InitializeAI Logo

How to Run an AI Readiness Workshop: A Step-by-Step Playbook

Learn how to facilitate a powerful AI Readiness Workshop that aligns stakeholders, identifies opportunities, and accelerates AI adoption in your organization. Based on InitializeAI’s proven playbook, this guide walks you through every step from pre-workshop prep to post-workshop activation.

How to Run an AI Readiness Workshop: A Step-by-Step Playbook

AI Strategy
5/23/2025
How to Run an AI Readiness Workshop: A Step-by-Step Playbook
Learn how to facilitate a powerful AI Readiness Workshop that aligns stakeholders, identifies opportunities, and accelerates AI adoption in your organization. Based on InitializeAI’s proven playbook, this guide walks you through every step from pre-workshop prep to post-workshop activation.

Organizations eager to explore AI often stumble—not due to lack of ambition, but lack of alignment. The solution? A well-structured AI Readiness Workshop. At InitializeAI, we use a methodical, cross-functional approach to unify stakeholders and catalyze AI initiatives.

This guide lays out a proven step-by-step framework to help you plan and execute your own high-impact workshop.


Why AI Readiness Workshops Matter

“AI success is rarely about the model—it's about stakeholder alignment, data readiness, and organizational momentum.”

AI Readiness Workshops create the necessary shared language, goals, and roadmap to bridge technical teams and business units. Done right, they:

  • Identify AI use cases grounded in business value
  • Surface blockers in data, talent, and culture
  • Build internal excitement and shared accountability
  • Accelerate leadership buy-in and budget alignment
AI Readiness Workshops

📍 Step 1: Define the Workshop Scope

Before sending a single invite, clarify the following:

  • Goals: Are you exploring use cases, prioritizing investments, or aligning teams?
  • Participants: Aim for a mix of exec sponsors, data owners, ops leads, product managers, and end users.
  • Format: Half-day or full-day? In-person or virtual?
  • Output: What deliverables will stakeholders walk away with?

📌 Pro tip: Start small—pilot with one department or line of business.

Define the Workshop Scope

🗂️ Step 2: Pre-Workshop Discovery

Successful workshops don’t start at the opening slide. They start with preparation.

Key Discovery Activities:

  • Conduct stakeholder interviews (10–20 min each)
  • Collect existing documentation (data maps, process flows, OKRs)
  • Send a brief survey to surface AI readiness, fears, and goals
  • Inventory available data systems and pipelines
Pre-Workshop Discovery

🧠 Step 3: Workshop Agenda

Here’s a sample half-day structure that we use at InitializeAI:

Time Activity
09:00 Welcome + Workshop Goals
09:15 AI Demystified: What AI Can (and Can’t) Do
09:45 Current State Mapping
10:30 Break
10:45 Use Case Brainstorming (guided templates)
11:30 Prioritization Exercise
12:00 Roadmap & Next Steps
12:30 Wrap-up & Feedback
Workshop Facilitation

💡 Step 4: Use Case Discovery & Prioritization

This is the heart of the session. Use pre-built cards or a digital whiteboard to guide teams through:

  • Problem Statement
  • Impact (cost, revenue, efficiency)
  • Data availability
  • Process ownership
  • Complexity (ML difficulty, change mgmt needs)

Apply a 2x2 matrix: Business Impact vs. Feasibility

📌 Outcome: A prioritized shortlist of 3–5 high-value, actionable AI use cases.

Use Case Discovery & Prioritization

🧱 Step 5: Assess Data & Capability Readiness

No AI without data.

Use this moment to inspect:

  • Where the needed data lives
  • Whether it’s labeled, clean, or accessible
  • Data sharing and compliance risks
  • Internal ML expertise or external partner needs

Visualize findings in a “Readiness Radar”:

  • Data
  • Talent
  • Infrastructure
  • Governance
  • Executive alignment
Assess Data & Capability Readiness

🛠️ Step 6: Draft the Roadmap

Turn workshop insights into a 30-60-90 day plan.

Sample Roadmap:

Phase Activities
30 Days Finalize use case(s), assign leads, define success metrics
60 Days Conduct feasibility assessments, gather data, prototype MVP
90 Days Deliver pilot, collect feedback, iterate or scale

Include who owns what—and ensure accountability.

AI Roadmap Creation

📨 Step 7: Post-Workshop Follow-up

Too many workshops die in a slide deck.

Your job now is to document, share, and activate:

  • Create a visual summary of outputs and priorities
  • Set up a recurring check-in cadence (biweekly or monthly)
  • Assign project owners and kick off quick wins
Post-Workshop Follow-up

📎 Resources You Can Use


AI pilot rollout, professionals analyzing data

👥 Real-World Success Story

A regional insurance company used this framework to align their underwriting, claims, and IT teams. Within 3 months, they had launched 2 pilots—one for claim triage automation and another for fraud detection. Both are now scaling org-wide.


🚀 Conclusion: From Workshop to Workflow

An AI Readiness Workshop isn’t just a feel-good meeting—it’s a strategic inflection point. When done right, it moves AI from an abstract ambition to a concrete plan with measurable results.

Start small. Align fast. Scale boldly.

Ready to bring this methodology to your org? Book a readiness call with InitializeAI →


AI StrategyDigital TransformationAI ReadinessEnterprise AIWorkshopsChange ManagementStakeholder Engagement