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

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“You're going to be working from outdated information and you're not going to be able to think and respond to new things that happen. And so what is much more helpful than understanding what your CEO thinks is I think understanding how your CEO thinks. And that goes for all sorts of levels of the company. I want to understand how all the strategic leaders 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 have confidence that these people understand how I think or I don't have confidence that they understand how this email or whatever it is is going to be received by this important person. And so I try to teach that to my team. And the way that I do that 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
“When I think about artifact based communication, so reading a strategy document, for example, everyone at the company reads strategy document. Great, everyone is working from the same idea of what the strategy is, but then things change, right? Like, especially if you're working in a really dynamic space, new competitive threats emerge, new opportunities emerge all the time. This is especially true now with AI. Obviously, everyone is lighting their strategies on fire and trying to figure out the best way to sort of transform their organization. And so, if the way that you understand what's going on at the company is from reading a document that was written six months ago,”
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 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 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 often say like, oh, it's a process problem. It's not a process problem. It's not an approval process problem. I think it's a transparency and it's communication problem, like downward communication, outward communication. And what I mean by that 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
“Gravitate toward that. And I totally get it. I totally get it. And you get paid better. Like no real judgment from me. I just, I wish I saw more, but I wish that 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 and really, really hard spaces. And I see you and I appreciate it. Shout out 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
“Well, if you are really in it just for pure love of the game, like you just love product management, 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 barrier, I mean, there's I don't want to, I don't want to act like I think this is easy to be clear, but in the like the grand scheme of things like I wish that The people who have this pure love of product management and have this pure love of building things that you would see more of that applied to building for low income people building for social services things like that that really really need that kind of work And I think there's a level of prestige obviously associated with working in certain companies and you know you get less of that in other industries and so people would naturally”
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 this is my hot take. Like, you know, you hear people talking about craft and taste and product management. It's all very wonderful. And I'm like totally onboard. Like I love it. I'm a sucker for that kind of thing. But 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
“The conversation moved on, whatever it is. And so so much of that skill, it's like a communication skill at its core. It's just how to express yourself verbally, but so much of the blocker of that is, I think, fear, fear of saying Granteng, fear of looking stupid, fear of just the discomfort of everyone in a room turning and looking at you, right? As you're kind of like trying to formulate a half-baked thought. And so if you can help people be less afraid of that, That's like 90% of the challenge of actually improving some of these skills. And so I think when you give people the skills of taking a punch, you are helping them feel less afraid of getting the punch in the first place. And that's why I think it's so important.”
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
“Than they would have been if there were fewer people in that meeting. And so one key piece of a meeting is like you usually have a problem you're trying to solve collectively as a group. And it's really hard to do that if people are being overly cautious about what they're saying because there's like too many people in there. So when I tell people this, I'm like, you know, it's really important that you earn your place in this meeting. And let's work on like how to do that. And the core piece of that is like you've got to say stuff that's valuable. And people always come up with all these excuses for why they can't do it. And one thing I've learned is that I think people are really good at coming up with very rational sounding reasons to not do things that just make them uncomfortable. But in their head, they're like, oh no, you know, like I'm too junior. Like nobody wants to hear what I have to say or everyone was already thinking it or, you know, I like to process things internally. And by the time I say.”
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, I think it's a big deal on two levels. One, it's a big deal because it can help you in a crisis or a minor crisis. But I actually think it's a bigger deal because I see so many people who don't put themselves out there because they're afraid of how it's going to go. And so I think of the like classic example of I'm often trying to encourage people to like speak up in meetings more to practice the skill of how you move a conversation forward in a way that contributes value, both because doing so, I think, is important because nobody wants to be in bad meetings, but also because it will help with your career, right? Like this is how you kind of get on people's radar as somebody who's like, oh, that person's got great ideas, thinks about things the right way, whatever it is. I think it's just, it's one of these things that I talk to people about it and they are interested in coming to the meeting and hearing about these big decisions that are getting made, but they just kind of want to sit there and observe. And I'm like, first of all, like every additional person in a meeting has a cost because every additional person in a meeting makes the people in that meeting less candid.”
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
“Many cases can be like the driver of burnout and the driver of I can't really handle the stress of this job anymore. And so I think of the take a punch concept is more just applied to that sort of specific problem of I'm struggling at work and I'm struggling largely because of my perceptions of other people and I want to feel more agency in that situation.”
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, that, yes, that's the taking the punch concept. The behavioral activation could be anything, right? 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 observation just conceptually is how are you taking action to reverse 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 so much of their self-identity is wrapped up in having the answers, being competent, getting things done. And so many of them have been people who have been really good at that for most of their careers, which is how they got into these jobs in the first place. I think that can be an extremely stressful thing for them.”
