How I AI How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop)
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May 19, 2025 
Hilary Gridley, Head of Core Product at Whoop, discusses how she leverages custom GPTs to enhance team management. She explains a method for creating GPTs that mirror her decision-making style, allowing her to focus on more strategic tasks. Hilary delves into the importance of clear evaluation rubrics for AI, uses AI to elevate team writing and presentations, and emphasizes how these technologies can democratize effective management practices. Her insights also highlight the need for inclusivity in AI, particularly for women in tech.
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Reverse Engineer Your Criteria
- Start by collecting examples of good and bad work to reverse engineer your decision criteria.
- Use these examples to help AI learn your preferences before tuning for specificity.
Create Clear Evaluation Rubrics
- Use AI to articulate core criteria that define good work based on your examples.
- Refine the AI's output by asking it to be more specific until the criteria perfectly reflect your standards.
AI Mirrors Managerial Evaluation
- AI tools naturally match managerial evaluation work, helping scale your management style.
- Creating GPTs to evaluate work like a leader boosts consistency and saves time.