Trello Migration: Move Work Without Losing History

List boards, lists, cards, checklists, and attachments in the current source (Sheets, another work OS, or email). Mark each: migrate live, archive as files, or drop. 1. Count live vs stale items — stale work should not become “To do” in Trello.

1. Capture owners, dates, comments, and attachments as first-class — not as a notes dump.
2. Write the exclusions: personal lists, duplicate boards, and the wrong job cluster (a portfolio PMO or an engineering issue tracker). Worked example: Harbor Marketing (a small campaign crew) inventories 14 spreadsheets and migrates two production boards. The rest become a read-only archive folder.

Build a field map: source column → Trello property → transform → owner. 1. Owners must resolve to real users, not free-text names.

1. Status values must match the lists you will actually use.
2. Dates and timezones need an explicit rule.
3. Comments/files either attach or get a documented “not migrating” label. Worked example: Harbor Marketing (a small campaign crew) refuses to import until 20 sample rows survive the map without a mystery column.

Import one site, one role, one client, or one squad. Then run create one board, move three cards across lists, and prove comments replace a side chat for that work on the pilot set. 1. Import, then immediately a contributor moves a card and a lead sees it without a Trello admin.

1. Ask a sceptic user to find “their” items without help.
2. Time how long a manager takes to answer “what is late?”
3. Fix the map before the next batch. Worked example: Harbor Marketing (a small campaign crew) will not schedule a cutover until the pilot can a contributor moves a card and a lead sees it without a Trello admin.

Run old and new in parallel for a week. Spot-check records sceptic users care about, then freeze the legacy source. 1. Dual-run rules: Trello is the write path; the old sheet is read-only after day 3 if the pilot held.

1. Daily: five sceptic spot-checks (late items, owners, attachments).
2. Connect remaining integrations only after the pilot week. Research names Zapier on the Trello side — confirm the connectors your work loop depends on.
3. Cut over on a quiet day — not month-end reporting. Worked example: Harbor Marketing (a small campaign crew) keeps the old export until Trello matches for seven consecutive days, then revokes edit access on the spreadsheet.