There is a difference between asking a good question once and asking it every week. Ask a competitor's pricing page what it says today and you learn almost nothing. Ask it every Monday for two months and you learn when they raised prices, what they stopped selling, and what they are suddenly pushing hard.
Claude and ChatGPT can both do the asking for you now, on a schedule, without you being there. This walkthrough covers why that matters more than it sounds, how to set one up in either tool, and eleven things worth watching, with prompts you can copy.
Time needed: about 5 minutes for your first task. It then runs forever.
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Why a scheduled question beats a good question
Most business questions are not hard. They are just easy to forget. You mean to check what your competitor is charging. You mean to see whether that supplier price came back down. You mean to look at your reviews. Then it is Thursday, something broke, and you did not.
A snapshot tells you a number. A series tells you a story.
Checking a competitor's site once gives you their prices today, which you cannot do much with. Checking it every week for two months gives you their direction: what they raised, what they quietly dropped, what they started leading with. Direction is the thing you can actually act on, and it only exists if somebody looked more than once.
Competitive analysis stops being a project
Nobody schedules a competitor audit, because it feels like a whole afternoon. So it happens once a year, usually because something went wrong. A weekly task turns it into four sentences in your inbox on Monday, and the change lands the week it happens rather than eleven months later.
Buying gets cheaper when somebody is watching
If you buy inventory, materials or equipment, the price you pay is mostly a function of when you happened to look. You cannot check daily and you should not try. A task can, and it only speaks up when something actually moves. That is the difference between paying the price and catching the dip.
It converts intentions into things that happen
"I should keep an eye on that" is not a plan. A recurring task is. The whole value here is not that the AI is clever, it is that it is consistent, and consistency is the exact thing a busy owner cannot supply.
How to set one up
Both tools do this now, and the setup takes about two minutes. The differences matter mostly if you are on a free plan.
| Claude | ChatGPT | |
|---|---|---|
| Where | claude.ai/scheduled-task | chatgpt.com/scheduled |
| Free plan | No paid plans only | Yes up to 3 active tasks |
| How many at once | Runs are capped per day rather than by task count | 3 free, 5 on Plus, 10 on Business, 15 on Pro and Enterprise |
| Timing | Hourly, daily, weekdays, weekly | Exact times and hourly need a paid plan. Free gets rough windows like morning or evening |
| Runs when your computer is off | Yes, it runs remotely | Yes |
| Can use your connected apps | Yes, connectors, skills and plugins | Yes, and paid plans can also trigger on Gmail, Slack or GitHub activity |
Claude
Pro, Max, Team or Enterprise- Go to claude.ai/scheduled-task, or click Scheduled in the sidebar.
- Click New task.
- Pick Create with Claude and describe what you want in plain English, and it will ask you the questions it needs. Or pick Set up manually to type the prompt, frequency and approval mode yourself.
- Choose how often: hourly, daily, weekdays or weekly.
- Save. Past and upcoming runs live on that same Scheduled page.
ChatGPT
Works on the free plan- Go to chatgpt.com/scheduled.
- Create a task, or just say it in a normal chat: "every Monday at 8am, check X and tell me what changed." It will offer to schedule it.
- Set the timing. On a paid plan you can pick an exact time or hourly. On free you choose a rough window and you get three active tasks.
- Results arrive as a notification and sit in your task list.
The one rule that decides whether you keep it
Tell it to stay quiet when nothing happened
The reason most people turn these off after a fortnight is that they produce a report every single day, including the many days when nothing changed. You stop reading it, then you stop seeing it, then you delete it.
Fix that in one line: "If nothing meaningful changed since your last run, just reply: no change." Now an email from the task actually means something, and you will read it.
A scheduled prompt needs five things
- What to look at. Name the exact pages, sites or sources. Vague inputs give vague output.
- What counts as a change. A price move over 5 percent, a new service, a review under 4 stars. Otherwise it reports noise.
- What to do when nothing changed. Say "no change" and stop.
- How to report it. Under 150 words, bullets, most urgent first.
- What not to do. Do not guess, do not fill gaps, say when you could not reach something.
Eleven things worth watching
Copy any of these as written and adjust the names and URLs. They all follow the five-part shape above.
Your competitors
The one most owners mean to do and never do. Weekly is plenty.
Every Monday at 8:00 AM, check these competitor websites: [paste 2 to 4 URLs, including their pricing and services pages]. Tell me only what CHANGED since your last run: - New or removed services - Any price change, with the old and new figure - New offers, guarantees or financing - Changes to what they lead with on the homepage - Anything new about hiring, locations or hours Keep it under 150 words, most important first. If nothing meaningful changed, just reply: no change. Do not guess at anything you cannot see, and tell me if a page would not load.
