in their identity and who they are because their action demonstrates that, um, it just gets them out of that negative thinking and it gets them through that trough of despair that comes after you. You feel like you took a punch. so the idea here is when you're afraid, somebody that matters in your career thinks ill of you of something that you did of you're not good at something or you think something that they're not happy about.. like this is a version of getting punched basically is you just feeling like someone thinks you're not doing a great job.., And so the tactic here is how to change their mind almost about you and give you something tangible to do.. Yeah,. okay.. And so the question to ask, and I wrote this down as you were talking, is this is what you ask of your reports?. what is the one thing that you can do that demonstrates the opposite of what you think this person thinks about you? exactly. and it's this comes up all the time, like there will be narratives that emerge, some are good, some are bad, um, about you and your career. and i think especially when people get to a place where they're putting themselves out there more, right? they're talking uh in more presentations, they're talking in more meetings. it's very natural for them to become uh concerned with the perception of themselves and it is scary because it it feels like something as i said you don't have control over. and so, exactly if it's if instead of focusing people around what do these people think of me, you focus them around, well, what are you going to do next to demonstrate that you are the person that you know yourself to be? uh, i think that can just be incredibly effective at giving people more of a sense of agency. i guess talk about the balance of i'm just gonna prove everyone wrong against what they think versus here's who i am and i know this is me and this person is mistaken and instead of debating them, i'm going to show them who i am. just like not overstressing about everyone thinking things about you in different ways. there is some value, i think, in having a little bit of a chip on your shoulder. i think that that's definitely been you see that people who are really successful, they do have a little bit of like i'm going to prove them wrong. and so i don't want to say that like you shouldn't think about it at all or you shouldn't care. like of course it's natural to care and of course, it's fine to care, but I do want to just sort of help help my team build this habit of doing the things that you know to be right and and having conviction in that and you know, being open to learning along the way and and sort of calibrating as you go. um,, but not not becoming overly concerned with your fears of what other people are going to think of you, Because I think especially for, uh, otherwise really thoughtful, you know,, really kind of the PE people who are kind of hard on themselves. I think that that just holds them back from being the person that they can be. so, a key part of this is this is going to help you stop just spiraling on thinking about what they think about you and gives you something to do that will change that. and then the other key point here is don't try to convince them otherwise. you're not going to go to your manager like, "oh, i'm i really think ketamine therapy and addiction is really important and i'm i didn't mean to say it this way." and that kind of thing. i, you know, i'm not interested in litigating the things that happened already when we can move forward. and i'm certainly not interested in litigating what another person thinks about a thing that happened. uh, i just i feel like i've spent so much time talking to people in meetings, whatever it is, where it's just this kind of like ruminating on something that has already happened, you know, it's very like anxious thinking pattern, i think. um, and people can just get stuck in it. uh, and so, you know, let them let let them do it. like i often think about uh it's like when you get bad feedback, right? uh or critical feedback and you kind of naturally have this reaction of oh well you know that's not fair 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 you naturally come up with these reasons why uh you're actually not wrong and and that's fine like it's i don't want to say like you should feel bad for doing that like let yourself have the pity party let yourself feel those things, but then but then you got to move on as quickly as possible because those feelings, they actually do tend to spiral and get worse um if you're not actively working against them. often times these sorts of lessons come from the person experiencing this themselves.. is this something that you dealt with when you were starting your career or even now?? and oh,, absolutely.., um, 100%. and I think it is more than just my career, but just my, like general mental health and my life. a lot of where this comes from is uh, a a concept in cognitive behavioral therapy called behavioral activation. and in my former job,, I was working for a company called Big Health and I was we make uh, digital therapeutics. So those are mobile apps that have been clinically validated to treat behavioral conditions like insomnia, depression, anxiety. and I was working on a new depression therapeutic. And so I went