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AI Effectiveness for Executive, Unit, and Team Leaders

 

This is a concise summary of the prompts used and the outputs generated to create the AI Effectiveness Initiative Plan during Jon’s “AI Effectiveness for Executive, Unit, and Team Leaders” webinar. It captures the framing, OKR setup, literacy diagnostic, and time-saving prompts that shaped the plan. During the live session, several GPTs were also DEMO’d and used to train participants—those GPTs and their links are not included in this document.

 

👉 If you’d like to experience the full session, visit [Insert Webpage Link] to sign up for a 60-minute private coaching session to develop your AI Effectiveness Initiative Plan and get access to weekly 15-minute FastTrack coaching sessions to help you implement the plan.

 

 

Part 1. Framing the Strategic Problem & Promise

What We Did:

  • You began by answering three key framing questions (Starting Point, Core Challenge, Desired Outcome).
  • We turned your answers (B, B, B) into a compelling Problem–Promise narrative and a crisp OKR.

Why It Mattered:

  • Executives and teams need a shared mental model of the current state, challenge, and target outcome.
  • The Problem–Promise framing created instant clarity and urgency.
  • The OKR turned an ambiguous “AI journey” into a measurable business objective (80% adoption, 20% cycle time reduction).

✅ Value Created:

  • Aligned strategic direction
  • Established a measurable north star
  • Provided a leadership narrative hook for communication

 

Prompt — Framing the Problem & Promise

Jon said (prompt):
“Framing the Problem and Promise

Step 1 — Frame the Starting Point
Q1: Where is your organization today on the path to AI Effectiveness?
B) Running scattered pilots, unclear ROI

Step 2 — Pinpoint the Core Challenge
Q2: What’s the biggest leadership barrier slowing your AI progress?
B) Limited team skills / inconsistent adoption

Step 3 — Clarify the Desired Outcome
Q3: What kind of result would make this webinar truly valuable for you and your team?
B) A specific, practical workflow to improve this quarter”

 

ChatGPT said (output):
Here’s a strong executive-ready framing of the Problem and Promise using your answers (B, B, B) — ideal for the opening 3–5 minutes of a webinar or strategy session:

Step 1 — Frame the Starting Point

✅ B) Running scattered pilots, unclear ROI
Strategic Narrative:
“Like many midsize companies, you’re experimenting with AI — launching pilots across teams — but the results are inconsistent and hard to quantify. It’s exciting, but also a little chaotic. The promise is there, but the path isn’t yet clear.”
Executive Hook (Metaphor):
“You’re like a team of explorers with great gear but no shared map — everyone’s heading in different directions, and no one’s sure which expedition will actually reach treasure.”

Step 2 — Pinpoint the Core Challenge

✅ B) Limited team skills / inconsistent adoption
Strategic Narrative:
“The barrier isn’t a lack of tools. It’s that your people don’t yet have the skills, shared playbooks, or rhythms to adopt AI consistently. Some are curious, some are cautious, and most are simply overloaded.”
Executive Hook (Pattern Insight):
“In our work with midsize firms, this is the single biggest gap between AI Pilots and AI Performance: not technology, but team capability.”

Step 3 — Clarify the Desired Outcome

✅ B) A specific, practical workflow to improve this quarter
Strategic Narrative:
“You don’t need more theory — you need a clear, practical workflow that can deliver measurable impact this quarter. Something your team can deploy next week, not next year.”
Executive Hook (Promise):
“By the end of this session, you’ll have a tested workflow you can plug into your business rhythm — one that improves performance, builds skills, and sets the foundation for AI Effectiveness.”

 

 

 


 

Prompt — OKR Builder

Jon said (prompt):
OKR Prompt:
“Using your answers from Q1–Q3, complete the statement below. Pick a specific metric that reflects impact (e.g., cycle time, error rate, waste %, throughput, adoption rate, decision speed, cost savings).”

OKR Template:
“By the end of this quarter, we will move from [Q1: current state] by addressing [Q2: core barrier] to achieve [Q3: desired outcome], measured by [specific KPI/business metric].”

