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Rupert Chesman
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Based on The AI-Native Playbook

AI-Native Leadership

3-Hour Intensive — From diagnosis to action plan.

Welcome

Introductions

Your name, your role, and the one workflow that keeps you up at night.

“

It wasn't slow because the people were stupid. It was slow because the architecture demanded it.

The AI-Native Playbook, p. 11

Agenda

Today's
3 Hours

  • Module 1 — The 97% Problem (35 min)
  • Module 2 — The Fork (30 min)
  • 10-minute break
  • Module 3 — The 16-Week Sprint (35 min)
  • Module 4 — The Inaction Tax (25 min)
  • Module 5 — Monday Morning (25 min)
Deliverables

What You
Leave With

Not notes. Not slides. Artefacts you can forward to your leadership team on Monday.

  • Friction Fingerprint — your organisation's unique friction profile
  • Legacy Tax Figure — the dollar cost of your current architecture
  • 16-Week EDGE Calendar — your implementation sprint plan
  • 90-Day Action Plan — Week One, Month One, Quarter One
Module 1 · 35 min

The 97% Problem

Your organisation isn't slow because your people are slow. It's slow because the architecture demands it.

01

The 97% Problem

Chapters 1–2 of The AI-Native Playbook

The Pricing Memo

  • A $2.3 million opportunity lands on someone's desk
  • It takes 42 days to approve — through 9 handoffs
  • Total actual work: 3 hours
  • $185,000 in margin erosion during the delay
  • Multiply by 200 similar decisions per year…
Silent Erosion
$37M

in annual silent erosion — from one company's approval architecture alone.

The Five Frictions

  • Latency — the VP's never-ending inbox. 60–80% of elapsed time.
  • Emotional Friction — jealousy, ego, turf wars. $359 billion annually in the US.
  • Inconsistency — same policy, same complaint, two completely different outcomes.
  • Information Loss — five handoffs = 23% lost. Ten = 40%. Fifteen = over half.
  • Scaling Limits — a team of 50 has 1,225 communication channels.
Interactive Tool

Five Frictions Diagnostic

15 min

Pick your highest-volume workflow. Score it across all five frictions. Watch your organisation's unique friction fingerprint appear.

Artefact: Friction Fingerprint (downloadable)

“

Your org chart is your biggest liability.

Chapter 1 title

Margaret's Billing Complaint
97%

of the workflow time was not work. It was waiting.

Interactive Tool

Legacy Tax Calculator

10 min

Enter your team size, average salary, and workflow volume. Watch the annual dollar cost of friction climb into six or seven figures.

Artefact: Legacy Tax Figure (downloadable)

“

You've given a Formula 1 engine to a horse and cart. The engine is magnificent. The cart is the problem.

The AI-Native Playbook, p. 27

The Patching Fallacy

  • Company deploys AI across every department. Drafts in minutes. Reviews 40% faster.
  • But the approval chain doesn't change. The architecture stays the same.
  • Net touch-time improvement: 92%. Net cycle-time improvement: 11%.
  • Your CFO sees a 92% productivity gain. Your customer sees 11%.
  • The AI made the fast parts faster. The slow parts didn't move.
Interactive Tool

Patching Fallacy Simulator

10 min

Model two scenarios for your workflow: patch it with AI copilots, or redesign from scratch. Watch where the two lines cross.

Module 2 · 30 min

The Fork

Stop trying to transform your existing organisation. Build the new one beside it.

02

The Fork

Chapters 3–5 of The AI-Native Playbook

“

The most dangerous thing you can do is try to transform your legacy business from the inside.

The AI-Native Playbook, p. 65

The Organisational Fork

  • Don't renovate the building. Build next door.
  • Run the legacy process and the AI-native process in parallel
  • Select a beachhead — one workflow, bounded risk, high visibility
  • This isn't a moonshot. It's a hedge. The downside is bounded. The upside compounds.
Interactive Tool

Organisational Fork Simulator

10 min

Select your highest-friction workflow from Module 1. Choose your path: transform from within, or fork and build beside. See the outcomes diverge.

Loop Compression

  • In the Loop — you approve every action
  • On the Loop — you monitor and intervene by exception
  • Above the Loop — you set the rules, the system executes
  • The goal isn't to remove humans. It's to put them where they're irreplaceable.
Interactive Tool

Loop Position Mapper

10 min

Select five of your key processes. For each, indicate where you sit: in the loop, on the loop, or above the loop. See your leadership position map emerge.

