You & AI workshop series

“I feel behind.”

That’s the most common thing I hear.

The truth? There will never be a better time to learn. The You & AI workshop series is designed not just help you catch up but to help you join the top 10% of AI users by changing how you interact with these tools entirely.

This isn’t a surface-level tour of prompting tricks. It’s a hands-on, practical experience designed to help you collaborate with AI in ways that actually move your work forward—faster, sharper, and with less friction.

The sessions

Each session builds a new dimension of AI fluency, compounding into greater confidence and capability.

  • AI isn’t a magic typewriter, but it can be a great collaborator throughout the writing process. Learn to build a writing partner that edits to your voice and preferences and coaches you in the ways you want to grow as a writer.

  • Projects can turn ChatGPT into a personal operating system—one that remembers your goals, holds relevant files, and evolves with your work. Learn to layer project instructions, prompting strategies, and token memory to create high-leverage workflows for tasks like writing, networking, and planning (whether your week or your meals). Think of it as training a junior collaborator who gets smarter with each interaction.

  • Explore how to turn AI into a knowledge partner—one that helps you remember what matters, synthesize across sources, and surface insight you didn’t know you had. You’ll learn to use tools like NotebookLM for source-grounded analysis, Internal Knowledge to mine your own drive, and Deep Research to explore unfamiliar terrain. Whether you’re working on long-term strategy, institutional memory, or deep content creation, this session shows how AI can help you think not just faster—but more coherently over time.

  • Learn how to turn AI into a lasting thought partner—one that evolves with your goals, adapts to your working style, and builds real memory over time. We’ll show you how to use persistent memory to keep projects coherent, sharpen your communication, and surface your own thinking patterns. By the end, AI becomes more than a tool—it becomes a mirror for your habits, strengths, and growth edges, helping you make smarter, more reflective decisions.

  • Learn how to use AI as an analytic partner that surfaces patterns, challenges assumptions, and pushes your thinking further. Whether you're working with surveys, financial data, or messy qualitative insights you’ll learn techniques to move from raw inputs to meaningful conclusions. We’ll walk through how to frame smart questions, guide AI through your data, and extract insights that go beyond the obvious.

Logistics

Duration: 5 sessions, 60 minutes each, on Zoom

Style: These are small live seminars, designed to be interactive

Enroll in an upcoming series

Fridays: July 11, 18, 25, and August 1 & 8 at 10:00am ET

Fridays: Aug 1, 8, 15, 22, & 29 at 12:00pm ET

Fridays: Aug 22, 29, Sept 5, 12, & 19 at 10am ET or 2pm ET

Past participants came from organizations like these

  • "The course has sparked so much new energy...and that has felt so electric and fun. This honestly might be the best professional development class I've taken in 25 years and several different industries."

  • “This course will save you so much time.”

  • “I came in with essentially zero familiarity and now feel like I know the fundamentals of what AI can do and how I can play with it, test its limits, and integrate it into my life.”

  • "I realized I was using 1% of what ChatGPT has to offer."

Your instructor

I’m Sarah Dillard, an entrepreneur and educator.

I first got interested in LLM tools after reading collected pieces about them in the 2020 Best American Science & Nature Writing. This led me to start experimenting before ChatGPT had even launched. When it did, it immediately felt like a game-changer. So much so that I wrote the first education sector op-ed on ChatGPT: “Schools Must Embrace the Looming Disruption of ChatGPT.”

I’m now founding The Rock Creek School, which blends timeless liberal arts ideas with modern tools like AI and data science. I also advise Harvard Business School on the design of their online entrepreneurship program, with a focus on how AI is reshaping what—and how—we teach.

I have an MBA from Harvard Business School & an MPP from the Harvard Kennedy School and started my career at Bain & Company. When not collaborating with AI, I enjoy hiking, hosting friends, and hanging out with my nieces (7 & 4).

FAQs

  • Some people start from no/low background & some start from daily professional use. The destination is the same either way: the series is designed to get people into top 10% of AI use.

  • If you can already do all of these things fluently, you may be looking for something more advanced:

    • Choose the right model (e.g., o3 vs 4o) based on the task

    • Use Projects as lightweight operating systems

    • Manage persistent memory to shape AI interaction

    • Activate hybrid routing to ensure the right tool is used behind the scenes

    If you have questions about fit, please feel free to contact me.

  • You'll need a ChatGPT account to participate. You don't have to pay for ChatGPT to join, but it will be easier to follow along and implement all that you are learning if you do.

    This course will focus on OpenAI's ChatGPT, and I'll be demoing from a paid ChatGPT account ($20-$30/month), which has more powerful features than free accounts.

  • If you add your email address here, I'll notify you when we open future trainings.

  • I'll send you a recording of the training for personal use that is good for seven days for personal use.

  • Unfortunately, once you're registered, we aren't able to offer refunds but can issue a credit that you can use to enroll in a future course.