Example OKRs:

  • “By the end of this quarter, we will move from scattered pilots by addressing disconnected workflows to achieve faster weekly reporting, measured by a 25% reduction in reporting cycle time.”
  • “By the end of this quarter, we will move from exploring ideas by addressing team skill gaps to achieve clear workflow execution, measured by 80% adoption of our daily production GPT tool.”
  • “By the end of this quarter, we will move from uneven success by addressing lack of clarity to achieve strategic alignment, measured by 100% of leadership teams having defined AI OKRs.”

 

ChatGPT said (output):

📝 Draft OKR

“By the end of this quarter, we will move from running scattered pilots with unclear ROI by addressing limited team skills and inconsistent adoption to achieve a specific, practical AI workflow that improves business performance this quarter, measured by an 80% team adoption rate and a 20% reduction in workflow cycle time.”

📊 Why This Works

  • Clear Starting Point— “Scattered pilots with unclear ROI” gives leadership a shared baseline.
  • Core Barrier— “Limited team skills / inconsistent adoption” targets the human factor, which is typically the real constraint.
  • Desired Outcome— “Specific, practical AI workflow” sets a tangible, short-term target.
  • KPI Alignment— Adoption rate (behavior) + cycle time reduction (impact) provides a balanced metric pair.

💡 Optional Variants

  • Operational Efficiency Focus— 25% reporting cycle time reduction
  • Adoption & Capability Focus— 80% team actively using AI workflow weekly
  • Strategic Alignment Focus— 100% leadership alignment on one AI use case

Part 2. Diagnosing AI Literacy to Target Capability Gaps

What We Did:

  • I generated 10 targeted multiple-choice diagnostic questions across leadership, decision-making, workflows, and strategy.
  • Each question came with scoring guidance and 1 actionable improvement suggestion.

Why It Mattered:

  • Before building solutions, great leaders diagnose capability and cultural gaps.
  • This tool gives an exec or unit lead a fast, structured way to assess AI readiness without a 3-week consulting project.

✅ Value Created:

  • Clear literacy map for leadership teams
  • Actionable next steps for targeted improvement
  • Reusable diagnostic you can deploy across units

 

Prompt — AI Literacy Diagnostic

Jon said (prompt):
“Ask me 10 multiple-choice questions to assess my AI literacy across leadership, decision-making, workflows, and strategy. Generate the choices for A, B, and C. Make D - Other (Please specify) and E - All of the Above. Provide a 1–10 score and one improvement suggestion for each.”

 

ChatGPT said (output):

Excellent — this is a smart move. Below is a 10-question AI Literacy Diagnostic tailored for leaders in midsize organizations, spanning leadership, decision-making, workflows, and strategy.

For each question, I’ve included:

  • ✅ Multiple-choice options (A–E)
  • 📝 Scoring rubric (1–10)
  • 💡 One improvement suggestion tied to that competency.

🧭 SECTION 1: Leadership & Vision

  1. How clearly have you articulated your organization’s vision for using AI?
  2. We haven’t articulated one yet
    B. We have a general idea but no clear vision statement
    C. We have a documented, shared vision with leadership buy-in
    D. Other (please specify)
    E. All of the above

Score:

  • A = 2 B = 5 C = 9 D = (estimate) E = 3
    💡 Suggestion:Craft a 1-sentence AI Vision aligned to business outcomes, then cascade it through your leadership team for alignment.
  1. How well does your leadership team understand AI’s strategic potential?
  2. Limited awareness; they see it as a tech fad
    B. Some curiosity; scattered understanding of use cases
    C. Strong grasp of opportunities and risks, with active discussions
    D. Other (please specify)
    E. All of the above

Score:

  • A = 1 B = 5 C = 9 D = (estimate) E = 3
    💡 Suggestion:Run a 90-minute AI Executive Briefing to establish shared language, examples, and urgency.

🧠 SECTION 2: Decision-Making & Data

  1. How is AI currently used to support leadership decision-making?
  2. Not at all; we rely on intuition and historical data
    B. Occasionally; ad-hoc analysis or pilots
    C. Regularly; integrated into dashboards and workflows
    D. Other (please specify)
    E. All of the above

Score:

  • A = 2 B = 5 C = 9 D = (estimate) E = 4
    💡 Suggestion:Identify one key decision (e.g., forecast, planning) and pilot AI-augmented decision support with clear metrics.
  1. How confident are you in the quality and accessibility of your organization’s data for AI use?
  2. Our data is fragmented and unreliable
    B. We have some clean data sets but limited access
    C. Our data is reliable, accessible, and structured for AI workflows
    D. Other (please specify)
    E. All of the above

Score:

  • A = 1 B = 5 C = 9 D = (estimate) E = 3
    💡 Suggestion:Run a Data Readiness Assessment and create a “Golden Dataset” for your first AI workflow.

