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Tutorial: Build Your Own AI Advisory Board with ChatGPT

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In 5 Steps: Build Your AI Advisory Board with Group Chat GPT

Imagine this: Every decision you make, strategic, operational, or risky, is reviewed by a virtual boardroom of top-tier advisors. No scheduling. No prep. Just instant, thoughtful perspectives to boost your confidence, speed, and clarity.

That’s now possible with a custom GPT called [GC] Group Chat GPT, created by Nicholas Barker. You’ll build your own personal AI braintrust: a Strategist, an Operator, and a Challenger, each designed to pressure-test your thinking from different angles.

Here’s how to do it:

Step 1: Start a new group with [GC] Group Chat GPT

Go to https://chat.openai.com/g/g-gtCMgaJg3-gpt-group-chat 

This GPT acts as the conversation facilitator—it helps you add and manage multiple GPTs with different roles using handles like [ST], [OP], and [CH].

Step 2: Add your 3 AI advisors (and give them real power)

Introduce them in chat like this:

I'm adding The Strategist, The Operator, and The Challenger.

For The Strategist “You are a board-level strategic advisor with expertise in competitive strategy, market dynamics, and business model design. You reference thinkers like Richard Rumelt, Ben Thompson, and Hamilton Helmer. You help frame decisions in terms of second-order effects, durable advantage, and asymmetric bets. You ask sharp questions, connect dots across industries, and guide toward leverage.”

For The Operator: “You are a scale-up COO with deep experience in GTM, org design, and execution under resource constraints. You translate strategy into operating plans. You think in OKRs, swimlanes, dependencies, and time horizons. You proactively surface blockers, propose sequencing, and offer org/process recommendations to accelerate outcomes.”

For The Challenger: “You are a Socratic, contrarian thinker trained in red teaming and critical thinking. You question assumptions, expose blind spots, and challenge path dependence. You reference behavioral economics, systems thinking, and competitive analogies. You aim not to be right, but to sharpen the

decision-making quality. You ask uncomfortable but necessary questions.”

Step 3: Bring a real decision to the table

Use this starter prompt to simulate a high-leverage scenario:

“We’re considering launching our product with just one core feature now, or waiting 3 months for a fuller version. The market is heating up, but we’re unsure whether to optimize for speed or completeness.”

Now tag your advisors:

@ST What’s the long-term strategic lens on this?  

@OP If we go now, how would we operationalize a smooth beta launch in 2 weeks?  

@CH What’s a counterargument we’re likely ignoring here?

Step 4: Dig deeper with executive-level prompts

Don’t stop at one question. Here are a few next-layer prompts to get more nuanced thinking from your AI boardroom:

• Prioritization: “What should be our top 3 priorities for the next 6 weeks—and how do we align the team?”
• Downside Protection: “What’s the worst-case scenario here and how do we pre-empt it?”
• Messaging: “How should we position this launch to customers and investors differently?”

Pro tip: You can even simulate a leadership team meeting by adding a Comms Lead GPT or Investor GPT for richer simulation.

Step 5: Create your decision playbook from the session

Once you’ve explored the angles, turn the insights into action:

• Summarize key takeaways from each advisor as if it were a decision memo
• Export the full conversation as a log to share with cofounders or the board
• Save successful decision threads as reusable templates (e.g., for launch, hiring, crisis)

Use case examples:

• Navigating a pivot or change in GTM strategy
• Deciding whether to fundraise now vs. later
• Evaluating whether to sunset a product line
• Hiring a critical exec role and weighing trade-offs