John P. Dentico, Ed.D., AIMP

Leadership Simulation Designer. Author. Podcast Host. Strategic Thinking Coach.

The Step Before It Becomes Code

Recognize why capable teams keep solving the wrong problem and what that actually costs once the specification closes.

See the costly step most teams skip

Watch a room settle on training or adoption, then see what gets permanently encoded as a result.

Watch the wrong diagnosis get accepted

Walk away clear on the one diagnostic move that has to happen before any system, tool, or plan hardens the wrong rules.

Leave knowing the missing step

Watch how decisions produce consequences across sessions, turning diagnosis into something you feel and remember.

Learn how consequence-driven simulations makes learning last

Move beyond execution and stand out for how you think, communicate, and shape decisions

Design Leader, ex-Slack, Pinterest

Goodnotes

Pinterest

Slack

The New York Times

Squarespace

Cheryl Chepusova

Staff-level designer with 15+ years leading product teams across 3 continents

June 2026

September 2026

AI is accelerating how quickly teams can produce work. As execution becomes easier, what differentiates senior designers isn’t output alone, it’s judgment.The designers who grow aren’t necessarily doing more work. They’re helping others understand the decisions behind the work, influencing direction, and making their impact visible in the moments that matter.This course is for senior product designers who consistently deliver great work but struggle to articulate their value. You may be known as reliable, collaborative, and highly capable, yet still find it difficult to communicate your thinking in stakeholder conversations, growth discussions, promotion cycles, or other career-defining moments.Together, we’ll focus on the skills that become increasingly important as your career grows: communicating decisions, building influence, navigating ambiguity, and making strong judgment visible to the business.This course includes: 👉 Weekly live group coaching sessions 👉 Async support on artifacts, communication, stakeholder situations, and other moments where you want feedback applying what you’re learning in practice 👉 Bonus 30-minute 1:1 coaching session

Grow from doing the work to owning your impact

Communicate Decisions More Effectively

Build Trust Through Visibility

Influence Across Different Stakeholders

Tell a Stronger Story About Your Impact

Senior product designers who ship consistently but are still seen as executors when promotions, reviews, and visibility matter

Designers on distributed teams who struggle to communicate judgment clearly across async updates, reviews, and reorgs.

Designers growing into strategic partners who want influence through strong thinking, not self-promotion.

Leave with a diagnosis of where your organization stands and a transformation plan your leadership can act on.

Frontier Tech Operator & AI Advisor 

Jory Des Jardins

AI Transformation Advisor | Frontier Tech, GTM, Future of Work | 30+ Companies

Founding Cohort -- Fall 2026

Most organizations are measuring the wrong things, restructuring before they've mapped anything, and calling it transformation.The professionals who get this right aren't the fastest adopters. They're the ones who understood what was at stake before everyone else did — and designed their organization's response deliberately.This course exists because that kind of thinking doesn't happen by accident. It requires a framework, a diagnostic process, and a peer community of senior operators who are navigating the same decisions you are.In four weeks you'll map your organization's AI trajectory, build a decision rights structure for your function, sequence a measurement plan your leadership can act on, and assemble a transformation design document you can walk into an executive conversation with the week after the course ends.Not a certificate. Not a survey of tools. A working artifact and a framework you'll use for years.

The leaders who get AI transformation right design it deliberately 

1. Diagnose where your organization's AI transformation is actually heading.  

"Pre-structure" how work gets done before you restructure who does it.

Sequence your transformation metrics correctly.

Protect your organization's judgment pipeline, and leave with an action plan.

Option to share your plan with Jory for direct review, during or post-course.

Senior operators — Chief of Staff, VP People, Head of Talent, function leaders responsible for how AI is integrated into their organization.

CHROs, CPOs, HRBPs at mid-to-large organizations navigating workforce restructuring, role redesign, capability planning during AI adoption.

Operators, senior managers, team leads, department heads, senior ICs leading AI transformation from the inside, strategy and execution.

Every coach knows when a program fails. 
Few know exactly why.

20+ Years Coaching Elite Athletes

Exos

Cleveland Browns

Munster Rugby

Denis Logan

Former EXOS Director. 20+ years coaching elite athletes & building systems.

