How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop)

How I AI

Hilary Gridley, Head of Core Product at Whoop, shares how she uses dozens of custom GPTs for her team that think and give feedback like her, allowing her to scale herself up and create time for higher-value work.

What you’ll learn:

1. A step-by-step process for creating GPTs that “think like you” by reverse engineering your own decision criteria

2. How to turn your management expertise into clear evaluation rubrics that AI can consistently apply

3. Practical techniques for improving team writing and presentations with AI-powered feedback

4. Why GPTs are the perfect tool for scaling good management practices without requiring prompt engineering skills

5. How to use AI to get invited to more strategic meetings by improving your written point of view

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Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Vanta—Automate compliance and simplify security

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Where to find Hilary Gridley:

Newsletter: https://hils.substack.com/

LinkedIn: https://www.linkedin.com/in/hilarygridley/

X: https://x.com/yourgirlhils

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Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

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In this episode, we cover:

(00:00) Intro

(02:52) Creating GPTs that think like you

(04:23) Demo: Reverse engineering a recommendation algorithm

(13:06) The value of articulating taste

(15:33) Demo: Creating a slide deck evaluator GPT

(19:19) Testing your new GPT

(21:32) Scaling GPTs across your team

(23:52) Demo: Using AI to improve your writing

(30:32) Lightning round and final thoughts

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Tools referenced:

• GPTs: https://chat.openai.com/gpts

• ChatGPT: https://chat.openai.com/

• Claude: https://claude.ai/

• Bolt: https://bolt.new/

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Other references:

• Whoop: https://www.whoop.com/

• Norwegian School of Economics: https://www.nhh.no/en/

• Researchers at NHH have uncovered significant gender disparities in the adoption of generative AI tools like ChatGPT: https://www.nhh.no/en/nhh-bulletin/article-archive/2024/september/study-reveals-gender-gap-in-ai-tool-usage-among-students/

• How to Become a Supermanager with AI: https://maven.com/hilary-gridley/ai-powered-people-management

• Girls in the Loop: https://grrlsintheloop.ai/

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