Dear Regina,

Step 1: AI Chatbots are your new, on-demand, personal tutor.

Two years ago, if you wanted to learn anything new, you had to slog your way through SO MUCH MEDIA. You had to sort through a chaotic cacophony of information and decide what was worth consuming, and what to throw away.

As a kid, library catalog cards were your best friend for learning.

When high-speed internet became widely available, Google suddenly became indispensable.

Today, AI Chatbots are your new BFFs.

If I were breaking into a new industry today, I would start every morning with ChatGPT. I deeply believe that we’re underutilizing what is probably the most patient, smartest, and always-available tutor in the world.

A lot of people use ChatGPT to think for them. They do this by asking ChatGPT to write, make decisions, and analyze for them. They outsource their thinking.

But there is no instruction manual on outsourcing your thinking.

I feel so strongly about this, you can read more about it on my personal Substack below:

Don’t be the 99% that uses ChatGPT to think for you. Instead, use it to learn. Use it to extend your thinking.

When I wanted to learn about real estate syndications, I had ChatGPT walk me through what a general partner does versus a limited partner. When I wanted to learn Mandarin, it helped me practice characters. When I was prepping for a deep dive on mergers and acquisitions, I had it give me an entire 101 rundown.

I use ChatGPT every day to learn everything from breaking down Bible verses I don’t understand, to learning about pregnancy and women’s fertility, to studying the economy.

The smartest operators I know aren’t afraid to look clueless for the sake of getting competent. If you embrace that early, you will accelerate past people who are trying to fake their way to understanding.

Step 2: Build your own vocabulary doc. Update it religiously.

In every industry, there’s a language. And if you don’t speak it, you’ll constantly feel like an outsider - even if you technically understand the concepts.

A few years ago, I spent time exploring lots of startup opportunities in a huge array of industries, including cloud kitchens, CPGs, community, IVF fertility clinics, enterprise SaaS, and AI. I knew if I wanted to do good deep dives, I had to talk to a lot of smart people. And it would be easier for them to take me seriously if I spoke the same language as them.

With each conversation I had, I built on my already-existing knowledge base and incorporated their vocabulary into my language. Every conversation made me sound smarter, and it created deeper resonance with whoever I was talking to. That made them more likely to want to talk to me and help me.

Learning the terminology creates scaffolding. It helps you:

• Understand written and verbal context faster

• Build credibility with the people around you

• Spot patterns more easily

• Ask sharper questions

Start a personal glossary (I suggest in Notion, obviously!), with:

• Definitions of jargon you hear on calls

• Acronyms (e.g., ARR, TPA, DAC, etc.)

• Visuals or analogies that help you remember the concept

This is one of those “small effort, big result” systems. You’ll retain more. You’ll ask sharper questions. You’ll start sounding like someone who’s been there a lot longer than a few months.

If you go through all these steps in a company you’re already working at, turn it into evergreen material. Make it part of an “Onboarding 101” for anyone new.

You will instantly build credibility and look like an insanely efficient, thoughtful operator. Add screenshots or “explainers” under each term, and share it with your team in your company’s Notion or Confluence. (We’ll come back to this in Step 4!)

Step 3: Learn from a variety of content.

Books and articles are not the only way to learn. You don’t have to jump into a longform book as your first step.

Instead, start by watching YouTube videos and listening to podcasts.

If there’s a book that’s interesting to you, chances are the author has gone on a “media tour” to promote their work.

This results in:

• Big Think videos

• TED talks

• Tim Ferriss podcast episodes (though! Tim says he will no longer host people who are just looking to promote their books, since it results in the same one episode on twenty different podcasts. I actually think this makes this podcast even more valuable, since you’re likely to hear different info than what you might find on your run-of-the-mill pod.)

The media tour will give you a great summary of whatever the book is about. I like starting at the podcast or video level because it gives me a 15-20 minute digest on what to expect from reading a more longform book. If I’m still interested after listening to the video or pod, I’ll pick up the book.

YouTube and podcasts are not replacements for longform learning! From these, you usually get:

• 101-level foundation

• Bigger picture of the industry

• High level exposure to expert thinking and macro trends

But if you want something deeper, you’ll need to consume longform content. There’s no way around it.

That being said, don’t immediately dismiss easier-to-consume content. Queue up the podcast for your walk, then be prepared to engage in active learning through longform content, feedback and repetition on the job, and asking increasingly nuanced questions to smart people.

Step 4: Turn your learning into internal documentation.

During my undergrad studies at USC, I would frequently host study groups at Doheny Library right before midterms and finals. I printed out comprehensive study guides for everyone who came (usually, about half the class) and “taught” everyone by quizzing them and pretending to be a lecturer.

What they didn’t know is that I was learning while “teaching” them. By saying things like a lecturer - in an assertive way - it reinforced my own learning. All my classmates thought I knew the lecture material backwards and forwards - but the reality was I was internalizing the knowledge as I was teaching them.

Sneaky, I know - but it works. (It also made me a great piano teacher at the same time because of my ability to speak confidently about stuff I was still actively integrating. Fake it til you make it?)

Every time you want to reinforce your own knowledge, teach it to someone else.

You don’t have to host “Education 101” sessions at your new job (though you could!). The easiest way to teach others is to write it down in a way that someone else could learn from it too.

👉 Start a Notion wiki. Use this hub template to keep it clean. 👈

In it, document:

• Key product features and how they work

• Who owns what internally

• Processes you’ve had to learn the hard way

• FAQs from customers or new hires

• Cheat sheets for things like onboarding, analytics, compliance, etc.

When you do this, you’re no longer “just” learning. You’re codifying tribal knowledge. That’s what separates someone who’s onboarding… from someone who’s operationally excellent.

Step 5: Share your learnings in public. (Yes, even when you’re not an expert yet.)

Write weekly digests. Summarize what you’ve learned. Share product insights, frameworks, or even “what surprised me this week” roundups.

You’ll be surprised how many people will read what you’ve learned and respect you for sharing your learnings. Here’s a format you can use:

• TLDR

• Key things I learned

• Questions I still have

When you share what you’re learning, three things happen. First, you retain the info better. Second, you show that you’re constantly willing to learn and stretch yourself. And lastly, you create a high-integrity learning culture where knowledge isn’t hoarded or gatekept.

This is the part where you go from “the new person who asks a lot of questions” to “the operator who just 10x’d our onboarding ramp for future hires.”

Linked Resources:

• Notion Wiki / Company Hub Template | Coaching Founder

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.