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AI TRAINING

AI Transformation Roadmap Design Workshop

Leave with a sequenced, dependency-mapped AI roadmap your leadership team has co-created and owns.

Format
workshop
Duration
12–16h
Level
practitioner
Group size
8–20
Price / participant
€1K–€3K
Group price
€15K–€35K
Audience
Chief Transformation Officers, CDOs, COOs, and their direct transformation or programme management teams
Prerequisites
Participants should hold decision-making authority over at least one functional area and arrive with a rough list of ongoing or candidate AI initiatives

What it covers

A facilitated 2-day working session that takes transformation leaders and their teams from scattered initiative ideas to a structured, prioritised roadmap. Participants conduct a maturity baseline assessment, inventory existing and planned AI initiatives, map interdependencies, and agree on a phased sequencing logic. The workshop closes with a communications plan and governance skeleton so momentum is sustained after the room disperses. Roughly 70% of time is hands-on facilitated exercises using the organisation's own data and context.

What you'll be able to do

  • Conduct an AI maturity baseline assessment using a structured diagnostic framework and identify the organisation's top capability gaps
  • Build a consolidated initiative inventory scored against value, effort, and strategic alignment criteria
  • Produce a dependency map that surfaces sequencing constraints and critical-path blockers across the portfolio
  • Draft a phased 12-to-24-month roadmap with clear milestones, owners, and success metrics
  • Design a stakeholder communication plan that addresses resistance and sustains executive sponsorship post-workshop

Topics covered

  • AI maturity baseline assessment and gap analysis
  • Initiative inventory and value/effort mapping
  • Dependency mapping and sequencing logic
  • Portfolio prioritisation frameworks (e.g. WSJF, impact/feasibility matrix)
  • Change management and stakeholder communications planning
  • Governance structure and decision-rights design
  • Quick-win identification versus long-horizon bets
  • Roadmap visualisation and executive narrative construction

Delivery

Delivered in-person or as a hybrid format with remote participants joining via facilitated breakout tools (Miro or equivalent). Two facilitators are recommended for groups above 12. Pre-work is required: participants complete a 30-minute maturity survey and submit their initiative list 5 business days in advance. Physical or virtual workbooks are provided. Day 1 focuses on diagnosis and inventory; Day 2 on sequencing, governance, and communications. A 2-week follow-up virtual session (2 hours) to pressure-test the draft roadmap is strongly recommended and can be added as an optional module.

What makes it work

  • Securing C-level sponsorship before the workshop so sequencing decisions carry real authority
  • Using the organisation's actual initiative list and real cost/effort estimates rather than hypothetical scenarios
  • Assigning a named roadmap owner who attends the full two days and commits to a 90-day review cadence
  • Pairing the roadmap with a lightweight governance forum that meets monthly to re-prioritise based on new information

Common mistakes

  • Inviting too many contributors without a clear decision-making owner, leading to a roadmap nobody actually owns post-workshop
  • Skipping the pre-work maturity survey so Day 1 is consumed by data gathering rather than diagnosis
  • Sequencing initiatives by enthusiasm rather than dependency logic, creating bottlenecks six months later
  • Producing a beautifully designed roadmap slide deck that is never operationalised into a governance or programme cadence

When NOT to take this

This workshop is not the right fit when an organisation has not yet run any AI pilots and has no cross-functional team with authority to make portfolio decisions — in that situation a foundational AI awareness programme for leadership should come first.

Providers to consider

Sources

This training is part of a Data & AI catalog built for leaders serious about execution. Take the free diagnostic to see which trainings your team needs.