I’ve written countless Product with Attitude articles about questions I was trying to answer for myself.
For a while, I trusted myself to remember those questions. This was optimistic. So I gave the remembering job to AI.
I now have a recurring task across ChatGPT Work, Claude Cowork, and Perplexity that sends me every long-tail question I asked during the previous week.
What Is a Long-Tail Question?
A long-tail question contains enough context to reveal the real problem someone is trying to solve.
“How do I grow a newsletter?” is broad.
“How can a small Substack newsletter become visible in ChatGPT and Perplexity without publishing five SEO articles a week?” is long-tail. It contains a platform, an audience size, a desired outcome, and a constraint.
That specificity is useful for two reasons.
First, it gives you a much better article seed.
Second, people ask AI search tools in full, context-heavy sentences. A question drawn from your own work can therefore point toward the language another person may use when searching for the same answer.
How to Create the Task in ChatGPT Work
Option 1: Open Scheduled in ChatGPT and create a new task. Paste the prompt I shared below, choose a weekly schedule, confirm your time zone, and select how you want to receive the result.
Option 2: You can also describe the job directly in Work and ask ChatGPT to schedule it.
Follow OpenAI’s Scheduled Tasks guide if you need help finding the controls.
Make sure you check Settings → Notifications, so you get notified in a way that works best for you.
How to Create the Task in Claude Cowork
Open Cowork and look for Schedule in the left sidebar. You can also type /schedule in the task command bar. Paste the prompt, set it to run weekly, and review which sources or integrations Claude may access.
This walkthrough documents the current Cowork scheduling flow.
If you already use Cowork heavily, connect this setup to my Claude Cowork guide for power users. The quality of the weekly report depends heavily on the context Claude can inspect.
How to Create the Task in Perplexity
Open Tasks from the main menu, create a new task, paste the prompt, and choose a weekly schedule. Perplexity Tasks can run saved prompts on a recurring cadence, including research requests. This launch summary shows the Tasks setup and supported recurring use cases.
If Tasks does not appear, check your plan and product version. Feature access changes, and a missing button is usually an account limitation.
What This Recurring Task Gives You
Once a week, the task reviews the conversations it is allowed to access and extracts questions that contain a specific problem, constraint, comparison, uncertainty, or desired result.
It skips simple commands such as “correct this sentence,” one-off admin requests, and questions that can be answered with a single fact. It groups the useful questions by theme and explains why each one may need more research.
The result is a small record of your real curiosity.
The list is still raw material. A scheduled task can collect your questions. You decide which ones contain enough experience, evidence, or original thought to become an article.