Hilary Gridley

16 statements across 1 episodes · 4 bullish · 2 bearish · 1 people on the record · first statement Jun 15, 2025 by Hilary Gridley · across every show →

On the record as a speaker too: Hilary Gridley's record, appearances and statements → this page counts the times other people say the name.

Everything said about Hilary Gridley, oldest first

Jun 15, 2025 negative
Opinion
Gridley: PMs should apply their craft to hard social problems, not SaaS
“Well, 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 doe…”
Hilary Gridley Jun 15, 2025 ▶ 26:27 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025 positive
Insight
Gridley: AI simulation tools radically accelerate PM learning feedback loops
“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, li…”
Hilary Gridley Jun 15, 2025 ▶ 1:30:03 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025 positive
Disclosure
Gridley built custom GPTs to give her team on-demand management feedback
“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-on…”
Hilary Gridley Jun 15, 2025 ▶ 1:24:29 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Litigating past criticism makes people look defensive, not effective
“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 o…”
Hilary Gridley Jun 15, 2025 ▶ 9:16 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Managers must prepare teams for failure, not just success
“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 gonna run into s…”
Hilary Gridley Jun 15, 2025 ▶ 8:24 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025 negative
Insight
Gridley: Every extra meeting attendee reduces participant candor
“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.”
Hilary Gridley Jun 15, 2025 ▶ 24:12 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Employees who disagree with their CEO's vision should leave
“And if you don't, if you disagree with it, like, you probably shouldn't be working in that company.”
Hilary Gridley Jun 15, 2025 ▶ 56:19 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025 positive
Insight
Gridley: AI adoption succeeds faster starting with non-work use cases
“I think a mistake a lot of people make when they start thinking about how to drive adoption is they're like, oh, we have to show people how to do their work with these tools. But I'm like, well, work is hard and If you are on a deadline for something, you've g…”
Hilary Gridley Jun 15, 2025 ▶ 1:04:19 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Shared mental models of leadership enable companies to move faster
“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 what level of, like, risk tolerance the company has, things like that, then you can actually start to move much, much…”
Hilary Gridley Jun 15, 2025 ▶ 31:44 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Approval bottlenecks are communication failures, not process problems
“I think people will often say like, oh, it's a process problem. It's not a process problem. It's not an approval process problem. It's a, I think it's a transparency and it's a communication problem, like downward communication, outward communication.”
Hilary Gridley Jun 15, 2025 ▶ 28:45 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Forcing reports to propose answers builds judgment and reduces dependency
“Like, when they come to me and they say, well, what do you think I should do? Or you know, what could I have done differently? I'll say, like, rephrase that as, tell me what you think you could have done differently, and then ask me if I agree. And when I do t…”
Hilary Gridley Jun 15, 2025 ▶ 43:37 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025 positive
Disclosure
Gridley uses LLMs to model colleagues' thinking and anticipate their objections
“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 like 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 …”
Hilary Gridley Jun 15, 2025 ▶ 1:35:49 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Assertive statements reveal mental models faster than open-ended questions
“Anytime you find yourself, like, tempted to ask an open-ended question to somebody whose brain you're trying to understand, stop yourself and say, like, let me just say that, let me say as a statement what I think, and then try to calibrate based on their reac…”
Hilary Gridley Jun 15, 2025 ▶ 44:30 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025 neutral
Insight
Gridley: Career anxiety pushes workers toward safe, low-risk problems
“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”
Hilary Gridley Jun 15, 2025 ▶ 6:55 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Disclosure
Gridley built Aristotle GPT to generate LSAT-style PM reasoning questions
“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 the scenarios of things that a PM would encounter.”
Hilary Gridley Jun 15, 2025 ▶ 1:27:27 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Jun 15, 2025
Insight
Gridley: Understanding how a CEO thinks matters more than what they think
“What is what much more helpful than understanding what your CEO thinks is I think understanding how your CEO thinks.”
Hilary Gridley Jun 15, 2025 ▶ 29:44 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
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