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

“Honestly, hyperleveraging myself with AI has been a big part of how I find time to do any of this stuff. And so I share a bunch about how I do that, how I use AI as a manager, building on a lot of the stuff that I shared on Claire's podcast as well, on how I AI. So you can find me on Maven there. We've got a couple cohorts coming up. And then, yeah, I encourage everyone to try out whoop. You can get a free month on me at join.com join.woop.com slash hilary. That's Hilary with 1L. And you can post at me or tweet at me on X and let me know what you think of it. And I would love everyone's feedback because we're really excited about it.”
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
“Great. Thank you. So, as I mentioned, I have a newsletter. It's hills.substack.com. That's H-I-L-S.substack.com. I'm also teaching a Maven class on being a supermanager with AI. So if you were listening to all this and you were like, oh, Hilary, that sounds so great, but I don't have time for any of that. How do you have time for all that?”
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
“As a product person, I always feel like I'm like living between these two, like the obsession and the responsibility. Like I just, I want to go so deep on this and I want to spend as much time as I possibly can just like sorting every little piece out. But like we live in a society. We exist in a business. I am trying to create value for shareholders and trying to like bring these two things together. I feel like A has been like the kind of defining struggle of my career. I think of many people's careers is like how you have something that you feel like you can really obsess over and have that flow over. Or have that flow when you're working on. But then like it's got to kind of like work in this broader system as well. And I think that that's sort of been like the thing that I think of as the guiding post for like what I want to do with my career and with my life.”
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
“There's a poem by Derek Walcott about it's called Sea Grapes, and it's about Odysseus. And he talks about Odysseus being driven by the ancient war between obsession and responsibility. And I read that line when I was like 18 years old, and it has always stuck with me. And I sort of mentioned earlier, I think about these like dualities that drive us. And I 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
“And I was like, that is so profound. Like that is what life is all about. It's just like, if it didn't have the parts that sucked, the cool parts wouldn't be as cool. And we're always chasing the cool parts. We want it all to be the cool parts, but it can't. So, thank 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
“I've obviously one that's been top of mind for me recently because I was talking about the highbrow fiction. I also will have to go lowbrow. I saw this clip of Beavis and Butthead online recently where they were watching music video for creep by Radiohead. And it starts off really slow. And one of them, I think maybe Butthead is like, oh, this sucks. And then the chorus comes and it starts getting like all hyped and they're like, they're like, oh, this rocks, this rocks. And then I'm not going to do my Deepson by Head Impression. So then it gets back to the slope art. And they're like, oh, wait, this stuff's again. And then Butthead is like, why don't they just play the cool part the entire time? And Beavis is like, because if they didn't have the part of the song that sucked, the cool part wouldn't be as cool.”
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 love my SWIFT. It's like a program that you can hook up a smart trainer to, like for an indoor cycling situation. And you kind of bike around like you're in Mario Kart and you're sort of in these virtual worlds biking with other people. I think for very serious cyclists, I am not a very serious cyclist. For me, it's been amazing as somebody who actually really like struggles to find time to exercise. They have sphere reward loops. They have one of the most amazing reward loops, which is you're biking along and you get into this track and a ghost of your previous self breaks out from you and starts racing alongside you at like your personal best for that track. And you have to beat your personal self or you have to beat this ghost version of yourself. And like nothing has ever motivated me more in my life than like past Hillary being like, I'm coming for you. And I'm like, I don't get that competitive with other people, but like past.”
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 have no, I feel like 10 different things. And I'm like, I have no words to any of the things that I'm feeling right now It's weird. It's weird stuff, but I'm enjoying 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
“The man is a freaky genius. Just when I thought that I had a good sense of all the human emotions that exist out there, like I watch this show and I feel things that I'm 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
“Now I really have to read. I was like kind of waiver. I was like, is this really what I'm going to want to read when I'm sitting by the pool? But I've come in.”
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. And it's like you got to be both, right? Again, fiction. I love dualities. There's a lot of dualities in fiction, a lot of like warring forces within people that is so driving for people, but can also be the source of so much anguish. I think it is important to live in both. I'm going to break down this problem. I'm going to structure it. I'm going to get out, but also like I'm going to sit here and I'm going to accept that there is no right answer and there is no perfect answer. And that's life. So, you know, you don't learn that to the extent that you learn that from a book at all, which maybe you don't, but I think you can learn it in 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
“Providing structure to ambiguous things and finding the way forward. And like to succeed at the job, you have to be able to do that. But I also think to succeed as a human in the job, you have to be able to sit in the mess and sit in the ambiguity. John Keith, the poet, talks about this concept of negative capability, which is the ability to remain in uncertainties, mysteries, doubts without any irritable reaching after fact and reason. And I love that.”