The Five Native Tests

  • Is the workflow data-complete? Can the system see everything it needs?
  • Is the decision logic codifiable? Can you write the rules?
  • Is the feedback loop closed? Does the system know when it's wrong?
  • Is the failure mode recoverable? Can mistakes be unwound?
  • Is the human value above the loop? Is judgment, not execution, the contribution?
Interactive Tool

Five Native Tests Assessment

10 min

Run five yes/no diagnostics on your chosen workflow. See whether it's ready for AI-native status — or still needs human architecture.

☕

10-Minute Break

Stretch. Get a coffee. Look at your friction fingerprint.
We resume with The 16-Week Sprint.

Module 3 · 35 min

The 16-Week Sprint

From diagnosis to implementation. The EDGE Method gives you a playbook you can hand to your team.

03

The 16-Week Sprint

Chapters 6–7 of The AI-Native Playbook

The EDGE Method

  • E — Evaluate
    Weeks 1–4: Score workflows, select your beachhead
  • D — Design
    Weeks 5–8: Build the AI-native workflow in parallel
  • G — Go Live
    Weeks 9–12: Run both systems side by side, measure
  • E — Expand
    Weeks 13–16: Scale what works, kill what doesn't
Interactive Tool

EDGE Method Planner

15 min

Work through four guided screens to build a 16-week implementation sprint calendar for your selected workflow.

Artefact: 16-Week EDGE Calendar (downloadable)

Interactive Tool

Data Readiness Scorecard

10 min

Five diagnostic questions that reveal whether your data infrastructure can support the AI-native workflow you're planning to build.

Governance at Speed

  • Five maturity levels: from ad hoc to autonomous governance
  • Kill switches: the thresholds that trigger human intervention
  • If your governance can't operate at the speed of your agents, you don't have governance — you have a backlog
  • The goal: guardrails that protect without paralysing
Interactive Tool

Governance & Kill Switch

10 min

Assess your governance maturity across five levels. Then configure kill-switch thresholds for your AI-native workflow.

Module 4 · 25 min

The Inaction Tax

The cost of waiting is already compounding. Every quarter you delay, the distance doubles.

04

The Inaction Tax

Chapter 8 of The AI-Native Playbook

“

The Inaction Tax doesn't send you an invoice. It compounds in silence.

The AI-Native Playbook, p. 173

Interactive Tool

Inaction Tax Calculator

15 min

Enter your revenue and competitor adoption data. See the compounding quarterly cost of delay — at 6, 12, and 24 months. This is the number that turns interest into action.

The Singularity Curve

  • Three timelines: fast, medium, and slow adoption
  • The capability gap between adopters and non-adopters widens exponentially
  • At some point, the gap becomes uncatchable — the singularity point
  • Different industries hit this point at different times
  • The first company to go AI-native gets a competitive advantage. The last one gets acquired — or disappears.
Interactive Tool

Singularity Curve Explorer

10 min

Select your industry. Explore three adoption timelines. See when the capability gap becomes uncatchable for your sector.

Module 5 · 25 min

Monday Morning

No new concepts. No new frameworks. Just synthesis and commitment.

05

Monday Morning

Epilogue + Appendices

Week One. Month One. Quarter One.

  • Week One — Share your friction fingerprint with your leadership team. Identify your beachhead.
  • Month One — Assemble the fork team. Run the Five Native Tests. Start the EDGE evaluate phase.
  • Quarter One — Go live with the parallel workflow. Measure. Expand or kill. Report to the board.
Interactive Tool

90-Day Action Plan Builder

15 min

Pull together every output from the previous modules into a concrete plan. Your friction fingerprint, your legacy tax figure, your EDGE calendar — all into one action plan.

Artefact: 90-Day Action Plan (downloadable)

Interactive Tool

Communication Playbook

10 min

Draft three messages: to your board, to your team, and to your direct reports. Each tuned for a different audience and tone.

Artefact: Communication Messages (downloadable)

“

This book was never about AI. It was about what your organisation becomes when the architecture changes.

The AI-Native Playbook, Epilogue

The Final Instruction

Start on Monday.

Act as if the fast timeline is real. Be pleasantly surprised if it's the medium one. In neither case will you regret having started.

Thank You

AI-Native Leadership

3-Hour Intensive · Based on The AI-Native Playbook by Rupert Chesman

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