Strategic Judgment for the AI Era: Master the Craft That Can't Be Automated
Kristi Pihl
Principal Advisor | Product, Tech & AI
Learn the craft that 20+ years and hundreds of deals actually teaches.
Everyone's scrambling to figure out what AI will replace. Not enough are asking what it can't.
Strategy is not a mindset or a skill you pick up from a masterclass. It's a craft—built from scar tissue, systems thinking, and judgment honed across decades of real constraints and tradeoffs. It's why CIOs still pick up the phone. Why PE firms call for a reality check. Why executives pay hundreds of dollars an hour to pressure-test their thinking.
LLMs can write strategies that sound good on paper. They can't be strategists that deliver results. Strategy manifests in the real—when budgets are tight, stakeholders don't align, and being wrong costs millions. It requires memory from watching transformations go sideways, go-to-market strategies miss regulatory gaps, and data lakes fail because no one agreed on what a customer is.
This course is for senior leaders who know AI is about to make strategic judgment exponentially more valuable.
True strategists aren't worried about being replaced. They're the ones executives call when the stakes are real.
What you’ll learn
This isn't strategy frameworks. It's the judgment that makes executives pick up the phone when the stakes are real and the plan is failing.
Learn to think in systems, read patterns, & spot unstated assumptions—the judgment that comes from watching failures replay again and again
Move beyond PPTs to master the interplay between economics, behavior, technical constraints, and human limits that shapes real outcomes
Speak across product, engineering, data, sales, and finance—from term sheets to technical debt tradeoffs to stakeholder incentives
Lead decisions that stick across complex organizations
Develop pattern recognition to identify leverage points, surface risk early, and know when to incur tech debt versus when it costs you later
Cultivate credibility that makes you the person CXOs phone for reality checks and PE firms trust to pressure-test roadmaps
Learn directly from Kristi
Kristi Pihl
Principal Advisor | Product, Tech & AI
Who this course is for
Senior product, engineering, or data leaders ready to move from execution into strategic advisory that executives trust
Strategy, ops, or transformation leaders sharpening their judgment to lead through ambiguity and deliver results across organizations
Experienced operators who know AI makes strategic thinking more valuable—and want to master the craft that can't be automated
Prerequisites
8+ years leading in complex environments
Experience in product, tech, data, ops, or strategy roles navigating real constraints, tradeoffs, and initiatives at scale
Comfort with strategic discussion
This is an apprenticeship, not a lecture series. You'll learn through active exchange, pressure-testing ideas, and interacting with peers
Commitment to live sessions
Judgment develops through real-time discussion, working through ambiguous scenarios, & learning from peers facing similar challenges
Schedule
Live sessions
2-3 hrs / week
This course is designed to fit into a busy executive schedule without requiring extensive evening or weekend time. It is built to run alongside your day job, so you can level up while immediately applying what you learn to in-flight initiatives.