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Hilary Gridley

Published podcast speaker

Claims
24
Episodes
1
Shows
1
Named items
3

Books, apps, and tools

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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

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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.

4 transcript-backed records

01 / 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

02 / 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

03 / 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

04 / 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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