very deep on this, um, and was working with a really wonderful clinical team full of clinical psychologists who helped me understand the techniques that therapists use, Uh, when they are working with people who have depression. And so much of depression is characterized by uh these negative thinking patterns and this like this feeling that i feel bad and i just need to wait until i feel better and then I'll start doing the things that are good for me. right? I don't feel like uh responding to this text, so i'm just not 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 I it that doesn't go away on its own especially if you have depression. um and it's something that again you you the idea of behavioral activation is uh you have to identify these actions that you can take that will reverse that negative spiral and will improve your mood. And so the the sort of like misconception is I'll feel better and then I'll act. and the thing that therapists try to teach people when they're working with them in therapy is I will act and then I will feel better. But acting is hard if you are in the throws of depression. and so easier said than done. uh, 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 I mean, I have a list of myself. I have 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 in around me. if I if I like feel myself kind of getting sucked into uh, like very low mood or negative thinking or whatever it is. And you can, you can see how effective that is at just getting you out of there versus the instinct to just sort of like, go and lie in bed and feel bad for yourself.., um, which I, I understand very well. And so that understanding that concept, which is, you know, at its core, a therapeutic concept used in cognitive behavioral therapy., um, but it kind of, it kind of changed how I see the entire world., um, and I, how I see, especially as a manager, the ways that people on my team think and behave, uh, and how easy it is to get stuck in some of these like downward spirals that you really need to actively push back on.., and as a manager, I want to help them do that., and I want to help them a, see that, like, see the ways they are in some ways sabotaging themselves, getting in their own ways um, with whatever is going on in their head. uh, and then I want to help them counterprogram it in themselves and also, you know, as I said, counterprogram the things that you are worried about out there as well.. so interesting.. so the core of this technique is what's a an action and you said this, it could be very small that you can take that in this case shows someone else you're not they're not you're not who they think you are like you're worried they think think about you in a certain way and you want to take an action that helps them see you're not that. so that yes, that's the taking the punch concept. the behavioral activation could be anything, right. it can be it can be picking up a piece of laundry off of the chair and putting it away and that's just sort of enough to get you out of the downward thing you're in.. so behavioral activation just conceptually is, uh, you know, how are you taking action to reverse the the downward feeling or the negative feeling that you're feeling? And then the take a punch concept is kind of that applied in the context of I'm in a working environment. I am very conscious of how I'm being perceived by other people that's causing me a great deal of stress. I think especially for product people who are, um, you know, so much of their self-identity is wrapped up in having the answers being competent getting things done. Um, and so many of them have been people who have been really good at that for most of their careers, which is how they got into these jobs in the first place. I think that can be an extremely stressful thing for them that in many cases can be uh, like the driver of burnout and the driver of like I I can't really handle the stress of this job anymore. um,, and so I think of the the take a punch concept is is more just applied to that sort of specific problem of I'm struggling at work and I'm struggling largely because of my perceptions of other people. uh,, and I want to feel more agency in that situation.. this is so cool.. okay,. on the idea of the specific take a punch concept, what kind of impact have you seen this have on people's mood and careers?? is this like how big a deal is this specific tactic? well,, I think it's a big deal Like on two levels. one, it's a big deal because it can help you in a crisis or a minor crisis, but i actually think it's a bigger deal because i see so many people who don't uh 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 um i'm often trying to encourage people to like speak up in meetings more. uh to practice the skill of how you move a conversation forward in a way that contributes value uh both because doing so i think is is important because nobody wants to be in bad meetings but also because it will help with your career right like this is how you 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 that you know they they are interested in coming to the meeting and hearing about uh these big decisions 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 than they would have been if there were fewer people in that meeting. and so, one