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. Okay, I'm going to go here. You know what I'm going to say? I'm like, I'm going to go full fiction on this. I'm going to say if you're going to read a book, like don't bother reading a business book. Even the business books I love the most that like shaped how I think I'm like, I kind of got the gist of them partway through. But fiction, I'm like, everybody should read East of Eden by John Steinbeck and everybody should read The Some Also Rises by Ernest Hemingway. Which is like my comfort book. I think what I love about fiction is it just It teaches you how to sit inside tension, right? I think so much of work.”
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
“Boney, you can't call something a lightning round and then ask me about books. That's like we could go for a whole other podcast”
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 Say one more thing, which is we also have opened a waitlist for advanced labs, and so pretty soon you're going to be able to have comprehensive lab work in the app. And I think we talk about the future of health of having control of all of your health data in one place and then being able to not just sort of find the signal in it and sort of understand how your sleep is impacting your metabolic health or things like that. But again, get really actionable coaching on actions that you can take to feel better and be a healthiest. And yeah, just pushing the limits of all the data that we're pulling into the global ecosystem. So really excited about that 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
“14 balery's life is insane. Like, I'm going on vacation tomorrow. And I'm like, I don't even need to bring a charger. Like, this is fantastic.”
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 HRV urrest and heart rate, things like that, that's your heart rate variability in your resting heart rate. Fluctuates throughout different times of your cycle. And even in the times leading up to that, like I headed not straightforward pregnancy journey and having these tools to really understand what was going on in my body was tremendously helpful and tremendously like empowering for me and honestly really has changed my life. I'm really excited about that. We have a lot of great new heart health features. We have a heart health screener with blood pressure insights and ECG. That's really cool. We got a lot of great stuff cooking. So even if you tried web in the past and thought it wasn't for you, I think the new experience is a real upgrade and it's something that I'm deeply proud of having worked on and really excited to have out in the world.”
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 I actually, part of how I found out I was pregnant was in seeing my whoop day. What? What? Which is remarkable. And the way that we have this cycle tracking now, you can see the way that your 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
“And I think that, as I mentioned earlier, I think it's really rewarding. We've also have a lot of personalized coaching to our AI in terms of actions that you can take to improve your Woop page, to improve your sleep, to feel better. And it's all part of our broader aim to make health more actionable and accessible. I think one thing I'm really excited about is we have a bunch of new women's health features. So we have hormonal insights with improved menstrual cycle tracking. I'm actually pregnant and I know.”
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
“We've really built something that can tell everyone be healthier and live better. I think we're, I would say we're no longer just for elite athletes. Like we're really now like a health and performance companion for anybody who wants to feel their best. For the first time in our company's history, we've updated our mission. So we're now saying that Woof exists to unlock human performance and health span. And health span, I think, is I mentioned earlier the speech I'm really excited about. because I do think it is kind of the most powerful version of like a longevity type feature I have seen because it is so focused on your behaviors and your habits today and we built it to be super super actionable so rather than just like giving you a score that you're kind of like okay that's nice if you start sleeping even like 20 minutes more 30 minutes more tonight like you're going to see how that changes your pace of aging you're going to see how that changes your”
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 really excited you got it. I know you tried it before. That's right. That's right. People who have tried who in the past maybe felt like it was very focused on like elite athletes. And that is exactly what I felt. And I think what we've done with our new experience 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
“I didn't want to admit this. There is a point at which it makes more sense for the company. Like if it is taking too long to develop something and there is a solution out there that works, like it is the right decision to acquire that. And I mean, I've worked at Dropbox for a while. I saw this happen all the time where we would acquire products that other teams internally have been working on. And it's just like, it's kind of heartbreaking when it happens. But I think there's like an urgency that that has instilled in me. that I think is actually really good and healthy, especially again, like working in this era where there is kind of this AI arms race and everyone's trying to move really quickly of like, yeah, there's always a shot clock. And you might not be aware of it, but it's there. And you got to, you got to build your heart out and you don't ship and you got to get things out because at any time like that clock might run out.”
