Trello vs Monday.com When Productivity Stops Making Sense

I was trying to automate a multi-step onboarding sequence for a client: data collection form → task list assignment → Slack DM to new hire → weekly status board update. I built it out in Monday.com last month because their automations finally don’t crash when assigning multiple people. Or so I thought. Mid-week, it just… stopped. Turns out? Board-level automations silently reset if you duplicate a template with outdated permission objects. No error. No webhook log. Just a fun little mystery 🙂 So while I was rebuilding it again (with logs this time), I started wondering why I ever left Trello.

Monday.com looks polished. Trello looks like sticky notes. But when you’re knee-deep in deadlines and boards that auto-sort themselves into chaos, appearances stop mattering. This is what I learned the hard way.

1. Interface speed and emotion under task pressure

Nobody talks enough about UI lag when boards get crowded. On Trello, I can open a card, drag it, archive it—done. Monday.com feels heavier. The beautiful timeline bars and visual overlays degrade fast once you’ve opened 30+ items. I had a coworker literally say, “I don’t want to open that board, it makes my laptop sound like a jet.”

Interaction-wise, Trello’s simplicity makes it usable in a panic. It’s tap-to-edit, not modal-on-modal. Monday.com sometimes nests status fields three clicks deep. In crunch mode—like late Tuesday when payroll builds miss something—fewer clicks matter. The irony is, Monday.com is objectively more powerful. It just throws too much visual noise at the wrong time.

When I redid a product roadmapping flow last spring, I started with Monday.com for color-coded dependencies. But once I reached 60+ items and 10+ automated status triggers, it slowed. Trello with Butler ended up being easier despite way fewer features.

2. Automation flexibility unraveled in actual usage

Here’s the truth: Monday.com’s built-in automation feels magical for five seconds… until it doesn’t match your use case. Trello’s Butler, while limited, reveals its quirks early, which is weirdly good. At least I know up front what’s possible.

For example, try writing a multi-condition if-else rule in Monday.com using only their visual builder. You can’t. You’ll hit a wall with the dreaded “one trigger per recipe” limitation. Want to skip sending a Slack message if task priority is low? That means building a second automation with a separate trigger. And good luck figuring out which one actually ran when something weird happens. No logs.

Trello’s automation, though less capable, gives you rule-based visibility. For instance: “When a card is added to list ‘Dev Complete’ by me, move it to ‘Staging,’ comment with ‘Ready for QA,’ and set due in 3 days.” You can’t build that nuance in Monday.com without stacking fragmented recipes.

There are breakpoints too. Trello Butler’s quota is hidden until you hit it. Monday will silently stop firing if you duplicate a board from a workspace without cross-permissions. I didn’t know that. Took me an hour to debug a missing sales follow-up ping that never triggered. :/

3. Real-time collaboration versus async clarity

Across teams, Trello works weirdly well when people work asynchronously. It’s harder to mess up. A card stays a card. Comments stay in one place. You won’t accidentally overwrite something because editing a checklist doesn’t trigger full reload.

Monday.com does co-editing fine… if everyone knows what they’re doing. I watched a sales teammate once accidentally delete half a column by dragging a cell an extra row. Undo took four clicks. And a team lead once updated 12 agents with the wrong instructions because statuses sync to separate mirrored boards—without a clear visual of which item links where. It was technically my fault. I forgot to train them.

In Trello, confusion shows slower. When someone misplaces a card, it’s obvious during weekly standup. In Monday.com, errors propagate silently. I once saw a cascading deletion because a dashboard widget referenced a formula column that got renamed. Monday didn’t warn us. It just displayed empty fields.

4. Mobile usage pain that reveals poor UI hierarchy

Trello on mobile felt like a 2008 app until recently. Cards barely loaded. But now? Its minimalism actually helps. Monday.com’s mobile app feels ambitious—but it’s frustrating. Fields collapse in weird ways. Entering time tracking data? That’s three screens deep. Good luck doing it during a subway ride.

I tried reviewing campaign tasks on my bed one night via Monday.com’s app. Accidentally tapped ‘Update’ instead of ‘Comment’ and added a weird note to the task descriptions. You can’t undo that easily, and there’s no version history for text fields.

Trello’s app still drops occasional drag-and-drop glitches, but it’s fast. One time I was in line at Chipotle and reassigned three due dates before even paying. That kind of lazy UX comfort matters more than we admit.

