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