🧰 SECTION 3: Workflows & Adoption

  1. How widespread is the use of AI tools in your team’s daily workflows?
  2. Very limited; only a few individuals experiment
    B. Moderate; small groups are trying them out inconsistently
    C. High; integrated into core workflows with measurable impact
    D. Other (please specify)
    E. All of the above

Score:

  • A = 2 B = 5 C = 9 D = (estimate) E = 4
    💡 Suggestion:Select one recurring workflow (e.g., reporting, planning, drafting) and integrate a single AI tool consistently over 2 weeks.
  1. How structured is your approach to identifying and scaling AI use cases?
  2. Unstructured — we explore ideas randomly
    B. Semi-structured — some prioritization but no repeatable process
    C. Structured — clear criteria, ROI assessment, and scaling process
    D. Other (please specify)
    E. All of the above

Score:

  • A = 3 B = 5 C = 9 D = (estimate) E = 4
    💡 Suggestion:Use a Use Case Funnel with 3 stages: Collect → Prioritize → Scale to build momentum systematically.

🧭 SECTION 4: Strategy & Scaling

  1. How well is AI aligned with your company’s strategic priorities and OKRs?
  2. Not aligned; AI sits in its own silo
    B. Some overlap, but not systematically tied to OKRs
    C. Fully embedded — AI initiatives map directly to strategic goals
    D. Other (please specify)
    E. All of the above

Score:

  • A = 2 B = 5 C = 10 D = (estimate) E = 4
    💡 Suggestion:Pick one strategic OKR and attach a high-impact AI initiative to make the value explicit.
  1. How ready is your organization to scale successful AI pilots company-wide?
  2. Not ready — no processes or infrastructure in place
    B. Partially ready — some teams can scale manually
    C. Ready — clear playbooks, governance, and tech foundations exist
    D. Other (please specify)
    E. All of the above

Score:

  • A = 2 B = 6 C = 10 D = (estimate) E = 4
    💡 Suggestion:Develop a “Pilot → Scale” Playbook documenting workflows, metrics, and change-management steps.

🪄 SECTION 5: Skills & Culture

  1. How would you describe your team’s AI skills and literacy?
  2. Very low — most don’t know where to start
    B. Mixed — a few champions, but no baseline training
    C. Strong — baseline training completed and active skill building
    D. Other (please specify)
    E. All of the above

Score:

  • A = 1 B = 5 C = 9 D = (estimate) E = 4
    💡 Suggestion:Roll out AI Effectiveness 101 training to build a shared baseline in 30 days.
  1. How open is your culture to experimenting and learning with AI?
  2. Resistant — fear and skepticism dominate
    B. Cautious — some curiosity but limited experimentation
    C. Open — experimentation is encouraged and celebrated
    D. Other (please specify)
    E. All of the above

Score:

  • A = 2 B = 5 C = 10 D = (estimate) E = 4
    💡 Suggestion:Launch a “Micro-Wins Challenge” to celebrate small, fast AI wins that build momentum and reduce fear.

📈 Scoring Summary

Range

Maturity Level

Description

10–30

Early Explorer

Just starting out; vision and skills need structure.

31–60

Emerging Practitioner

Some traction, but adoption and alignment are inconsistent.

61–90

Strategic Adopter

Strong foundation; next step is scaling and integration.

91–100

AI-Effective Leader

Strategic, systemic, and cultural alignment achieved.

 

 


 

Part 3. Installing Daily Leverage Loops (Time Buy-Back Prompts)

What We Did:

  • Identified 3 daily prompts to save 5+ hours/week through workflow acceleration, decision clarity, and sprint reflection.
  • Tied each to your OKR for compounding strategic impact.

Why It Mattered:

  • Executives are time-constrained. These prompts turn routine strategic work into repeatable leverage loops.
  • They drive daily execution without adding meetings.

✅ Value Created:

  • Time savings (~5 hrs/week)
  • Improved decision speed & alignment
  • Daily focus on strategic priorities

 

Prompt — Save Me time (WEAK)

Jon said (prompt):
“Provide me 3 prompts that can save me time.”

