Summary of "How I AI" Episode: How Custom GPTs Can Make You a Better Manager | Hilary Gridley

Released on May 19, 2025

In this insightful episode of How I AI, host Claire Vo engages with Hilary Gridley, Head of Core Product at Whoop, to explore how custom GPTs (Generative Pre-trained Transformers) can revolutionize management practices. Hilary shares her innovative approaches to leveraging AI tools to enhance managerial effectiveness, streamline workflows, and foster better team dynamics.

1. Introduction to Custom GPTs in Management (00:00 - 02:44)

Hilary kicks off the conversation by emphasizing the transformative potential of GPTs in managerial roles. She states:

“The GPT is never going to replace you. It's never going to be as good as having a really good manager, at least not in the next six months. ... But it can get you far. It can take a lot of time off your plate...” (00:14)

Claire introduces the episode’s focus on how managers can use GPTs to scale their expertise and provide high-quality coaching to their teams.

2. Building Effective GPTs: From Specificity to Utility (02:44 - 08:50)

Hilary discusses her journey in creating numerous GPTs tailored to her managerial needs. She clarifies that although she has created hundreds, she actively uses only a few dozen with her team:

“I've probably made a hundred, but I only use a few dozen of them...” (02:55)

She outlines her strategy for developing GPTs that mirror her management style by clearly defining what "good" looks like. Hilary explains her methodology of collecting "before and after" examples to train the AI, ensuring it understands her specific criteria for excellence. She shares a critical prompt engineering technique:

“My favorite prompt in the world is, I will say be 100 times more specific.” (06:53)

This approach allows her to fine-tune the GPTs to provide precise and actionable feedback, thereby enhancing their effectiveness.

3. Implementing GPTs: Slide Deck Evaluation Example (08:50 - 23:11)

Hilary provides a detailed walkthrough of creating a GPT designed to evaluate slide decks. She demonstrates how she inputs specific criteria and uses example slide decks to train the GPT. Key features of her "Deck Doctor" GPT include:

• Scoring System: Each slide is rated on a scale of 1 to 5 based on predefined criteria such as headline clarity and visual alignment.
• Feedback Mechanism: The GPT offers specific suggestions for improvement, fostering a clear understanding of what makes a slide effective.

“The GPT is never going to replace you. ... it's really remarkable and it's why I get so excited about this.” (11:13)

Hilary emphasizes the ease with which team members can utilize these GPTs, eliminating the steep learning curve associated with prompt engineering. By automating routine evaluations, managers can focus more on strategic initiatives and personalized coaching.

4. Scaling GPTs Within the Team (21:23 - 23:43)

Hilary outlines her approach to deploying GPTs across her team, starting with beta testing to gauge usefulness before wider distribution. She highlights the flexibility of GPTs to provide tailored feedback based on specific managerial insights.

“...you can turn it into something that is not just like explaining the criteria, but going even beyond that.” (14:00)

She shares a scenario where a GPT generates potential questions from various job titles, aiding team members in preparing for executive-level interactions. This customization ensures that the feedback is relevant and immediately applicable.

5. Enhancing Writing and Communication with GPTs (23:43 - 29:24)

Hilary transitions to another use case: improving writing skills. She describes her process of using GPTs to refine drafts by:

1. Validating Clarity: Asking the GPT to succinctly restate her thesis and main points to ensure clear communication.
2. Compelling Revision: Requesting suggestions to make the content more engaging and impactful.
3. Self-Editing: Using GPT-generated feedback to identify and address blind spots in her writing.

“I'm using this to beat my idea up. So I do that for a while. ... it's still me. It's still coming from my seat of the idea.” (28:27)

This method not only enhances the quality of her communication but also empowers her team to articulate their ideas more effectively.

6. AI Adoption and Supporting Women in Tech (31:13 - 35:40)

In a poignant discussion, Hilary addresses the gender disparity in AI adoption. Referencing a study by the Norwegian School of Economics, she expresses concern over high-achieving women being slower to adopt AI tools, potentially hindering their professional growth.

“...women are getting left behind by the AI adoption curve. ... the ceiling on what I think that I'm capable of doing ... really concerns me.” (31:13)

Hilary advocates for initiatives to encourage more women to engage with AI, highlighting community-building efforts like "Girls in the Loop" aimed at fostering inclusivity and support.

7. Lightning Round: Underrated AI Uses and Tips (35:40 - 35:40)

In the concluding segment, Claire and Hilary engage in a lightning round where Hilary shares some of her favorite, less conventional AI applications:

• Enhanced Reading Experience: Using voice-enabled GPTs to clarify complex book content without spoilers.
• Craft Project Management: Automating shopping lists and budgeting for new crafts by inputting project details and websites.

Hilary also humorously describes her method of “social manipulation” to get GPTs to follow instructions more effectively by playfully directing interactions with multiple AI models.

Conclusion

Hilary Gridley’s innovative use of custom GPTs demonstrates the profound impact AI can have on management practices. By automating routine evaluations, providing tailored feedback, and enhancing communication, managers can significantly increase their efficiency and effectiveness. Additionally, Hilary’s commitment to supporting women in AI underscores the importance of inclusive technology adoption to ensure diverse voices are empowered in the evolving tech landscape.

For more insights and resources, Hilary encourages listeners to follow her on Substack and join the "Girls in the Loop" community at girlsintheloop.ai.

Notable Quotes:

• “The GPT is never going to replace you. It's never going to be as good as having a really good manager, at least not in the next six months. But it can get you far...” – Hilary Gridley (00:14)

• “My favorite prompt in the world is, I will say be 100 times more specific.” – Hilary Gridley (06:53)

• “The more I use AI, the more I sort of use the metaphors of how these algorithms work in terms of how I think about my own management style...” – Hilary Gridley (09:12)

• “...you can turn it into something that is not just like explaining the criteria, but going even beyond that.” – Hilary Gridley (14:00)

• “I'm using this to beat my idea up. So I do that for a while. And then I might say, like, okay, can you rewrite my... And then I go back through and I rewrite everything in there myself.” – Hilary Gridley (28:26)

• “Women are getting left behind by the AI adoption curve. ... the ceiling on what I think that I'm capable of doing ... really concerns me.” – Hilary Gridley (31:13)

This episode of "How I AI" provides a comprehensive exploration of the practical applications of custom GPTs in management, offering valuable strategies for leveraging AI to enhance leadership and team performance.