Read Time: 5 minutes. |
Note: this playbook looks longer than normal, but most of the words are prompts for you to copy and paste. |
From Setup to Action |
Last week, you built your AI executive coach with three layers of context: your business, your leadership profile, and your coaching style. Start with Part 1 if you missed it. |
Or maybe you joined the 1002 leaders at our Lightning Lesson on Thursday to explore this topic together (you can still get the recording here). |
Now comes the hard part: actually using it. |
Most leaders set up their AI coach, ask one question, get disappointed with the response, and never come back. |
The problem isn't the AI. Most models have an IQ greater than 90% of the population. And they've been trained more knowledge than any human consume. |
The problem now is mostly likely how you're using it. |
Great coaching—human or AI—requires the right approach for the right situation. You wouldn't ask your coach the same questions about firing someone as you would about entering a new market. |
Here are the three most common coaching modes, plus three real scenarios that show you exactly how to get the most from your AI coach. |
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The Three Coaching Modes |
Mode 1: Socratic Questioning (When You Need Clarity) |
Use this when: You're stuck, confused, or can't see the real problem. |
How it works: Your coach asks questions that help you discover your own answers. |
The prompt structure: |
"I'm struggling with [SITUATION]. I feel [EMOTION/CONFUSION]. Don't give me answers yet. Ask me questions (one at a time) that help me think through this more clearly. Challenge my assumptions. Help me see what I'm missing."
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Why this works: Sometimes you won't really hear advice. You need to think out loud with someone who asks better questions than you're asking yourself and get to the conclusion yourself. |
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Mode 2: Stress Testing (When You Have a Plan) |
Use this when: You've made a decision but want to pressure-test it before committing. |
How it works: Your coach pokes holes in your thinking and surfaces risks you haven't considered. |
The prompt structure: |
"Here's my plan: [YOUR DECISION/APPROACH] My reasoning: [WHY YOU THINK THIS IS RIGHT] Stress test this. What am I missing? What could go wrong? What assumptions am I making that might be wrong? What alternatives should I consider?"
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Why this works: Confirmation bias is real. Your AI coach has no ego and no stake in your decision. It can dispassionately challenge you without any political undercurrents. |
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Mode 3: Expert Advice (When You Need a Recommendation) |
Use this when: You're out of ideas, short on time, or need an outside perspective fast. |
How it works: Your coach gives you clear recommendations based on your context. |
The prompt structure: |
"Here's my situation: [CONTEXT] Here's what I've tried: [PAST ATTEMPTS] Here's what's at stake: [CONSEQUENCES] Given everything you know about me and my business, what would you recommend I do? Be direct."
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Why this works: Sometimes you just need someone to tell you what they'd do in your shoes. |
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| | | | Our Next Cohort Starts in 10 Days | MGMT Accelerator - Eight 90-minute sessions over four weeks plus 3 group coaching sessions starting February 18 at 11:00 AM ET. | Perfect for leaders with 3-10 years of experience who want to refine their systems to deliver more impact and level up as a leader. | Don't wait! We cap this program at 50 leaders to ensure an intimate learning experience. | |
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Scenario 1: Handling an Underperformer |
The situation: You have a team member who's been missing deadlines and delivering subpar work for two months. You've had one "soft" conversation that didn't change anything. |
The wrong approach:
"How do I fire this person?" |
Why it's wrong: You're jumping to the solution before diagnosing the problem. |
The right approach (Socratic Mode): |
"I have a team member who's been underperforming for two months. I had one conversation about it that didn't change anything. I'm frustrated and considering letting them go. Before I make that decision, help me think through this: - What might I be missing about why they're struggling? - Have I been clear enough about expectations? - Is this a skill gap, a will gap, or something else? - What would I need to see to know whether this is fixable? Ask me questions that help me diagnose this properly."
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What good coaching looks like: |
AI Coach: "Let's start with clarity. When you had that first conversation, what specifically did you say their performance needed to improve? And what did they commit to doing differently?" |
You: "I told them they needed to be more reliable with deadlines. They said they'd work on it." |
AI Coach: "That's pretty vague. Did you define what 'reliable' means? Did you set specific metrics or checkpoints? And did you explore why they've been missing deadlines?" |
You: "No, I assumed they knew what I meant." |
AI Coach: "There's your starting point. You can't hold someone accountable to expectations you haven't made explicit. Before you consider termination, you need to have a clear conversation about specific outcomes, timelines, and consequences. What would that conversation look like?" |
The outcome: You realize you haven't actually managed the situation directly yet. You've hinted at it in ways that may not have been heard. Now you have a clear next step. |
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Scenario 2: Making a Big Investment Decision |
The situation: You're considering hiring two senior engineers at $200K each. It would accelerate your roadmap but strain your budget. |
The wrong approach:
"Should I hire these engineers?" |
Why it's wrong: Your AI coach doesn't have enough context about the tradeoffs. |
The right approach (Stress Testing Mode): |
"I'm considering hiring two senior engineers at $200K each. My reasoning: - We're 6 months behind on our product roadmap - These hires would cut that to 3 months - Faster time-to-market could generate $500K in additional revenue this year - But it would consume 40% of my remaining budget Here's my plan: Hire both, cut discretionary spending elsewhere, and bet on the revenue upside. Stress test this decision. What am I missing? What could go wrong? What alternatives should I consider?"
