Hilary Gridley: How to coach product teams to take a punch

1. 0:00 – 4:31

   Hilary’s background

   1. HGHilary Gridley0:00

      Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive.

   2. LRLenny Rachitsky0:07

      You spend a lot of time thinking about how to help your team learn to take a punch.

   3. HGHilary Gridley0:10

      If they come to me and they're upset, I try to focus them less around how you litigate another person's impression of you and more on what is the action that you can take to counter-program the narrative that you are afraid that this other person has of you. What are you going to do next to demonstrate that you are the person that you know yourself to be?

   4. LRLenny Rachitsky0:28

      Do you have specific tactics that you teach your team to deal with hardship?

   5. HGHilary Gridley0:31

      I would really love it if more people were like, "Screw it. I'm gonna do something that's probably gonna fail. It's important and it's worth doing and I'm gonna do it well."

   6. LRLenny Rachitsky0:37

      Is there something you've learned about when your leader tells you to do something you disagree with?

   7. HGHilary Gridley0:41

      People think that the game is all about influencing the CEO, influencing the people around them. You come up thinking like you're the protagonist. But in the story of work, you are probably not the protagonist. You're not special.

   8. LRLenny Rachitsky0:53

      Today my guest is Hillary Gridley. Hillary is head of core product at Whoop. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox. Even more importantly, she wrote what is now the sixth most popular post of all time in my newsletter, How to Become a Supermanager with AI. She's also the first ever crossover guest between this podcast and our sister podcast, How I AI with Claire Veaux. And not just that, her episode with Claire is on track to be the most popular episode of the podcast. So all that to say Hillary is incredible and I'm so excited to continue learning from her. This conversation is packed with advice that will make you a better product leader, builder, and also just a better human. If you know what's good for you, you don't wanna miss this episode. A big thank you to Sam Proppas, Danielle Reynal, and Kelvin Wong for sharing suggestions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including Superhuman, Notion, Linear, Perplexity, and Granola. Check it out at lennysnewsletter.com and click bundle. With that, I bring you Hillary Gridley. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point your customers will start asking for enterprise features like SAML authentication and SCIM provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by WorkOS, including ones you probably know like Vercel, Webflow, and Loom. WorkOS also recently acquired Warrant, the fine-grained authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, SCIM, or user management, you should consider WorkOS. It's a drop-in replacement for Auth0 and supports up to one million monthly active users for free. Check it out at workos.com to learn more. That's workos.com. This episode is brought to you by Persona, the adaptable identity platform that helps businesses fight fraud, meet compliance requirements, and build trust. While you're listening to this right now, how do you know that you're really listening to me, Lenny? These days, it's easier than ever for fraudsters to steal PII, faces, and identities. That's where Persona comes in. Persona helps leading companies like LinkedIn, Etsy, and Twilio securely verify individuals and businesses across the world. What sets Persona apart is its configurability. Every company has different needs depending on its industry, use cases, risk tolerance, and user demographics. That's why Persona offers flexible building blocks that allow you to build tailored collection and verification flows that maximize conversion while minimizing risk. Plus, Persona's orchestration tools automate your identity process so that you can fight rapidly shifting fraud and meet new waves of regulation. Whether you're a startup or an enterprise business, Persona has a plan for you. Learn more at withpersona.com/lenny. Again, that's withpersona.com/lenny.

2. 4:31 – 17:57

   Teaching teams to handle criticism and setbacks

   1. LRLenny Rachitsky4:33

      Hillary, thank you so much for being here and welcome to the podcast.

   2. HGHilary Gridley4:39

      Thank you, Lenny. I'm so excited to be here.

   3. LRLenny Rachitsky4:41

      I talked to a bunch of people that work with you about what we should talk about and what you're amazing at. Uh, first of all, every one of them loves working with you so much. One, one of them is like, "I joined Whoop just to work with Hillary and to report to her."

   4. HGHilary Gridley4:53

      Aw.

   5. LRLenny Rachitsky4:53

      And of that, a theme... There's kind of this theme that emerged that I think is a good kind of overarching theme for our conversation, and it's something that you spend a lot of time thinking about, and it's how to help your team and how to help people within your company learn to take a punch. Essentially, how to help them deal with hard stuff and do hard stuff and build hard things. So I guess just broadly, does that ring a bell? Does that resonate?

   6. HGHilary Gridley5:16

      Yeah, absolutely. It's, uh, it's something I care a lot about. I've been, I think, pretty lucky in my career. I've been very drawn to working on hard product problems, uh, regulated areas, uh, really hard business models, uh, things with pretty high emotional stakes for the users of the products. Um, you're really likely to run into a lot of setbacks along the way, and I think this is really relevant today because I look out and I, I talk to a lot of people and I hear fear and I hear uncertainty, and I think it comes from a few places. I think, um, obviously I'm really excited about AI and how it's transforming the way we work, and I think a lot of people are, but I think a lot of people are scared too, and they're embracing these tools. They're learning these tools.... but a lot of them have a question in the back of their mind, like, "What does this mean for the future of my job?" And in many cases, "What does this mean for, for my identity," right? Like, I think it, it makes people question, um, even just how we provide value as humans in society. And I also think, you know, uh, people, especially young people today haven't even necessarily been in a career environment where there wasn't always kind of a threat of layoffs or things like that. And I think that's taken a real psychic toll on a lot of people. And so, I think all managers now really need to be able to lead their teams through uncertainty, through fear, through hard things. Um, and I love the concept of taking a punch. I've got a, a couple other tools that I, I like to use. Um, but I think it, it can teach people how to thrive in these environments, and it's really important to me because I would love if more people took on hard things. I think there's so many really hard, challenging problems out there to solve. And the more people are kind of fearful about the future of their careers or the future of work, I think the more they gravitate toward things that they feel like they're likely to succeed at. And I think that's wonderful. We need that too. Uh, but I would really love it if, if more people were like, "Screw it. I'm gonna do something that's probably gonna fail. And, uh, it's important and it's worth doing and I'm gonna do it well."

   7. LRLenny Rachitsky7:15

      There's so many (clears throat) kind of Venn diagrams of why this skill is so important, especially today. One is it feels like the easy stuff is, is done. (laughs) Like, the stuff left to build is hard. Like, it feels like hardware, deep tech is where things are heading. Also, just, like, machine learning, AI skills. Just, like, stuff that's really hard. And then the other is just AI is just changing so much. It's just such a s- stressful time and hard time for a lot of people. Let's actually walk through some of the things that you have learned about how to help people get good at these things, about how to learn, how to help people learn to take a punch. Uh, AK, do your things, deal with struggle. The first is you actually actively teach them. Like, you have specific tactics that you teach your team to deal with hardship and to take a punch. So what are some of those things? What are some of the things that you teach your team and help them develop the skill?