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 how easy it is to get stuck in some of these downward spirals that you really need to actively push back on. And as a manager, I want to help them do that. I want to help them, A, see that, like see the ways they are in some ways sabotaging themselves, getting in their own ways with whatever is going on in their head. And then I want to help them 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.”
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 a lot of the work is in how you help people identify specific actions that they can take that will reliably lift their mood. And I mean, I have a list of myself. I've had a list on my phone of my behavioral activations. And it's things that I know I can do if I start feeling like the walls are closing around me. If I feel myself kind of getting sucked into very low mood or negative thinking or whatever it is, and 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, which I understand very well. And so that understanding that concept, which is that, you know, at its core, a therapeutic concept used in cognitive behavioral therapy, but it kind of changed how I see the entire world and how I see, especially as a manager, the ways that people in my team think and behave.”
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
“Wait until I feel better, and then I will start doing the things that are good for me, right? I don't feel like responding to this text, though I'm just not going to do it, but I'll respond when I feel better. I don't feel like working out, so I'm not going to do it, but I'll do it when I feel better. And the truth is that doesn't go away on its own, especially if you have depression. And it's something that, again, the idea of behavioral activation is You have to identify these actions that you can take that will reverse that negative spiral and will improve your mood. And so the sort of like misconception is I'll feel better and then I'll act. And the thing that therapists try to teach people, they're working with them in therapy is I will act and then I will feel better. But acting is hard if you are in the frozen depression. And so easier said than done.”
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, absolutely. 100%. And I think it is more than just my career, but just my general mental health in my life. A lot of where this comes from is a concept in cognitive behavioral therapy called behavioral activation. And in my former job, I was working for a company called Big Health. And we make digital therapeutics. So those are mobile apps that have been clinically validated to treat behavioral conditions like insomnia, depression, anxiety. And I was working on a new depression therapeutic. And so went very deep on this and was working with a really wonderful clinical team full of clinical psychologists who helped me understand the techniques that therapists use when they are working with people who have depression. And so much of depression is characterized by these negative thinking patterns and this like this feeling that I feel bad and I just need”
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 fine. I don't want to say you should feel bad for doing that. Like, let yourself have the pity party. Let yourself feel those things. But then, but then you got to move on as quickly as possible because those feelings, they actually do tend to spiral and get worse if you're not actively working against them.”
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, I'm not interested in litigating the things that happened already when we can move forward. And I'm certainly not interested in litigating what another person thinks about a thing that happened. I just, I feel like I've spent so much time talking to people in meetings, whatever it is, where it's just this kind of like ruminating on something that has already happened. You know, it's very anxious thinking pattern, I think. And people can just get stuck in it. And so, you know, let them let them do it. Like, I often think about it's like when you get bad feedback, right? Or critical feedback. And you kind of naturally have this reaction of, oh, well, you know, that's not fair because they don't understand. I actually have numbers I have to deliver on or like I only had 10 minutes to do this. So like, of course it wasn't perfect. Like you naturally come up with these reasons why you're actually not wrong.”
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 is some value, I think, in having a little bit of a chip on your shoulder. I think that's definitely when you see that, people who are really successful, they do have a little bit of like, I'm going to prove them wrong. And so I don't want to say that you shouldn't think about it at all or you shouldn't care. Of course, it's natural to care, and of course it's fine to care. But I do want to just sort of help my team build this habit of doing the things that you know to be right and having conviction in that. you know, being open to learning along the way and sort of calibrating as you go, but not becoming overly concerned with your fears of what other people are going to think of you because I think, especially for otherwise really thoughtful, you know, really kind of the people who are kind of hard on themselves, I think that just holds them back from being the person that they can 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
“Exactly. This comes up all the time. Like, there will be narratives that emerge. Some are good, some are bad about you and your career. And I think especially when people get to a place where they're putting themselves out there more, right? They're talking in more presentations. They're talking in more meetings. It's very natural for them to become concerned with the perception of themselves. And it is scary because it feels like something, as I said, you don't have control over. And so exactly if instead of focusing people around, what do these people think of me? You focus them around, well, what are you going to do next to demonstrate that you are the person that you know yourself to be? I think that can just be incredibly effective at giving people more of a sense of agency.”
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's something that you could do to show them that's not true? Because you know it's not true. And I think giving people that power to focus on the next step they can take and the action that they can take that helps them feel more secure in their identity and who they are because their action demonstrates that. It just gets them out of that negative thinking and it gets them through that trough of despair that comes after you feel like you took a punch.”
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 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 think there's evidence for that. Is there evidence for that? And even if there is, it doesn't really matter.”
