Why your team still doesn't "get" category design (and how to fix it)

This is a 🏴‍☠️ Founding Members–Only 🏴‍☠️ post. Founding Members get access to the Pirate Eddie Bot to ask category design questions, weekly actionable insights, the full library with 20+ audiobooks 150+ mini-books, and more. See the Founders Deck here.

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Dear Friend, Subscriber, and Category Pirate,

We get this question all the time:

“How do I transfer category design to my team?”

It’s a reasonable question. You’ve read the mini-books. You’ve internalized the frameworks. You see the world differently now—and you want your team to see it too.

So what do most people do?

They drop a pile of reading assignments on their team’s desk. “Here, read these 20 mini-books. Then we’ll talk.”

And then nothing happens.

The problem isn’t your team. The problem is the approach.

Pirate Tom Schwab, founder of Interview Valet, ran into this exact wall.

He’s all in on category design. He wanted to teach it to his team. But he knew dumping a mountain of content on them wasn’t going to work.

So he tried something different.

He opened up the Pirate Eddie Bot—and started talking.

Not typing. Talking.

In about 30 minutes, Tom had a conversation with the Pirate Eddie Bot about who he was trying to teach, what he wanted them to learn, and what the end goal was. The Pirate Eddie Bot broke it down into a 3-month curriculum—what to focus on each month, each week, and which specific mini-books would have the biggest impact for his team.

30 minutes. A full training plan. Built by conversation.

Tom is now using that plan to execute and evangelize category design across his entire team.

You don’t transfer knowledge. You install thinking.

This is the distinction that changes everything.

When you give someone a stack of books, you’re asking them to do the synthesis work themselves. To connect the dots. To figure out what matters and what doesn’t. To translate theory into their specific context.

That’s a lot to ask—especially when they’re also doing their actual job.

Your team still needs to read. That’s how thinking changes.

But there’s a massive difference between “here’s 20 mini-books, good luck” and “here are the 3 mini-books that will shift how you see our business—read them in this order, and here’s what to focus on in each one.”

The first approach is overwhelming. The second is a path.

Your team doesn’t need to read everything. They need to read the right things, in the right order, for the right outcome.

That’s what the Pirate Eddie Bot helps you figure out.

It’s trained on every Category Pirates mini-book. Every framework. Every nuance. So when you have a conversation with it, you’re not guessing which content matters most—you’re getting a curated curriculum designed around your team, your business, and your goals.

Not sure what matters most for your team to learn?

Start there. Ask Eddie.

Tell him what your business does, where your team seems stuck, and what you’re trying to accomplish. He’ll help you figure out where the biggest gaps are and what will move the needle most.

When you implement this, here’s what changes:

You stop being the bottleneck.

Right now, every category decision runs through you. Every POV conversation. Every strategic call that requires someone to think different—it’s all waiting on you.

When your team thinks this way, they can move without you in the room. They can have conversations with customers you’re not part of—and nail the POV anyway. They can push back on “best practices” without needing you to give them permission.

You get people to jam with. People who speak the language. People who see what you see.

And the business?

It scales beyond your personal bandwidth. Your vision stops being stuck inside your head—and starts moving through your entire organization.

And the result?

You become the bottleneck for your own company’s growth. The thing you see so clearly can only move as fast as you can move. Your vision is stuck inside your head.

Tom figured this out. Now you can too.

Here are the 5 steps to build a category design training plan for your team:

Using the Pirate Eddie Bot.