Gridley uses LLMs to model colleagues' thinking and anticipate their objections
Hilary Gridley · How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop) · Jun 15, 2025 · at 1:35:49
Hilary Gridley (Head of Core Product at Whoop) discusses using generative AI tools like ChatGPT or Claude to simulate how specific coworkers think based on notes from past interactions.
0:00 / 0:17exact quote · 17.5s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“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 it for myself.”
quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →
More from Hilary Gridley
Gridley: Product leaders fail if they push personal vision over the CEO's
“When you're reporting to the CEO and like 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 like influencing the CEO, influencing the people around them to make it so. An…”
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…”
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.”
Gridley: Product management has no right answers, only least wrong options
“Cause I think in product, like I like to joke, there's no right answers, right? You're just, there's only wrong answers and you're just trying to execute well on like the least wrong answer that's available to you.”
Gridley: Teams succeed more by committing to flawed directives than fighting them
“If it's not a, like a obviously terrible answer, and sometimes even if it is an obviously terrible answer, you're still more likely to succeed if you just sort of like sort of reorient yourself around a world where it's not a terrible answer and then just try …”