I gave myself a board

I wanted another opinion on the jewellery business we’re building.

There are people I know who are much better at business than me. People who would spot something obvious while I’m still working out which question to ask.

I kept thinking about who I could speak to. Then one day I asked ChatGPT who would make a useful board of advisors for this particular business.

I spent quite a while working out who should be on it.

I now have three simulated advisors: a Naval-inspired leverage strategist, an experienced bootstrapped jewellery operator, and a sceptical capital allocator.

They look at the same situation separately, challenge one another, then give me a recommendation. They can disagree. Doing nothing has to be an option.

Nobody had to accept an invitation.

That is the bit I keep coming back to. I can think about whose perspective would help, then try a digital version without needing an introduction, a meeting or anyone’s permission.

Who, not how, has become much more available than I was treating it.

The Naval-inspired one was an obvious choice for me. Freedom, ownership, leverage, building something that doesn’t require you to become its permanent employee. His interest in Eastern philosophy resonates with a lot of the inner work I’ve gone through too.

I like the way he thinks.

And, interestingly, that advisor often gives the answer I was already leaning towards.

The jewellery operator is the more useful discomfort.

That is probably my weakest seat. The practical commercial brain. What are we selling, to whom, at what margin? Can somebody we pay run the event profitably? What actually needs to happen before a customer can buy?

Otherwise, I could go off in my Navalisms for quite a while.

The capital allocator wants to know what we can lose, when the cash comes back, and whether this deserves any money in the first place.

Those are useful people to have in the room when I’m getting excited.

The most useful thing the board said in its recent review was that we had become much better organised, but had not yet demonstrated better economics.

Fair.

We had clearer priorities, people taking ownership, a growth roadmap and a lot of things worked out. The board kept asking whether any of that had turned into repeatable, profitable sales.

It gave me something specific to look at.

AI can be sycophantic. It can become an echo chamber. I’ve put instructions in place asking it to care more about truth than agreeing with me. I think that helps to a degree.

But the choice of seats matters too. I want perspectives that make me examine things I would otherwise skip.

And I still have to check what comes back. Three simulated advisors agreeing that an event looks profitable doesn’t establish whether it will be.

The slightly embarrassing realisation is how little I’ve extended this beyond myself.

If somebody owns commercial operations, why shouldn’t they have help examining an event’s economics? A perspective looking at staffing and practical delivery. Another checking the assumptions in the forecast.

They still own the outcome. They can use those perspectives to arrive with a better recommendation.

I’m already using AI for so much of my work, yet I keep catching myself trying to supply every kind of judgment from my own head.

There’s a lot I don’t know. Learning how to deal with that seems more useful than expecting to become good at everything.

So I’m trying to remember to slow down before disappearing into the how.

What outcome do we need? Who would be useful here? What would they look for?

Try a digital version. See what it catches. Get an actual person involved where that is what the situation needs.

There is still something I haven’t worked out, though.

When another human being believes I can do something I haven’t done before, it lands differently. Their conviction can make the next move feel possible.

Sometimes I’m asking for an assessment. Sometimes I think I’m asking to feel comfortable taking a step that hasn’t been proved yet.

I can now convene a board whenever I want.

I’m still finding out what makes me close the chat and act faster.