How to build GPTs you’re proud of

Hosted by Hilary Gridley and Ben Erez

Wed, Mar 11, 2026

6:00 PM UTC (30 minutes)

Virtual (Zoom)

Free to join

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Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking
Ben Erez
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What you'll learn

How to pick what's worth building

Not every piece of judgment should be a GPT. What makes something a good candidate vs. a waste of time?

How to write instructions that capture nuance

The difference between a GPT that gives generic advice and one that sounds like you.

How to iterate when the output isn't good enough

The specific moves for diagnosing why a GPT is falling flat and what to change.

Why this topic matters

Most custom GPTs “work,” but barely. The output is generic, the tone is off, and you stop using them. The issue isn’t mechanics. It’s that no one teaches you how to encode real judgment. In this session, we’ll break down GPTs we’ve built and show the specific iterations that turned loose advice into high-leverage AI-powered tools others can rely on.

You'll learn from

Hilary Gridley

Product Leader (Whoop, Dropbox, Nike)

Hilary was most recently the Head of Core Product and AI at WHOOP, overseeing the company's AI coaching platform and core app experience. A longtime product builder, she also teaches a popular course on practical AI for managers and writes a popular Substack on AI-native leadership. Her work focuses on how AI is reshaping how we work, think, build, lead, and live.

Ben Erez

Former Meta PM and PM interview coach (coached 200+ PMs, 17K+ students)

Ben teaches a popular Maven course (includes his AI Copilot) focused on product sense and analytical thinking interviews at top tech companies like Meta, OpenAI, Stripe, DoorDash, etc. Ben also co-hosts the Supra Insider podcast and offers PM interview guides at Insider Loops. Ben is a frequent guest contributor on Lenny's Newsletter.

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