Software Switching and Migration Checklist

A step-by-step checklist for evaluating, migrating to and retiring an AI productivity tool.

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Decide

Evaluate

Migrate

Roll out

Retire

Switching software is less about the new tool and more about the sequence of small steps that protect your data, your budget and your team's patience. This checklist groups the work into five stages: decide, evaluate, migrate, roll out and retire. Work through it in order and tick items as you complete them; your progress is kept in your browser on this device.

How to use it. Treat the Decide stage as a gate. If you cannot write down the problems you want to solve, a switch will probably recreate them in a new interface. In the Evaluate stage, insist on testing exports and pilots with real work, because demos are built to impress. In the Migrate stage, move in waves rather than all at once so that mistakes affect one team, not everyone.

Example. A 15-person agency using this list found, during the evaluation stage, that its current tool exported documents but not comment history. It decided to archive important threads as PDFs before migrating, which added half a day but avoided losing client decisions.

Limits. The list is general. Regulated businesses may need additional steps, such as legal review of vendor data-processing terms. Adapt it to your contracts and compliance duties.

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