key piece of a meeting is like you usually have a problem you're trying to solve uh collectively as a group. and it's really hard to do that if people are being overly cautious about what they're saying because there's like too many people in there. so, uh, when i tell people this, i'm like, you know, it's really important that you earn your place in this meeting. uh, and let's work on like how to do that. and the core piece of that is like you've got to say stuff that's valuable. and people always come up with all these excuses for why they can't do it. and one thing i've learned is that i think people are really good at coming up with very rational sounding reasons to not do things that just make them uncomfortable. uh but in their head they're like, "oh no, you know, like i'm i'm too junior. like nobody wants to hear what i have to say or everyone was already thinking it or uh you know, i you know, i like to process things internally and by the time i say them, the conversation's moved on, whatever it is." um and so so much of like that skill, it's like a communication skill at its core. it's just how to express yourself verbally. uh but so much of the the blocker of that is i think fear. uh fear of saying the wrong thing, fear of looking stupid, fear of just the the discomfort of everyone in a room turning and looking at you, right, as you're kind of like trying to formulate a half-baked thought. and so if you can help people be less afraid of that, that's like 90% of the challenge of actually improving some of these skills. um, and so i think when you give people the skills of taking a punch, you are helping them feel less afraid of getting the punch in the first place. um, and that's why i think it's so important. that's profound. the second order effect of the skill. there's something you mentioned when we were chatting earlier that um, stuck with me with this idea that too many pms and too many people are playing on easy mode and not trying hard things. oh, leaving myself in trouble here. okay, let's do it. say more. oh, i think this is my hot take. like, you know, you hear people talking about craft and taste and product management and it's all very wonderful. um, and i i'm like totally on board. like, i love it. i'm i'm a sucker for that kind of thing. but i'm like, well, if if you are like really in it just for pure love of the game, like you just love product management. like why are you building products for people exactly like you who have all your exact same problems at a company that sells to other companies that doesn't worry about pricing like there's no real I mean there's I don't want to i don't want to act like i think this is easy to be clear. um, but in the like the grand scheme of things like I wish that the people who have this pure love of product management and have this pure love of building things that you would see more of that applied to building for low-income people building for, you know, social services, things like that that really, really need that kind of work. uh, and I think there's a you a level of prestige obviously associated with working uh in certain companies and you know, you get less of that in in other industries. And so people would naturally gravitate toward that.. uh, and I you know, I totally get it. I totally get you get paid better, like no, no real judgment for me.. uh, I just I wish I saw more but I wish you would see more people and I'll say this I know there's a lot of you out there. I know there's a ton of people out there doing really really important work in really really hard spaces. uh and I see you and I i appreciate it and shout out to you. awesome,. okay,, I'm glad you shared that. thank you. I think this will resonate with a lot of people. I want to move on to another trait skill that you are good at and help people learn which is being very transparent in what's happening within the organization within your thinking. you almost help people think the way you think and see the way you think so that they can operate at a higher level. just talk about that, what that looks like and why that's important.. it's interesting. I think another thing I hear a lot of people complain about in organizations is like the why do 10 people have to sign off on this email before I send it kind of problem. And I think the answer to that is like because those 10 people all have different information, different context and in many cases completely different like working models for how the CEO of the company and other strategic leaders in the company think and it makes things super inefficient. I think people will often say like, oh, it's a process problem.. it's it's not a process problem. it's not an approval proc problem.. it's a i think it's a transparency and it's communication problem like downward communication, outward communication and what I mean by that is um, when I think about like artifactbased 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, uh, new competitive threats emerge, new opportunities emerge all the time. This, this is especially true now with AI. obviously, everyone is lighting their strategies on fire and trying to figure out the best way to, to sort of transform their organization.. and so, if you're you're if the way that you understand what's going on at the company