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Hilary Gridley

Published podcast speaker

Claims
24
Episodes
1
Shows
1
Named items
3

Books, apps, and tools

The evidenced stack.

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tool / likes

Custom GPTs

“When I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about, is how can I make sure that when a person does this, they feel really great? And part of why I like Custom GPTs as a tool for helping people learn to use LLMs, and I talk about this on the podcast I did with Claire, on how I AI, is because if you put in the prompt, you as the person building the custom GPT, you write the prompt, you put it in, you design it such that somebody can upload a specific document.”

Lenny's Podcast · 15 Jun 2025

Evidence receipt · Source ↗

book / likes

The Sun Also Rises

“Even the business books I love the most that shaped how I think I'm like, "I kind of got the gist of them part way through," but fiction, I'm like, everybody should read East of Eden by John Steinbeck and everybody should read The Sun Also Rises by Ernest Hemingway, which is my comfort book.”

Lenny's Podcast · 15 Jun 2025

Evidence receipt · Source ↗

book / likes

East of Eden

“Even the business books I love the most that shaped how I think I'm like, "I kind of got the gist of them part way through," but fiction, I'm like, everybody should read East of Eden by John Steinbeck and everybody should read The Sun Also Rises by Ernest Hemingway, which is my comfort book.”

Lenny's Podcast · 15 Jun 2025

Evidence receipt · Source ↗

Claim ledger

What Hilary said.

24 transcript-backed records

01 / recommendation

Likes East of Eden. Likes The Sun Also Rises.

“Even the business books I love the most that shaped how I think I'm like, "I kind of got the gist of them part way through," but fiction, I'm like, everybody should read East of Eden by John Steinbeck and everybody should read The Sun Also Rises by Ernest Hemingway, which is my comfort book.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

02 / uncertainty

I feel like I've had so many of those times where I don't know, when I was growing up, I felt so confident in how I felt about everything.

“I feel like I've had so many of those times where I don't know, when I was growing up, I felt so confident in how I felt about everything.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

03 / belief

I'll say one more thing, which is we've opened a wait list 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 understand how your sleep is impacting your metabolic health or things like that.

“I'll say one more thing, which is we've opened a wait list 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 understand how your sleep is impacting your metabolic health or things like that.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

04 / belief

We got a lot of great stuff cooking. So even if you tried WHOOP 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.

“We got a lot of great stuff cooking. So even if you tried WHOOP 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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

05 / uncertainty

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

“There's so much cool stuff we're doing right now. I'm like, I don't know if I want to get into it all right now, but I can.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

07 / uncertainty

You should do that. But again, it's like you do that 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.

“You should do that. But again, it's like you do that 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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

08 / belief

I try to find ways that I really am impressed with my team, and the ways that they take care of themselves outside of work, because I think that makes them better at their jobs, frankly, and just happier humans.

“I try to find ways that I really am impressed with my team, and the ways that they take care of themselves outside of work, because I think that makes them better at their jobs, frankly, and just happier humans.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

09 / belief

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.

“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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

10 / belief

What's something that you could do to show them that it'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 in 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.

“What's something that you could do to show them that it'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 in 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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

11 / belief

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.

“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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

12 / belief

If you're just pushing yourself at 100% of your physical capacity all the time, not only are you going to burn out, but you're literally going to suffer performance decline. And in the same way, I think in the athletic world, there's so much more, just acceptance of, I don't even want to say limits, but just like, you have to take the time to do the things you need to be your best.

“If you're just pushing yourself at 100% of your physical capacity all the time, not only are you going to burn out, but you're literally going to suffer performance decline. And in the same way, I think in the athletic world, there's so much more, just acceptance of, I don't even want to say limits, but just like, you have to take the time to do the things you need to be your best.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

13 / belief

" Obviously that's not going to set your team up for success or make anybody happy about it, but you do hear that, you do see that happening. And so I think what I try to do in those situations is separate out my opinion from it, from the, " Well, what is the insight that makes it make sense to this person" and explain their rationale.

“" Obviously that's not going to set your team up for success or make anybody happy about it, but you do hear that, you do see that happening. And so I think what I try to do in those situations is separate out my opinion from it, from the, " Well, what is the insight that makes it make sense to this person" and explain their rationale.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

14 / belief

Being open to learning along the way and 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, really the people who are hard on themselves, I think that that just holds them back from being the person that they can be.

“Being open to learning along the way and 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, really the people who are hard on themselves, I think that that just holds them back from being the person that they can be.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

15 / belief

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.

