How to build your own board of advisors in Claude

I built an AI board of advisors recently, and it came out of a conversation that went badly.

I was heads down on our AI work, project managing and product managing it week to week, so far in the weeds that I was mostly thinking about what we were shipping in the next few days. Then I sat down for breakfast with a few venture capitalists, and the conversation fell flat. They'd ask where the business was going (thinking in a 5-10 year time horizon), and I'd answer where it was going to be in December. It was a completely different mental model, and it made me realize I had these blind spots.

When I'm running the business I'm deep in the details, and when I go talk to people outside of it who are thinking on totally different time horizons and asking different questions, I'm not in that headspace at all.

So I built a board to get myself there.

It's a set of personas in Claude, each one a business leader or long-term thinker I'd love to have in the room. Steve Jobs is on mine. He might be the best salesman and pitchman who ever lived, which makes him worth having around before any big pitch, and now I'll literally use him to practice or get into the right headspace before a big conversation.

Tique and I talked through all of this on a recent episode of the podcast. Here's how to build one worth using.

A board is only valuable if it's built around the things you're weak at. So before you pick anyone, get honest about where your gaps are, and then ask who's good at that.

If you're a travel advisor, your first instinct might be another advisor you admire, or a travel influencer you follow. That can work. Just know that the value you get from a persona scales directly with how much Claude already knows about the person, because that's what lets it actually embody them.

Steve Jobs works with almost nothing from you. There are decades of books and interviews about how he thought, so his name alone carries a point of view. Someone who isn't well known and doesn't have much written about them comes through thin, because the model has little to draw on.

So think big here. You want people who are famous enough, and have had enough written about them, that Claude can step into the persona just from the name.

Examples you may consider:

I wish I was better at business strategy —> Consider someone like Jeff Bezos, Steve Jobs, or Jim Collins
I wish I was better at the numbers —> Consider an investor like Warren Buffett, Bill Gurley, etc.
I wish I was better at creating that incredible client experience —> Consider someone like Brian Cheksy from Airbnb or Danny Meyer.

If you don’t know, try asking Claude or your AI of choice who the best people in the world are at a particular task.

Give each person a real job

"You are Steve Jobs" is a weak instruction. It's much better to be clear about what you want that persona to do.

I want Jobs on my board because he was one of the best storytellers and showmen who ever existed, and I want him showing up thinking about the sale and how we build a movement around what we're doing. I also want his ruthlessness about focus. When I bring the board a plan, I want Jobs pushing me to cut everything that isn't essential.

Doug Leone is on there for a different reason. I want him zeroing in on the economics and pushing until every single thing I'm saying holds up from a finance perspective. Give each persona that kind of context, tell the AI what to pull from, and the board gets far more useful than a list of famous names.

Be honest about how you show up

The more honest you are when you build this, the more you get out of it.

Something else came out of that breakfast. One of the VCs was generous enough to tell me, straight, how I came across in the room. I came across less serious because I’d couch beliefs in hedges. I thought I was being polite but I was perceived as unsure.

I took that feedback and fed it into the board. Now it knows the specific ways I tend to fall short, like skipping steps because they're obvious to me, or slipping into cautious operating language when I should sound urgent. Once the board knows your failure modes and the habits you fall into by default, it can use the personas to catch you in the act.

Tell it how you want it to behave

You also get to tell the board how to act.

In mine, I set up a few different modes depending on what I need. On some problems I told the board to slow down and understand what I'm asking before it says anything, and only start poking holes once it gets it. Other times I want it to go straight at a draft and tear it apart.

Use this to cover your own habits. If you know you tend to give the AI too little to work with, tell the board to ask you a batch of questions first, before it weighs in at all. The more you know about your own strengths and weaknesses, right down to how you work with AI, the more the board gives back.

Here's what mine looks like

I've built a few of these now. The one I lean on before a fundraise is 4 people, each there for a specific job.

Bill Gurley is the VC across the table. His job is to ask whether the story survives after I leave the room, when the partner who liked me has to repeat it to their own partnership and win them over without me there.

Brian Chesky is there for translation. He catches the moments where I jump from A to M because the middle steps are obvious to me and invisible to everyone else.

Andy Raskin works on the narrative before anything else. He makes me write the strategy in 200 words a 14-year-old could follow. If I can't, we don't move on.

Frank Slootman handles urgency and ambition. He flags every place I sound like I'm rationing runway instead of pressing an open window, and every place the language is too small for what we're building.

Yours won't be about talking to venture capitalists. If you run a travel business, your board might be someone who's brilliant on marketing, a hospitality legend for the client experience, and someone who makes you defend your pricing.

Save it as a skill

Once you know who's on your board, save the whole thing as a skill.

You could build it as a project, but a skill is better, because you can use it everywhere in Claude. Once it's set up, you just type / and the skill name in any chat or project and your board is there. And you don't have to figure out how to write it, because Claude knows how to make skills. You describe what you want and it builds it for you.

Here's a prompt to get you started. Open Claude and say something like this:

I want your help creating a skill we'll call Travel Agency Strategist Board. I want these 5 people on the board:

Steve Jobs, for storytelling and getting people to want what I sell
Danny Meyer, for hospitality and the client experience
Jeff Bezos, for long-term thinking and customer obsession
Doug Leone, for the economics and the finances
Seth Godin, for marketing and standing out

Here's what I want the board to push me on:

Whether my pricing and margins actually hold up
Whether my client experience is memorable or just fine
Whether I'm building for this year or the next 10
Whether my marketing gives people a reason to choose me
Whether I can tell the story of my business in a way that makes people act

The goal of the board isn't consensus. It's to push my thinking and help me get better. What else do you need me to tell you about this board to truly create a world-class board that will help me grow my business?

Swap in your own people and your own list. Those 5 are just a starting point.

That last question is the one that matters. It gets Claude to interview you before it builds anything, so you end up with a much better board.

Then start using it. Bring it a decision you're stuck on or a pitch you're about to give, and let the board push on it.

The full conversation with Tique is on the podcast if you'd rather hear it out loud.

How to build your own board of AI advisors