This year, I had a delightful experience with ChatGPT. When I checked on Whole Foods’ Thanksgiving catering, it didn’t just tell me the slots were available — it asked, “Would you like me to notify you when pickup slots become available?”

I said yes.

And just like that, I realized how naturally AI can slip into everyday life — not as a gadget or a gimmick, but as a quiet helper that saves time and reduces friction. This simple feature made me smile and reminded me why I love using AI for all sorts of things.

How I Let ChatGPT Track My Thanksgiving Order

If you’ve ever tried to order Thanksgiving catering from Whole Foods, you know the story. The turkey dinners open for ordering in late October, pickup slots vanish in a blink, and you’re left hitting refresh on your browser like it’s Ticketmaster in 1998.

So this year, I asked ChatGPT to do it for me.  I simply told it to “Search for Whole Foods Market Redwood City Thanksgiving catering pickup windows and notify me when they are posted or change.”

That single sentence created what’s called a conditional automation — a simple, intelligent reminder that checks every day and lets me know when something changes. No app installation. No calendar juggling. Just quiet background intelligence.

A ChatGPT Plus Exclusive

Conditional automations like (“check Whole Foods pickup windows daily and notify me”) are only available in ChatGPT Plus or Team/Enterprise plans — i.e., the paid GPT-5 version. Free ChatGPT (which runs GPT-4-mini) can set ordinary reminders within a single chat session (e.g., “remind me to order turkey tomorrow”), but it cannot keep checking automatically or send notifications later once the session ends. I could not find this feature in Microsoft Copilot, Gemini, or Perplexity.

What’s Actually Happening Behind the Scenes

When I gave that command, ChatGPT set up a recurring check that runs every morning at 9 a.m. Pacific time. Each time, it searches the Whole Foods Redwood City catering page to see whether Thanksgiving pickup windows have been posted or updated.

If there’s a change — new time slots, menu updates, or a pickup window opening — I get an automatic notification. If nothing’s changed, it stays silent.

In short: it’s a “check-and-notify” loop that lives entirely in natural language. You don’t have to know scripting, APIs, or webhooks. You just describe what you want to monitor and how often to check, and ChatGPT handles the rest.

Why This Matters (Beyond Turkey)

This might sound like a small convenience, but it represents something much bigger.

AI assistants are moving from being reactive (“answer my question”) to proactive (“watch this for me”).

The same pattern works beautifully for professional use cases:

• Monitoring when an RFP or grant opportunity is published.
• Tracking airline fare drops for mission travel.
• Watching for security advisories or vendor updates.
• Following stock or fund thresholds for budget management.

Instead of remembering to check, you let the system check for you.

The Bigger Picture for Nonprofits and Foundations

At CGNET, we see this kind of automation as part of the next wave of AI-enhanced productivity.

It’s not about replacing people — it’s about removing the friction of “when will that update?”

For nonprofits and foundations already stretched thin, this kind of invisible automation can reclaim time and reduce missed opportunities. Imagine being alerted the moment a grant portal reopens, a security patch drops, or a donor dashboard refreshes.

It’s small wins like these that add up to bigger impact.

Try It Yourself

If you want to experiment, try saying something like: “Check the CDC travel advisory site every morning and notify me if guidance for Kenya changes.” Or “Monitor flights from San Francisco to Nairobi and alert me if the fare drops below $900.”

You don’t need a developer — just a clear request.

And maybe an extra slice of pumpkin pie as a reward for the time you’ll save!

Want to learn more? AI has been a subject of my writing for several years, and CGNET has offered AI user training and implementation for both large and small scale organizations.   I would love to answer your questions! Please check out our website or drop me a line at g.*******@***et.com.