is from reading a document that was written six months ago,, you're going to be working from outdated information and you're not going to be able to, like think and respond to new things that happen. And so what is, what much more helpful than understanding what your CEO thinks is, I think, Understanding how your CEO thinks. Um, and that goes for all sorts of levels of the company. I want to understand how all the strategic leaders in my company think and I want my team to understand how I think. And when I feel confident that people on my team understand how I think like I don't need to read their emails, I don't need to approve things. The times where I feel like I need to do that is because I'm working with people where I'm like, I don't I don't have confidence that these people understand how I think or I don't have confidence that they understand how this uh this email or whatever it is is going to be received by this important person. um, and so I try to teach that to my team. And the way that I do that is a few ways. uh, first I'm in meetings with people like important people at the company. um,, so I'm constantly hearing the things that they're saying and paying attention to sort of the note behind the note. why do i think they're saying this? what do i what insight do they have that they're bringing to this conversation that might not be obvious? um, and i try to make an effort every week, i don't always do it, but i try to send my team just a quick rundown in slack of here are the most important conversations or the most interesting conversations i had this week. here's what that person said verbatim. again, i i write a lot of notes, so i' i've got it. um, if you've got a transcriber, maybe that'll help you. and here's here's what i interpret that as. here's why i think they say that. here's where i think that's coming from. and here's what i'm going to do differently as a result. and these aren't long. and sometimes if i don't have time, i'll just like in a team meeting, i'll literally just go through my notes from the week and sort of voice over stuff and editorialize it as i go. um, and over time i think my my team has like a pretty good sense of what people are saying and and how to think about uh the thinking behind it and how this person thinks, how this person thinks and how i think. and i think when you get an entire organization working that way where everyone's working from the same models of like how what the ceo thinks matters uh what level of like risk tolerance the company has things like that then you can actually start to move much much faster and communication becomes much much much less painful. so the tactic here is to help your team kind of build a mental model of everyone in the company that matters so that it's like the way you put it almost is when they're emailing them or asking for something they they already know how they're going to respond. is there is there an example you could share of something like this of just like something a person at whoop of how they think. I don't know, maybe you can keep it anonymous just to make this a little real of the kind of mental model you might want to build around someone. so, our CEO, will, is uh, somebody who obsesses over pixels in a way that um, is, you know,, challenging to get things through a design review, but I think results in a product that is a thousand times better than it would be if uh, he were accepting "TJAKDJALSDK" How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop) Product Leadership: Learning to Take a Punch and Thrive in Uncertainty This blog post summarizes key insights from a podcast interview with Hillary Gridley, Head of Core Product at Whoop, focusing on product leadership, dealing with hardship, and leveraging AI for skill development. Introduction - The podcast episode centers around helping teams learn to "take a punch"—navigating challenges and setbacks. Hillary Gridley, with her extensive experience at Whoop, Big Health, and Dropbox, shares valuable insights on this topic, along with strategies for transparency and habit formation within organizations. The conversation also touches upon the transformative power of AI in learning and skill development. Helping Your Team Learn to Take a Punch - The Core Concept: Taking a punch refers to handling setbacks and critical feedback. It's about focusing on actionable steps rather than dwelling on others' perceptions. Counterprogramming Narratives: Instead of litigating others' impressions, focus on actions that demonstrate the opposite of what you fear they think. Example: After a misunderstanding, Hillary researched an emerging public health concern to show she takes such issues seriously. The Key Question: What's one thing I can do to demonstrate the opposite of what I'm afraid this person thinks of me? Challenging Negative Thinking: Managers should challenge negative self-talk, focusing on actions to prove those thoughts wrong. Behavioral Activation: This CBT technique emphasizes action to reverse negative spirals. Act first, feel better afterward. Hillary maintains a personal list of behavioral activations. Impact on Mood and Careers: The "take a punch" tactic helps people overcome fear, leading to increased participation and career growth. Avoiding "Easy Mode" and Embracing Hard