 

ChatGPT said (output):

Here are 3 high-leverage prompts designed specifically to save you time as a strategic leader driving AI adoption and execution. Each is built for speed, clarity, and immediate business impact 👇

⏱️ 1. Rapid Workflow Optimizer

Use when: You want to quickly improve a team process or routine task without a long analysis session.

Prompt:

“Act as a Lean Process + AI Workflow Expert. Here’s the current workflow: [insert brief description or steps]. Identify:

  • 🚫 Top 3 time-wasting steps
  • 🤖 2–3 ways AI could automate or accelerate those steps
  • 📝 A recommended ‘future state’ 3-step workflow I could implement this week.”

✅ Time Saved: 30–60 min of meeting + brainstorming per workflow.
💡 Pro Tip: Run this for one process each week and build a “Quick Wins Library.”

 

🧠 2. Decision Brief Generator

Use when: You need a clear, 1-page decision brief for leadership or clients—fast.

Prompt:

“Summarize this situation into a concise executive decision brief. Include:

  • 🧭 Context (why this matters)
  • ❓ Key Decision(s) Needed
  • 📊 2–3 Options with Pros & Cons
  • 📝 Recommended Next Step
    Text: [paste email thread, meeting notes, or scenario].”

✅ Time Saved: 45+ min of drafting and structuring.
💡 Pro Tip: Use this before strategy meetings to ensure discussions are focused and actionable.

 

📈 3. Strategic Sprint Planner

Use when: You want to turn an idea or challenge into a 2-week sprint plan without starting from scratch.

Prompt:

“Convert this initiative into a focused 2-week sprint plan.
Initiative: [insert description].
Create a concise table with columns for Objective, Key Activities, Owner, Expected Outcome, and Success Metric. Ensure it’s realistic and execution-ready.”

✅ Time Saved: 60+ min of planning + alignment work.
💡 Pro Tip: Use this to accelerate quarterly OKR execution cycles or team improvement projects.

 

⚡ Summary Table

#

Prompt Name

Best Use Case

Typical Time Saved

1

Rapid Workflow Optimizer

Streamlining recurring workflows

30–60 min

2

Decision Brief Generator

Structuring decisions clearly

45+ min

3

Strategic Sprint Planner

Turning ideas into executable sprints

60+ min

 

Prompt — Save Me time (STRONG)

Jon said (prompt):
“Given my OKR, provide me 3 prompts that I can use daily to buy back 5 hours of time each week.”

 

ChatGPT said (output):

Excellent — this is exactly how strategic leaders get leverage with AI.
Your OKR is:

“By the end of this quarter, we will move from running scattered pilots with unclear ROI by addressing limited team skills and inconsistent adoption to achieve a specific, practical AI workflow that improves business performance this quarter, measured by an 80% team adoption rate and a 20% reduction in workflow cycle time.”

The key here is to design daily prompts that act like repeatable “force multipliers” — helping you standardize workflows, delegate thinking, and reduce context switching.

Here are 3 powerful daily prompts designed to buy back 5+ hours/week (≈ 1 hour/day) by turning routine strategic work into fast, structured outputs 👇

🧭 1. Daily Workflow Accelerator Prompt

Goal: Streamline 1 recurring activity or process each day.
Time Saved: 15–30 minutes/day (1.5–2.5 hrs/week)

Prompt:

“You are my AI Workflow Optimizer. Each day, I’ll give you one recurring task or workflow that eats up time.
Workflow: [Describe in 1–3 sentences]
Generate:

  • 🚫 2–3 steps I can eliminate, delegate, or automate immediately
  • 🤖 1 AI-powered shortcut or template I can apply today
  • 📝 A cleaner 3-step version of the workflow I can test with my team this week.”

💡 Why it works: This prompt builds a daily habit of continuous improvement — compounding workflow savings over time.

 

🧠 2. Decision Clarity Prompt

Goal: Turn messy inputs (emails, updates, meeting notes) into clear decisions fast.
Time Saved: 20–30 minutes/day (2–2.5 hrs/week)

Prompt:

“Summarize the following situation into a clear executive decision brief. Include:

  • 🧭 Key context and why it matters
  • ❓ Decision(s) required
  • 📊 2–3 options with pros/cons
  • 📝 Recommended next step(s)
    Text: [Paste content or describe situation]”

💡 Why it works: Instead of mentally sorting through complexity, you get a ready-to-use 1-pager for fast, confident decisions or delegation.

