YouSaid · the spoken record

Hilary Gridley

lines on the record: 134
first: 2025-06-15
most recent: 2025-06-15
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Make them feel like a million bucks for doing something that in many cases they might think, oh, am I allowed to have this other job outside work? Like, is this okay? And so, yeah, you gotta, you gotta proactively build those reward loops.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Handelbar. She's a fitness instructor in her spare time. And so whenever we have like a long meeting, I'll be like, oh, Emily, why don't you 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. Like Emily's doing her thing and I'll be like, you know, everyone come check out Emily at Handlebar in Charlestown this Saturday, 10 a.m. And by the way, like you all out there in the podcast world should do that if you're in the Boston area. She's great. Shout out to Emily. But it's things like that. Like it's just finding these small ways to because people are already laughing. People are already smiling. We're doing the silly thing. Everyone's in a good mood. And I'm like, boom, perfect time to give someone a shout out.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly, but no, like people see that and people respond to it. I think 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. And it's something that like I'm always trying to model for my team and make it really visible the ways that I'm doing this and sort of like having my hobbies and my other various things. 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 stand till 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 try to do the opposite. Like I try to find ways that I really am impressed with my team and the way.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I didn't think a lot of it is just shound 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 a thing. And people respond to that. Like people will see, I mean, maybe it's because I work at Woop and we're all obsessed with reward loops. So we're all like loop.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Based on how your behaviors and your activities change every single day. And the colors change when you're doing better and when you're doing worse. And you can kind of see it all broken down how you sleep, your VO2 max, the consistency of your sleep, how much time you're spending in different heart rate zones, how much time you're spending strength training, things like that. And we found that, again, it's just this incredibly powerful reward loop because we're taking something that historically has been really, really hard, which is like when I make healthy changes today, not only do I not see the results of those for decades, but the short term reward loop of those often feels pretty bad because change is hard and it feels bad before it feels good and trying to 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“And then I think continuing to have that data where you can look back at your data and see 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 find ways to do this in a longer term way. Because when you have these short reward loops, it's easier where it's like, I did a thing and 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 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 20, 30, 40 years. And so we have something similar where we have this, we call it the amoeba. It has your whoop age in it. It's like it has colors and sort of kind of moves around. And that changes.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 manages to override like whatever was driving people to do it in the first place.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Because I think there's something Woop is really good at. So I think one of the most interesting kind of anti-reward loops on Woop is around alcohol. Woop has this recovery system. You get a recovery score every morning. You drink and you're on whoop, you will very quickly learn that if you anytime you drink, you get a red recovery. And it's so interesting because”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“without any of the despair of, oh, I'm not very good at prompting and this didn't really work and I'm frustrated. And so I just always think about that in general. Like if I'm trying to build any kind of habit on my team, it's less about like the accountability of like how I'm forcing this and more about like how I make it so rewarding for people to do it that they do it naturally.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Powerful, it needs to be immediate, and it needs to be emotional so that when this person does the thing that you want them to do, they feel like a million bucks. And so when I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about is like, how can I make sure that when a person does this, they feel really great. And part of why I like custom GPTs as a tool for helping people learn to use LLMs, and I talk about this on the podcast I did with Claire on how IAI 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 joy of like, oh, this helps me. This was cool.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Working on, oh, I put this into ChatGPT and I didn't really get a good answer, and now I'm frustrated because this thing's taking longer than I need it to take or whatever. And so, you know, I start with things that are just fun, simple use cases, like, you know, it might be coming up with times to take a vacation or a place to do 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 going to 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”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“For asking, it is hills.substack.com h-l-s.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 a mistake 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. 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 hotkeys are all different or whatever. And so I actually think like using it in 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?”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“And just sort of like a kind of generic get work done way. And so I have this little tool if you sign up for my newsletter, I'll send it to you.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“My creating habits around using this. And for me, there's a couple of things there. So it's consistency. How are you getting someone doing something every single day? And to do that, like it has to start small. It has to start super easy. You have to give them things that take no more than a minute or two to do. And I actually, I have like 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 a hundred times more confident in their skills and actually using it every day as a habit because it's built like as a habit formation tool and not an education tool this is”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I'm kind of obsessed with habit formation and reward loops and behavior change and 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 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 I think if you think about it more in the context of behavioral psychology, it actually works a lot better. And so I'll give you an example. I've, like many leaders, have been trying to think about how to drive AI adoption, AI upskilling on my team, and what that can look like. And when I talk to people about this outside of the company, I'm always surprised because they're like, well, how, you know, how do you measure it and how do you enforce it? And I don't really think about any of that stuff. I'm thinking about how.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“You will see that ideas, and you do have an obligation to try to convince them that it's a bad idea. And you're going to be right sometimes, and you're not going to be right every time. And I think that's why it's so hard to talk about these things in absolutes, because sometimes you're right and sometimes you're not right. And it is important to get really good at knowing the difference and knowing where you go from there.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And that's where I think it's time to have some humility around it. But this, you know, it's a journey. You don't start from like, well, I got nothing to say here. So I think it's, you know, knowing where you are on that journey is important too.