Problems - Hillary advocates for applying product management skills to challenging problems, including those in underserved areas or social services. While acknowledging the appeal of prestigious companies and higher salaries, she encourages pursuing impactful work, even if it's more challenging. Transparency and Shared Mental Models - The Problem: Inefficient processes often stem from a lack of transparency and shared understanding of leadership thinking. The Solution: Build shared mental models by sharing important conversations, interpretations, and actions taken. This reduces the need for constant approvals and speeds up decision-making. Understanding "How" Leaders Think: It's more valuable to understand the reasoning behind decisions than simply knowing the decisions themselves. Example: Hillary explains how her CEO's focus on "building the future" translates into specific product improvements, emphasizing high-impact, low-effort changes. The "What If I'm Wrong" Exercise: This helps understand others' perspectives and potentially discover blind spots. Respecting Different Points of View: Maintain your perspective while respecting others' views and considering their potential validity. Handling Disagreement with Leaders - Understanding the Rationale: Before disagreeing, thoroughly understand the leader's perspective. Ask clarifying questions, even if the answers aren't straightforward. Respectful Candor: Express disagreement respectfully, explaining the leader's rationale even if you don't agree with it. Focus on Execution: Don't get bogged down in debates; focus on executing the plan and learning from the outcome. Magic Questions: Use statements ending with "Do you agree?" or "Is that right?" to understand others' mental models by observing their responses to your assertions. This helps calibrate judgment and reduces reliance on the leader for answers. Building Good Habits and Designing Reward Loops - Habit Formation over Education: Focus on creating consistent, low-friction habits with powerful, immediate, and emotional reward loops. Consistency: Start small and aim for daily actions. Reduced Friction: Use AI tools for tasks unrelated to work to minimize initial barriers. Reward Loops: Design powerful, immediate, and emotional rewards for desired behaviors. Example: Whoop's recovery score provides immediate feedback on the impact of actions. Examples: Publicly acknowledging AI usage, celebrating team members' self-care practices, and using Whoop's data visualization to create positive feedback loops. Shifting Reward Focus: Intentionally reward behaviors you want to encourage, rather than inadvertently rewarding undesirable behaviors. Creating Space for Creativity and Deep Work - Modeling Self-Care: Leaders should model self-care practices and normalize taking breaks for creativity and deep work. Understanding Individual Needs: Recognize that different people need different things to thrive. Ask about what brings them joy. Behavioral Activation for Joy: Help team members identify and incorporate joy-inducing activities into their daily routines. Permission Structure: Provide a permission structure for team members to prioritize self-care and avoid burnout. Underestimating the Power of AI - Accelerated Learning: AI can significantly accelerate learning by shrinking feedback loops and providing on-demand, personalized guidance. Aristotle GPT: An example of an AI tool that provides personalized feedback on logical reasoning skills in product-related scenarios. Increased Reps: AI tools enable individuals to get significantly more reps than through traditional methods, leading to faster skill development. Pivotal Corner: A Career Inflection Point - Hillary's pivotal moment was transitioning to report directly to the CEO at Big Health. This experience fostered a deeper understanding of leadership perspectives and the importance of humility in acknowledging potential blind spots. Fail Corner: Learning from Setbacks - A heartbreaking project failure at Big Health taught Hillary the importance of acknowledging the "shot clock" in product development and the necessity of balancing obsession with responsibility. Whoop 5.0 and Future Innovations - Hillary discusses Whoop's new features, including improved cycle tracking, heart health features, and a longer battery life. She highlights the focus on making health data more actionable and accessible. Lightning Round - Favorite Books: East of Eden and The Sun Also Rises . Fiction helps navigate ambiguity and tension. Favorite Movie/TV Show: The Rehearsal . Favorite Product: Zift, an indoor cycling program with a powerful reward loop. Life Motto: The "cool parts" of life are enhanced by the "sucky parts." Fiction Book Impacting Product Building: Derek Walcott's poem "Seag," emphasizing the balance between obsession and responsibility. Conclusion Hillary Gridley's insights offer a powerful framework for product leaders. By focusing on helping teams develop resilience, fostering transparency, building good habits, and leveraging AI, leaders can create more effective, fulfilling, and less stressful work environments. Her emphasis on understanding others' perspectives and embracing both obsession and responsibility provides a valuable roadmap for navigating the complexities of product leadership and life itself.