A migration trial usually fails long before the contract or the cutover plan. It fails when the new workspace still feels like a staged demo while the old tool still looks like the place where real work lives.
That is why the first win is not feature parity. The first win is making the trial look enough like current work that a team can trust what it sees.
Do not import history just because it exists
Linear open-only pilot import before archive drag is the cleanest move in this batch. If the team is still evaluating the product, the workspace should answer today's planning questions first. Old backlog can wait.
It belongs next to reviewable import assistant with bulk reimport safety. One keeps the scope small. The other makes the first pass reversible.
Separate hierarchy cleanup from the main migration job
Linear top-level team import before sub-team polish sounds operational because it is operational. That is also why it matters. The switch gets calmer when the team can land the data first and rearrange the org shape second.
A lot of migrations go sideways because they try to solve every structural preference in the same pass. Buyers do not need that much elegance on day one. They need continuity.
Identity drift kills trust faster than missing polish
Linear Jira personal-account link before assignee drift is the move I would check first in any dual-run trial. If the new issue says the wrong person owns it, the workspace stops feeling real immediately.
That pairs naturally with dual-run sync during trial before full Jira cutover. A dual run only helps if the mirrored work still points to the people who actually own it.
Filter the sync before the old system floods the new one
Linear JQL webhook filter before sync flood fixes another quiet trial failure. The new product gets judged by every low-value queue, stale bug class, and legacy ticket type it never needed to inherit.
A narrower sync is not cheating. It is a cleaner test of whether the new workflow handles the work you actually care about.
The project should produce a believable timeline early
Linear start and target dates before graph guesswork is where the workspace stops being a container and starts being a planning tool. Once the graph can show scope, velocity, and a live completion estimate, the buyer has something better than a promise.
I would read that beside project overview starts with resources, docs, and milestones. One makes the room feel ready. The other makes the timeline feel alive.
If I were tightening one migration this week, I would import only the live slice, avoid hierarchy fuss during the landing, link every Jira identity that matters, trim the sync with JQL, and put real dates into the project graph early. That is how the switch starts looking like current work instead of a rehearsed demo.
If you want help turning a migration trial, project workspace, or switcher path into a cleaner product-led conversion system, the advisory CTA is here: work with Ian Goh.