Crafting Your Digital Transformation Roadmap
A hands-on workshop to drive cross-functional collaboration for business-critical digital transformation initiatives

Half day on Friday, September 5
Cost: $595

WORKSHOP LEADER

Rebecca Solano
Senior Manager, Organizational Change Management
Crowe

Overview:

Digital transformation delivers its greatest impact when teams work together, aligned on clear objectives and equipped with practical roadmaps. In this immersive half-day workshop, you’ll work through a case study to identify milestones, define outcomes, and surface risks using industry-proven templates. By the end of the day, you’ll walk away ready to craft your digital transformation roadmap for your enterprise initiatives.

What You’ll Gain?

  • Guidance on how to rank and select your top 3–5 digital projects, backed by ROI criteria and business alignment.
  • Identify and map key sponsors, champions, and frontline teams with a tailored influence matrix.
  • Populate milestones, owners, and KPIs into a Roadmap.
  • Define and apply mitigation strategies while considering common challenges.

Who Should Attend?

  • Transformation & Change Leaders responsible for cross-functional rollout
  • IT/OT & Digital Executives driving roadmap approval and resourcing
  • Business-Unit Heads seeking clarity on digital-initiative impact
  • Implementation & Consulting Teams supporting enterprise-wide adoption

Agenda:

9:00–9:15    Welcome & Objectives

  • Introduction, workshop goals, and deliverables overview
  • Icebreaker: “What has held back our success?”

9:15–10:00    Module 1: Prioritize High-Impact Initiatives

  • Mini-lecture: ROI criteria and business alignment guidance
  • Exercise: Score and select top 3 projects using case study

10:00–10:45    Module 2: Identify & Map Stakeholders

  • Template: Stakeholder-Influence Matrix
  • Group activity: Build your map and anticipate challenges

10:45–11:05    Break 

11:05–11:55    Module 3: Populate Your Roadmap Blueprint

  • Walkthrough: phases, milestones, owners, KPIs
  • Hands-on: Draft two phases in the roadmap

11:55–12:25    Lunch Break 

12:25–1:15    Module 4: Integrate Risk & Change-Management

  • Identify top risks for collaboration
  • Role-play: Aligning cross-functional teams and collaborators

1:15–2:00    Module 5: Acceleration Tactics during Challenges

  • Rapidly assess challenges to pivot
  • Exercise: Addressing common challenges

2:00–2:40    Module 6: Finalize Your 90-Day Action Plan

  • SMART-objective next steps
  • Paired peer review: Refine next steps, actions, and anticipated challenges

2:40–3:00    Wrap-Up & Next Steps

  • Consolidated toolkit delivery (templates, checklists, guidance)
  • Q&A and feedback