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 mean, I think the one that probably looms largest in my mind is I mentioned this depression therapeutic that I spent about a year working on. And ultimately, the company ended up acquiring Merging the two of them, and a lot of the stuff that we had initially built that I have really loved about this product we were working on didn't really ever end up seeing the light of day beyond the kind of testing that we had done around it. And it was heartbreaking because like I still, I wish this product existed. Like I look at it and I'm like, this was a great product. And we put so much heart and soul into it. And I think the lesson that I learned from that is I think there's always a shot clock, right? When you're working, especially on a zero to one product, I think it can be very easy to feel like you have the luxury of time of just like, you know, we got it. We got to take the time to figure this out and get it right. And that's what's most important. But the sort of build versus buy question is always live and it's always fair. And whether you want to admit it, if you're the one working on it and you probably don't,”
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
“Great question, hypothetically, you know, I told you that I take all these notes on here's what this person said and here's how I interpret it. And LLMs are really good at pattern matching and sort of spotting the like, you could feed all of those in and just say, you know, come up with the like 10 criteria that this person is most likely to use to assess a possible recommendation or path forward or give me like the top 10 ways that this person is likely to pick apart an argument or object to something and you're going to get a good answer.”
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 will admit that I have tried this. And I think it's a great idea. I think it does help. I have not gotten to a point where I'm comfortable sharing it with other people, nor have I told anyone that I have tried to do this for them, but I've certainly done it for myself. And I think it would be helpful because you could say things like you could upload or whatever and be like, what are the free questions that this person's going to ask me about it? And then you could be prepared for the questions that that person's going to ask you. And that's great”
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, and to the point of like when you start talking to people and you start trying to build this mental model of how they think, like that's exactly what you learn, right, is, well, I can see how this person kind of, you know, worked at this company at this time. And I can see how this person had this kind of relationship with this other person. And like all of these things shape the way that we approach problems and the way that we try to, you know, just move through the world. And it is like it is understanding those types of things that allow you to understand how a person thinks.”
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
“Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive. And, you know, I think it's right. Like, as I said, it is so often this feeling like there is not a clear right answer and not even necessarily a good answer. And everyone is looking to you for clarity and everyone is looking to you to make the right decisions. everyone sees the errors or at least like everyone can spot the flaws in whatever decision you make or whatever recommendation you make and you know you as i said like every path forward has flaws that can be poked in it and so understanding that like the existence of potential ways to be criticized about something does not does not warrant criticism in a way that like can i think often result in a lot of negative self-talk for people”
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, I was terrified Yeah. Big time terabyte. And then, I mean, this is also like what I was saying about why it's so important to like be regimented about having these things outside of work that allow you to continue to thrive even in the face of just like utter feelings of failure, of like, I am not doing a good job. This is not going well. I don't know what I'm doing. You know, I'm always at that time. Kelman actually gave me some great advice that was that this is maybe kind of scary advice. When I asked him when his advice for me at the time was and he said,”
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
“That's, I mean, that's what it is. Like, I feel like I've had so many of those times where I don't know when I was growing up, I was just so, I felt so confident in like how I felt about everything. And then you get out there and you're just like, oh, I was missing some things. And after a while, you're kind of like, okay, maybe I should approach these situations a little differently with the with the possibility that maybe I'm missing something.”
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
“Definitely trial by fire, but it made me understand so many things that seemed like they didn't make sense to me before when I was just like in the rank and file of like a big tech company earlier in my career. You get in the room and you talk to these people and you're like, oh, this like this actually makes sense. Like I understand why this person has come to these conclusions. And some of it's like understanding the pressure they're under. Some of it's understanding, again, like the way they view the world. But I think that was, you know, to get to our earlier point around like the humility of understanding that like maybe this person is right about something that I don't see and maybe I can start by if I start by giving them the benefit of the doubt it is not only like a nice thing to do but it is also like it will get me it will help me understand why they're doing the things that they are and I think I would have been so much less frustrated earlier in my career if I understood that instead of 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
“I mean, I think it was at my former company at Big Health when my former boss left the company and I started reporting into the CEO. And again, I think it was my first time just having like up close, like working with a CEO so closely. And it just 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
“Here's the scope that's being proposed. If you had a t shirt size this, like which one would you choose and why? And you can say, oh, you know, this sounds small or whatever. And it'll say, oh, actually, like, these types of integrations tend to be complex for these reasons. So it's probably going to end up being more like a large. And it doesn't have enough context to like really inform you in the way that your tech stag at your company is, although I guess you could build it and give it that information and then it would. That would be cool. You should do that. But again, it's like you do that like as a PM, you might get a chance to do that, I don't know, a couple times a week, maybe, maybe less often than that. And when you have this little tool, you can do it infinity times. You can do it, you know, you can spend an afternoon doing it. And so again, like both the speed of those loops and the like, the number of those loops that you're able to get is just like radically different.”