 

📝 3. Strategic Sprint Progress Prompt

Goal: Automate daily reflection and keep sprints moving without extra meetings.
Time Saved: 20–30 minutes/day (2–2.5 hrs/week)

Prompt:

“Act as my Strategic Execution Assistant. Summarize today’s work on our AI workflow OKR using this structure:

  • 🟢 Wins / Progress made today
  • 🧱 Blockers or issues that need escalation
  • 🚀 Top 3 priorities for tomorrow
  • 📊 Any quick insights on cycle time or adoption trends (if mentioned)
    Notes: [Paste bullet points, Slack messages, or mental notes]”

💡 Why it works: This replaces manual journaling, debrief emails, or sync huddles — while keeping your OKR front and center daily.

 

📈 Summary Table

#

Prompt Name

Daily Use

Time Saved (Est.)

Strategic Leverage

1

Daily Workflow Accelerator

Streamline recurring tasks

1.5–2.5 hrs/week

Shrinks cycle time, builds efficiency muscle

2

Decision Clarity

Turn messy inputs into structured decisions

2–2.5 hrs/week

Increases decision speed & clarity

3

Strategic Sprint Progress

Automate daily OKR tracking

2–2.5 hrs/week

Keeps execution rhythm tight

 

 


 

Part 4. Defining Strategic Bets, Flanks, and Extensions

What We Did:

  • Converted your OKR into 5 Strategic Bets, 5 Protect the Flanks, and 5 Extend Victories plays.
  • Each move was tied to execution levers (training, workflows, champions, comms, governance).

Why It Mattered:

  • This gave you a portfolio view of strategic moves — not just a to-do list.
  • Balanced offensive and defensive plays create sustainable momentum.

✅ Value Created:

  • Strategic clarity for sprint planning
  • Risk mitigation built in
  • Clear storytelling for leadership and team alignment

 

Prompt — Generate Ideas for Strategic Bets, Protecting the Flanks, and Extending Victories

Jon said (prompt):
"Act as a strategy consultant. Based on my OKRs, provide 5 strategic bets, 5 protecting the flanks, and 5 extending victories moves."

 

 

ChatGPT said (output):

Excellent — this is exactly the kind of strategic clarity that turns an ambitious AI Effectiveness OKR into a winning execution play.

Let’s restate your core OKR first for alignment:

“By the end of this quarter, we will move from running scattered pilots with unclear ROI by addressing limited team skills and inconsistent adoption to achieve a specific, practical AI workflow that improves business performance this quarter, measured by an 80% team adoption rate and a 20% reduction in workflow cycle time.”

Using this OKR as the anchor, here’s a strategic moves map across three categories:

🧭 1. Strategic Bets (5)

Purpose: Identify high-leverage, high-impact moves that can create step changes in performance.
These are your big plays for unlocking transformation this quarter.

#

Strategic Bet

Why It Matters

1

Install One Hero AI Workflow in a core operational area (e.g., reporting, planning, or production scheduling)

Creates a proof point with measurable ROI, accelerates adoption through visibility

2

Run a 30-Day AI Effectiveness Training Sprint for a cross-functional team

Quickly levels up team literacy and builds a shared language, solving the “limited skills” barrier

3

Launch a “Daily AI Wins” Dashboard tracking adoption and cycle time impact

Builds transparency, creates competitive energy, and aligns teams to the OKR metrics

4

Empower 3 Internal AI Champions to drive peer-led adoption

Shifts from top-down push to bottom-up momentum, sustaining cultural change

5

Tie AI Workflow Adoption to One Quarterly Business Priority/OKR

Ensures relevance, executive sponsorship, and integration into the strategic rhythm

👉 Strategic bet theme: Focus and momentum through one workflow, one training sprint, and visible wins.

🛡 2. Protecting the Flanks (5)

Purpose: Anticipate and neutralize risks or vulnerabilities that could derail progress.
These are defensive plays that create strategic safety.