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What good coaching looks like: |
AI Coach: "Let's test your assumptions. You're betting that faster time-to-market generates $500K in additional revenue. How confident are you in that number? What's it based on?" |
You: "It's based on our sales pipeline and what customers are asking for." |
AI Coach: "Okay. Now let's test the downside. If you hire these engineers and the revenue doesn't materialize, what happens? Can you sustain $400K in additional payroll without that upside?" |
You: "No. We'd have to cut elsewhere or raise more money." |
AI Coach: "So you're making a high-risk bet. Here's an alternative: What if you hired one engineer now and made the second hire contingent on hitting a revenue milestone in Q2? That cuts your risk in half while still accelerating the roadmap." |
The outcome: You realize you can de-risk the decision by sequencing the hires instead of making both at once. |
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Scenario 3: Resolving Team Conflict |
The situation: Your head of sales and head of product are constantly at odds. Sales says product is too slow. Product says sales overpromises. It's affecting the whole company. |
The wrong approach:
"How do I get these two to stop fighting?" |
Why it's wrong: You're treating the symptom, not the disease. |
The right approach (Direct Coaching Mode): |
"My head of sales and head of product are in constant conflict. Sales says product is too slow to ship features customers need. Product says sales overpromises and creates unrealistic expectations. This has been going on for three months. I've tried mediating but nothing changes. It's starting to affect team morale and our ability to execute. Given what you know about me and my business, what would you recommend I do? Be direct."
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What good coaching looks like: |
AI Coach: "Here's what I'm seeing: This isn't a personality conflict—it's a structural problem. Sales and product have misaligned incentives. Sales gets rewarded for closing deals, even if product can't deliver. Product gets rewarded for quality and stability, even if it means slower feature development. |
You need to do three things: |
Create shared metrics. Both leaders should be measured on customer satisfaction and retention, not just their functional goals. This aligns their incentives. Establish a decision-making framework. Who has final say on roadmap priorities? Right now it sounds like they're both trying to drive, which creates constant conflict. Have a come-to-Jesus conversation. Tell them both: 'This conflict is hurting the company. I need you to figure out how to work together, or I'll make changes.' Then give them two weeks to propose a solution.
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Which of these feels most urgent to address first?" |
The outcome: You realize you've been trying to fix a relationship problem when you actually have a systems problem. Now you have a clear action plan. |
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Advanced Techniques |
Part of what makes a coach so helpful is they force you to close the loop. |
The loop of converting advice into action. The loop of examining attempts for patterns. The look of holding yourself radically accountable.
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You'll want your AI coach to do the same. |
The Action Loop |
After your AI coach gives you advice, don't just take it and run. Engage: |
"That's helpful. Let me play that back to make sure I understand: [SUMMARIZE THE ADVICE] Now help me think through implementation: What's the first conversation I need to have? What could go wrong? How do I know if it's working?"
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The Analysis Loop |
Use your AI coach to spot patterns across multiple situations: |
"Over the past three months, I've brought you three different team conflicts. What patterns do you see in how I'm handling these? What might I be doing (or not doing) that's contributing to these issues?"
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The Accountability Loop |
Set up regular check-ins with your AI coach: |
"Every Monday morning, I want you to ask me: 1. What did I commit to last week? 2. What did I actually accomplish? 3. What got in the way? 4. What's my focus for this week? Hold me accountable to following through."
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Tip: Copy and paste your Called Shots template to make this even easier. |
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Your Next Move |
This week, use your AI coach for one real leadership challenge: |
Identify the situation: What's the toughest thing you're dealing with right now? Choose your mode: Socratic questioning, stress testing, or direct coaching? Have the conversation: Use the prompt structures above Take action: Don't just collect advice. Implement it! Report back: Tell your AI coach what happened and what you learned
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Remember: Your AI coach is only as good as the questions you ask and the context you provide. |
You can get expert guidance, but it requires being radically honest. |
With your coach. And with yourself. |
Good luck. |
Dave |
PS - I'd love to hear how it goes. Drop us a note to give me any feedback on how your coach it working. |
PPS - Our February MGMT Accelerator is 10 days away 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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