found out I was pregnant was in seeing my what? What? What? Which is remarkable and the way that we have this cycle tracking now you can see the way that you're different you know your HIV, your rest and heart rate things like that that's your heart rate variability and your rest and heart rate.

1:42:20Flush your weights for other times of your cycle and even in like the times leading up to that like I had a not straight forward pregnancy journey and having these tools to like really understand what was going on 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 features we have a heart health screener with blood pressure insights and ECG that's really cool. We got a lot a lot of great stuff cooking so even if you tried to open the past and thought it wasn't for you I think the the new experience is a real upgrade and it's it's something that I'm deeply proud of having worked on and really excited to have out in the world.

1:43:03I'm generally very excited about this like you could do a you said blood pressure and VO2 max it's and I know the battery is even longer to you. There's just like so much stuff. Oh, the 14 day battery life. I didn't even say we have these beautiful new leather bands. Oh wow. Okay. 14 day batteries life is is insane like I'm going on vacation tomorrow and I don't need to bring a charger like this is fantastic. Oh man. Like this sounds like a whoop ad but I'm like very excited about this. I will say one more thing which is we also have we've opened a weightless for advanced labs and so pretty soon you're going to be talking 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 and yeah just pushing pushing the limits of all the data that that we're pulling into the ecosystem.

1:44:04So really excited about that too. I'm hoping the whoop can actually take my blood and labs. Is that is that where is this is going because that would be so convenient. Okay. It would be like it'd be weird but also awesome. I don't think I'm going anywhere to do that. Hey Larry we covered so much ground. Okay. Before we get to 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 or less nugget you wanted to leave listeners with. I don't think so. I feel like we covered everything. We did. We covered so much in the best way possible.

1:44:34With that we 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. But 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're created a time box for it. Yeah exactly. Okay I'm going to go year and a half and 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 I 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 part way through.

1:45:12But fiction I'm like everybody should read East of Eden by John Steinbach and everybody should read the Sun Also Rises by Ernest Hemingway. It was just 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 forward and like 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.

1:45:50John Keith Sapoet talks about this concept of negative capability which is the ability to remain an uncertainties, mysteries, doubts without any irritable reaching after that dim reason and I love that. That sounds like a perfect quote for all PMs to. Exactly and it's like it's like you got you got to be built right again fiction. I love dualities there's a lot dualities and 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.

1:46:27I'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 that's life. So you know you don't learn that through to the extent that you learn that from a book at all which maybe you don't but I think you can I think you can learn in fiction. I don't know how you feel about this book. I think you'll be proud of me. I'm really Anna Krennan right now. Oh I was I'd literally that's the book that I'm bringing on vacation with me so you've never even ever read it. I've never read it. Cool me neither.

1:46:58Okay. Well exchange some notes it's very long. I'm really like because I'm reading on the Kindle like only 12 % okay. 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 but I'm like saying about the pool but I'm going to do it. Another guest recommended it and I saw on some lists recently and then like I should read that. What? So yeah okay great. Next question 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 and I don't know if he saw his previous thing that he did.

1:47:32Oh yeah it's called okay he's so hilarious and such a genius Nathan for you oh my god I haven't seen the new season now. The main is the freaky genius like I just when I thought that I had like a good sense of all the human emotions that exists out there like I watch the show and I feel things that I'm like I have no I feel like 10 different things and I'm like I have no words. I'll leave the things that I'm feeling right now. It's weird it's weird stuff but I'm enjoying it. I gotta watch it. Do you have a favorite product you've recently discovered that you really enjoyed other than the whoop.

1:48:08I love my swift. Swift it's like a program that you can hook up a smart trainer too like for an indoor cycling situation 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 a very serious cyclist 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 a 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 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 uh this I can't let happen so I I think it's a great product.

1:49:08I'm thinking about how to use that tech that uh I don't know mode for other use cases like the ghost version of something to motivate you. I didn't know many product meetings where I'm like can we make like a ghost version of your self? Yeah okay like shut up about the ghost. Okay amazing okay two more questions 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 told by mine recently because I was telling about the high brow fiction. I also have to go low brow. I saw this uh clip of Beavis and Butthead online recently where they were watching a music video for creep by radio head and it starts off really slow and one of them I think maybe Butthead is like uh the sucks and then the chorus comes and it starts getting like all hyped and they're like they're like oh this rocks this rocks and then I'm not sure if I need some butthead impression.

1:50:02So then it gets back to the slow part and uh they're like oh wait this sucks again and then Butthead is like why do 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 that is what life is all about is 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 part but it can't so thank you Beavis and Butthead. Thank you Beavis and Butthead. Okay file question I love that you're talking about fiction books because this is where my question was gonna go what's a fiction book that most impacted your product building approach or career or the way you think about product.

1:50:52Can I give a poem? 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 um and I you know I sort of mentioned earlier I think about these like dualities that that drive us and um I think as a 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 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 we we live in a society uh we exist in a business uh 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 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 um or have that flow when you're working on but then like it's got it's got to kind of like work in this broader system as well uh and I think that that's sort of been like the the thing that I think of as the guiding post for like what I want to do with my career and with my life um so I think it's got to be Derek Walcott what a beautiful way to end it Hillary two final questions work in folks find you online if they want to reach out maybe follow up on stuff that you talked about and how can listeners be useful to you great thank you um so as I mentioned I have a newsletter it's hills .substack .com that's h -i -l -s dot substack .com um I'm also teaching a maven class on being a supermanager uh 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 has been a big part of how I find time to do any of this stuff um and so I share a bunch about how I do that how I use AI as a manager um building on a lot of the the stuff that I shared on Claire's podcast as well um how I AI um so you can find me on maven there we've got a couple cohorts coming up and then uh yeah I encourage everyone to try out whoop you can get a free month on me at join dot com join dot whoop dot com slash Hillary that's Hillary with one L and you can you can post it me or tweet it me on x and let me know what you think of it 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 and you can also I realize that if you google super manager you will find me so that is my new plan to fame.

1:53:56Oh my god that's so great uh 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 this was so fun it's 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 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 dot com see you in the next episode