#

Flank Move

Why It Matters

1

Clarify AI Use Guardrails early (ethics, compliance, data security)

Prevents fear-based resistance and avoids compliance surprises mid-sprint

2

Identify 3 Key Skeptics Early and bring them into pilot design

Neutralizes passive resistance and converts potential blockers into co-creators

3

Protect team bandwidth by eliminating 1–2 non-critical projects this quarter

Avoids initiative overload that kills focus and adoption

4

Secure quick IT support & data access agreements upfront

Prevents bottlenecks that often slow workflow automation projects

5

Set clear success metrics and check-in cadence

Keeps everyone aligned and prevents drift into vague, non-measurable outcomes

👉 Flank protection theme: De-risk adoption by aligning people, governance, and capacity before scaling.

🏆 3. Extending Victories (5)

Purpose: Amplify early wins into broader organizational impact and create compounding advantages.
These are offensive scaling plays.

#

Extending Move

Why It Matters

1

Package and share the Hero Workflow case studyinternally within 30 days

Turns one success into a rallying story that accelerates follow-on adoption

2

Replicate the winning workflow across 1–2 adjacent functions

Expands impact without reinventing the wheel

3

Create a “Top 5 AI Wins” quarterly recognition program

Builds cultural momentum and celebrates champions publicly

4

Invite external partners or clients to see the workflow in action

Positions the company as an AI-effective leader, creating strategic differentiation

5

Embed the workflow into next quarter’s strategic planning process

Institutionalizes the win, ensuring it’s not a one-off pilot but part of the operating rhythm

👉 Victory extension theme: Codify, replicate, celebrate, and institutionalize.

📝 Strategic Moves Summary Table

Category

Strategic Intent

Core Levers

Strategic Bets

Create breakthrough momentum

Hero workflow, training sprint, champions, dashboards

Protect the Flanks

Remove adoption blockers early

Governance, skeptics, bandwidth, IT/data, metrics

Extend Victories

Scale and embed wins

Storytelling, replication, recognition, external positioning, planning integration

 

 


 

Part 5. Converting Strategy into a 90-Day Sprint Plan

What We Did:

  • Mapped the 5 Moves into a 12-week execution plan with milestones at weeks 2, 4, 6, 8, 10, and 12.
  • Defined roles, KPIs, and rhythms to drive accountability and compounding execution.

Why It Mattered:

  • Many teams stall after setting OKRs because they lack execution rhythm.
  • This plan gives executives a clear playbook to go from strategy → skills → workflow → adoption → scale.

✅ Value Created:

  • Execution clarity
  • Role accountability
  • Predictable sprint rhythms for adoption

Prompt — 90-day AI Effectiveness Initiative Plan

Jon said (prompt):
"Convert the 5 Moves in the 90-day AI Effectiveness Model into a sprint plan for my OKR with milestones at weeks 2, 4, 6, 8,10, and 12. Assign roles, KPIs, and Sprint Rhythms."

 

 

ChatGPT said (output):

Perfect — this is exactly the kind of strategic execution structure that turns a bold OKR into a 12-week AI Effectiveness sprint with clear ownership and compounding wins.

Let’s anchor first:

🧭 Your OKR

“By the end of this quarter, we will move from running scattered pilots with unclear ROI by addressing limited team skills and inconsistent adoption to achieve a specific, practical AI workflow that improves business performance this quarter, measured by an 80% team adoption rate and a 20% reduction in workflow cycle time.”

🧩 The 5 Moves — 90-Day AI Effectiveness Model

These are the backbone for your sprint plan:

  1. Strategic Alignment– Set the vision, choose the right use case.
  2. Skill Acceleration– Rapidly level up AI literacy.
  3. Workflow Integration– Implement one high-impact AI workflow.
  4. Adoption & Rhythm– Build habits, accountability, and team momentum.
  5. Scale & Institutionalize– Extend wins and lock in operating rhythm.

🚀 90-Day Sprint Plan for Your OKR

Below is a 12-week sprint structure with milestones, roles, KPIs, and rhythms.
This plan assumes biweekly sprint reviews and weekly standups.