Where you rank for the searches that matter
Pick five real phrases a customer would type, not industry jargon.
Every Monday morning, search for these phrases and tell me who is showing up: [list 5 phrases, e.g. "emergency plumber Tampa"]. For each one tell me the businesses in the top few results, whether my site [yourdomain.com] appears, and anything new: a competitor who was not there last week, a new ad, or a change in the local map results. Under 200 words. Flag anywhere I lost ground since your last run. If nothing changed, say: no change.
Your inbox, before you open it
Needs your email connected. Turns 40 unread into a list of what actually needs you.
Every weekday at 7:30 AM, read the emails that arrived since yesterday morning and give me: 1. Needs a reply from me today, with who and what they want 2. Anything mentioning a deadline, an invoice or a dollar amount 3. Anything that looks like a new enquiry or a new customer 4. Everything else in one line Under 200 words. Do not reply to anything, do not send anything, do not delete anything. This is a briefing only.
A news brief for your industry, not the world
The trick is being specific about your trade and your area. Generic news briefs get ignored.
Every weekday at 7:00 AM, give me a short brief on news from the last 24 hours that could affect my business. I run [describe your business] in [your area]. Cover only: changes to regulations or licensing, material or supply costs, anything major happening to local competitors, and local news that changes demand such as weather, construction or big employers moving. Five bullets maximum, one line each, with a link. Skip national politics and general business news. If nothing relevant happened, say: nothing today.
Christmas gift prices, from now until you buy
Start it in autumn. The point is catching the drop, not checking on the day.
Every day at 6:00 PM, check the current price of these items: [paste product names and links]. Tell me only if something changed: a price drop of 10 percent or more, an item coming back in stock, or a coupon or sale that applies. Include the price you saw last time next to the new one. One line per item. If nothing moved, just reply: no change. Do not recommend alternatives, I only want these.
Running shoes, or any specific thing in your size
Size and colour is where price watching usually falls apart. Say them explicitly.
Twice a week, check the price of [exact shoe model] in [size] at [list the retailers you would actually buy from]. Only tell me when the price drops below [your target price], or when my size comes back in stock after being sold out. Include the retailer, the price and the link. If nothing qualifies, reply: nothing yet. Do not suggest a different model or a different size.
What it costs you to buy, so you order at the right time
The inventory version of the shoe task, and the one most likely to pay for your subscription.
Every Monday and Thursday, check the current price of the materials and products I buy most: [list items, with supplier links if you have them]. Tell me anything that moved more than 5 percent either way since your last run, with the old and new price. Flag anything showing as out of stock or on extended lead time, because that matters more than the price. Under 150 words. If nothing moved, reply: no change.
Your reviews, the day they appear
A bad review answered within a day reads very differently from one answered in three weeks.
Every day at 5:00 PM, check for new reviews of [your business name] in [your city] on Google, Facebook and [any other site that matters to you]. For each new one give me the rating, the site, and what they actually said. Put anything under 4 stars at the top and draft a short, calm reply I could post, without arguing and without offering money. If there are no new reviews, reply: none today.
Three more worth setting up
What goes wrong
It reports every day and I stopped reading it
The most common failure by far, and it is a one-line fix. Add "if nothing meaningful changed, just reply: no change" to the prompt. A task that only speaks when something happened is a task you keep.
It says something changed and nothing did
Usually because you never defined what a change is. "Tell me if prices changed" catches a rounding difference. "Tell me about price moves over 5 percent" does not. Put a number on it.
I set up nine of them and now it is noise again
Start with two. Live with them for a month. The plan limits are actually doing you a favour here: three on a free ChatGPT account is roughly the number a person can genuinely keep up with.
It cannot see the page I asked about
Some sites block automated access, and some content sits behind a login. The task cannot get in either. Ask it to tell you when a source failed rather than quietly skipping it, or it will report "no change" on a page it never actually read.
Can it just buy the thing when the price drops?
No, and you should not want it to. It watches and it tells you. Buying stays with you. Treat anything it reports as a prompt to go and look yourself, especially where money is involved.
Your checklist
Two tasks, set up properly, beat nine you ignore.
Want to build your first one with help?
We run a free workshop every Friday at 2 PM Eastern. Bring the name of one competitor and we will build the watch task live, together, and you leave with it running.
Plan limits and features checked in September 2026 against Anthropic's and OpenAI's own documentation. Both companies change these often, so if your screen shows something different from this page, trust your screen.