Executive AI Coaching
Live strategic thinking — now amplified by AI
Think clearly. Decide faster. Move with confidence.
“Hold on ... we can do that?”
“That’s how we get there?”
“This came together so fast”
“Wow, that unlocked it!”
This is real-time, high-leverage coaching for leaders navigating complex decisions — with AI as a precision tool, not the point.
We start with a real challenge, fly live with AI, and think through it from every angle — surfacing blind spots, reframing assumptions, and build what matters: the lens to decide, the language to align, or the clarity to move.
AI isn’t the star. But it’s the jet fuel — accelerating insight, surfacing patterns, and helping us test strategy in real time. What makes it work is the combination: smart framing, live sense-making, and the ability to hold complexity without rushing to false clarity.
This is strategic thinking — designed to move you forward.
Formats that fit real leaders
Two ways to work together — grounded, focused, and high-trust.
None of this is off-the-shelf. Both flex to your context. One is a structured coaching program with AI woven throughout, the other is a longer-term partnership for steady clarity.
AI Coaching for Strategic Thinking
Use AI to think better, not just faster
BEST FOR: Leaders curious about AI who want to apply it to real work, not hypotheticals
FORMAT 5 sessions over 8 weeks
OUTCOME: Sharper thinking, faster momentum, and a practical way to use AI in strategy
1:1 Thinking
Partnership
Ongoing clarity and momentum, powered by AI
BEST FOR: Executives who want a trusted thinking partner — not just a coach to listen.
FORMAT: Bi-weekly sessions over 4 months
OUTCOME: Clear direction, usable outputs, and AI woven in where it helps most
What Each Looks Like in Practice
Here’s how each format works in practice — who it’s for, the rhythm of the work, and what you’ll walk away with
AI Coaching for Strategic Thinking
Applying AI to real challenges, not hypotheticals.
WHEN THIS HELPS
When you’re facing a decision that feels high-stakes and ambiguous. When you want to see how AI can sharpen your options without replacing your judgment. When you need to move quickly from scattered inputs to clearer framing and actionable next steps.
HOW IT WORKS
Five sessions over eight weeks. Each one begins with a live challenge you’re navigating. We use AI prompts and structured questions to explore options, test assumptions, and frame the problem from multiple angles.
WHAT YOU WALK AWAY WITH
Sharper framing of a current challenge or decision
Practical AI prompting styles and strategic thinking techniques you can reuse in your own work
Session artifacts — decision criteria, maps, or draft narratives you can act on right away
WHY IT’S DIFFERENT
This isn’t a course on AI or a generic coaching session. It’s structured experimentation on your real work — using AI as a live thinking partner to get to sharper insights, faster.
1:1 Thinking Partnership
WHEN THIS HELPS
When the pace is relentless and you need structured space to step back and think. When you’re carrying multiple big choices and want to sharpen them before moving. When the complexity around you feels noisy, or when you want someone who won’t just nod, but will push, test, and expand your ideas.
HOW IT WORKS
We work together over four months, meeting every other week. Each session flexes to your context: sometimes about clarifying a decision, sometimes about shaping a tricky narrative or team dynamic. AI is used selectively, when it adds structure or speed.
More than a sounding board - a partner to frame, test, and sharpen your decisions over time.
WHAT YOU WALK AWAY WITH
A reliable rhythm of space to step back and think strategically
More confidence in decisions because they’ve been tested and stretched in dialogue
Working frameworks or maps that help you bring clarity back to your team
WHY IT’S DIFFERENT
This isn’t “classic executive coaching.” It’s a long-term thinking partnership: steady space to step back, sharpen choices, and build clarity you can take back to your team.
Why coaching? Why now?
You’ve got the instincts. AI sharpens the edge.
Frame complex questions — from fuzzy to structured
Surface what’s hidden — assumptions, blind spots, patterns
Use AI to deepen insight — without noise, fluff, or filler
Decide with clarity. Lead with confidence.
You’ll leave with something concrete: a clarified strategy, decision support tool, or a new narrative — and handpicked resources from my own strategic vault.
What we might work on
Framing tough decisions — clarifying trade-offs, setting decision criteria, avoiding blind spots.
Sharpening roles and responsibilities — cutting through ambiguity in teams and org design.
Shaping narratives that stick — whether for your team, your board, or the wider organization.
Exploring AI in context — testing how AI can accelerate your actual work, not just hypotheticals.