When It Feels Like You’re Never Going To Reach The Promised Land
Introduction
In 2018, a well-known global retailer announced a bold digital transformation initiative. The goal was to migrate their aging inventory system to a cloud-based solution. On paper, it looked like a textbook upgrade. But what followed was anything but simple: delays, cost overruns, employee frustration, and a loss of trust in leadership. What had been planned as a technology migration became a strategic quagmire.
Some migrations aren’t just complex—they’re wicked. Whether you’re upgrading an ERP, replacing a CRM, or shifting to a new HRIS, system migrations can trigger a cascade of unforeseen issues, entrenched resistance, and strategic uncertainty. These projects often defy linear timelines and best practices because the problem itself evolves as you try to solve it. That’s the very definition of a “wicked problem,” a term coined by Horst Rittel to describe challenges with no clear solution.
Rittel’s 10 Properties of Wicked Problems
So what makes a problem wicked? Rittel identified ten characteristics that distinguish wicked problems from tame ones. Let’s apply those directly to the context of system migrations:
1. No Definitive Formulation
Stakeholders disagree on goals: modernization vs. compliance vs. agility.
2. No Stopping Rule
Go-live is just the start. Iterations, fixes, and training follow.
3. Good-or-bad, not true-or-false
Evaluation depends on politics, perception, and outcomes.
4. No Ultimate Test
Real issues emerge only in live environments.
5. One-Shot Operation
Once cut over, there’s no rolling back.
6. No Exhaustive List of Solutions
Many possible vendors, configurations, and pathways.
7. Essentially Unique
Even similar migrations play out differently across orgs.
8. Symptom of Other Problems
Often exposes deeper cultural or operational issues.
9. Framing Defines Action
“Tech upgrade” vs. “strategic shift” leads to different designs.
10. No Right to Be Wrong
Leaders bear consequences regardless of complexity.
What You Can Do to Save Your Migration
Each wicked attribute presents risks — but also opportunities. Here are three concrete tactics you can use to manage each of Rittel’s 10 properties during a system migration:
1. No Definitive Formulation
- Hold stakeholder alignment workshops before scoping requirements.
- Use storyboards or personas to visualize competing definitions of success.
- Create a dynamic problem statement that evolves as more input is gathered.
2. No Stopping Rule
- Shift mindset from “go-live” to “ongoing value realization.”
- Budget for continuous improvements and post-launch optimization.
- Celebrate milestones to maintain momentum rather than declaring finality.
3. Good-or-bad, not true-or-false
- Establish a shared success rubric that includes qualitative and emotional factors.
- Use pulse surveys to capture perception gaps across teams.
- Conduct storytelling sessions to surface what success means on the ground.
4. No Ultimate Test
- Run simulations or dry-runs with actual users in advance.
- Use post-launch retrospectives to capture unintended effects early.
- Monitor long-tail metrics like turnover or adoption 6–12 months out.
5. One-Shot Operation
- Create rollback plans for critical modules (even if imperfect).
- Use shadow systems or parallel run periods where feasible.
- Document assumptions explicitly so they can be revisited.
6. No Exhaustive List of Solutions
- Use design thinking to broaden idea generation before down-selecting tools.
- Engage vendors in sandboxing new workflows.
- Map decision trade-offs transparently to build shared understanding.
7. Essentially Unique
- Benchmark cautiously — don’t assume what worked elsewhere fits your context.
- Ask “What’s different about us this time?” in kickoff meetings.
- Tailor communication and training based on role and culture.
8. Symptom of Other Problems
- Use migration as a mirror to surface broader system health issues.
- Include non-technical stakeholders early to capture systemic causes.
- Don’t isolate migration from HR, finance, or culture transformation efforts.
9. Framing Defines Action
- Test different problem framings before committing to a solution path.
- Use “how might we…” questions to stay exploratory.
- Design roadmaps that reflect multiple interpretations, not just one vision.
10. No Right to Be Wrong
- Be transparent about risks and trade-offs with sponsors and staff.
- Create blame-free spaces to surface issues before they escalate.
- Model humility and learning publicly to encourage psychological safety.
How To Tame Your Wicked Migration
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