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Think to your point about pushing back because you asked about this Again, I never wanted to sound like I'm just like defeat us, 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 teach my team like. You have to be really good at forming arguments and 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 the qual and the quant and moving it together.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's that level of like, I'm going to fight with you about how the world's going to work in five years where I think you're just fighting a losing battle.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a product? Like what does that mean for if it has to be true that take woop, for example, if there's a vision of the future where you have all of your health data in one place and we're able to detect health issues before you even know you have them and we're able to do really hyperpersonalized coaching to help you understand like how your behaviors today are impacting how healthy are going to be in decades? What does that mean for what Woop 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? And I do think that's exactly where the like the people in the rank and file can be tremendously influential.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“The vision is in many ways, I mean, in some ways it's execution based, but in many ways it's a vision of what the world is going to look like in five years, in 10 years. And so in some ways, I would say like your job is if you can understand that and you can understand, here's what this person thinks the world is going to look like, assuming all that is true.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Places that you can put yourself. And so I think it's just like kind of constantly feeling out for like where are the places that I'm really spiky? Where are the things that I think I do really well? Where are the gaps? And again, you can only find those if you're engaging in really good faith and engaging earnestly and like really understanding how other people think.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Know it's all, it's almost like if you're playing Jenga and you're sort of trying to feel around to find like, okay, well, where are the pieces that can move? And when you know how somebody else thinks, A, like you can find that there are immovable forces. Those are not the battles worth fighting. But there are also areas where maybe they don't know as much. And there's also areas where maybe like they're actually kind of scared because they don't 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 have been tremendously influential, but you can only do that if you have a good frame for kind of what the model is and where are the things where it's like, okay, we are operating on a person's insight here that is, it is itself extremely unique and extremely valuable. 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there's so many decisions all the way down, and there's so many micro places where you can zig where others would have zagged. And I think I personally, like a lot of where my fulfillment comes from is from feeling like if somebody else were in this job, it would be done differently and like something about the product is different because I was the one who worked on it because I was in the job. And that comes from like my unique perspective, my unique point of view, the experiences I've had in the past, like my various influences. And I think it's trying to like figure out the right level for it so that you're not pushing against an immovable force.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, like 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 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. It becomes extremely painful because you're just everyone's just fighting all the time. And so in some ways, it feels like you're kind of like if it sounds almost defeatist, like I'm always worried about the sounding like I'm just like, yeah, just do whatever the boss says. And that's not how I feel at all. Like, I think it's incredibly important to bring your skills and your talents and your perspective to the job you have and really your taste and your craft and all of these things. But I do think this idea of like understanding how to build.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, you are probably not the protagonist. And as much as it, you know, can feel kind of weird to say that, I genuinely think 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 going to fail because actually like what your job is to do is to understand what the CEO's vision is and like what they care about again, sort of how they think about things and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of product. And that was just such a like 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 could be the protagonist in your life. You can be the protagonist in the story of your family, but in the story of your work, like of a company.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's really interesting. My 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 shut that apart by Stripe for a ton of money. 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And all these other people have no unique, beautiful, perfect concise, just wrong opinions. And so I feel like that's been like a big area of growth for me, honestly, is like learning to approach people that way. It's not just like. This is a nice thing to do, but I think it genuinely makes me a happier person. And yeah, I think a lot of it comes from reading fiction.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's so easy to look at another 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 is the world of this person where the thing that they're saying makes sense? And I feel like in my life, honestly, like a lot of my frustration has come from being frustrated with other people. And so this is something that I've had to learn over time because when I come home from work and I'm just like, oh, this person said this and it didn't make any sense and this person's totally out to lunch and leadership doesn't know what's going on.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“I agree so much. I'm a proud former English major, and so I'm a huge proponent of reading fiction and reading in general. I feel like that's where so much of this comes from for me. It's just like a curiosity for in what world does this make sense for this person?”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Not what I'm talking about. If your goal is to understand and you are coming from help me understand how I'm wrong, help me understand what I'm getting wrong here and approach it with that sort of like curiosity and humility and make sure that you're like caring yourself and presenting yourself to this person in a way that shows that, that you're not coming in like hostile or forceful or something. Yeah, because there are absolutely circumstances where you're doing that and you're going to get bad intel because you're making the person uncomfortable. So they're going to lie to you. But that's like a I think a whole set of interpersonal skills that we probably don't have time to talk about today”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“You know, it's funny because I'm 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 in pure of heart. Like, you've got to go in. 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, here's what I think. Like you agree, you agree. Like, of course, alien.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Their judgment over time. So they're actually forcing themselves to make this assertion, and then they're kind of calibrating how close that was to like how I would think about it, which will get you much faster, much further than just asking open-ended questions and getting the answer. And then the second part of it is they don't become reliant on 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 want to help them, you answer the question, and then you find that they come to you with all their questions and you're kind of like, yeah, you got to solve some of these on your own. So again, I think like the magic questions to me, 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, 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“And so when I first started working in a regulated space, I would find this kind of frustrating and confusing because I would say, can you just like give me the rule so I can understand what's right and what's left of it? And they'd be like, oh, well, it depends, it depends, depends. And so I learned that if I 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, you know, what could I have done differently? I'll say like rephrase that as tell me what you think you could have done differently and then ask me if I agree. And when I do this, I think it has a few benefits. One, it helps them kind of calibrate.