Legacy system migration strategies: A comparison guide

Migrating to a new design system can be a challenge. Legacy systems are often deeply embedded in workflows, and teams are usually busy with other priorities. For adoption to succeed, the strategy matters as much as the system itself. There is no one-size-fits-all solution—different organizations need different approaches.

This article is based on insights from the panel discussion Legacy System Migration Strategies, featuring Chela Giraldo, Robin van Zessen, and Jeremy Dizon.

The challenge of migration

The main problem is not technical. It is about people, timing, and priorities. Teams resist change when it feels forced or when benefits are unclear. Design system teams struggle to balance speed, quality, and adoption. The result is that migration projects can stall or fail if not managed carefully.

To overcome this, several strategies have emerged. Each one has its own philosophy, strengths, and trade-offs. The right choice depends on the organization’s culture, resources, and timeline.

Strategy comparison

1. The Trojan horse approach

Philosophy: Piggyback adoption onto existing feature work.
Best for: Tight budgets, frequent updates, and minimizing resistance.

• ✅ Low friction and incremental progress
• ❌ Progress depends on existing team workstreams

2. Strategic team selection

Philosophy: Start with willing adopters, build case studies, then expand.
Best for: Small DS teams and organizations with mixed team maturity.

• ✅ High success rate, strong success stories
• ❌ May leave reluctant teams behind

3. Incremental micro-adoption

Philosophy: Adopt in layers—tokens, core components, then patterns.
Best for: Complex systems and teams afraid of big changes.

• ✅ Gradual learning, reduced disruption
• ❌ Longer timelines, temporary inconsistencies

4. Value-first communication

Philosophy: Lead with benefits, not compliance.
Best for: Organizations with strong team autonomy.

• ✅ Builds genuine buy-in, sustainable adoption
• ❌ Needs upfront investment in proof and support

5. Start small strategy

Philosophy: Begin with foundations, scale up step by step.
Best for: Teams new to design systems.

• ✅ Clear progression path, quick early wins
• ❌ Feels slow if teams want faster change

6. Shared responsibility models

Different views:

• Design System team leads: DS team drives adoption and reports issues.
• Product team owns: DS provides tools, product teams enforce compliance.
• Partnership: Shared accountability, regular check-ins, mutual support.

Choosing the right approach

The decision framework looks like this:

• Trojan Horse → Minimal friction, budget-limited, relationship-focused.
• Strategic Selection → Limited DS capacity, need case studies.
• Micro-Adoption → High complexity, gradual learning.
• Value-First → Voluntary adoption, culture change.
• Start Small → New to DS, systematic rollout.

In practice, hybrid approaches often work best. Combining strategies can balance speed, trust, and sustainability. For example:

• Trojan Horse + Start Small → Token adoption during existing feature work.
• Strategic Selection + Value-First → Partner with willing teams, show benefits.
• Micro-Adoption + Partnership → Layered adoption with shared ownership.

Conclusion

Migrating a legacy system is not only about technology. It is about people, trust, and timing. The best strategy depends on your context, but success usually comes from mixing approaches rather than sticking to one. With the right plan, migration can be less painful and more effective—turning adoption into collaboration instead of resistance.

About the panelists

• Chela Giraldo – Colombian product designer at Realtor.com, focusing on design systems and accessibility.
  ✦ “Design System Designer Diaries” article · Personal site

• Robin van Zessen – UX designer since 2009, specializing in design systems since 2016.
  ✦ Instagram: @ux.robin

• Jeremy Dizon – Lead product designer at Disney Streaming, systems experience since 2014.
  ✦ Medium profile

Cheatsheet: Migration strategies at a glance