   8. HGHilary Gridley8:05

      Uh, so at its core, when I say take a punch, what I mean is you're going to run into situations where something has gone wrong. Uh, maybe you have misstepped. Maybe you are just hearing someone speak critically about your work. Whatever it might it, might be, you're gonna feel like you have taken a punch. Like, it's a very physical feeling. And I think as managers, you spend a lot of time teaching your team how to be successful, right? You, you want to prepare them to maximize the chances of a good outcome. But if you don't also prepare them for what happens when that outcome isn't as good, uh, you're gonna run into some problems. And so when I think about how to take a punch, what I say to my team is, if they come to me and they're upset because something has happened, um, maybe they said something in a meeting that wasn't received well, or again, they're hearing somebody else talk about them in some way, whatever it is, I try to focus them less around whatever happened and how you litigate another person's impression of you based on something that has already happened, and more on what is the action that you can take next to counter-program the narrative that you are afraid that this other person has of you? And I think the counter-program piece is really important because whenever we feel our ego's injured, I think it's very natural for all of us to say, like, "Well, that's not fair. I wanna correct the record." When you do that, I, I think more than often, more often than not, you come off as, as just looking defensive and you kind of start obsessing over things that you don't actually have control over, uh, which is what another person thinks of you, and you don't even necessarily have that information. And so I always ask myself in these moments, "What is one thing that I can do, small, that will demonstrate the opposite of what I'm afraid this person thinks of me?" And so I'll give you an example of this. Um, I was in a meeting a while ago and we were talking about different things that we wanted to start tracking in the Whoop journal. And our chief technology officer suggested ketamine tracking, and I thought she was making a joke and I laughed. And she looked at me very seriously and was like, "This isn't funny, Hillary. Like, this is a serious issue for a lot of people. Uh, and it's, it's an emerging, uh, problem in some cases, and I think we should take it seriously, and I think there's a lot of value we could provide here." And I was completely humiliated. Uh, humiliated because I actually take this stuff really seriously. Like, I take addiction really seriously. I have a ton of empathy for, for people who struggle with it, and I also think of myself as somebody who embraces new ideas and wants to be on the forefront and, uh, would never laugh off something that kind of seems like a fringe issue that's, I think, becoming actually more and more, uh, a, a big part of what's happening today. And so, I realized that in that moment, I was having that reaction because of the, the feeling that it gave me about who I am as a person. And I became so worried that this other person had the wrong impression of me. And I wanted to follow up with her after and, and say, like, "Let me explain myself." Like, "Let me explain why I didn't mean that," or whatever it is. But I just, as I said, I think, I think usually that you're fighting a losing battle when you're trying to do that and it draws attention to the thing that you kind of did poorly, uh, and you don't really wanna draw more attention to it, right? You wanna move on, take action, move forward. And so I thought about, "Well, what, what am I afraid that she thinks of me? I'm afraid that she thinks that maybe I don't take, uh, some of these health issues seriously. I'm afraid she thinks that maybe I'm somebody who, uh, kind of, like, laughs off emerging trends." Um, and so I thought about, "What's something that I could do to demonstrate the opposite of that?" And I did some research very, very quickly on, um, you know, what are some, like, emerging public health concerns that people really aren't talking about that would be interesting to track? And I found some interesting research about sports betting and especially young people and sports betting, and it's sort of becoming this thing that a lot of public health experts are very worried about. And-So I very quickly just sent her an, uh, note that said, "Wanted to build on this idea you had today. Um, I really liked that idea, by the way. I, you know, I saw this, uh, this article or saw this research about this other emerging thing, sports betting, and I think it'd be really e- interesting for us to start tracking that because we could maybe draw some correlations between people's stress." We have a stress monitor in Whoop. We can track your stress. Uh, "We could draw interesting correlations between betting behaviors and stress levels." Um, and so that's all I did. It took me five, 10 minutes total. Um, but I think it, it's a great example of show- sort of showing this idea of, like, counterprogram that narrative. Don't, don't fight about the narrative. And so when I teach this to my team, I'm always doing the same thing. They come to me. Uh, they seem kind of agitated about something, and I say to them, like, "It seems like this is really bothering you. What, what's going on in your head? What are you afraid of? What are you worried about?" And often it will emerge, you know, "I'm worried that this other person thinks I'm bad at my job. I'm worried that this person thinks I'm an idiot," whatever it is. And I challenge that. I think this is really important for managers too, to kind of challenge this negative thinking when you see it happen, and not just sort of validate it and allow them to go down these negative spirals. I challenge it and I say, "First of all, I don't, I don't think there's evidence for that. Is there evidence for that? And you know, even if there is, it doesn't really matter. What's, what's something that you could do to show them that it's not true? Because you know it's not true." Um, and I think giving people that, that power to focus on the next step they can take, the action that they can take that helps them feel more secure in their identity and who they are because their action demonstrates that, um, it just gets them out of that negative thinking and it gets them through that trough of despair that comes after you, you feel like you took a punch.

   9. LRLenny Rachitsky13:52

      So the idea here is when you're afraid somebody that matters in your career thinks ill of you, of something that you did, of you're not good at something or you think something that they're not happy about, like, this is a version of getting punched basically, is you just feeling like someone thinks you're not doing a great job. And so the tactic here is how to change their mind almost about you and give you something tangible to do.

   10. HGHilary Gridley14:16

       Exactly.

   11. LRLenny Rachitsky14:17

       Okay, and so the question to ask, and I, I wrote this down as you were talking, is... And this is what you ask of your reports. What is the one thing that you can do that demonstrates the opposite of what you think this person thinks about you?

   12. HGHilary Gridley14:28

       Exactly. And it's, uh, uh, this comes up all the time. Like, there will be narratives that emerge, some are good, some are bad, um, about you and your career. And I think especially when people get to a place where they're putting themselves out there more, right? They're talking, uh, in more presentations, they're talking in more meetings, it's very natural for them to become, uh, concerned with the perception of themselves. And it is scary because it, it feels like something, as I said, you don't have control over. And so exactly. If, if it's in- if instead of focusing people around, "What do these people think of me?" you focus them around, "Well, what are you going to do next to demonstrate that you are the person that you know yourself to be?" Uh, I think that can just be incredibly effect- effective at giving people more of a sense of agency.

   13. LRLenny Rachitsky15:12

       I guess talk about the balance of, "I'm just gonna prove everyone wrong against what they think," versus, "Here's who I am and I know this is me and this person is mistaken and instead of debating them, I'm gonna show them who I am." Just, like, not over-stressing about everyone thinking things about you in different ways.

   14. HGHilary Gridley15:30

       There is so- some value, I think, in having a little bit of a chip on your shoulder. I think that that's definitely been, you see that, people who are really successful, they do have a little bit of like, "I'm gonna prove 'em wrong." And so I don't want to say that, like, you shouldn't think about it at all or you shouldn't care. Like, of course it's natural to care and of course it's fine to care, but I do want to just sort of help, help my team build this habit of doing the things that you know to be right and, and having conviction in that and, you know, being open to learning along the way and, and sort of calibrating as you go. Um, but not, not becoming overly concerned with your fears of what other people are going to think of you, because I think especially for, uh, otherwise really thoughtful, you know, really kind of, the pe- people who are kinda hard on themselves, I think that that just holds them back from being the person that they can be.

   15. LRLenny Rachitsky16:21

       So a key part of this is this is gonna help you stop just spiraling on-

   16. HGHilary Gridley16:25

       Exactly.

