Manage the People Side of a Systems Migration
Digital Transformation · Ongoing · Intermediate
The job
Plan the employee experience around a major systems change, not just the technical cutover.
What the sponsor gets
Each canvas and map from this playbook — Stakeholder Map, Empathy Map, Pre-Mortem Canvas, Retrospective Canvas, Journey map — exports as a PDF, or as PowerPoint on Pro, straight from the session, and the whole run exports as one PowerPoint for the sponsor. Nothing is redrawn.
The method
Assess the change impact
Map which teams are affected, how their daily work changes, and how much disruption to expect. Interview people who rely on the current system to understand what they'll lose, not just what they'll gain.
Tip: The biggest people risk isn't the technology — it's losing the workarounds and tribal knowledge that made the old system actually work.
Map migration stakeholders
Create a Stakeholder Map plotting everyone affected by influence and impact. Identify who needs hands-on support, who needs communication, and who can champion the change.
Tip: The super-users of the old system are your biggest risk and your biggest asset — invest heavily in them.
Understand the most affected group
Create an Empathy Map for the team whose daily workflow changes most. What do they fear losing? What frustrates them about the current system? What would make the new system feel like a genuine improvement?
Tip: If you can't articulate a genuine benefit for the most affected group, your change communications will ring hollow.
Map the migration experience
Create a Change Management journey map from announcement through training, cutover, and stabilisation. Map the emotional experience — anxiety peaks at cutover, not at announcement.
Tip: Plan for a "valley of despair" 2–4 weeks after cutover when people are slow on the new system and nostalgic for the old one — this is when you need the most support.
Pre-mortem the people risks
Run a pre-mortem focused on people-side failures: inadequate training, data quality issues, loss of productivity, shadow systems emerging, key person leaves.
Tip: Ask: "What will people do when the new system can't do something the old system could?" — the answer reveals your training and support gaps.
Design training and support
Build role-specific training paths (not one-size-fits-all), identify floor-walkers for the first 2 weeks post-cutover, and create a rapid-response support channel for migration issues.
Tip: Schedule training as close to cutover as possible — training 6 weeks before go-live means people forget everything by day one.
30-day post-migration retrospective
Run a retrospective one month after cutover. What's working? What's painful? Where have shadow systems or workarounds emerged? Use the findings to prioritise stabilisation work.
Tip: If people are maintaining spreadsheets alongside the new system, the migration isn't complete — find out why and fix it.
The canvases and maps
- Stakeholder Map
- Power against interest in four quadrants, so engagement effort goes where it matters and nobody important is handled by accident.
- Empathy Map
- The goal first, then what the person sees, says, does, hears, thinks and feels, so the room separates what it has observed from what it is guessing.
- Pre-Mortem Canvas
- It starts from failure — the project, how it failed, root causes, mitigations and early warnings — so people can voice doubts as foresight rather than dissent.
- Retrospective Canvas
- What went well and what to improve, then start, stop and continue, so reflection ends in actions rather than a list of complaints.
- Journey map
- Stages run across and lanes run beneath them, so the experience reads in the order people live it and each low point lines up with what causes it.
What it doesn't do
It doesn't run the room for you or decide for the client. The steps, canvases and duration are a starting point you adapt; the judgement stays yours.