When both ClickUp and Asana started plugging AI into their platforms, I went in skeptical. Not in a cynical way—just honest curiosity. What actual project management friction would AI smooth over in either of these tools? Not marketing slogans—real usage improvements. So I tested the AI features side by side with a few freelance and agency project templates, tracking three things:
Thank you for reading this post, don't forget to subscribe!
How many steps the AI actually removed
If the AI suggestions matched how real teams write tasks and projects
Where things broke or got weird
Quick recap for context:
Feature
ClickUp AI
Asana Intelligence
Task generation from prompt
✔️ Native inside Docs/Tasks
✔️ Inside description field + project setup
AI-written summaries
✔️ Available inside comments, Docs, chats
✔️ In comment threads only (for now)
Automation with natural language
❌ Not available
✔️ Predictive rules for workflows
Output consistency
Medium–High
High (semantic alignment improves over time)
So, side by side, they’re nudging in slightly different directions with their AI. ClickUp turns AI into a writing assistant inside the app: tasks, comments, even chat threads can be AI-augmented. Asana is designing AI into the structure of work itself—automating next steps, surfacing overdue tasks intelligently based on project goals, or summarizing task activities. Neither approach is wrong, but the utility really depends on your team’s friction points.
The bottom line is: You won’t get a “perfect” AI experience with either yet, but they’ve both become surprisingly good at reducing repetitive—and frankly mindless—PM tasks.
Task Writing and Content Generation Comparison
Let’s talk about AI-powered writing inside project management tools. That means things like: generating subtasks based on a generic objective, rewriting instructions in a better tone, or summarizing a chat thread into action points.
ClickUp AI reacts more like a creative assistant. If you’re inside a task and say “Break this down,” it actually rewrites the description and suggests subtasks. One time I gave it:
“Launch website for new campaign by next Friday. Includes copy, images, and basic analytics.”
Not bad. Little too generic (“basic navigation” felt vague), but decent starting point.
Asana’s version doesn’t auto-generate subtasks like that. But it does suggest labels and auto-fills task fields if you type out a lot in one go. You paste a paragraph, it’ll recommend structure—set due date to next Friday, assign to design team, etc. It’s trying more to understand your intent than click buttons for you.
This also happens when you’re building a new project: if you start typing something like “Launch campaign for May 2024 with email + social + landing page,” Asana will actually start suggesting tasks (like drafting posts, reviewing subject lines, assigning inbox support) without you asking. ClickUp doesn’t do that natively.
Ultimately, ClickUp wins at transforming vague ideas into tangible subtasks. Asana wins at understanding existing structure and optimizing it intelligently.
AI-Powered Automation and Workflow Triggers
This is where the gap widens. Asana Intelligence currently leads here with its predictive workflow triggers and rules. You can literally type:
“When task is overdue and unassigned, remind project owner every 2 days until completed.”
And it sets up the rule.
I tested it by creating fake overdue tasks on a Friday and watched the reminders show up automatically by Monday morning. ClickUp can’t do this—yet. It relies on traditional Rule-based automation (IF-THEN structure), which you have to manually configure. Yes, ClickUp automations are super flexible… but not AI-infused.
Another area: Asana’s AI sometimes suggests new automation triggers just based on your behavior. I noticed after ignoring a task update for two days, it floated this:
“Would you like to create a rule to remind you when a task you created hasn’t been updated in 48 hours?”
Not subtle. But effective.
ClickUp hasn’t built prediction into automation yet. You won’t get suggestions like that unless you pore through automation templates yourself.
To conclude, ClickUp wins on possibility if you prefer custom setup, but Asana wins on actual time saved through AI-predictive nudges.
Summarizing Comments and Cross-Project Threads
ClickUp AI lets you ask for summaries in nearly any field: chat threads, Docs, task comments. This feels like a timesaver, especially on long feedback threads. I tested it in a full QA comment history for a homepage update—around fifteen comments back and forth—and the output was shocking. It nailed the gist:
“Summary: Consensus reached on updated hero section (ver2B), change CTA button to orange, and remove testimonial carousel. Awaiting final approval from Jack before live update.”
I reread the thread after. It got almost everything right. Only thing it missed was a comment deeper in suggesting to delay until product photos came in. Understandable miss—it was buried.
Asana, meanwhile, only unleashes its summarizing AI inside comment threads. And even that behaves oddly if the comment structure isn’t clear (multiple people replying to different things). When it worked, it was clean—but when it hiccups, you either get skipped points or worse, a warped meaning.
For less linear discussions, ClickUp did better. It aggregates the context more accurately, possibly because its internal AI model ingests more than just recent history. Asana’s summaries are solid when projects are tidy but fragile with messy threads.
To sum up, if you have chaotic comments, ClickUp AI gives you breathing room. With neat teams, Asana holds up well.
AI-Assisted Templates and Onboarding
Both tools have turned to AI to fast-track the process of getting a new user up and running. ClickUp has a prompt-first onboarding—ask for a “client onboarding project with deliverables and meeting schedule,” and it’ll not only generate Doc templates but try to spawn dashboard widgets and automations (although the automations were flaky). Asana guides new users through premade AI-recommended templates based on role and project type, and those are driven more by structured data than freeform prompts.
ClickUp’s AI templates felt more like scaffolding—fast and rough. You’ll still have to balance dates, reorder sections, and interpret placeholders. Asana’s auto-onboarding created cleaner workspaces that felt ready to go faster. I prefer ClickUp’s speed for experienced teams who tweak later; I prefer Asana’s polish for new users who want less guesswork.
Overall, both have value—but their usefulness again comes down to how much freedom you want in your early project setup.
Natural Language Support and Global Actions
One of Asana Intelligence’s major flexes is understanding natural language across the app. Tell it “show tasks overdue by more than 3 days in all marketing projects” and it’ll run the search. ClickUp doesn’t yet support this kind of semantic search or filtering. Even their AI chat requires distinct prompts like “Summarize task X.”
This also comes into play in mobile. Asana iOS users can tap the AI button and say things like “I’m running late—delay this by 2 days” and it manages dates and dependencies. I tried this while commuting. It worked… but if my task lacked a clear dependency tree, the AI hesitated and just postponed one item without flagging the chain.
ClickUp’s mobile AI still leans on the editor more. You’d use it to rewrite comments, simplify instructions, or label thoughts—not control work structures globally with voice or command line.
As a final point, if your workflows are heavy on quick commands and voice shortcuts, Asana’s AI is much more aligned with how people want to interact on the go.
Choosing ClickUp AI or Asana Intelligence
If your team wants:
Creative flexibility transforming vague instructions into structured work
AI assistance in writing, rewriting, summarizing anywhere inside the interface
Embedded Docs or chat that benefit from AI voicing
Then ClickUp AI is your best shot. It acts like a supercharged intern who can write your task drafts, not a robot manager making decisions for you.
If you’re looking for:
An AI system that flows smoothly in structured companies
Rule-based automations that improve and adapt based on behavior
Voice, search, and shortcut-based management of large projects
Then Asana Intelligence is where you’ll feel more at home. Instead of helping you write things better, it helps you manage things faster.
Finally, there’s cost: both offerings may be limited based on plan level, and AI features evolve fast—so check if these features are on by default before assuming access just because you updated the app.
