Building an AI Board of Directors: AI-Powered Strategy for CEOs

Key takeaways

• Access instant expertise: Create an “always-on” advisory group of historical and contemporary business legends to stress-test your strategies.
• Eliminate risk: Use your AI board of directors to ask “dumb questions” and test radical ideas without risking credibility with your fiduciary board.
• Scale your decision-making: Move from solitary problem-solving to dynamic dialogue by leveraging diverse AI perspectives.

In the high-stakes world of executive leadership, decision-making often feels like a lonely endeavor. CEOs constantly navigate complex challenges — from strategic pivots to personnel issues — often with limited time and imperfect information. While a formal Board of Directors provides invaluable governance, a new, unconventional capability has emerged for the executive toolkit: The “AI Board of Directors.”

In a recent episode of The Markup AI Podcast, we discussed a concept that bridges the gap between traditional mentorship and generative AI. Matt Blumberg shared his experience building a virtual board comprised of business legends like Steve Jobs, Warren Buffett, and Clayton Christensen. This isn’t science fiction — it’s a practical application of Large Language Models (LLMs) that reshapes how leaders approach problem-solving.

This guide explores the concept of the simulated board, how it works, and how you can build your own to elevate your decision-making with the precision of Markup AI.

The concept: What’s an AI board of directors?

At its core, an AI board of directors is a set of custom-built AI agents designed to simulate the advice and perspectives of historical and contemporary business luminaries. Unlike a standard generative model that offers generic business advice, this tool is precision-engineered to role-play specific individuals based on their known philosophies, public statements, and behavioral patterns.

The CEO in our podcast describes his board as having “15 or 20 business luminaries on it.” This diverse group includes visionaries like Steve Jobs, value investors like Warren Buffett, and academic giants like Clayton Christensen. The goal isn’t to replace human advisors but to create an “always-on” sounding board that offers distinct, high-level perspectives on demand.

How it works under the hood

The effectiveness of an AI board of directors lies in the depth of its preparation. You can’t simply ask an LLM, “What would Steve Jobs do?” To retrieve truly valuable insights, the AI requires deep context and strict guardrails.

Deep research profiles

For every member of this board, you must generate a comprehensive behavioral profile. This goes beyond biography; it analyzes how that person acts as a board member. Does this person focus on product purity? Financial discipline? Disruptive innovation?

Why you need an AI board of directors (and why your real board isn’t enough)

You might wonder why a simulated board is necessary if you have a real Board of Directors. As our podcast guest emphasizes, “There’s no substitute for a real board.”

A real board has legal fiduciary duties and deep historical context. They are irreplaceable for governance. However, they have limitations regarding availability and the stakes involved. You often want to present polished strategies to a real board, not rough thoughts.

The simulated board fills these gaps:

• Instant availability: Consult your board at 2 a.m. There is no scheduling, no agendas, and no time limits.
• Risk-free environment: Test your wildest ideas without fear of judgment or losing credibility.
• Diverse perspectives: Instantly triangulate a problem through radically different lenses to reveal friction and new paths forward.
• Thought partnership: Turn the solitary act of thinking into a dialogue.

Case study: “What would Steve Jobs do?”

One of the most compelling examples involves the Steve Jobs persona. While the AI version of Jobs doesn’t shout, it captures the essence of his rigorous standards.

If you pitch a feature-heavy roadmap to a generic AI, it might say, “Ensure your product is user-friendly.” However, a specific “Steve Jobs” agent — enforced by Markup AI guardrails — might retort, “This interface is cluttered. Simplify it or don’t launch.”

The emotional weight and specific framing of the feedback push a CEO to think differently. Similarly, a Clayton Christensen persona would view problems through the lens of The Innovator’s Dilemma, looking for low-end disruptors rather than competitor features.

By toggling between these viewpoints, you run a stress test on your strategy against the greatest business minds in history.

How to build your own simulated board

You don’t need to be an AI engineer to assemble your cabinet of legends. Follow this framework to create your own board using today’s tools.

1. Select your board members

Do not just pick famous names. Select archetypes that balance each other out:

• The Visionary (e.g., Steve Jobs) for quality and imagination.
• The Strategist (e.g., Michael Porter) for theoretical soundness.
• The Operator (e.g., Sheryl Sandberg) for process and scaling.
• The Skeptic (e.g., Warren Buffett) for risk assessment.

2. Create the deep research profiles

Teach the AI who it is pretending to be. And use the AI to generate these baselines.

• Prompt action: “Write a detailed profile on [Name] focusing on their style as a strategic advisor. Highlight core philosophies, decision-making frameworks, and communication style.”

3. Craft the system prompt

This acts as the instruction manual for your session. Define the roles clearly.

• Structure: “You are a simulated Board of Directors. I’ll present a problem, and you will role-play a discussion. Steve Jobs: Focus on product excellence. Warren Buffett: Focus on long-term value. Rule: Debate and offer conflicting advice based on your unique perspectives.”

4. The board meeting

Present your dilemma. Watch as the personas argue their specific viewpoints. This friction is where the insight lives.

The future of executive coaching

The simulated board is just one example of how AI is moving from a tool for production to a tool for cognition. It represents a democratization of wisdom, making the mental models of elite leaders available to any entrepreneur.

However, remember that this is a simulation. The AI does not know your secrets, can’t predict the future, and lacks the moral weight of a human mentor. But as a tool for overcoming writer’s block and expanding your strategic horizon, it is unmatched.

So, the next time you face a “bet the company” decision, call a meeting with your simulated board. Steve, Warren, and Clay are waiting in the lobby.

Frequently Asked Questions (FAQs)

Is a simulated board a replacement for real advisors?

No. A simulated board lacks fiduciary responsibility, human nuance, and deep knowledge of your specific internal team dynamics. It’s a tool for ideation and stress-testing strategies, not for final governance decisions.

How does Markup AI improve the simulated board experience?

Generic LLMs often “drift” into generic advice. Markup AI Content Guardian Agents^SM ensure consistency. They scan the generated responses, score them against the specific persona profile (e.g., “Is this aggressive enough for Steve Jobs?”), and rewrite the content to ensure the advice stays authentic to the simulated character.

Can I use this for confidential information?

You should always prioritize data security. Ensure you are using an enterprise-grade instance of your LLM or API that guarantees your data isn’t used to train public models. Markup AI integrates with secure pipelines to ensure your content and prompts remain protected.