Executive Workshop

AI-Native Leadership
3-Hour Intensive

Based on The AI-Native Playbook by Rupert Chesman. This workshop gives executives the diagnostic tools, implementation frameworks, and urgency metrics to lead AI transformation — and leave with a concrete 90-day plan.

3 Hours
5 Modules
13 Interactive Tools
4 Artefacts
211-Page Book

What You'll Leave With

Four executive-grade artefacts and the frameworks to lead your organisation's AI-native transition.

Friction Fingerprint

Diagnose the five frictions costing your organisation 97% of its workflow time — with your specific numbers.

Legacy Tax Figure

Calculate the annual cost of maintaining legacy workflows — the number that gets the board's attention.

EDGE Implementation Calendar

A colour-coded 16-week sprint calendar for your first AI-native workflow rebuild.

90-Day Action Plan

Week One, Month One, Quarter One — the executive-grade plan you can pin to your wall on Monday morning.

Workshop Curriculum

5 modules, 180 minutes, from diagnosis to action plan.

01

The 97% Problem

3 lessons · 35 min

The Five Frictions Diagnostic — map your workflow's hidden costs
Legacy Tax Calculator — your annual cost of doing nothing
The Patching Fallacy Simulator — why incremental AI fails
02

The Fork

3 lessons · 30 min

The Organisational Fork Simulator — patch or rebuild?
Loop Compression Mapper — where does your team sit?
Five Native Tests Assessment — has your workflow crossed the line?
03

The 16-Week Sprint

3 lessons · 35 min

EDGE Method Planner — build your 4-phase implementation calendar
Data Readiness Scorecard — are your systems ready for agents?
Governance at Speed — maturity assessment and kill switch configurator
04

The Inaction Tax

2 lessons · 25 min

Inaction Tax Calculator — the compounding cost across four dimensions
Singularity Curve Explorer — where is your industry's tipping point?
05

Monday Morning

2 lessons · 25 min

90-Day Action Plan Builder — synthesise every module into Week 1 / Month 1 / Quarter 1
Communication Playbook — three ready-to-send messages with tone controls

Who This Workshop Is For

C-Suite Executives

Who need to understand what AI-native means for their competitive position and lead the transformation.

VP / Directors

Responsible for implementing AI strategy and needing a structured framework — not just a buzzword.

Heads of Transformation

Running digital or AI programmes who need governance frameworks, data readiness tools, and implementation playbooks.

Board Members

Who need to evaluate AI investments, understand the Inaction Tax, and ask the right questions of management.

The AI-Native Playbook by Rupert Chesman

Based on the Book

The AI-Native Playbook

Every interactive tool in this workshop is mapped to specific pages and frameworks from The AI-Native Playbook by Rupert Chesman. 211 pages covering the Five Frictions, the Organisational Fork, Loop Compression, the EDGE Method, Governance at Speed, and the Inaction Tax — with precise data, case studies, and implementation guides.

211 Pages
8 Chapters
8 Appendices
30+ Data Points

Frequently Asked Questions

It’s only 3 hours. Can it really change how we approach AI?

Three hours is deliberate. Executives don’t need a semester — they need a forcing function. This workshop is structured so you spend every minute doing the work: diagnosing your specific friction points, calculating your actual Legacy Tax figure, building your EDGE implementation calendar, and drafting your 90-day action plan. You leave with four concrete artefacts, not a set of slides to review later. The constraint is the point.

Do I need technical knowledge to get value from this?

Not at all. This workshop is designed for executives, not engineers. Every concept is explained in business terms with real-world case studies. The 13 interactive tools do the heavy lifting — you provide the strategic context and organisational knowledge. If you can run a P&L review, you can do this workshop.

How is this different from a standard AI strategy course?

Most AI courses teach you about AI. This one makes you do the work with your own numbers and your own organisation in mind. You’ll calculate your actual Legacy Tax, build your real EDGE implementation calendar, and draft the three messages you’ll actually send on Monday morning. The output is artefacts you take away and act on, not theoretical frameworks you forget by Friday.

Is this relevant to my industry?

The Five Frictions framework and the EDGE Method are industry-agnostic — they apply to professional services, manufacturing, financial services, education, government, healthcare, and everything in between. The workshop uses your specific organisational context throughout, so the artefacts you produce are tailored to your situation, not generic templates. If your organisation has workflows, meetings, and decisions, this is relevant.

Can I take this with my leadership team?

That’s the ideal format. The workshop is designed for facilitated group sessions where leadership teams work through the tools together, building shared understanding and alignment on the 90-day plan. When your CFO has calculated the Legacy Tax alongside you and your COO has mapped the beachhead workflow, you leave with collective commitment — not a lone champion trying to convince everyone else.

What’s the relationship between this workshop and The AI-Native Playbook?

The workshop is built on the frameworks from The AI-Native Playbook by Rupert Chesman — the Five Frictions, the Organisational Fork, Loop Compression, the EDGE Method, and the Inaction Tax. The book provides the full depth: 211 pages of data, case studies, and implementation detail. The workshop takes those frameworks and turns them into an interactive working session. You don’t need to read the book first, but many participants find it valuable as a reference for implementation afterwards. The book is available on Amazon in 14 countries.

What exactly do I walk away with?

Four executive-grade artefacts: your Friction Fingerprint (a diagnostic of the five frictions costing your organisation 97% of its workflow time), your Legacy Tax Figure (a dollar estimate of what inaction is costing you), your EDGE Implementation Calendar (a phased 90-day plan with specific milestones), and your 90-Day Action Plan (including Week One actions, your beachhead workflow, and the team you’ll assemble). These aren’t aspirational documents — they’re working tools built from your real numbers.

What if our organisation is already using AI?

Most organisations using AI are patching — bolting AI tools onto existing workflows without rethinking the workflows themselves. This workshop helps you assess whether you’re genuinely AI-native or just AI-assisted, measure the gap, and decide where to make the architectural leap. The Five Native Tests in Module 2 will tell you exactly where you stand. Many participants discover that what they thought was an AI strategy is actually a tool adoption programme.

How soon can we start implementing the 90-day plan?

The plan is designed to start on Monday. The first EDGE cycle takes approximately 16 weeks, but it begins with Week One actions you can take immediately — running the Inaction Tax calculation with your CFO, naming your beachhead workflow, and assembling a four-person team. The second cycle compresses to 10–12 weeks as your organisation builds the muscle. By your fifth cycle, you’re running 4–6 week iterations.

Is this a one-off workshop or an ongoing engagement?

The 3-hour intensive is self-contained — you leave with everything you need to execute. However, organisations often find value in follow-up sessions to review progress against the 90-day plan, recalibrate priorities, and plan subsequent EDGE cycles. Get in touch if you’re interested in ongoing advisory support or want to run the workshop across multiple leadership teams in your organisation.

About the Expert

Rupert Chesman

AI Educator · Filmmaker · Author of The AI-Native Playbook

Rupert has trained thousands of professionals across corporate workshops, online courses, and live intensives — turning complex AI concepts into practical, immediately applicable skills. As an filmmaker and creative technologist, he brings a unique perspective that bridges technical capability and real-world application.

Ready to Start?

The gap between AI-native and legacy organisations doesn't close over time. It compounds. Start on Monday.