Why Most Tool Migrations Fail on Day One
Switching project management tools is one of those decisions that sounds clean in a strategy meeting and gets messy the moment it hits a real team.
The executive decision is straightforward: "We're moving from Trello to monday.com. monday.com has better automation, better dashboards, better scaling for our growing team. Migration starts next Monday."
Then reality kicks in. That "migration starts next Monday" turns into weeks of chaos because it ignores a fundamental truth: work doesn't pause for tool migrations. Teams have active Trello boards with cards in progress, checklists half-completed, attachments people need to reference, and comment threads containing critical context that took months to accumulate.
The cold-turkey approach — export everything from Trello, import it into monday.com, and shut down Trello on a set date — works in theory. In practice, it creates three problems:
The context gap. Trello board histories, card comments, and attachment contexts don't transfer perfectly to any new tool. Even the best import tools lose formatting, break links, and flatten the relational structure that made the Trello board useful in the first place. Teams spend weeks after migration hunting for information that "used to be on the Trello board."
The two-system problem. During migration, some work is in Trello and some is in monday.com. Nobody is sure which is the source of truth. Team members check both tools, trust neither, and start keeping their own side-lists in notebooks or personal spreadsheets. The migration was supposed to create clarity; instead, it created confusion.
The resistance spiral. People who were comfortable in Trello — especially long-tenured team members who had built personal workflows around Trello's card system — push back. Not because monday.com is worse, but because the migration disrupted their flow. The harder you push the switch, the more resistance you get, and the more likely it is that adoption stalls halfway through.
The Bridge Approach: Trello Inside monday.com
The team in this case — a mid-size organization with project management and operations teams spread across Europe — took a different approach. Instead of replacing Trello overnight, they ran both tools simultaneously, with Trello embedded inside monday.com.
Using Trello Embed for monday.com, they brought their existing Trello boards directly into the monday.com workspace. This created a transition period where monday.com was the single interface everyone used, but Trello boards remained fully accessible and interactive within that interface.
Here's how the migration phased out:
Phase 1: Reference Mode (Weeks 1–4)
In the first phase, the team simply embedded their active Trello boards on corresponding monday.com boards. No migration of data. No recreation of boards. Just visibility.
The monday.com board became the new "home" for each project. It had the team's new task tracking, automations, and dashboards — all built fresh in monday.com using its native features. But right alongside it, the embedded Trello board showed all the historical context: completed sprints, archived cards, comment threads from the last six months, attachments that people still needed to reference.
This immediately solved the context gap. When someone needed to check "what was the decision we made about that feature in March?" they didn't need to log into Trello separately. The answer was on the same monday.com board, in the embedded Trello view, three scrolls down from the active work.
Phase 2: Parallel Operation (Weeks 4–8)
In the second phase, some teams started new work exclusively in monday.com while continuing to reference Trello for ongoing projects. The Trello embed served as the bridge — legacy work stayed visible and interactive in the embedded view, while new work was created directly in monday.com.
This eliminated the two-system problem. There was only one tool to open: monday.com. Yes, some of the content inside monday.com was technically a Trello embed — but from a user's perspective, everything was in one place. No one had to decide which tool to check. The answer was always "open monday.com."
Crucially, during this phase the team could still interact with their Trello boards through the embed. If a legacy project required a card update, they could do it within monday.com without navigating to Trello. This meant Trello access was preserved without Trello being a separate destination.
Phase 3: Wind-Down (Weeks 8–12)
As legacy projects completed and active work shifted fully to monday.com, the Trello embeds became progressively less relevant. Some boards were kept as read-only archives — a project history reference that team members could check if they needed to trace a decision back to its origin. Others were removed entirely once the team confirmed all critical information had been captured in monday.com.
By the end of the third month, the team was operating entirely in monday.com. Trello wasn't shut off abruptly — it simply became unnecessary, one board at a time.
Why the Gradual Approach Works
It Respects Muscle Memory
People don't resist new tools because they're irrational. They resist because switching tools means temporarily becoming less effective at their job. The person who could find any card on any Trello board in three seconds is now fumbling through an unfamiliar monday.com interface. That gap in competence is frustrating, and it's the number one reason tool migrations stall.
The Trello Embed approach lets people access their familiar Trello boards while they learn monday.com. The Trello muscle memory keeps working even as the new monday.com muscle memory develops. By the time the Trello embeds are no longer needed, everyone is comfortable in the new system.
It Preserves Tribal Knowledge
Every team has institutional knowledge buried in their project management tool. Comment threads where a critical decision was debated and resolved. Card descriptions that document the "why" behind a process. Attachment chains that piece together the evolution of a deliverable.
This knowledge almost never survives a data export/import. It's too context-dependent, too embedded in the tool's specific structure. But with the Trello board embedded in monday.com, it doesn't need to survive a migration — it's still right there, in its original form, accessible whenever someone needs it.
It Lets Teams Migrate at Their Own Pace
Not every team in an organization moves at the same speed. The tech-forward marketing team might be fully native in monday.com within two weeks. The operations team with fifteen active Trello boards and six months of project history might need two months. The Trello Embed approach lets each team transition on its own timeline while still creating organizational alignment around monday.com as the single workspace.
Who This Is For
The Trello-to-monday.com bridge approach is designed for:
- Organizations actively migrating from Trello to monday.com that want a gradual, low-disruption transition instead of a hard cutover
- Teams with significant Trello history — months or years of board activity, card comments, and attachments that contain important institutional context
- Managers leading change management who need to reduce team resistance by preserving familiar tools during the transition period
- PMOs and operations teams that can't afford productivity dips during migration because active projects can't pause
- International and distributed teams where coordinating a simultaneous tool switch across time zones and regions adds additional complexity to the migration
Get Started
If your team is planning or mid-way through a Trello-to-monday.com migration, the Trello Embed integration can serve as the bridge that makes the transition smooth rather than disruptive.
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