   17. LRLenny Rachitsky16:26

       ... thinking about what they think about you and gives you something to do that will change that.

   18. HGHilary Gridley16:30

       Mm-hmm.

   19. LRLenny Rachitsky16:30

       And then the other key point here is, don't try to convince them otherwise. You're not gonna go to your manager, like, "Oh, I'm, I really think ketamine therapy and addiction is really important and I'm, I didn't mean to say it this way," um, that kind of thing.

   20. HGHilary Gridley16:45

       I, you know, I'm not interested in litigating the things that happened already, when we can move forward, and I'm certainly not interested in litigating what another person thinks about a thing that happened. Uh, I just, I feel like I've spent so much time talking to people in meetings, whatever it is, where it's just this kind of, like, ruminating on something that has already happened. You know, it's a very, like, anxious thinking pattern, I think. Um, and people can just get stuck in it. Uh, and so, you know, let 'em, let, let them do it. Like, I often think about, uh, it's like when you get bad feedback, right? Uh, or critical feedback, and you kind of naturally have this reaction of, "Oh, well, you know, that's not fair 'cause they don't understand. I actually have numbers I have to deliver on," or, like, "I only had 10 minutes to do this, so like, of course it wasn't perfect." Like, you, you naturally come up with these reasons why, uh, you are actually not wrong. And, and that's fine. Like, it's, I don't want to say, like, you should feel bad for doing that. Like, let yourself have the pity party. Let yourself feel those things. But then, but then you gotta move on as quickly as possible, because those feelings, they actually do tend to spiral and get worse, um, if you're not actively

3. 17:57 – 22:59

   Behavioral activation and mental health in the workplace

   1. HGHilary Gridley17:57

      working against them.

   2. LRLenny Rachitsky17:58

      Oftentimes these sorts of lessons come from the person experiencing this themselves. Is this something that you dealt with when you were starting your career or even now and...

   3. HGHilary Gridley18:08

      Oh, absolutely. Um, 100%. And I think it is more than just my career, but...... just my, like, general mental health and my life. A lot of where this comes from is, uh, a, a concept in cognitive behavioral therapy called behavioral activation. And in my former job, I was working for a company called Big Health and I was... We make, uh, digital therapeutics. So those are mobile apps that have been clinically validated to treat behavioral conditions like insomnia, depression, anxiety. And I was working on a new depression therapeutic. And so I went very deep on this, um, and was working with a really wonderful clinical team full of clinical psychologists who helped me understand the techniques that therapists use, uh, when they are working with people who have depression. And so much of depression is characterized by, uh, these negative thinking patterns and this, like, this feeling that I feel bad and I just need to wait until I feel better and then I will start doing the things that are good for me, right? "I don't feel like, uh, responding to this text, so I'm just not gonna do it, but I'll respond when I feel better. I don't feel like working out, so I'm not gonna do it, but I'll do it when I feel better." And the truth is, like, it, that doesn't go away on its own, especially if you have depression. Um, and it's something that, again, you, you... The idea of behavioral activation is, uh, you have to identify these actions that you can take that will reverse that negative spiral and will improve your mood. And so the, the sort of, like, misconception is I'll feel better and then I'll act. And the thing that therapists try to teach people when they're working with them in therapy is, "I will act and then I will feel better." But acting is hard if you are in the throes of depression. And so easier said than done. Uh, and a lot of the work is in how you i- help people identify specific actions that they can take that will reliably lift their mood. And I, I mean, I have a list of it myself. I've got a, a list on my phone of my behavioral activations and it's things that I know I can do if I start to feel like the walls are closing in around me, if I, if I, like, feel myself kind of getting sucked into, uh, like, very low mood or negative thinking or whatever it is. And you can, you can see how effective that is at just getting you out of there versus the instinct to just sort of, like, go and lie in bed and feel bad for yourself, um, which I, and I understand very well. And so that, understanding that concept, which is at, you know, at its core a therapeutic concept used in cognitive behavioral therapy, um, but it kind of, it kind of changed how I see the entire world. Um, and, uh, how I see, especially as a manager, the ways that people on my team think and behave, uh, and how easy it is to get stuck in some of these, like, downward spirals that you really need to actively push back on. And as a manager, I wanna help them do that. I wanna help them, A, see that, like see the ways they are, in some ways, sabotaging th- themselves, getting in their own ways, um, with whatever is going on in their head. Uh, and then I wanna help them counter-program it in themselves and also, you know, as I said, counter-program the things that you are worried about out there as well.

   4. LRLenny Rachitsky21:22

      So interesting. So the core of this technique is what's a s- an action, and you said this, it could be very small-

   5. HGHilary Gridley21:28

      Very small.

   6. LRLenny Rachitsky21:28

      ... that you can take that, in this case, shows someone else you're not, they're not, you're not who they think you are. Like, you're worried they think, think about you in a certain way and you want to take an action that helps them see you're not that.

   7. HGHilary Gridley21:40

      So that, yes, that's the taking the punch concept. The behavioral activation could be anything, right? It can be, it can be picking up a piece of laundry off of the chair and putting it away and that's just sort of enough to get you out of the downward thing you're in. So behavioral activation just conceptually is, uh, you know, how are you taking action to reverse the, the downward feeling or the negative feeling that you're feeling? And then the take a punch concept is kind of that applied in the context of I'm in a working environment, I am very conscious of how I'm being perceived by other people. That's causing me a great deal of stress. I think especially for product people who are, um, you know, so much of their self-identity is wrapped up in having the answers, being competent, getting things done, um, and so many of them have been people who have been really good at that for most of their careers, which is how they got into these jobs in the first place. I think that can be an extremely stressful thing for them that, in many cases, can be, uh, like the driver of burnout and the driver of, like, "I, I can't really handle the stress of this job anymore." Um, and so I think of the, the take a punch concept is, is more just applied to that sort of specific problem of, "I'm struggling at work and I'm struggling largely because of my perceptions of other people, uh, and I wanna feel more agency in that situation."

   8. LRLenny Rachitsky22:58

      This

4. 22:59 – 27:51

   The importance of putting yourself out there

   1. LRLenny Rachitsky22:59

      is so cool. Okay, on the idea of the specific take a punch concept, what kind of impact have you seen this have on people's mood and careers? Is this... Like, how big a deal is this specific tactic?