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 that's, you know, we were talking about a similar one with understanding engineering benchmarks. I don't have an engineering background. So this was really hard for me when I was moving into product is just getting an instinct for what types of things tend to be easier or harder for engineering teams. And so we can have one similar that's saying.”
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
“Make one that is like literally so specific to you and your life, but is like testing and sort of like training you on this broader skill set. And I think you can, you know, you can make things more fun that way, even in just like the school context in terms of doing that in a way that's just relevant to a person's interest, relevant to the things they care about. I think there's a ton of really interesting potential there too.”
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 have like a version of this that's very specific to whoop and working in consumer health, but you could do it for anything, or you can just do generic, you know, however you want to do it. And it's actually kind of fun because it gives you the scenario and it's like, you know, the sales team is telling you that we need to invest in feature A and the, I don't know, the engineering team is telling you that we only have time to do feature B. And the metrics are telling you that people who get this feature retain better. Like it just sort of gives you these little things and it's like, follow that logic, which is the logically best path from this. And it gives you a little multiple choice answer. You select one and then explain why you're right and wrong. And so I think that's just like another example of, you know, you can't create those like hyper personalized learnings where I can.”
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, so this came from, I was talking earlier about learning how to make a really strong logical argument or just like a strong argument for your point of view in general. And the sort of fundamental skill for that, in my view, is logical thinking, logical reasoning. And when I think about like the best way we have to test that today, at least like the best is maybe not the right word, but the standard way we have to test that. The LSAT, like the test that you take to get into law school, that is what that tests. And it sort of gives you these different scenarios. And we'll try to say like, you know, if A is true, then which of the following is true is not true, like sort of testing some of these different logical relationships. And so what I did was I made a GPT that I basically told it, like create LSAT style questions to test logical reasoning, but put them in this scenarios of things that a PM would encounter.”
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
“Task you're doing like you can be a you can be a film editor just like sitting there pouring over the film deciding like what to edit what to cut what to you know put into the trailer or whatever it is you're making that's an incredibly tedious job that takes forever and I think there's no reason we can't like make that way more efficient with AI in ways that make the learning like more fun And so I just, yeah, I think that that's sort of my hot take is Yes, it is like there is this threat of a lot of these jobs that are things that seem like you can just automate them away that might happen But like we absolutely still need to be investing in people's skills I just don't think we need to be investing in them historically in the way that we always have and I think in the future we'll find that those ways actually seem quite inefficient compared to what what's possible 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
“Try again, like it actually is really inefficient when you think about it. And the sort of learning applications around AI that I get really excited about are how do you shrink that loop? So in my podcast with Claire, I showed her how like I build these GPTs that kind of think like me. And the purpose of that is so that my team can get feedback that is at least 80% close to the feedback that I would be giving them. But instead of having to wait until I get to their message or until our one-on-one, they can get that on demand as many times as they want forever. And I think there's a lot of things like this of like ways that things that require other people just naturally slow things down, require getting feedback from other people just naturally slow things down. We can build AI tools that in my view there's no reason why the amount of reps that you get at whatever”
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 the fear that I hear, at least, is if you're not getting those reps early in your career, like maybe it's not contributing so much value to the company at that moment, but it's how you learn to be great later on. And so there's a fear that in five, ten years, like we're just not going to have that class of people who have learned to do the jobs well and who have built judgment in that way. But what I think that misses is it assumes that You know, you go and you do this analyst job for two years and at the end of it you have a person who knows how to make models really well, knows how to do a few things really well. But like, why does that have to take two years? And why does that model of like you grind over this thing, you wait for feedback, eventually you get that feedback? Maybe that feedback's good. Maybe it's not. You go back.”
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 was sore. And if you had to get a link in there, like good luck to you. But oh my gosh, my ability to just like look at something written today and just. So, I think people see the way that there's a threat of companies not wanting to hire as much entry-level talent because it's like, oh, this is the kind of work that AI can do”
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
“Terms of my own judgment and my own taste and how I think about just making like very quick judgment calls now I just wouldn't have been able to do that if I didn't spend years learning like you know I used to do social media like the skill of having to condense something that I want to say into like 120 characters or whatever it used to be on old Twitter 240 I can't remember I forget 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
“Yeah, I think we are not being nearly creative enough when it comes to how to think about learning with AI. And I think, you know, you hear people worry about entry-level jobs. And when you think about an entry-level job, it is sort of inefficient by design because you have taken an analyst, sort of a classic entry-level role. They're doing grunt work. They're doing really tedious work, but they're getting a lot of reps in. because that's exactly how you learn the judgment to do higher level jobs well. And I hear this in creative fields too. I hear this like from every, I certainly feel this way. Like the work that I did in the beginning of my career, it didn't feel like it was all that important in terms of the impact it was having, but it did feel like it was transformative.”