5. Permissions and role confusion in cross-functional teams

Monday.com has granular access. Great in theory. Bad in practice if you don’t remember which workspace owns what. Trello’s permissions are primitive, yes. But that means you can’t overthink it.

A client once asked me why her events team could edit the accounting board. I’d copied a template board in Monday.com and forgot that automation access rules default to the creator. All coworking automations fired using my name for three weeks. We didn’t notice until a teammate commented “who the heck is automating this stuff?”

In Trello, responsibility is clearer. Cards show the last editor. Boards are owned outright—no layers of workspace-admin-thread. When someone automates something with Butler, it’s visible in the card back. None of that is true on Monday.com.

And then there’s the bulk permissions bug. I once added viewers from Airtable-form input via Monday’s API bulk invite—and all were granted Editor access by default. The permission string was ignored because of malformed syntax. No error message. Just… full access.

6. Timelines and due dates that behave differently than expected

Monday.com’s timeline blocks are beautiful. But underneath? Deadlines trail ghosts. You can’t easily tell who added a due date, and changing a date doesn’t notify watchers unless a separate automation exists. One coworker relied on Monday timelines for launch planning, and only found out a critical task had been quietly delayed after glancing at the board Friday afternoon.

Trello’s due dates are dumber—but more honest. You miss your date, it turns red. You get a notification at exactly 24 hours. No timeline, no dependencies, no auto-adjust. But that’s also why they’re safer.

There’s also the problem of cascading updates. Move a parent task in Monday and you might assume child item dates shift too. They don’t. Unless you scripted it. I learned this the hard way when planning async sprints with a remote team. Shifted by two launch days, but the backend tasks did not.

A few specific things to watch:

• Monday.com duplicate tasks may retain outdated dependency links
• In Trello, checklist due items don’t roll up to board level—that confused two interns
• Changing start dates in Monday does not back-propagate milestones
• Recurring tasks in Monday might duplicate in weird sequence if the week starts on a Sunday
• Trello’s recurring card automation needs a manual label to filter correctly

7. Reporting and dashboards when leadership needs answers

Monday.com shines here. You can build real dashboards. Widgets. Charts. The sort of stuff leadership loves seeing at a glance. But… the devil shows up in the data source logic.

I had a weekly metrics dashboard pulling from three boards. One week it gave obviously wrong conversion numbers. Turns out a quote status column was renamed “Quote Sent (Q2),” which broke an unnamed filter. No error shown. Just silently dropped those rows.

Trello? Lol. You get calendar view or card counts—and third-party tools. That’s it. But at least it doesn’t pretend to be more. I’ve exported Trello boards into Airtable for proper reports more than once. It’s brute-force but accurate.

8. Cost efficiency when scaling across departments

Here’s where Trello quietly wins. You can go shockingly far for free. Even with paid Butler quotas, small teams can live on the free or cheap plan for years. Monday.com? It punishes non-uniformity. Want just 3 editors? Too bad, pay per seat in fixed blocks.

I once tried onboarding a part-time contractor on Monday for one week. There was no trial slot left. So we had to purchase another full seat just to add them. Trello? I created a temporary shared board with power-up limits—done in 5 minutes.

9. Unexpected friction when boards go stale

Stale data doesn’t surface easily in Monday.com. It’s possible to have archived cards still affecting dashboard filters. I once spent 20 minutes debugging why a status pie chart showed 2% “In Progress” when no active boards had any. Answer: a hidden board copy in a workspace no one used.

Trello, ironically, surfaces staleness by being dumb. Archived cards vanish. Old checklists don’t affect anything. But Butler won’t act on archived items either, so if you forget that, automations may just stop for no visible reason. Very annoying, but fixable.

10. Real-world examples where one platform cracked

I built a CRM workflow for a solar client using Monday. Pipe of leads came in through a form fill → CRM board → forecast board → deal board → close-tracking dashboard. Looked great! Until someone removed one label column and all automations stopped. Entire pipe collapsed quietly. No alerts. No backups. Took hours to notice.

About three months later, rebuilt the same structure in Trello with card links and checklist triggers via Butler. Messier UI. Fewer visuals. But every misfire shows up instantly. And rebuilding it after bugs took 30 minutes, not 3 hours.

¯\_(ツ)_/¯