   2. HGHilary Gridley23:13

      Well, I think it's a big deal, like, on two levels. One, it's a big deal because it can help you in a crisis or a minor crisis. But I actually think it's a bigger deal because s- I see so many people who don't, uh, put themselves out there because they're afraid of how it's gonna go. And so I think of the, like, classic example of, um, I'm often trying to encourage people to, like, speak up in meetings more, uh, to practice the skill of how you move a conversation forward in a way that contributes value. Uh, both because doing so, I think, is, is important because nobody wants to be in bad meetings, but also because it will help with your career, right? Like, this is how you kinda get on people's radar as somebody who's like, "Oh, that person's got great ideas, thinks about things the right way," whatever it is. I think it's just, it's one of these things that I talk to people about it and they, you know, they, they are interested in coming to the meeting and hearing about, uh, these big decisions that are getting made, but they just kinda wanna sit there and observe. And I'm like, first of all, like, every additional person in a meeting has a cost because every additional person in a meeting makes the people in that meeting less candid than they would have been if there were fewer people in that meeting.And so one key piece of a meeting is like, you usually have a problem you're trying to solve, uh, collectively as a group, and it's really hard to do that if people are being overly cautious about what they're saying because there's, like, too many people in there. So, uh, when I tell people this, I'm like, "You know, it's really important that you earn your place in this meeting. Uh, and let's work on, like, how to do that." And the core piece of that is like, you've got to say stuff that's valuable. And people always come up with all these excuses for why they can't do it. And one thing I've learned is that I think people are really good at coming up with very rational sounding reasons to not do things that just make them uncomfortable. Uh, but in their head they're like, "Oh, no," you know, like, "I'm- I'm too junior," like, "Nobody wants to hear what I have to say," or, "Everyone was already thinking it," or, uh, "You know, I," you know, "I like to process things internally and by the time I say them, the conversation's moved on," whatever it is. Um, and so, so much of, like, that skill, it's like a communication skill at its core, it's just how to express yourself verbally, uh, but so much of the- the blocker of that is, I think, fear. Uh, fear of saying the wrong thing, fear of looking stupid, fear of just the o- the discomfort of everyone in a room turning and looking at you, right, as you're kind of like trying to formulate a half-baked thought. And so if you can help people be less afraid of that, that's like 90% of the challenge of actually improving some of these skills. Um, and so I think when you give people the skills of taking a punch, you are helping them feel less afraid of getting the punch in the first place. Um, and that's why I think it's so important.

   3. LRLenny Rachitsky25:57

      That's profound, the second order effect of this skill. There's something you mentioned when we were chatting earlier that, um, stuck with me, was this idea that too many PMs and too many people are playing on easy mode and not trying hard things.

   4. HGHilary Gridley26:10

      (laughs) Uh-oh. Maybe I got myself in trouble here.

   5. LRLenny Rachitsky26:12

      Okay, let's do

   6. NANarrator26:12

      (laughing)

   7. LRLenny Rachitsky26:13

      ... Say more.

   8. HGHilary Gridley26:15

      Oh, I think this is my hot take. Like, you know, you hear people talking about craft and taste in product management and it's all very wonderful. Um, and I- 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- 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 b- I mean, there's b- I don't wanna, I don't wanna act like I think this is easy, to be clear. (laughs) Um, 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. Uh, and I think there's a, a level of prestige obviously associated with working, uh, in certain companies and, you know, you get less of that in- in other industries, and so people naturally gravitate toward that. Uh, and I, you know, I totally get it. I totally get it. And you get paid better. Like, no- no real judgment from me. Uh, I just, I wish I saw more of it. I wish you would see more people. And I'll say this. I know there's a lot of you out there. I know there's a ton of people out there doing really, really important work in really, really hard spaces. Uh, and I see you and I- I appreciate it, and shout out to you.

   9. LRLenny Rachitsky27:47

      Awesome. Okay. I'm glad you shared that. Thank you.

   10. HGHilary Gridley27:50

       (laughs)

   11. LRLenny Rachitsky27:50

       I think this will resonate

5. 27:51 – 38:10

   Transparency and communication in leadership

   1. LRLenny Rachitsky27:51

      with a lot of people. I want to move on to another trait/habit/skill that you are good at and help people learn, which is being very transparent in what's happening within the organization, within your thinking. You almost help people think the way you think and see the way you think so that they can operate at a higher level. Let's talk about that, what that looks like and why that's important.

   2. HGHilary Gridley28:13

      It's interesting. I think another thing I hear a lot of people complain about in organizations is like the, "Why do 10 people have to sign off on this email before I send it," kind of problem. And I think the answer to that is like, because those 10 people all have different information, different context, and in many cases, completely different, like, working models for how the CEO of the company and other strategic leaders in the company think. And it makes things super inefficient. I think people will often say like, "Oh, it's a process problem." It's- it's not a process problem. It's not an approval proce- problem. It's a, I think it's a transparency and it's a communication problem. Like, downward communication and outward communication. And what I mean by that is, um, when I think about, like, artifact-based communication, so reading a strategy document, for example. Everyone at the company reads the 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, uh, new competitive threats em- 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- to sort of transform their organization. And so if you're- you're- if 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 gonna be working from outdated information and you're not gonna 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. Um, and that goes for all sorts of levels of the company. I want to understand how all the strategic leaders at 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. I don't need to approve things. The times where I feel like I need to do that is because I'm working with people where I'm like, I don't- I don't have confidence that these people understand how I think, or I don't have confidence that they understand how this, uh, this email or whatever it is is going to be received by this important person. Um, and so I try to teach that to my team.And the way that I do that is, uh, a few ways. Uh, first, I'm in meetings with people, like important people at the company. Um, so I'm constantly hearing the things that they're saying and paying attention to sort of the note behind the note. Why do I think they're saying this? What do I... what insight do they have that they're bringing to this conversation that might not be obvious? Um, and I try to make an effort every week, I don't always do it, but I try, to send my team just a quick rundown in Slack of here are the most important conversations or the most interesting conversations I had this week. Here's what that person said verbatim. Again, I, I write a lot of notes, so I've, I've got it. Um, if you've got a transcriber, maybe (laughs) 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. And 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. Um, 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, uh, 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, uh, what level of, like, risk tolerance the company has, things like that, then you can actually start to move much, much faster and communication becomes much, much, much less painful.

   3. LRLenny Rachitsky32:03

      (clears throat) So the tactic here is to help your team s- 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 or asking for something, they w- they already know how they're gonna respond.

   4. HGHilary Gridley32:17

      Exactly.

   5. LRLenny Rachitsky32:17

      Is there, is there an example you could share of something like this of just, like, something, a person at Whoop of how they think? I don't know. Maybe you can keep it anonymous just to make this little reel of the kind of mental model you might wanna build around someone.

   6. HGHilary Gridley32:29

      So our CEO, Will, is, uh, somebody who obsesses over pixels in a way that, um, i- is, you know, challenging to get things through design review, but I think results in a product that is a thousand times better than it would be if, uh, he were accepting of, you know, small, uh, 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, um, and he doesn't compromise. And I think this can sometimes get misconstrued, and I think a lot of people might think that he just wants, like, maximal scope on everything. Um, and I think that is a misunderstanding of what he cares about. Uh, 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." A lot of people hear that and they're kind of like, "Oh, gosh," like, you know, "We're never gonna get this thing done on time," like, "we can't make any sort of sacrifices to scope or anything like that." But when I hear that, like what I hear is more that with... we have this AI coach in the product, we have all this amazing data in the product, uh, you know, we're tracking every single one of your heartbeats, and we're pulling in 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, uh, VO2 max, which is the... you know, a measure of your cardiovascular health, you can explain that to people with static content or you can explain that to people by bringing their data into, you know, the, 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 gotta 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 out the, the, um, signal from the noise on that in these really small and elegant ways. And so for something like that, like, I would get that feedback in design review or I'd hear that in a design review and maybe one of my PMs would be in that design review. Um, and so I bring that to the team. And I hear things like that in a few different design reviews. So I bring those back to the team and I'm like, "I've noticed that recently we are consistently getting this type of feedback. Uh, here's why I think it's really important to Will, uh, because I think he's really focused on building, you know, the, the health company of the future." And I don't want you all to think that this just means, like, we have to just throw AI at everything and we have to just throw, like, maximum scope at everything. I think the key is understanding, like, on the matrix of, uh, cost and effort for, uh, impact. Like, what are those high impact but low cost ways that we can just find and sprinkle through the experience, um, and, and really try to make that magical? Uh, so I'm connecting the dots for my team, right? I'm saying, "You weren't in all these meetings, but I saw it. Here's what I heard. Here's my interpretation of what I heard." Um, "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."

