Best Project Management Apps Teams Are Actually Using in 2025

1. Notion blends task tracking and documentation until it breaks

If you’re trying to combine projects, notes, and team docs in one place, Notion feels like the obvious answer — right up until that one teammate creates a database view with 85 filters and suddenly your Kanban board loads like molasses on a 2009 Chromebook. At the surface, it’s clean and modular, but under the hood, database relations can spiral out without anyone really noticing.

We had a team board that linked to client pages, each client page had tasks, each task linked to subtasks, and then subtasks had priority rollups. Somewhere along the line, dragging one item between groups caused a sync lag so bad that the team started Slack DMing each other instead of trusting the board.

Things that mess with Notion logic fast:

• Multiple people adding filter groups on the same board
• Calculated rollup fields triggering re-indexing every refresh
• Linked views edited in different team spaces (without anyone noticing)
• Accidentally copying a view, editing it, and overwriting the source database’s sort
• Using AI summaries inside recurring templates (causes unexpected duplication delays)

A weird one we hit: date properties don’t always obey timezone offsets when used in rollups. If someone logs a task in UTC+5 but the project manager views it in PST, the automation tagging “Due Today” fires incorrectly. There’s no warning — just mismatched tags floating around.

One community thread had this gem from a PM: “Whenever I use Notion to manage a launch, I spend two weeks setting it up and one day abandoning it after the backend spaghetti regenerates.” Not wrong.

2. ClickUp is feature complete until someone creates a second space

The onboarding pitch works well. ClickUp nails that full-visibility illusion: nested tasks, custom fields, time tracking, workload views. But move beyond one space and the mental model collapses. For some reason “Spaces” behave more like separate instances than like categories — automations and views don’t travel cleanly between them.

One client made a separate space for Dev, Design, and QA — and couldn’t figure out why none of the global dashboards were populating their widgets. Turns out widgets pull from spaces individually unless you re-select each list manually. You have to dig into dashboards → settings → data source → check every list again. Nothing about that is intuitive from the UI.

Also, recurring tasks sometimes duplicate weirdly when combined with automation triggers. We had a “Send email when task is due today” script that started double-sending whenever the due date updated automatically via recurring config. Contacted support, was told: “Yep, happens sometimes when time triggers sync at the same time as the recurrence regeneration.” Huh.

The aha moment: Using task custom fields + list grouping lets you fake cross-space joins, but it involves manually mirroring status types, which is just as fragile as it sounds. Fast way to build resentment with ops leads.

3. Asana stays friendly until dependencies get circular or stuck

Everyone loves Asana’s layout until you start relying heavily on subtasks with dependencies. There’s an undocumented case where two tasks set as blocking each other in a loop won’t break the app — they just never mark complete. You’ll sit there wondering why your critical path status is stuck waiting on itself.

We ran into this while automating milestone completion triggers. Task A depended on B, and B depended on Task A (accidentally, from a cloned template), and it caused an entire priority indicator system to hang. No error, just silent failure. If you try calling the API to get blocked_by fields, it returns both refs — so not even validation rejects it.

Another issue: if one user adds a date, another removes it, and then you re-add it within a few seconds, the priority automations fire twice. There’s no lockout on concurrent field changes. You can spot it in the task activity log, but barely — you’ll see rapid back-to-back entries like “Due Date changed to June 12” → “Due Date removed” → “Due Date changed to June 12” all in under 5 seconds. Asana thinks each is new.

Annoying workaround: use a Slack webhook aggregator and delay all Asana POST commands by 2 seconds to prevent race conditions firing instant triggers. Nobody documents this, nobody warns you.

4. Trello is unbeatable for visual simplicity until scale or labels grow

Trello is always deceptively fast. You paste a checklist, it becomes items. You move cards, everyone sees it. Then a few months in, somebody color-codes every card by mood or priority or both, and suddenly filters break because people keep assigning labels differently. One board had green = “review later,” and another used green = “in QA.” Nobody was wrong, but suddenly automation rules became meaningless.