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 that's why. Here's the thing. Here's the thing the reason I'm so regimented about this is because like. If I'm not, I will fall apart. Like there's this quote. I can't remember where I saw this, but I love it. It's like, you know, I have exercised the demons from my head, but they are outside and they are doing push-ups. Like the threat of the demons coming back is always there. And so I take this stuff really seriously because I know if I let myself start to slide into like I'm not doing the things I need to do to take care of myself. I'm going to have a bad time. The walls are going to start closing in around me. And I'm not like shy about that. And so to me, there's no point in torturing myself and like just working so, so, so, so, so, so, so hard and having no room for joy and having no room for creativity, even just from a practical standpoint. Like it's not, I'm not, I'm just not going to succeed.”
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
“In terms of being able to have creative breakthroughs of any kind, it's just so important to have active rest. It's so important to have heads downtime. Like this stuff is all very well documented. We know it all, but we just come up with excuses to like not give it to ourselves. I think it's kind of self-sabotaged at a certain point.”
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 it's so funny because so much of this stuff, it's like obvious when you apply it to an athletic context. And obviously, I talked about the like recovery score. This concept of like athletes need to recover is very obvious. Like no one, I think, would argue with that. If you're just pushing yourself at 100% of your physical capacity all the time, like not only are you going to burn out, but like you're literally going to suffer performance decline. You know, in the same way, like I think in the athletic world, there's so much more just acceptance of I didn't want to say limits, but just like. You have to take the time to do the things you need to be your best. And that's not just running into the wall all day. And I think we forget that at work, but I think, I mean, the analog is 100% there. I also think about this with.”
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
“Do you even know what those things are? Because I think a lot of people don't. And a lot of people, it's great. Like they're like, oh, I need to be getting X number of hours of exercise, X hours of sleep. Like I know I need to eat lunch right at 12 or else I turn into a pumpkin. And if it's somebody who like knows what all those things are and you're just there to kind of help them carve out time, that's one thing. But I think in a lot of times people don't even know. And then your kind of behavioral activation them where you're like, all right, well. Why don't you try some things and get back to me and like, let me know what seemed to work, what seemed to make a difference. But I do think so much of it is like a permission structure because people feel the pressure to be like, oh, I'm so busy. I'm so busy. I'm meetings all day. I can't decline these meetings. I can't not do these things. And so in many ways, I think just modeling it gives them the permission structure to start to take back their life.”
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 I think just like showing people that it's possible, like showing people that you can do these things. And I talk about them and I bring them to lessons. I have like a book club that I sometimes require at work. And then I say maybe I don't need to require this anymore. But like ways to just make it really visible, make sure people know that I'm doing it. And then ask them about it. And in my one-on-one checking in with people, I'm asking them like, what do you do for joy? Like, are you doing something every single day that's bringing you joy in your life? And if they say, no, I'm like, that's a problem. Like, what are we going to do about that?”
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, as I said, modeling it, like I try to always tell people, like, here's how I'm doing these things. Like I talk about them so it's really normalized because I think, I mean, a lot of PMs are like, oh my gosh, I'm so busy. I have no time in meetings all day. But like that's a little bit self-inflicted, I think. At some point, like you have to be the one responsible for getting yourself out of the weeds. And it's hard to do, but it's doable.”
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
“To the point of behavioral activation, like understanding what the things are that a person needs to be happy, to be their best self, to be a high functioning person. And that depends on their values. It depends on a lot of things about them. So, you know, for Emily, it's fitness, it's teaching, it's these things. For me, it's having my crafts that I do, my illustration, my writing, my reading, all of these sorts of things. I think that that's the first step is just as a leader, like understanding what those are for people on your team.”
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 funny. I'm glad to hear people think I'm going to do this because I'm like, I'm terrible at organizing events. My team's always like, oh, we should do like a fun event. I'm like, yeah, that's a great idea. And then I don't organize it. So I like the thing I do this in other ways. And I do think one of them is just like in modeling how to carve out space for things. And a couple things. I think there's the creativity, which for me is like probably more outside of work. And for me, it's creativity. But again, it's like a big part of.”
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