Talk at LDX3 by Camille Fornier. https://leaddev.com/software-quality/escaping-the-rewrite-trap
This is targeted towards platform teams, but interesting.
Principles for success:
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vision (need something compelling to engineers vision (need something compelling to engineers & stakeholders; Could include features that would ONLY be deliverable with the new world.. one of the things like the attached photo)
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consider adjacent systems (could we absorb sibling systems to reduce overall complexity? reconsider OSS/vendor components)
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right-size the effort to the company right-size the effort to the company & rate of growth (don’t design for millions when you do low thousands)
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factor in migration costs (this is the biggest risk)
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determine the major 12-month wins (ideally targeted across multiple stakeholders since they can have moving attention spans)
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sell the plan (to the team, stakeholders)
Execution gotchas:
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Beware the new external hire manager/tech lead (they lack context, so they shouldn’t be running the project)
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Minimize disruption to users (reminder for platform people)
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Correctness (investment in the test harnesses to ensure the new rearchitected thing still works)