The real trouble comes when Butler rules try to trigger off normalized label sets. One card moves → triggers three overlapping rules → creates cards on three other boards. Then someone renames a label and nothing works anymore. There’s no way to make Butler rules dependent on label *IDs*, only label *names*. That means automation routing can silently break if one PM changes “Needs Review” to “Staged.” Not a warning in sight.

This snippet from an internal Trello/Butler audit was enlightening:

actionError: "Label not found: Needs Review", context: boardId=abc123

Yep, despite labels being objects behind the scenes, Butler only binds by name unless you’re using the API manually.

I still use Trello for partnerships and small-team planning. But the moment you add more than one automation per board column, it’s a minefield. If the board’s visible to contractors, it gets even more fragile — people unfamiliar with the naming patterns create chaos with the best intentions.

5. Jira has the deepest config but fights every attempt at customization

If your team is two engineers and a PM, Jira is overkill. If your team has ten squads and HIPAA compliance, probably required. The admin interface is robust, but holy hell does it hate you editing workflows after launch. There are flows that once activated cannot be changed unless you clone and relink the entire project config schema — something that’s barely hinted at in their UI.

We once switched an In Progress → Staged state and learned that existing automation rules hardcoded the old status name. Even though the UI seemed dynamic. Fun fact: some Automations use status *IDs*, some default to *text match by display name*, and there’s no way to convert reliably unless digging through raw JSON in the admin export.

Jira didn’t always update entity references across automations either. You can add a new custom field, attach it to your screen, and still not see it in rule builders unless a ticket already exists with the field value saved. Why? No clue. Atlassian forums gave us a partial answer: Automation runner can’t bind to a field unless it exists in a previously indexed issue. That one cost an entire Friday.

The only consistent fix was to manually create a dummy issue with sample values in staging, then wait a few minutes before configuring rules. Hacky, and definitely not documented anywhere on atlassian.com.

6. Basecamp avoids complexity but can’t scale past verbal coordination

Everyone who loves Basecamp swears by it because “it gets out of the way.” But that only works if your org runs on updates, not ownership. Once you need recurring accountability on tasks across teams, its intentionally light structure starts tripping over itself.

There’s no dependencies. No automations. You can’t even assign subtasks under a broader umbrella unless you hack them in via links or nested to-do lists. We ran a design review setup where every review cycle had 5 sub-items, each needing a different stakeholder — and we ended up tagging people in the comments instead because assigning checklist items didn’t notify them clearly enough.

The root issue: Basecamp doesn’t track change systematically. You get notified, or you ask. There’s no history of who updated what field when, because there are no fields. The upside is simplicity. The downside is zero pattern discovery.

Their support did confirm one thing: if you rename a to-do list, it doesn’t impact old references. But if you copy a project with renamed lists, sometimes the cross-links preview the *old* name for a few minutes via cached metadata. Happens once or twice a week and then fixes itself.

7. Monday.com works until item IDs get misaligned in automations

This one’s sneaky. Monday seems flexible, and their automation UI almost feels fun to use — drag, set, rule, done. But behind the scenes, items aren’t tied to consistently exposed IDs in the way you’d expect. An item duplicated from an automation might reuse a name but get a new ID, breaking any Zapier flow expecting an earlier reference.

The trapdoor: when duplicating a board with reusable automations, the action verbs clone, but the linked columns don’t re-bind — so your rules will silently fail unless you manually rewire every mapping. No warnings, no soft fails. Just nothing happens.

We spent close to two hours wondering why newly moved leads weren’t syncing to Airtable. Turned out it was because we duplicated a board template but didn’t reselect the email column inside the automation rules. Yep — the field name was the same, but internally, it was a different column ID.

Make.com has better tooling around this, because at least the module config exposes those IDs. Monday’s own UI doesn’t — unless you dig through the dev tools.