Stop Guessing Your Programming: Build a System (For Strength Coaches)

Ask ten coaches why a program failed, and you'll get ten different answers.Too much volume.Wrong exercises.Poor recovery.They're not wrong. They're just not specific enough to act on.Here's the better question:When a program fails, which decision broke first?This workshop gives you a five-step diagnostic you can run on any program:Constraint — What's actually limiting the outcome?Alignment — Does the intervention match the constraint?Dosage — Is the athlete getting enough of the right stimulus?Time to Emergence — Has enough time passed to expect adaptation?Interference — Is something else suppressing the result?Underneath it all is Recovery—not another programming decision, but the context that determines whether adaptation is even possible.Once you can diagnose where a program fails, you can build with confidence instead of guessing.This is a live build session.Bring a real athlete.Leave with a sequenced program, a load and taper plan, and a repeatable method for diagnosing both.

Diagnose why programs fail, build with confidence, and stop guessing every programming decision.

Diagnose exactly where a program fails — not just that it did

Build a complete program for a real athlete — in the right order

Know exactly when to push, when to back off, and when to peak

Return to the diagnostic with real tools in hand

Coaches who can feel when a program isn't working but don't have a precise way to say why

Trainers who are designing programs session by session and want a repeatable method for catching problems before they cost an athlete

Strength coaches who make load and periodization decisions by feel and need a framework that holds up across different athletes and blocks

Build on your product skills to excel at team-building, improving performance, seeing what others are missing and enabling impactful change.

Excellence & Impact for Product Leaders

Sascha Brossmann

Fractional CPO · Executive Advisor · Community Builder

Cohort 1

Research is clear: <a target="_blank" rel="noopener noreferrer nofollow" href="https://hbr.org/2009/05/why-teams-dont-work">most teams underperform</a>. To make it worse, many organisations struggle to define how their employees will be successful at teamwork. People are complex – they require work to make the work work. :)This can be hard even for seasoned leaders. As a rookie manager, the challenge becomes even more daunting: suddenly you're facing entirely new problems that require equally new skills. It often feels like assembling your parachute while already falling.It does not have to be that way.I've been that manager. Muddling through, failures along the way. Until something clicked:As product people we habitually point all our skills outward, at users. Our organisations and the people we work with remain a blind spot.This changes fundamentally when we reframe what we already know.People Discovery turns our skills inward: to understand the people we work with, surface needs and capabilities, and convert that into trust, cohesion, and visibly better work. A win/win for people and performance.With that we can approach our teams and organisations like a product: human-centric, outcome-focused, agile, strategic, intentionally designed.It profoundly changes the game. Like to see how?

Turn your product skills inwards to become a high-impact leader

The unlock: Reframe your product skills for management and leadership

The backbone: Build situational awareness with people and business discovery

The heart muscle: Turn insights into effective team agreements that stick

Benefit from people discovery across the team lifecycle

Diagnose and fix performance and culture issues

The growth hormone: Leverage product skills beyond leading teams

You have senior work experience in a product-related role. You're confident with your skills so that you can start building on them.

Senior product-related experience

Both a team you're leading or one of equal peers (e.g. exec team) works. No team? We will also use roleplay and an AI team for course work.

Ideally: you have a team to get right into practice

New managers coming from a product, design, tech, or related role who want to hit the ground running.

Experienced managers looking for new ways to improve both team performance and talent attrition.

Senior leaders discontent with the status quo who want to align human flourishing with business impact.

Agentic AI

Coding with AI

AI Workflows

Claude Code

OpenClaw

Vibe Coding

AI Evals

AI Transformation

RAG & Search

AI for PMs

AI for Engineers

AI for Designers

AI for Marketers

AI for Founders

Product Sense

Product Discovery

User Research

Prototyping

Growth

Analytics

Tech Foundations

Strategy

Influence

Leadership

Career Growth

Machine Learning

LLM Ops

Context Eng

Security

System Design

Figma

Design Systems

Visual Design

Design Strategy

Automation

Content Marketing

Demand Gen

Go-to-Market

Product Marketing

Positioning

Social Media

Brand

B2B Marketing

SEO & AEO

AI for Leaders

AI Governance

Communication

Management

People Operations

Exec Presence

Storytelling

Goal-setting

Personal Brand

Fundraising

Everyone

Operators

Data Scientists

Business Analysts

User Researchers

Customer Success

Project Managers

HR Professionals

Sales People

Lawyers

Finance

Investors

Real Estate

Educators

Creators

Product managers who drive strategy, development, and launch of products.

Executives and senior leaders who set strategy, lead teams, and drive organizational outcomes.

Setting strategic direction, making high-stakes decisions, and translating vision into execution.

Identifying opportunities and validating what to build through customer research, experimentation, and prioritization.

Developing intuition for what makes a great product — evaluating ideas, understanding user needs, and making tradeoff decisions.

The Step Before It Becomes Code

What you'll learn

Why this topic matters

You'll learn from

John P. Dentico, Ed.D., AIMP