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 I very quickly just sent her a note that said wanted to build on this idea you had today. I really liked that idea, by the way. I saw this article or I saw this research about this other emerging thing, sports betting. And I think it'd be really interesting for us to start tracking that because we could maybe draw some correlations between people's stress. We have stress monitoring whoop. We can track your stress. We could draw interesting correlations between betting behaviors and stress levels. And so that's all I did. It took me five, ten minutes total, but I think it's a great example of showing this idea of like counter program that narrative. 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. They seem kind of agitated about something. And I say to them, like, it seems like this is really bothering you. What's going on in your head? What are you afraid of? What are you worried about? And often it will emerge, you know, I'm worried that this other person thinks I'm bad.”
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 just, as I said, I think usually you're fighting a losing battle when you're trying to do that. And it draws attention to the thing that you kind of did poorly. You don't really want to draw more attention to it, right? You want to move on, take action, move forward. And so I thought about, well, what am I afraid that she thinks of me? I'm afraid that she thinks that maybe I don't take some of these health issues seriously. I'm afraid she thinks that maybe I'm somebody who kind of like laughs off emerging trends. And so I thought about what's something that I could do to demonstrate the opposite of that. And I did some research very, very quickly on what are some emerging public health concerns that people really aren't talking about that would be interesting to track. And I found some interesting research about sports betting and especially young people in sports betting. And it's sort of becoming this thing that a lot of public health experts are very worried about.”
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
“Problem in some cases. And I think we should take it seriously. I think there's a lot of value we could provide here. And I was completely humiliated because I actually take this stuff really seriously. Like I take addiction really seriously. I have a ton of empathy for people who struggle with it. And I also think of myself as somebody who embraces new ideas and wants to be on the forefront and would never laugh off something that kind of seems like a fringe issue that's, I think, becoming actually more and more a big part of what's happening today. And so I realized that in that moment I was having that reaction because of the feeling that it gave me about who I am as a person. And I became so worried that this other person had the wrong impression of me. And I wanted to follow up with her after and say, let me explain myself. Like, let me explain why I didn't mean that or whatever it 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
“And so I'll give you an example of this. I was in meeting a while ago, and we were talking about different things that we wanted to start tracking in the WOOC journal. And our chief technology officer suggested ketamine tracking. And I thought she was making a joke. And I laughed. And she looked at me very seriously and was like, This isn't funny, Hillary. Like, this is a serious issue for a lot of people, and it's an emerging.”
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
“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 want to correct the record. When you do that, I think more than often, more often than not, you come off as just looking defensive and you kind of start obsessing over things that you don't actually have control over, which is what another person thinks of you. And you don't even necessarily have that information. And so I always ask myself in these moments, what is one thing that I can do small that will demonstrate the opposite of what I'm afraid this person thinks of me?”
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 at its core, when I say take a punch, what I mean is you're going to run into situations where something has gone wrong. Maybe you have misstepped, maybe you are just hearing someone speak critically about your work, whatever it might be, you're going to feel like you have taken a punch. Like it's a very physical feeling. And I think as managers, you spend a lot of time teaching your team how to be successful, right? You want to prepare them to maximize the chances of a good outcome. But if you don't also prepare them for what happens when that outcome isn't as good, you're going to run into some problems. And so when I think about how to take a bunch, what I say to my team is if they come to me and they're upset because something has happened, maybe they said something in a meeting that wasn't received well or again, they're hearing somebody else talk about them in some way, whatever it is. I try to focus them less around”
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 would really love it if more people were like, screw it, I'm going to do something that's probably going to fail. And it's important and it's worth doing. And I'm going to do it well.”
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
“Even just how we provide value as humans in society. And I also think people, especially young people today, haven't even necessarily been in a career environment where there wasn't always kind of a threat of layoffs or things like that. And I think that's taken a real psychic toll on a lot of people. And so I think all managers now really need to be able to lead their teams through uncertainty, through fear, through hard things. And I love the concept of taking a punch. I've got a couple other tools that I like to use. But I think it can teach people how to thrive in these environments. 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.”
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, absolutely. It's something I care a lot about. I've been, I think, pretty lucky in my career. I've been very drawn to working on hard product problems, regulated areas, really hard business models, things with pretty high emotional stakes for the users of the products. You're really likely to run into a lot of setbacks along the way. And I think this is really relevant today because I look out and I talk to a lot of people. I hear fear and I hear uncertainty. And I think it comes from a few places. I think obviously I'm really excited about AI and how it's transforming the way we work. And I think a lot of people are, but I think a lot of people are scared too. And they're embracing these tools. They're learning these tools. But a lot of them have a question in the back of their mind, like, what does this mean for the future of my job? And in many cases, what does this mean for my identity, right? Like I think it makes people quite.”
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
“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.”
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
“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.”
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
“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?”
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.”
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