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 the most helpful way for kind of trying to understand a person's mental model is to just like put facts in front of them and see when they say no to and what they say yes to. And then if you can get them to explain great. And if they're good communicators, they often can. But if they're not, like, you don't have to let that stop you. And so, I mean, I'll do this even just as an example in a non-leadership context with if I'm working with 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 if we were to take this path, would that be okay? Would that not be okay? And sometimes that's not straightforward. Sometimes there's regulatory areas that are up to interpretation.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 on like the least wrong answer that's available to you. And so I think it is like, you know, the sort of reasonable people can disagree about this stuff at all of, you know, like this is what I think and this is how I'd approach it. I think this is what they think. And I think this is why they would approach it this way. And again, like the only chance we have of succeeding is not being torn apart on that. And so at the end of the day, like if it's not like a obviously terrible answer, and sometimes even if it is an obviously terrible answer, you're still more likely to succeed if you just sort of like sort of reorient yourself around a world where it's not a terrible answer and then just try to will that into existence.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Obviously, that's not going to set your team up for success or make anybody happy about it. But you do hear that. You do see that happening. And so I think what I try to do in those situations is separate out 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. 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. 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Where, like, it's still respectful. 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 a job. So we have to do it.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“First, I do try to go through the what if I'm wrong exercise. I think a lot of people just sort of like expect that if you ask somebody an open-ended question like, why are we doing this, you're going to get a straightforward answer. And oftentimes the answer is not straightforward for various reasons. Like maybe there's confidentiality reasons. Maybe there's just like, you know, somebody is acting on a hunch, but that hunch is informed by years or decades of reps of developing judgment. And like they're probably really on to something. And it's not just like this kind of arbitrary feeling. But whatever it is, like I really try to get to the bottom of, let me really make sure that I have done my best to understand this person's point of view. 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 relatively candid about that, but candid in a way.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Your team have the emotional maturity to exist and thrive in an organization is helping them think that way, like helping them understand you have a point of view. Your point of view is important. But on some level, you do kind of have to have respect for these other points of view and have the humility to think that like maybe they're onto something that you're not onto and it's amazing how much you can like learn and intuit without having to have all the Oftentimes you will find that X, Y, and Z is happening.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, Andrew, 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, 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 and agree with it. I might still, you know, think I'm right or whatever. But oftentimes it forcing myself to think that way forces me to think about how this other person thinks it. And if I do that enough, I will be like, oh, this makes sense. I think this makes sense if I think this makes sense if. And oh, maybe this other thing is true. And I think when I hear the people, the people who are like, I don't know what's going 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 help.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Those high impact but low cost ways that we can just find and sprinkle through the experience and really try to make that magical. So I'm connecting the dots for my team, right? I'm saying you weren't in all these meetings, but I saw it. 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 across our products going forward.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“Conscious of the fact that this product knows so much about me and is able to sort of sort out the signal from the noise on that in these really small and elegant ways. And so for something like that, I would get that feedback and design review or I'd hear that in a design review. And maybe one of my PMs would be in that design review. And so I bring that up to the team. And I hear things like that in a few different design reviews. So I bring those back to the team. I'm 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 AI at everything and we have to just throw like maximum scope at everything. I think the key is understanding on the matrix of cost and effort for impact. Like what are”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 VO2 max, which is a measure of your cardiovascular health, you can explain that to people with static content, or you can explain that to people by bringing their data into 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 feels like the future. This feels like I'm very...”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“A 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 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 We have this AI coach in the product, we have all this amazing data in the product, we're tracking every single one of your heartbeats and we're pulling all this other data.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, our CEO will is somebody who obsesses over pixels in a way that is 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 small excuses here and there for, oh, well, this 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 misconstrued. And I think a lot of people might think that he just wants like maximal scope on everything. And I think that is a misunderstanding of what he cares about. We often get feedback from him that's like, you know, this doesn't feel like the future and everything that we're building needs to feel like the future.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And over time, I think my team has like a pretty good sense of what people are saying and how to think about the thinking behind it and how this person thinks how this person thinks and how I think. And I think when you get an entire organization working that way where everyone's working from the same models of like how what the CEO thinks matters, what level of 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.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source
“A few ways. First, I'm in meetings with people, like important people at the company. So I'm constantly hearing the things that they're saying and paying attention to sort of a note behind the note. Why do I think they're saying this? What insight do they have that they're bringing to this conversation that might not be obvious? And I try to make an effort every week. I don't always do it, but I try to send my team just a quick rundown and slack of here are the most important conversations or the most interesting conversations I had this week. Here's what that person said verbatim. Again, I write a lot of notes, so I've got it. If you've got a transcriber, maybe that'll help you. Here's what I interpret that as.”
2025-06-15 · Lenny's Podcast · 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) · IDENTIFIED FROM THE TRANSCRIPT · source