How We Use Custom Fields + Automations to Run Projects in ClickUp
Key Takeaways
- Custom fields + automations together are far more powerful than either one alone - they let you auto-assign tasks, apply templates, and enforce consistency at scale
- Use a Role custom field on templates so new tasks auto-assign to the right person per client or project via automations
- ClickUp automations are literal (if this, then that) while ClickUp AI interprets intent - use each for what it does best
- Name your automations clearly so your team can manage, debug, and toggle them without confusion
- Task name contains filters can trigger template applications automatically - great for content calendars and repeatable workflows
Episode Summary
Most teams use ClickUp automations at a surface level. Basic status changes and notifications. Without custom fields powering them, you are leaving most of the value on the table.
Gray walks through a real-world example of combining a Role custom field with automations to auto-assign tasks per client or project. Instead of bulk-assigning work every time you spin up a new client engagement, the automation reads the role and assigns automatically. The back half covers when automations beat AI agents, best practices for naming automations, and a detour into where AI-built software converges and where it stays bespoke.
One of the densest episodes of the series for anyone doing serious automation work.
What We'll Cover
MCP Update
Quick but important. ClickUp MCP now supports adding tasks to additional lists and moving tasks. Those were two features previously limited to the native app.
Having them in MCP opens up a lot of agent-driven workflows that used to require API glue. For the broader MCP context see episode 9.
ClickUp Automations vs. ClickUp AI
Before diving into the walkthrough, Gray draws an important distinction. ClickUp AI interprets what it thinks you mean. You ask a question in natural language and it gives you its best answer.
Automations are literal. If this exact condition is met, then this exact action happens. No interpretation, no guessing. Knowing when to use each is the difference between a system that scales and one that stalls.
Role Custom Field + Task Templates
The core use case in this episode starts with a ClickUp template for a deliverable. A campaign with tasks for strategy, writing, editing, and design.
Each task has a Role custom field baked into the template, but the assignee is left blank. The person filling each role changes per client or project, so leaving it blank lets the automation take over.
How to Group and View Tasks by Role
Gray shows how to group and filter tasks by the Role custom field. You can quickly see every task requiring a specific role across a project.
This view by itself is useful for resource planning, but it also sets up the automation pattern in the next segment.
Building the Automation: Trigger + Custom Field Filter + Action
At the client level, Gray builds an automation that says: when any task is created and the Role field equals Senior Strategist, automatically assign it to Jeff.
That one automation eliminates the need to manually bulk-assign across every new project for that client. Multiply across 40+ roles on an enterprise team, and the time savings compound fast.
Naming Your Automations (Best Practice)
A tiny discipline that matters: name your automations clearly. “When Role = Senior Strategist, assign to Jeff” is infinitely better than “Automation #47.”
Your team needs to be able to find, debug, and toggle automations months after you built them. Good names are how they do that.
Auto-Applying Templates with Task Name Filters
Another powerful pattern: using “task name contains” as an automation trigger. If you’re running a content calendar and a task name contains “blog,” ClickUp can automatically apply your blog post template and leave a comment tagging the right person.
Same for video, podcast, or any other repeatable content type. One of the highest-leverage ClickUp tips for content teams.
AI Agents vs. Automations: Cost and Efficiency
When should you use traditional automations versus AI agents? Automations are free, deterministic, and fast. AI agents are flexible but come with token costs that add up at scale.
Gray’s rule: use automations for anything that follows a predictable pattern, and save AI agents for tasks that genuinely require interpretation or judgment. For the deeper dive on building your first three agents, see episode 5.
Humans as the AI Moat
A quote from Zeb Evans that Gray keeps coming back to: humans are the moat in the AI era.
Models commoditize, agents commoditize, workflows commoditize. The judgment to know what to build and how to run it stays with people who have done the work at scale. The practical implication is to invest in your team’s ability to design systems, not just to use them.
Vibe Coding and the Website Builder Parallel
The back half of the episode explores a broader idea: AI-built software is following the same pattern as AI-built websites. The low-level skill of coding a basic site gets commoditized.
Higher-order work like strategy, design, and positioning becomes more valuable. Gray draws the parallel to how ClickUp implementations will evolve as AI gets better at the tactical work.
Jason Fried on Bespoke vs. Convergent Software
A closing detour into an idea Jason Fried wrote about. Software converges toward big platforms, but there is an explosion of niche, bespoke tools happening at the same time.
Both are true simultaneously. ClickUp is a convergent platform. VibeUp from episode 13 is how it keeps room for the bespoke.
Trivia & Wrap-Up
This week’s trivia, plus a reminder that the ZenPilot methodology walks through how to combine custom fields, automations, and AI agents into a single coherent system. If you are stuck building automations that feel fragile, book a call with the team.
Transcript
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