   7. LRLenny Rachitsky36:06

      Essentially these are principles or values or tenets per person of what matters to them.

   8. HGHilary Gridley36:11

      Exactly.

   9. LRLenny Rachitsky36:11

      So for Nick it's, this needs to feel like we're living in the future. It can't just be, like, another, uh, heartbeat tracking app.

   10. HGHilary Gridley36:18

       Yeah. Yep.

   11. LRLenny Rachitsky36:18

       This is so cool.

   12. HGHilary Gridley36:19

       Cool.

   13. LRLenny Rachitsky36:19

       And there's so much ch- trickle down benefit to this. One is people feel like they're aware of what's happening. That's one of the most common, I think, piece of feedback people have with big companies, like, "I don't know what's happening." So there's so much visibility, all the secretive stuff happening in the meetings, like, "I don't know."... where people were deciding my fates and all these discussions. So, I think just even knowing that you're sharing all this is so powerful.

   14. HGHilary Gridley36:40

       Well, and on th- on that note, like, when I approach these conversations, I always try to think of them as, um, even if I don't agree with the feedback, if I don't agree with the decision, like, what is the insight that I'm missing? Like, how am I wrong about this? In ways, like, what would be true for this other person to be right? And I'll go through that thought exercise, and I might not get to the other side a- and agree with it. I might still, you know, think I'm right or whatever. But oftentimes, it- forcing myself to think that way forces me to think about how this other person thinks it. And I- 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 s- when I hear the people, the people who are like, "I don't know what's going on with 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, is helping them think that way. Like, helping them understand you have a point of view, your point of view is important, um, but on some level, like, you do kind of have to have respect for these other points of view and have the humility to think that, like, maybe they- they're onto something that you're not onto. And it's amazing how much you can, like, learn and intuit without having to have all the facts just by doing that. If you're like, "Well, this person's behavior makes sense in a situation where X, Y, and Z is happening," oftentimes you will find that X, Y, and Z is happening.

6. 38:10 – 41:49

   How to respectfully disagree with your manager

   1. HGHilary Gridley38:10

   2. LRLenny Rachitsky38:10

      I'm glad you went there. I wanted to actually follow this thread, which is kind of a different direction, but I think a lot of people are always struggling with this as a leader. When your leader disagree- does, says something that you completely disagree with, but you still need to represent that as like, here's the thing we're doing. But you don't want to be like, "Oh, just 'cause Nick said so," you know, 'cause you lose power as a leader. Do you have any just, is there, like, something you've learned about how to do that well when your leader tells you to do something you disagree with and you still need to get your team to do it?

   3. HGHilary Gridley38:39

      First, I, I do try to go through, like, the, the what if I'm wrong exercise. Uh, I think a lot of people just sort of, like, expect that if you ask somebody a, a, a s- open-ended question, like, "Why are we doing this?" you're gonna get a straightforward answer, and oftentimes the answer is not straightforward for various reasons. Like, maybe there's confidentiality reasons. Uh, maybe there's just, like, you know, s- 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 onto something that's not just, like, this kind of arbitrary gut feeling. But whatever it is, like, I really try to get to the bottom of, let me, let me really make sure that I have done my best to understand this person's point of view. Um, and I have some sort of tools for doing that, which I can also talk about. But if I've done that and I still disagree, I'm, like, relatively candid about that, but candid in a way where, like, it's still respectful. Like, I think what you want to avoid is a situation where as a manager you're like, "Ah, this, you know, I have no control. This sucks. This decision is so stupid, but, like, that's the job, so we have to do it." Like, obviously that's not gonna, 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. And so I think what I try to do in those situations is separate out, like, my opinion from it from the, like, well, what is the insight that makes it make sense to this person? And explain their rationale even if I'm comfortable saying, like, you know, "I don't necessarily think... Like, this isn't how I would do it," or, uh, "I don't even really agree with how they're thinking about it, but from their point of view, from their perspective, uh, 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 gonna find out if we are all squabbling about whether this is a good idea the whole time. Like, the only way we're gonna find out is if we give it the best shot that we have and try to do it. And if we're wrong, like, that happens sometimes, and we try again.

   4. LRLenny Rachitsky40:41

      I like that this comes back to your m- mental model orientation of here's their mental model.

   5. HGHilary Gridley40:46

      Mm-hmm.

   6. LRLenny Rachitsky40:46

      Here's what their experience has been like. Here's how they see the world, the trends, and then this is why they think the way they think. And so instead of encouraging your team or yourself even to be like, "No, no, you're wrong here," it's more, "Okay, here's their dataset. Let's try this, and this will inform the dataset and maybe change their mind."

   7. HGHilary Gridley41:03

      Yeah, 'cause I think in product, like, I like to joke there's no right answers, right? You're just, i- there's only wrong answers, and you're just trying to execute well on, like, the least wrong answer that's available to you. Uh, and so I think it is, like, you know, the sort of reasonable people can disagree about this of it all of, you know, like, this is what I think and this is how I would 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 a, like a obviously terrible answer, and sometimes even if it is an obviously terrible answer, you're still more likely to succeed if you just sort of, like, sort of reorient yourself around a world where it's not a terrible answer and then just try to will

7. 41:49 – 49:54

   How to use “magic questions” to decode how people think

   1. HGHilary Gridley41:49

      that into existence. (laughs)

   2. LRLenny Rachitsky41:50

      You said that you have some tools to help you understand someone's point of view. I can't help but ask more about that.

   3. HGHilary Gridley41:56

      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 as, like, the most helpful way for kind of trying to understand a person's, uh, mental model is to just, like, put facts in front of them and see what they say no to and what they say yes to. And then if you can get them to explain, great. And if they're good communicators, they often can. Um, but if they're not, like, you don't have to let that stop you. And so, I mean, I, I'll, I'll do this even just as an example, uh, in a non-leadership context with, uh, if I'm working with, like, legal teams or compliance teams or things like that. They're often working from a, a literal set of rules, right? There are laws. There are regulations.Um, and you are trying to understand, like, what i- i- you know, if we were to take this path, would that be okay or would that not be okay? And sometimes that's, that's not straightforward. Um, sometimes, like, it, there's regulatory areas that are, um, 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, the rules so I can understand what's right and what's left of it?" And they'd be like, "Oh, well, it depends, it depends, it depends." And so I learned that if I had kind of flipped that and approached 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, "Well, what do you think I should do?" Or, um, you know, "What could I have done differently?" I'll say, like, rephrase that as, "Tell me what you think you could have done differently, and then ask me if I agree." And when I do this, I think it ha- 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, um, 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, um, they don't become reliant on me for answering these questions. I think that's kind of a trap that a lot of managers fall into, is you, people come to you with questions, you wanna 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 gotta solve some of these on your own." So again, I think, like, the magic questions to me, is that right? Do you agree? And any time 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, "Well let me just say that, let me say as a statement what I think, and then try to calibrate based on their reaction." And like, I think that's the fastest way to understand how another person thinks.

