Trello vs Monday for Remote Teams Who Click Too Much

Table of Contents

1. Creating task templates behaves wildly differently on each platform

With Monday.com, duplicating a task or item keeps its subitems unless you’ve toggled that off. Trello, on the other hand, treats every card template like a brand new card with zero context — no checklists, no labels, not even a due date if you blink wrong. I built a recurring weekly production checklist in Trello using card templates and Butler, and during testing, half the checklist items just didn’t show up. Why? Turns out if you edit the original template after automations are referencing it, Trello may not recognize it as a valid source anymore. Absolutely zero warning — the automation just says success, but nothing happens.

Monday’s item templates are a bit more predictable, but they often bring over column configurations you forgot were part of the original board — automations, status colors, field types. One time I cloned a template across four boards and ended up with automations firing on old status names that no longer existed in the new context. Debugging it felt like trying to fix a broken lamp by wiring a lightbulb into four different walls hoping one would turn on.

2. Board-level user permissions work until automation gets involved

If your team uses shared boards but not everyone is an admin, you’ll hit snags differently on both platforms. Monday lets you restrict column edits, but if an automation tied to your own permissions tries to modify a restricted column, it silently fails. There’s no red flag, just a workflow that sits there mocking you. Trello doesn’t support granular permissions per field at all — so you live in fear of someone dragging a card into the wrong list while trying to scroll.

One of the weirdest misbehaviors I ran into: a Trello webhook setup in Zapier that triggered when a card was moved to a specific list… unless that list had been archived and recreated. Same name, same board, but the webhook would randomly ignore it. I only caught this because a team member insisted her task moved but the automation didn’t generate a Slack post. Dug into the logs — the list ID changed invisibly during board reconstruction, so the filter quietly ignored it.

3. Visual timelines exist but are mostly aesthetic in Trello

Trello technically offers a timeline view under the “Premium” plan, but it behaves more like a glorified calendar overlay with odd mapping logic. If a card has dates attached, it appears — except for checklist items with due dates. Those just vanish. Compare that to Monday, where timeline columns are a native field — you can drag and resize, and project owners can instantaneously see bandwidth issues when multiple items collide.

That said: Monday’s visual timelines break completely if you import a CSV that lacks start dates. It’ll still create items but leave them floating in limbo, even though the view tries to load them. The result? A partially rendered Gantt chart where some bars float, but others just… don’t exist. No warning. No tooltip. You’ll think your browser broke. It didn’t — the platform just mapped “no start date” as non-existent rather than defaulting to the item’s creation date.

4. Slack integrations trigger differently on identical-looking actions

This one’s especially annoying if your remote team lives inside Slack. Trello’s Slack integration announces card moves and comments, but ONLY if they happen manually. If a Butler automation performs the same move, nothing gets sent. It’s like the Slack bot is unionized and only watches human labor. Monday does hook into automations for Slack notifications, but if you create an automation that uses multiple condition branches, only the first one with a Slack step actually sends a message. The rest silently fail unless explicitly cloned per condition.

A tip I found by accident (seriously — I was renaming an automation and misclicked): in Monday’s automation builder, opening the “custom message” box and saving it makes it persist more reliably across duplicated boards. Before that, my messages kept reverting to generic templates whenever I copied a board. Never documented, never mentioned in their official tutorial. No one on support chat had heard of it either, which was comforting and also deeply cursed.

5. Mobile apps show completely different data priorities

Using the Trello mobile app, especially on Android, surfaces a lot of hidden assumptions. For example, labels are collapsed unless you open the card fully. If your team uses color-coded labels to indicate project status, scrolling through a list shows none of that. Monday’s mobile app plays nicer with structured data — status columns and assignees preview cleanly — but it won’t respect custom sorting unless you remember to manually save a view.

Half of a team meeting last month involved one person swearing the task was due Friday based on what he saw on his phone. Turns out it was — but only for his personalized view, which no one else had access to. Monday lets individuals filter per device, local to the app, but doesn’t flag that difference anywhere. Another classic case of “Why are we seeing two separate realities on the same task?”

6. Cross-board automations feel robust until the edge cases show up

With Monday.com, moving or cloning an item to another board is frictionless — unless your automations reference people or status fields that use custom values. Then you’re in dropdown mismatch hell. The automation will still move the task, but assign it to a user who doesn’t exist on that board, or worse, map the wrong status entirely. Trello doesn’t even offer true cross-board automation without 3rd-party tools or messing with Butler in very specific non-intuitive ways.

Checklist of high-risk cross-board operations:

Moving cards with labels into boards without those label definitions (Trello)
Assigning a person in Monday when that person isn’t added to the destination board
Mapping a status column to another board where status colors differ
Using template items that contain dependencies not visible in the target board
Zapier automations triggered on card creation may miss cards added through clones
Monday automations with cross-board moves break if a field name matches but the field type differs

One surprise: in Trello, I created what I thought was a foolproof “move card to another board when checklist is complete” rule. Worked great for two months. Then one day, it stopped mid-flow. Logs said “invalid target board” even though the board still existed. I had renamed the target board’s name — but the automation was referencing board name, not board ID. It had been working off a lucky match the entire time.

7. Native reporting options are either overkill or basically nonexistent

Trello gives you almost nothing unless you’re using third-party plugins or exporting JSON and parsing it yourself. Monday has a full dashboard builder… except most widgets require all your relevant data to be in one board, or perfectly synchronized columns. You can’t visualize progress on a board that uses checklist-like subitems unless you manually propagate status from child to parent with automations. I learned that the hard way during a client monthly review where half the data showed 100 percent incomplete. Turns out it wasn’t. Parent items had zero updates, but their subitems were all done. Monday doesn’t calculate nested progress by default.

It’s possible to rig a workaround with a combination of mirrored columns and roll-up automations, but then your reporting views get deeply brittle — rename a column, and the whole thing nukes itself with an error.

8. Board templates create more chaos than consistency for teams

I tried setting up a pristine board in Monday with all the right automations, column types, colors, and rules — then turned it into a workspace-wide template. When a team member spun it up, half the automations were missing. Why? Some automations aren’t transferrable unless the user spinning up the board has full automation permissions, which we had forgotten to give. Trello avoids this by treating automations as user-specific unless explicitly shared, but that also means it’s easy to forget Butler rules lurking under someone else’s login until they leave the company.

Most disturbing moment: I opened a freshly templated board and watched a card move to another list even though no active rule managed that action. What it was actually doing: replaying a stale webhook from Zapier that had been tied to a previous user token… which somehow still fired because the board’s name had been reused. Not kidding.