The AI Leadership Playbook
Discover where AI can create the greatest leverage in your business.
AI is an incredible employee… but a terrible CEO.
If there's one thing I hope you remember from today's presentation, it's this:
AI is an incredible employee… but a terrible CEO.
Most business owners don't need another AI tool. They don't need another list of prompts. They need clarity. They need to answer one simple question:
If AI became my next employee tomorrow, what is the most valuable job I could give it?
This workbook is designed to help you answer that question.
Before you begin:
- Open a new ChatGPT conversation.
- Work through each Leadership Conversation in order.
- Keep everything in the same chat.
- Don't skip ahead — each conversation builds on the previous one.
The more AI understands your business, the better it can help you. By the end of this workbook, you'll know exactly where AI can create the greatest leverage in your business — and you'll have a clear first project to begin.
Meet Your New AI Employee
Imagine you hired an incredibly intelligent employee tomorrow. They can research, write, analyze, organize information, brainstorm ideas, solve problems, and learn quickly. But before you assign them work… they need to understand your business.
Copy the conversation below into ChatGPT.
I want you to act as my CEO coach and business advisor. Your first job is not to solve problems. Your first job is to understand my business. Ask me one question at a time. Keep asking questions until you're confident you understand: • My business model • My customers • How I make money • My team • Where I spend most of my time • My biggest frustrations • What repeatedly gets pushed aside • Where I believe I'm the bottleneck • My biggest growth opportunities • What I wish I had another employee doing Do not recommend solutions until you fully understand my business. When you're ready, identify the five highest leverage opportunities where AI could create value. Rank each opportunity based on: • Business impact • Time savings • Frequency • Ease of implementation • Return on investment • Whether I am personally the bottleneck Explain why each opportunity earned its ranking. If you disagree with where I think AI should help, challenge my assumptions.
Choose the Right First Job
Not every opportunity deserves your attention today. Continue the same conversation.
Let's focus on Opportunity #1. Before we move forward, I want you to challenge this decision. Play devil's advocate. If you believed another opportunity deserved a higher priority, what argument would you make? Help me decide whether this is truly the best first project for AI.
Define the Real Problem
Great leaders don't solve unclear problems. Before discussing solutions… make sure everyone understands the problem.
Now help me define the real problem. Ask me one focused question at a time. Keep digging until you're confident you understand the root cause. When you're ready, summarize: • The real problem • Why it exists • The impact it's having • What happens if I never solve it Don't recommend solutions until I agree with your summary.
Define the Mission
Now think like the CEO. If you hired a real employee to solve this problem… what would success actually look like?
Now help me define the mission. Help me clearly identify: • The outcome I'm trying to achieve • What success looks like • What should be prioritized above everything else • Any important constraints Challenge anything that isn't clear before moving forward.
Give Your AI Employee Better Context
Great employees make better decisions when they understand your business. Great AI works exactly the same way. Before asking AI for recommendations, gather as much relevant information as possible.
Before making recommendations, review everything I've shared. Tell me what additional information would help you better understand my business before moving forward. If there are gaps in my thinking, point them out.
Hire Your AI Employee
Up until now, you've been interviewing your AI employee. Now it's time to start working together.
Based on everything we've discussed, I want you to become my AI employee for this project. Tell me: • What you should own • What I should continue owning as CEO • What information you'll need from me on an ongoing basis • What we'll work on together • The first thing we should do tomorrow morning • The biggest mistakes we should avoid • How we'll know we're succeeding
Final Thought
AI will continue to get smarter. New models will be released. New tools will come and go. But leadership doesn't change.
The business owners who get the greatest value from AI won't be the ones who know the most about AI. They'll be the ones who know the most about their business — communicate clearly, think strategically, and lead AI like the incredible employee it is.
Because AI is an incredible employee… but a terrible CEO.