   4. LRLenny Rachitsky44:51

      There, it makes me think about a lot of people... Like, it sound, it could come across as it's, like, a weird manipulative way of asking someone stuff. But it turns out th- like, we're not good at really knowing what we think or know a lot of times, and you need someone almost to interview you in a really effective way to get out all this knowledge. And this is just a really simple way of getting that out of your head.

   5. HGHilary Gridley45:09

      But it, you know, it's funny 'cause I'm like, uh, when I talk about this, I ge- I get that reaction a lot where people are like, "Well, doesn't it feel coercive?" And I'm like, "Well, you gotta go in pure of heart. Like, you've gotta go in-"

   6. LRLenny Rachitsky45:19

      (laughs)

   7. HGHilary Gridley45:19

      "... o- open to being wrong and even expecting to be wrong." And you have to make that clear to them, right? Like, if you're coming in and you're like, "Rrr, here's what I think. Like, you agree? You, you agree?" Like, of course you're not gonna get the answer you want. Or, I mean, you might get the answer you want, you might get a yes. If your goal is to get to yes, that's not what I'm, that's not what I'm talking about. If your goal is to understand and you are coming from like a, help me understand how I'm wrong, help me understand what I'm getting wrong here, um, and approach it with that sort of, like, curiosity and humility, um, and make sure that you're, like, carrying yourself and presenting yourself to this person in a way that, that, that shows that, that you're not coming in, like, hostile or forceful or something. Um, yeah, 'cause it, it, there are absolutely circumstances where you're doing that and you're gonna get bad intel because you're making the person uncomfortable so they're gonna lie to you. But that's like a, I think a whole set of interpersonal skills that we probably don't have time to talk about today. (laughs)

   8. LRLenny Rachitsky46:09

      I wanted to come back to you said this, uh, f- interesting insight about your CEO, that he wanted to build something that, uh, was, felt like the future. Uh, I would, just wanted to share there's a story that has always stuck with me at Airbnb. There was a, a big launch coming up and there was a designer sitting at, late in the office trying to re- update the website to include this new product. It was a launch of Airbnb Neighborhoods like, I don't know, 10 years ago. And he's, and she was just like, "Hey Joe," and this is Joe Gebbia, was walking around the office, and she's like, "Hey Joe, what do you think I should h- what do you want the website to be? What do you want it to look like? What should we try to..." And it was gonna launch in two days. He's like, "Build something the internet has never seen before." And now this makes me, like, it's interesting 'cause when I th- always think about that story and tell that story, it's like, this is a crazy ask. And now, as you share an approach for how to handle something like that, it really changes my perspective to like, okay, what's Joe's worldview? Why, why is that the way he saw the world and why we needed to build a site like that? Which I, I could start thinking about but that's a really interesting way to just, like, handle things that sound absurd and out of nowhere.

   9. HGHilary Gridley47:18

      I agree so much. I, uh, proud former English major and so I'm a huge proponent of reading fiction and, and reading in general. And, um, I, I feel like s- that's where so much of this comes from for me, is just, like, a curiosity for, like, in, i- in what world does this make sense for this person? Uh, and it's so easy to look at an other person's behaviors and another person's actions and what they say and just be like, "That doesn't make any sense." And I just, I find that, I don't know, like your relationships become so much richer, even just in a work context, like, when you approach it with that, like, what, what is the world of this person where the thing that they're saying makes sense? And I'd 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, "Ah, this person said this and it didn't make any sense and this person stole the out to lunch and leadership doesn't know what's going on," like, all I was doing was making myself miserable. Uh, 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, "No, nobody appreciates my perfect, unique, beautiful insight." Um, and all these other people have no unique, beautiful, perfect insights, just wrong opinions. And so I feel like that's been, like, a big area of growth for me honestly, is, uh, like, learning to approach people that way. It's not just like-... oh, this is a nice thing to do, but I think it, it, like, genuinely makes me a happier person. Uh, and yeah, I think, (laughs) I think a lot of it comes from reading fiction.

   10. LRLenny Rachitsky48:55

       Hmm. 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 in, around you. And I...

   11. HGHilary Gridley49:04

       (laughs) I feel like this is just making me sound like a crazy person.

   12. LRLenny Rachitsky49:06

       No! There's so much power to this. Like, it's, uh, it's, as you talk I'm like, wow, there's so much value here. 'Cause 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 with the CEO or the chief product officer, designer. Just like, "Ah, I hate this. What are they just asking all these ridiculous things, keeping the bar way too high." It's just, nothing's ever good enough. But not only does it help you feel better about their asks, because you can understand where they're coming from, it also helps you be more effective in helping them change their mind, potentially, and see a different perspective. Because now you see the data that informs their perspective and you could help adjust that or, or kind of poke at it like, "Hey, are you sure this is true? Are you sure, like, I don't know, your competitor, and this is how they see it? Maybe it's not. Let's, let's look into that a little deeper."

8. 49:54 – 52:48

   Why you’re not the protagonist at your company

   1. LRLenny Rachitsky49:54

   2. HGHilary Gridley49:54

      Yeah, it's really interesting. I, uh, I, at my last company, when I started reporting to the CEO, um, 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 has just got acquired 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 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 gonna 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, um, and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of a product." And that was just such a, like, radically different way from what I ever thought my job was. Uh, again, to go back to sort of the fic- 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 real 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, uh, like, you are probably not the protagonist. And as much as it, you know, can feel kind of weird to say that, I, I genuinely think, like, some of the best advice I've got in my life in terms of things that have just not only transformed how I see the world and how I act in it, but just, like, my own sense of happiness? Is like, you're not special. And it's, like, I used to spend so much time and energy just being like, "Oh, like, people aren't, people don't see it my way, and I have to convince them." And when you're in an organization, like it's a, it's an ecosystem, right? Like it's a, it's an organization full of people who are all trying to work together to get a thing done, and if every single one of those people is operating from their own, like, protagonist viewpoint of, "This is how I actually see the world. This is what I think we're here to do, and I need to convince everyone around me at all times." Like, it becomes extremely inefficient and it becomes extremely painful, 'cause you're just, everyone's just fighting all the time. And so, in some ways, like, it feels like you're kind of, uh, like if, it sounds almost defeatist. Like, I'm always worried about this sounding like I'm just like, "Yeah, just do whatever the boss says." Um, and that's not how I feel at all. Like, I think it's incredibly important to bring your skills and your talents and your perspective to the job you have, um, and, and really, your taste and your craft and all of these things. Um, 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, um, actually just makes work a lot better for everybody.

