How Team Project Management Tools Break When Scaling Up

1. Airtable bases collapse fast under messy team permissions

We were using Airtable to track feature requests for two teams inside a single base. Simple enough, until someone created a shared view for the wrong grid, someone else changed a field type from single-line text to multiple select, and suddenly three Zaps broke with no error logs. What’s wild is that Airtable doesn’t throw permission errors if a shared view is deleted — it just acts like the view never existed, so anything dependent on it waits silently until timeout.

Hidden fields shift orders when toggled on and off again across views — you’ll notice the field positions jump inside automations if the automation was built by dragging fields in from the UI when setting outputs. Super annoying if your team is using custom forms or synced bases, because the intake fields don’t match the data structure anymore.

Temporary workaround: export the full base schema with something like the Airtable API and run a diff when contributors change views or field types. We now have a Friday morning script that snapshots all base schemas and flags deviations in Slack.

2. ClickUp custom fields break automations when task types change

We left Jira for ClickUp because we wanted something more “friendly.” Except ClickUp lets you assign custom fields only at the Space, Folder, or List level — and when you move a task across those boundaries, even if the fields have the same name, they’re not the same object under the hood.

We had an automation that copied a “Complexity Estimate” field when a task moved from Design to Development. It died quietly because both lists had their own version of that field. It took four of us and two hours of testing to realize we were copying from null to null.

“You can have multiple fields named ‘Complexity Estimate’ and ClickUp won’t warn you they’re different objects.”

Honestly just manually re-assigning field templates per folder is safer when automating anything across ClickUp Spaces. ClickUp Help says field merging isn’t supported “at this time,” which feels like code for “good luck out there.”

3. Notion databases choke when synced with tasks by multiple users

Every time someone says “let’s just manage everything in this Notion database,” I pause. Because if more than two teammates are writing to the same page inside a synced block view, the write-order roulette starts. We’ve had a task marked “done” in a filter view but still showing up as open in a linked board because one synced block hadn’t refreshed yet.

What actually helped: Disable database syncing across multiple workspaces if any automations are involved. Also force everyone to toggle off Showcase mode — that thing doesn’t play nice with table filters. There’s a weird edge case where database updates triggered from Zapier show in the Activity log but don’t reflect visually until a full page reload. Not the same thing as cache — this is some weird front-end inconsistency.

An updated task status in Notion takes anywhere from 3 seconds to a full minute to display in a different filtered view across a synced page. That’s a huge delay in multi-user workflows — especially if someone is relying on that status to kick off another step in Coda or Slack.

4. Asana rules fail silently when using subtasks with form submissions

We built an intake form where submissions generate tasks with pre-populated subtasks. Form automation works fine on the top-level task, but half of the subtask-based rules trigger inconsistently. You won’t see this in the UI — Asana doesn’t throw an error. The subtask just… doesn’t run the rule.

Why? Because Asana’s rules engine doesn’t officially support subtask triggers unless you manually enable rule inheritance or add them to a project directly. And buried deep in the forums is a note that form-generated subtasks aren’t treated the same way as user-created ones. They inherit the top-level metadata after task creation, meaning you’re trying to trigger a rule based on data that doesn’t exist yet.

We now run a Make.com scenario that force-writes top-level metadata into all child subtasks five seconds after each intake. Solved it, but wow — not intuitive.

5. Trello Butler automations stall with large board action queues

What nobody tells you: Trello’s Butler has automation quotas, but they’re not consistent across teams. Your rule might work in a small board but fail quietly when imported into a client workspace with big queues. We duplicated a working Butler rule set across six boards — three boards worked, two delayed by five minutes, one just dropped every third action with no notification.

What surfaced it?

I saw a label being applied to the wrong card, then realized it wasn’t being applied at all on others. Butler doesn’t log failures in-app — you have to scroll endlessly in the command log for “skipped” items. One board had nearly 1000 skipped events. There’s no API for this, so we ended up using screenshots and manual comparison just to trace it.

If you’re doing any serious automation with Trello Butler:

• Keep rule complexity below 5 actions
• Avoid card moves across boards unless necessary
• Don’t apply labels and due dates in the same rule if board is large
• Space out triggers or add artificial delays using webhooks
• Test on boards with active users, not just test cards

Even board visibility affects triggers — a member-only board will handle rules faster than a public-facing board with lots of watchers. No solid documentation on that either, just observed behavior after a month of slowly losing my mind.

6. Team adoption nosedives if mobile notifications are unclear or late

Doesn’t matter how clean your automations are. If someone gets a notification that says “New task created” without context, they won’t tap it. Worse, mobile push notifications from most project management apps (especially ClickUp and Monday) group triggers in a way that erases task metadata. We ran a survey with five team leads and found they only read around 20% of task assigns on mobile if the title wasn’t specific.

Zapier doesn’t help unless you custom-build mobile logic. We ended up patching this through Slack instead — each assigned task now includes a brief summary pulled from a single-line field truncated to around 50 words. That field is generated by an OpenAI function that parses the task body and grabs the most concrete sentence.

{ “summary”: “Follow up on Retool deployment error showing incorrect dates” }

That alone boosted actual click-through taps on mobile Slack notifications — based on Slack link metadata — by maybe 60-something percent.

7. Calendar integrations flake out when meetings get reassigned twice

I thought this was a Google Calendar issue, but turns out it’s the way task tools like Monday and Asana interpret ICS feeds. If a meeting is assigned to Person A then reassigned to Person B and back again, many tools duplicate it both in the feed and in associated task comments. In one case, it created two tasks and two ICS events — both dated the same, both still linked in Slack automations.

The kicker is that most integrations just watch the summary + start time. They identify events by that combo, so if just the attendee changes and then reverts, the system treats it like a new event that should still exist.

Found this by inspecting the ICS payload:

UID:76jklsd9-event-1234
SUMMARY:Client kickoff status sync
ATTENDEE:mailto:angelo@example.com

Reassigned that same event, UID doesn’t change — so tools ignore it. Doesn’t matter that it’s reassigned. So now our booking automations strip UID tracking for reassignments unless the host changes too.