Prompting Techniques and Model Calibration

Rachel Wolan, the chief product officer at Webflow, has embraced AI not just as a product leader but as a hands-on builder. A coder since age 16, Rachel has returned to her technical roots by creating a custom AI chief-of-staff application that helps manage her executive workload. In this episode, she demonstrates how she uses personal AI software to prep for meetings, triage her calendar, manage emails, and even get brutally honest feedback about how she’s spending her time.

What you’ll learn:

1. How Rachel built a custom AI chief-of-staff application that integrates with her calendar, email, and more
2. Why building personal software can be a gateway to understanding AI’s capabilities for executives
3. How her AI agents help her prep for podcasts, dinners, and meetings with just-in-time information
4. The technical approach to building personal AI software using markdown files, API tokens, and multiple LLM interfaces
5. How Rachel organized company-wide “builder days” that dramatically increased AI tool adoption across her organization
6. Why she believes executives must lead by example in AI adoption to authentically drive organizational change

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Brought to you by:

Graphite—Your AI code review platform

Atlassian for Startups —From MVP to IPO

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In this episode, we cover:

(00:00) Introduction to Rachel Wolan

(02:26) Why Rachel started leaning into AI

(06:26) Building an AI chief of staff

(08:17) Prepping for the podcast

(10:00) Rachel’s morning flow with her AI chief of staff

(14:14) Designing a personalized interface with custom note cards

(16:34) Getting “brutal truth” feedback from your AI assistant

(19:34) Email triage and management workflows

(23:31) Prepping for networking dinners and events

(28:18) The result of building an AI chief of staff

(30:09) Organizing “builder days” to drive AI adoption

(35:38) Measuring the impact of AI adoption initiatives

(38:00) Lightning round and final thoughts

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Tools referenced:

• Claude: https://claude.ai/

• Claude Code: https://claude.ai/code

• Cursor: https://cursor.com/

• Google Calendar API: https://developers.google.com/calendar

• Gmail API: https://developers.google.com/gmail

• Webflow: https://webflow.com/

• Figma: https://www.figma.com/

• Make: https://www.make.com/

• Hex: https://hex.tech/

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Where to find Rachel Wolan:

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

X: https://x.com/rachelwolan

Webflow: https://webflow.com

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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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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.