9. 52:48 – 1:01:02

   Aligning with the CEO's vision

   1. HGHilary Gridley52:49

   2. LRLenny Rachitsky52:49

      So then, a lot of people, like you said, I love that you went there, is just like, if you're...'Cause it could sound like, okay, your job is just to execute what the CEO tells you, there's no value to your insights and perspectives, and you're just, get out of the way, you're just this get everyone to do the thing the CEO wants. Where do you, I guess, in your experience, or just advice on where's the fulfillment for you then as a CPO, or example, or a director of product, where, you know, it's not that fun just to be there executing a CEO's vision and not have any input?

   3. HGHilary Gridley53:20

      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 zig where others would have zagged. And I think I personally, like, a lot of where my fulfillment comes from is from feeling like if somebody else were in this job, it would be done differently. And like, something about the product is different because I was the one who worked on it, because I was in the job. And that, that comes from, like, my unique perspective, my unique point of view, the experiences I've had in the past. Like, my various influences. Um, and I think it's trying to, like, figure out the right level for it so that you're not, you're, you're not pushing against an immovable force. Um, you know, it's a- it's almost like if you're playing Jenga and you're sort of trying to feel around to find like, okay, well where are the pieces that can move? And when you know how somebody else thinks, A, like you can find that there are immovable forces. Those are not the battles worth fighting. But there are also areas where maybe they don't know as much, and there's also areas where maybe, like, they're actually kind of scared 'cause they don't know as much. And maybe that's an area where you have an interesting point of view. And so you can step into that role and be tremendously valuable and, and be tremendously influential. But you can only do that if you have a good, like, uh, frame for kind of what you're, what the, 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 y- it is u- itself 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? Uh, and there's millions of different places that, that you can, you can put yourself. Um, and so I think it's just, like, kind of constantly feeling out for, like, where are the places that I'm really spiky? Where are the things that I think I do really well? Uh, where are the gaps? And again, you can only, you can only find those if you're engaging in really good faith and engaging earnestly in, in, like, really understanding how other people think.

   4. LRLenny Rachitsky55:19

      There's two really interesting thoughts that I have as you're talking that I think will even further crystallize what you're saying. One is that you're just saying this is the way the world works. It makes me think about Jeffrey Pfeffer. He was a guest on this podcast. He teaches this class at Stanford Business School about how to, how to gain power in the world, so like, the rules of power. And, uh, he talks about, you know, it's like, it's... 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, would be." And what you're describing is the way a company works is the CEO is in charge there (laughs) and your job is to, you know... they're the boss. And the sooner you understand their vision trumps your vision, the easier everything gets. Like, you're not there to tell the CEO, "Here's what we should be building," right? Their job is to own the vision of the business and the company.

   5. HGHilary Gridley56:18

      Yeah, I think that's true. And if you don't... if you disagree with it, like, you probably shouldn't be working at that company.

   6. LRLenny Rachitsky56:22

      Yeah. The other piece is th- it's just the vision. Like, here's the vision of the future of where we are heading. If we win, here's what will be true and the world will look like. 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, the director of products, all those sorts of folks working together.

   7. HGHilary Gridley56:40

      And, uh, and everyone at that level.

   8. LRLenny Rachitsky56:42

      Everyone at the company.

   9. HGHilary Gridley56:43

      And I think that what, what, 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 execution-based, but in, 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 gonna look like, uh, 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 does that mean for our product? Like, what does that mean for, uh... If, if it has to be true that, like, you know, take Whoop, for example. If, uh, if there's a vision of the future where you have all of your health data in one place and we're able to detect health issues before you even know you have them, and we're able to do really hyper-personalized coaching, uh, to help you understand, like, how your behaviors today are impacting how healthy you're gonna be in, in decades. Uh, what does that mean for what Whoop needs to be today? And what does that mean for how it needs to evolve in the next couple of years in order to both make that a reality, but also, like, win in that world? Um, and I do think that's exactly where the, like, the people in the rank and file can be tremendously influential. It's that level of, like, "I'm gonna fight with you about how the world is gonna work in five years," where I think you're, you're just fighting a losing battle.

   10. LRLenny Rachitsky58:13

       And if you don't like the vision, you could leave, right? It's like... Or change, try to change it. Like, those are the two options.

   11. HGHilary Gridley58:18

       And I think to your, to your point about pushing back, 'cause you asked about this, like, I, again, I, I never want it to sound like I'm just, like, defeatist, like, just accept it. Like, I'm a very opinionated person. Uh, like, I go to the mat for things that I think are true. And so I've, I've, 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 qual and the quant and moving it together. Um, but you have to be able to advocate for what you think is true in the most compelling way possible, and you have an obligation to do it. And if you have done it and you've done it well and it didn't work, that's when it's time to say, "Well, maybe there's something here that, you know, that I wasn't seeing previously." Um, and that's where I think, you know, it's, it's time to have some humility around it. But there's... You know, there's... It's a, it's a journey. You don't, you don't start from, like, "Well, I got, I got nothing to say here." Um, so I think it's, you know, knowing where you are in that journey is important, too.

   12. LRLenny Rachitsky59:18

       This reminds me. There's a PM leader at Airbnb who ended up leading a new initiative, and they ended up doing a bunch of stupid stuff. And he's like, "I just... I'm realizing that it's me that needs to be pushing back on stuff now that I'm in charge of this product team. Uh, I'm the person that needs to convince the CEO this is a bad idea, and I, I, I'm just realizing that after doing a bunch of stuff that was stupid."

   13. HGHilary Gridley59:43

       And you do. Like, you will see bad ideas, and you do have an obligation to try to convince them that it's a bad idea. And you're gonna be right sometimes, and you're not gonna be right every time. And I think that, like, that's why it's so hard to talk about these things in absolutes, because, like, sometimes you're right and sometimes you're not right. And it is important to get really good at knowing the difference and knowing, uh, where you go from there.

   14. LRLenny Rachitsky1:00:03

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10. 1:01:02 – 1:11:14

    Building effective habits

    1. LRLenny Rachitsky1:01:03

       wanna move on to another skill you're really good at. But first of all, something I noted that I wanted to touch on real quick. You mentioned that Whoop now does VO2 max, and I'm not, and this is not a promotion for Whoop, but that's so cool. That's like a huge thing to track. That, this is like the thing that Peter T. and all these guys are always saying this is the thing you want to track to understand your health and progress is your VO2 max. It's like your blood oxygen level. I don't even know exactly what it is, but, uh, but that's cool that new Whoop lets you do that.

    2. HGHilary Gridley1:01:28

       There's so much cool stuff we're doing in Whoop right now. I'm like, I don't know if I wanna get into it all right now, but I can.

    3. LRLenny Rachitsky1:01:33

       We'll, we'll get back to it. We'll get back to it.

    4. HGHilary Gridley1:01:34

       All right, let's get back to it.