Week

Milestone

Key Activities

Roles

KPIs

Sprint Rhythm

2

Strategic Alignment Complete

• Identify and prioritize one Hero AI Workflow (e.g. reporting, planning) 
• Define success metrics (ROI, adoption, cycle time) 
• Set AI Vision & OKR alignment

CEO/VP Ops (Sponsor), Strategy Lead (Facilitator), Team Leads (Input)

• Hero Workflow selected 
• Baseline metrics established 
• Leadership alignment

• Kickoff workshop 
• Weekly standup

4

Skill Acceleration Sprint Complete

• Run AI Effectiveness 101 training (2–3 sessions) 
• Identify 2–3 AI Champions 
• Launch Daily Wins channel/dashboard

AI Coach (Trainer), Champions, Team Leads

• 80%+ team trained 
• Champions nominated 
• 1st daily wins shared

• Weekly standup 
• Biweekly sprint review

6

Workflow Pilot Implemented

• Design & implement Hero AI Workflow v1 
• Test in 1–2 teams 
• Set up quick feedback loops

Workflow Owner (Ops), AI Champion, IT/Data Support

• Workflow live in pilot team 
• First measurable cycle time improvements

• Daily syncs during launch week 
• Weekly standup

8

Adoption & Rhythm Established

• Expand workflow to 2nd team/function 
• Track adoption & cycle time KPIs weekly 
• Integrate into team meetings and huddles

AI Champions, Team Leads, Ops Lead

• ≥50% team adoption 
• 10%+ cycle time reduction 
• Dashboard reviewed weekly

• Weekly standup 
• Biweekly sprint review

10

Scaling Momentum

• Package success case study 
• Share wins org-wide 
• Start extending workflow to adjacent functions

Strategy Lead, Comms, AI Champions

• Case study published 
• 1–2 adjacent teams onboarded 
• Leadership endorsement

• Weekly standup 
• Sprint review

12

Institutionalize & Lock In

• Embed Hero Workflow into standard operating rhythm 
• Formalize governance (metrics, accountability) 
• Identify next 1–2 workflows to scale

Leadership Team, Strategy Lead, AI Council

• 80%+ adoption 
• 20% cycle time reduction 
• Next workflows identified

• Sprint retrospective 
• Leadership review

🧠 Role Clarity

Role

Description

Typical Person

Sponsor

Provides strategic air cover, removes barriers

CEO / VP Ops

Strategy Lead

Orchestrates sprint plan, aligns milestones

You / Transformation Lead

Workflow Owner

Designs & runs the Hero Workflow

Ops / Process Lead

AI Champions

Peer leaders who drive adoption & skill transfer

Selected functional team members

IT/Data Support

Ensures infrastructure, access, and data readiness

IT Lead / Data Analyst

Comms Lead

Crafts internal stories and dashboards

Marketing / Internal Comms

📊 Key KPIs Across the Sprint

KPI

Target

Why It Matters

Workflow Adoption Rate

80%+ by Week 12

Core OKR metric — behavior change

Cycle Time Reduction

20% by Week 12

Tangible operational impact

Training Completion

80%+ by Week 4

Capability foundation

Champion Activation

≥3 Champions leading workflows

Culture + scaling

Case Study Published

Week 10

Momentum multiplier for scaling

🔄 Sprint Rhythms

Rhythm

Cadence

Purpose

Weekly Standup (15 min)

Weekly

Track workflow progress, remove blockers, surface wins

Biweekly Sprint Review (45 min)

Weeks 4, 8, 12

Check milestone progress, adjust plan, celebrate wins

Leadership Review (30 min)

Monthly

Strategic alignment, unblock resources, scale decisions

Daily Wins Updates

Asynchronous

Build momentum & visibility of progress

📝 Strategic Execution Flow

Weeks 1–4 → ALIGN & UPSKILL
✅ Choose Hero Workflow, train team, appoint champions.

Weeks 5–8 → PILOT & ADOPT
🚀 Launch workflow, establish rhythms, track KPIs.

Weeks 9–12 → SCALE & LOCK IN
📈 Extend victories, embed into operations, pick next plays.

🪄 Why This Works

  • Focuses energy on ONE workflowto avoid scattered pilots.
  • Builds capability + rhythm before scaling— solving your core leadership barrier.
  • Aligns execution to clear KPIs and sprint cadences, which drives accountability and adoption.

 

 

Ready to turn AI potential into real business results?


Take the next step by joining Jon for a 60-minute private coaching session where you’ll build a clear, actionable AI Effectiveness Initiative Plan tailored to your company, unit, or team. You’ll also unlock access to weekly 15-minute FastTrack coaching sessions, designed to keep your team focused, aligned, and implementing effectively—week after week.