People asked for this after I mentioned it on Threads, so here is the concrete version.
This is not a thought experiment. It’s not a “demo app.” It’s a working tool I use daily.
The simplest description is: I built myself an executive team that lives in Slack.
The Problem
Most people approach AI with a single chat thread and a single assistant persona.
It’s convenient, but it carries two failure modes:
First, the assistant becomes “generically helpful.” It tries to be agreeable, comprehensive, and safe. When you ask a vague question, it answers with a vague blanket.
Second, you end up with one dominant perspective. Even if the assistant is smart, it’s still one voice, one posture, one set of defaults. Real decisions rarely improve under a single posture.
What I wanted instead was closer to how high-stakes decisions happen in practice: specialized opinions, disagreement, and a bit of productive discomfort.
Real executive teams do not converge by default. They argue. They challenge. They correct each other.
If you want clarity, you want tension.
The Solution (The Calm Way)
The “AI Executive Board” is a set of narrowly-defined personas that share a workspace.
Each executive has:
- a clear mandate (what they are responsible for)
- a narrow success metric (how they judge “good”)
- a strong bias (what they protect, what they refuse)
The most important design choice is that they do not try to be helpful in general.
They try to be correct in their domain.
That constraint changes the texture of the conversation. Instead of one assistant trying to cover everything, you get multiple specialists pulling in different directions.
Example: Chief Reality Officer
The Chief Reality Officer is brutally grounding and profit-focused. She’s allergic to delusion, and she’s not interested in protecting my feelings.
I assigned her to a project I emotionally love: the kind of project you defend with taste and identity and a quiet hope that the world will “eventually see it.”
The problem is that emotional love does not pay rent.
Her job is to confront the mismatch between what I’m attached to and what produces monetary results. When I propose a plan, she asks the questions I’d rather avoid:
What is the actual business model?
What is the evidence that anyone wants this?
What is the next measurable step, not the next build step?
It creates friction. That friction is the point.
Example: Chief Growth Officer
The Chief Growth Officer is focused on growth through communication: talking to people, outreach, feedback loops, distribution.
She exists to counter my default tendency to build quietly and hope people will “just find it.”
She often contradicts the CRO. Where the CRO will try to cut, the CGO will push for experimentation in the market. The arguments are not bugs; they are the mechanism.
What It Feels Like
The surprising part is not that the answers are good.
The surprising part is that it feels like internal debate externalized into a system.
I’m not asking, “What should I do?”
I’m watching arguments unfold, then choosing which argument is most aligned with reality.
Sometimes it’s annoying. Sometimes it’s uncomfortable. It is almost always useful.
That’s how decision-making should feel when you’re taking it seriously.
The Technical Foundation (Minimal, On Purpose)
I intentionally kept the first version simple:
- Node / TypeScript
- a Slack app (private workspace)
- Supabase for storing the executive definitions and state
The first working version took about 2 - 3 hours.
Not because it was “easy,” but because I didn’t overbuild it. I treated it like an Operator project: define the flow, define the constraints, then let the system execute.
Guardrails and Power-Ups
After the initial version proved useful, I added guardrails and a cost reporter.
The biggest unlock, by far, was file support.
Text-only messages are fine for opinions, but limiting for real work. Once executives could read a document, a screenshot, a spreadsheet, or a draft, the quality of analysis jumped. It stopped being “chat about work” and started being “work.”
Hiring, Firing, and Noise Control
Executives are defined in Supabase.
Hiring is a row. Firing is a boolean flag.
No redeploys, no ceremony, no drama.
The second key is keeping the system quiet.
I use two simple rules:
If I tag an executive, they respond.
If I don’t tag them, they respond only when a relevance threshold is met.
That prevents the board from turning into a constant interruption machine. It stays available without being noisy.
Context Management (Underrated Feature)
The board has a “general context” that I can add to and remove from inside Slack.
Most people treat forgetting as a failure mode. In practice, forgetting is a feature. Old context becomes stale. Old constraints become accidental laws.
The ability to subtract context keeps the system light.
It’s the same principle as good software: remove what is no longer true.
Cost vs Value
The monthly cost is roughly $5.
The value is not subtle: constant strategic pressure, clearer decisions, and less self-deception.
It’s not that the board “tells me what to do.”
It makes it harder for me to lie to myself.
Operator Takeaway
This is not about “AI replacing executives.”
It’s about delegated perspective and intentional friction.
A single assistant optimizes for being helpful.
An executive board optimizes for being correct in conflict.
And for an Operator, that’s the whole point.