    5. LRLenny Rachitsky1:01:35

       (laughs) Okay, cool. Yeah, um, okay. So another habit/skill that you are really good at that I've heard from folks is, and you've mentioned this a couple times, is just building habits, helping your team build good habits, and coming back to the CBT stuff, just like behavior loops and things like that. Talk about just what that is, why that's important, what you help your team learn there.

    6. HGHilary Gridley1:01:58

       Yeah. I'm kind of obsessed with habit formation and reward loops and behavior change and all of these things. And, um, when I think about trying to change behavior on your team or just trying to, like, 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, like, more of like an education model where it's like, you know, you teach the thing, you assess the thing, and then you, there's like some accountability around the thing. And, um, I think if you, if you think about it more in the context of behavioral psychology, it actually works a lot better. And so I'll give you an example, um, I've, like many leaders have been trying to, uh, think about how to drive AI adoption and AI upscaling on my team, and what that can look like. And, uh, when I talk to people about this outside of the company, I'm always surprised 'cause they're like, "Well, how, you know, how do you measure it and how do you enforce it?" And, uh, I don't, I don't really think about any of that stuff. Like, I'm thinking about like how am I creating habits around using this? And for me there's a couple things there. So it's, uh, consistency. Um, how are you getting someone doing something every single day? And to do that, like, it has to start small. It has to start super easy. You have to give them things that take no more than a minute or two to do. Um, and I actually, I have like a 30 days of GPT I call it, of like a list of 30 things to do, one every single day, that I don't know anyone who has gone through this and, like, not come out the other side feeling 100 times more confident in their skills and actually using it every day as a habit. Um, because it's built, like, as a habit formation tool and not an education tool. Um, and it-

    7. LRLenny Rachitsky1:03:41

       And this is using a specific GPT build, or building their own GPT? Or what's the habit there?

    8. HGHilary Gridley1:03:44

       Uh, the habit is using ChatGPT or Claude or any of these-

    9. LRLenny Rachitsky1:03:48

       Got it. Oh, oh okay, got it. Got it, got it.

    10. HGHilary Gridley1:03:49

        ... uh, these models, all of 'em, tools to get their work done-

    11. LRLenny Rachitsky1:03:51

        Yeah.

    12. HGHilary Gridley1:03:51

        ... um, in just sort of like a kind of generic get work done way.

    13. LRLenny Rachitsky1:03:54

        Mm-hmm.

    14. HGHilary Gridley1:03:55

        Um, and so I have this little tool. If you sign up for my newsletter, I'll send it to you. Um-

    15. LRLenny Rachitsky1:04:01

        Uh, what's the URL to the newsletter while you, as you mention that?

    16. HGHilary Gridley1:04:03

        Oh, thanks for asking.

    17. LRLenny Rachitsky1:04:04

        (laughs)

    18. HGHilary Gridley1:04:04

        It is hills.substack.com, H-I-L-S dot substack.com.

    19. LRLenny Rachitsky1:04:08

        Sweet.

    20. HGHilary Gridley1:04:09

        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. Uh, reducing friction. I think a mistake a lot of people make when they start thinking about how to drive adoption is they're like, "Oh, we have to show people how to do their work with these tools." But I'm like, well, work is hard, and if you are on a deadline for something, you've gotta get something done, the last thing that you ever want is more friction associated with getting it done. Like, it is so annoying when you're trying to get a thing done and, like, your tools are being changed on you and you don't know how the thing works and, like, you know, the hot keys are all different or whatever. Um, and so I actually think, like, using it in, uh, like, situations that have nothing to do with your work, um, are way easier because you're removing all of that friction of like, "Oh, wait, I gotta go think about, all right, what's the project that I'm working on? Oh, I put this into ChatGPT and I, like, didn't really get a good answer and now I'm frustrated 'cause this thing's taking longer than I need it to take," or whatever. Um, and so, you know, I start with things that are just like fun, simple use cases, uh, like, you know, it might be coming up with times to take a vacation or places to go on vacation, or it might be like uploading your calendar into ChatGPT 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 gonna make it like an unpleasant experience. So consistency, reduce friction, and then most importantly, designing reward loops. And this is something that when I'm talking to people about designing for behavior change, the number one thing I always tell them is, "You are not thinking enough about the reward loop." And the reward loop needs to be powerful, it needs to be immediate, and it needs to be emotional so that when this person does the thing that you want them to do, they feel like a million bucks. And so when I think about any kind of habit I'm trying to, to build on my team, that's something that I'm, I'm always thinking about is like, how can I make sure that when a person does this, they feel really great? And part of why I like custom GPTs as a tool for helping people learn to use LLMs, 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, uh, document, and then they can get a specific output, like feedback on that document, um, or, you know, maybe something more fun than feedback, uh, an, an improved written version of that document, they get the, like, the joy of like, "Ooh, this helped 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 and I'm frustrated." And so I'm ju- 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, that they, they do it naturally.

    21. LRLenny Rachitsky1:07:15

        I'm go- I wrote down notes as you were talking. So, hmm, kind of the four parts of habits, and I wanna, I'm gonna 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 consis- the three things you wanna focus on, consistency, friction, and reward loop. And within reward loop, you want it to be powerful, immediate and emotional. What is an example of this?

    22. HGHilary Gridley1:07:40

        Yeah, I can give some actually examples of, like, how we do this in product, if that would be interesting?

    23. LRLenny Rachitsky1:07:45

        Absolutely.

    24. HGHilary Gridley1:07:45

        Um, 'cause I think this is something Whoop is really good at. So I think one of the most interesting kind of anti-reward loops on Whoop is around alcohol. Um, Whoop has this recovery system. Uh, you get a recovery score every morning. It's red, yellow or 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 dr- anytime you drink, you get a red recovery. And it's so interesting because it's not like people who were drinking weren't getting hangovers before, or like, they weren't like... They, 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, "Ooh," 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, uh, y- "I- I've been, you know, I've had problems with my drinking for years and 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, 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 you can see, "Oh, that was the red day, that was the day that I, I did this thing." Um, and it's something that we've actually been trying to, uh, you know, find ways to do this in a longer term way because when you have these short reward loops, it, it's easier where it's like, "I did a thing and then 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 Healthspan that, uh, 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, uh, we call it the Amoeba. Um, it has your Whoop age in 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. Uh, and you can kind of see it all broken down how you sleep, your VO₂ max, the consistency of your sleep, uh, how much time you're spending in different heart rate zones, how much time you're spending strength training, things like that. Um, 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, the short term reward loop of those o- often feels pretty bad because change is hard and it feels bad before it feels good and trying to, like, build that reward loop that is, is more rewarding for people to see those numbers change and to see those colors change, um, so that they're actually able to make those changes and see that progress and feel really good about it.

    25. LRLenny Rachitsky1:10:59

        I love that you're using all these, uh, habit building tactics that folks have been using historically to get you to check your Instagram likes and your Facebook posts, uh, for actual good, for helping people live longer and happier. Uh, that makes me very happy.

11. 1:11:14 – 1:14:28

    Promoting team well-being

    1. LRLenny Rachitsky1:11:14

       Is there an example of doing this sort of thing with your team of helping them build... And you talk about AI, like learning to use, you know, Claude, ChatGPT?

Episode duration: 1:54:39