“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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

16 / commitment

For the first time in our company's history, we've updated our mission, so we're now saying that WHOOP exists to unlock human performance and health span. And health span I think is, and I mentioned earlier this feature I'm really excited about, because I do think it is kind of the most powerful version of a longevity-type feature I have seen because it is so focused on your behaviors and your habits today.

“For the first time in our company's history, we've updated our mission, so we're now saying that WHOOP exists to unlock human performance and health span. And health span I think is, and I mentioned earlier this feature I'm really excited about, because I do think it is kind of the most powerful version of a longevity-type feature I have seen because it is so focused on your behaviors and your habits today.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

17 / evaluation

I mean I worked at Dropbox where I saw this happen all the time where we would acquire products that other teams internally had been working on and it's just like, it's heartbreaking when it happens. But I think there's an urgency that that has instilled in me that I think is actually really good and healthy, especially again working in this era where there is kind of this AI arms race and everyone's trying to move really quickly of, yeah, there's always a shot clock.

“I mean I worked at Dropbox where I saw this happen all the time where we would acquire products that other teams internally had been working on and it's just like, it's heartbreaking when it happens. But I think there's an urgency that that has instilled in me that I think is actually really good and healthy, especially again working in this era where there is kind of this AI arms race and everyone's trying to move really quickly of, yeah, there's always a shot clock.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

18 / commitment

" 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, I'm not doing the things I need to do to take care of myself, I'm going to have a bad time.

“" 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, I'm not doing the things I need to do to take care of myself, I'm going to have a bad time.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

19 / evaluation

One thing that he said to me that really stuck with me is when you're reporting to the CEO and as a chief product officer, the big mistake that people make is they think that the game is all about getting what is inside their head and influencing the CEO, influencing the people around them to make it so, and if you go into the role trying to do that, you're going to fail because actually what your job is to do is to understand what the CEO's vision is and what they care about, again, sort of how they think about things and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of product.

“One thing that he said to me that really stuck with me is when you're reporting to the CEO and as a chief product officer, the big mistake that people make is they think that the game is all about getting what is inside their head and influencing the CEO, influencing the people around them to make it so, and if you go into the role trying to do that, you're going to fail because actually what your job is to do is to understand what the CEO's vision is and what they care about, again, sort of how they think about things and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of product.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

20 / preference

When I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about, is how can I make sure that when a person does this, they feel really great? And part of why I like Custom GPTs as a tool for helping people learn to use LLMs, and I talk about this on the podcast I did with Claire, on how I AI, is because if you put in the prompt, you as the person building the custom GPT, you write the prompt, you put it in, you design it such that somebody can upload a specific document.

“When I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about, is how can I make sure that when a person does this, they feel really great? And part of why I like Custom GPTs as a tool for helping people learn to use LLMs, and I talk about this on the podcast I did with Claire, on how I AI, is because if you put in the prompt, you as the person building the custom GPT, you write the prompt, you put it in, you design it such that somebody can upload a specific document.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

21 / recommendation

You have to give them things that take no more than a minute or two to do. And actually, I have a 30 days of GPT, I call it, of a list of 30 things to do, one every single day, that I don't know anyone who has gone through this, and not come out the other side, feeling a hundred times more confident in their skills, and actually using it every day as a habit, because it's built as a habit formation tool, and not an education tool.

“You have to give them things that take no more than a minute or two to do. And actually, I have a 30 days of GPT, I call it, of a list of 30 things to do, one every single day, that I don't know anyone who has gone through this, and not come out the other side, feeling a hundred times more confident in their skills, and actually using it every day as a habit, because it's built as a habit formation tool, and not an education tool.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

22 / uncertainty

I think that that's why it's so hard to talk about these things in absolutes, because sometimes you're right, and sometimes you're not right.

“I think that that's why it's so hard to talk about these things in absolutes, because sometimes you're right, and sometimes you're not right.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

23 / evaluation

" And I have 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, however you want to do it. And actually it's kind of fun because it gives you the scenario and it's like, "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.

“" And I have 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, however you want to do it. And actually it's kind of fun because it gives you the scenario and it's like, "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.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast

24 / evaluation

I think we are not being nearly creative enough, when it comes to how to think about learning with AI. And I think, 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 analyst, sort of a classic entry level role.

“I think we are not being nearly creative enough, when it comes to how to think about learning with AI. And I think, 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 analyst, sort of a classic entry level role.”
Speaker
Hilary Gridley
Publisher
Lenny's Podcast
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