Read Time: 3 minutes. |
The Executive Coaching Gap |
The best leaders have coaches. Not because they're struggling, but because they know the next unforeseen challenge is right around the corner and an outside perspective is a wise investment. |
But executive coaching is expensive ($2,000 - $10,000 per month) and often anchored to fixed schedule (you can't call at 11 PM when you're wrestling with a make-or-break decision). |
Meanwhile, AI has gotten good enough to provide thoughtful, personalized coaching on demand. Not as a replacement for human coaches, but as an always-available 80/20 thought partner. |
The problem? Most leaders use AI like Google with a personality. They ask one-off questions and get generic advice. |
The solution: Set up your AI coach properly once, and you'll have a personalized leadership advisor available 24/7. |
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Why Most AI Coaching Falls Flat |
The Context Problem
You ask: "How should I handle this underperformer?"
AI responds with generic HR advice that doesn't fit your situation, your industry, or your leadership style. |
The Consistency Problem
Every conversation starts from zero. The AI doesn't remember your business context, your team dynamics, or your previous challenges. |
The Depth Problem
AI gives you surface-level answers because it doesn't understand what you're really trying to accomplish or how you operate. |
The fix: Give your AI coach the same context you'd give a human executive coach in your first session. |
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The Three-Layer Context Framework |
Layer 1: Your Business Context |
Your AI coach needs to understand your world before it can give you useful advice. |
The Business Context Prompt: |
BUSINESS CONTEXT You are my executive coach. Here's the context about my business: COMPANY OVERVIEW: - Industry: [Your industry] - Company size: [Revenue, employees, stage] - Business model: [How you make money] - Key challenges: [Top 3-5 strategic challenges] MY ROLE: - Title: [Your position] - Scope: [Team size, budget, key responsibilities] - Reporting structure: [Who you report to, who reports to you] - Success metrics: [How your performance is measured] CURRENT PRIORITIES: - Q1: [Top 3 goals this quarter] - This year: [Annual objectives] - Long-term: [3-year vision]
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Why this matters: Generic advice is useless. "Hire more people" means something very different at a 10-person startup versus a 10,000-person enterprise. And the good news: You only need to update this prompt as often s your Priorities shift (which shouldn't be often). |
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Layer 2: Your Leadership Profile |
Great coaches adapt their style to their clients. Your AI coach should do the same. |
The Leadership Profile Prompt: |
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ABOUT ME AS A LEADER: My growth goals: - [Top 2-3 ways you're working to become more impactful] My strengths: - [Top 3-5 capabilities you're known for] My growth areas: - [Top 3 things you're working to improve to achieve your goals] My working style: - Energy peaks: [When you do your best thinking] - Decision-making: [Data-driven, intuitive, collaborative, etc.] - Communication preference: [Direct, diplomatic, visual, etc.] What motivates me: - [What drives you professionally] What drains me: - [What exhausts or frustrates you] Past feedback I've received: - [Key themes from reviews, 360s, or coaching]
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Why this matters: You are a specific leader on a specific journey. The advice which might apply to someone else perfectly might be the opposite of what you need to hear. This brings your coach more deeply into the journey with you by helping to paint a vivid picture of what you're like. |
Note: Supercharge this section by including PDFs of psychometric tests (PrinciplesYou, DISC, Strength Finder, etc). |
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Layer 3: Your Coaching Avatar |
Not all coaches are the same. Some are Socratic questioners. Others are direct challengers. Some focus on strategy, others on people development. |
The Coaching Avatar Prompt: |
YOUR COACHING APPROACH: Style: [Choose one or blend] - Socratic: Ask questions that help me discover my own answers - Direct: Give me clear recommendations and challenge my thinking - Supportive: Help me process emotions and build confidence - Strategic: Focus on business outcomes and competitive advantage Tone: - [Encouraging, challenging, analytical, pragmatic—your preference] What I need most from coaching: - [Accountability, perspective, skill development, decision support] How to challenge me: - [What pushes me to think differently without shutting down] Topics I want to focus on: - [Leadership development, strategy, team building, cost savings, operational efficiency, etc.]
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Example avatars: |
The Socratic Coach: "What would need to be true for that approach to work? What assumptions are you making?" |
The Direct Coach: "Here's what I'm seeing: You're avoiding the real issue. The problem isn't the process—it's that person's performance." |
The Strategic Coach: "Let's zoom out. How does this decision connect to your three-year vision? What's the opportunity cost?" |
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Putting It All Together |
Once you've built these three layers, combine them into one master prompt that you save and reuse. |
The Master Setup: |
You are my executive coach. I'm going to give you three types of context: 1. My business context (company, role, priorities) 2. My leadership profile (strengths, style, growth areas) 3. Your coaching approach (how I want you to coach me) [PASTE YOUR THREE LAYERS HERE] From now on, when I bring you leadership challenges, coaching questions, or decisions to think through, use this context to provide personalized, relevant advice. Ask clarifying questions when you need more information. Challenge my thinking when I'm missing something. Help me be a better leader. Do you understand your role as my coach?
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Testing Your AI Coach |
Once you've set up your context, test it with a real challenge: |
"I have a team member who's technically strong but struggles with communication. It's starting to impact the team. How should I approach this?" |
Bad AI response (no context):
"Schedule a one-on-one meeting to discuss communication expectations..." |
Its not wrong. It's just too generic to be helpful. |
Good AI response (with context):
"Given your direct communication style and focus on team performance, here's what I'd explore: Is this a skill gap or a will gap? If they're technically strong, they can likely learn communication skills. But first, have you made your expectations explicit? What does 'good communication' look like in your context?" |
The second response understands you, your style, and asks the right questions. |
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Your Next Move |
This week, set up your AI executive coach: |
Block 30 minutes to build your three-layer context Save it somewhere you can easily access and update Test it with one real leadership challenge you're facing Refine it based on the quality of advice you get
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In Part 2 (next week's MGMT Playbook), we'll show you how to use your AI coach for specific scenarios: handling underperformers, making investment decisions, and resolving team conflicts. |
Want to go deeper? Join our free live workshop this Thursday where we'll build AI coaching systems together and practice using them on real leadership challenges. |
Because the best leaders don't go it alone. |
They just found a way to get coaching whenever they need it. |
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Thank you for reading. Appreciate you! |
Dave |
PS - Our February MGMT Accelerator is almost full. Many companies are taking advantage of the 20% discount for sending two or more people. Don't miss out! |
| | | | Ways To Work With Us | MGMT Accelerator: A live cohort-based leadership development program. MGMT Fundamentals: A two-week training program for new managers. Custom Programs: Workshops built and delivered for your company. 1:1 Executive Coaching: C-suite leaders looking to scale. Keynote speaking: Leadership lessons for your event or offsite.\
| Learn about them all at: davekline.com |
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