The holidays are the biggest project of the year, and nobody ever writes a plan for it. This year, let AI help you write one.
Thanksgiving is two weeks away. After that, it’s a sprint to New Year’s. At work, I’m a CTO, and nothing ships without a plan. At home, I’m a dad with two daughters, and the holidays show up every year with no plan at all.
So this post is a practical guide to using AI for the holidays. It covers three jobs you can hand off this weekend, with prompts you can copy. Then it covers the part nobody likes to talk about: the scammers have these tools too.
The 60-Second Version of PIE
In my book, Practical AI for the Rest of Us, I teach a simple framework called PIE. It stands for Prompt, Iterate, Execute.
- Prompt: Tell the AI what you want, with real detail.
- Iterate: Treat the first answer as a draft and push back.
- Execute: Take the result out of the chat window and use it.
That’s it. The idea behind the whole book is “what you know, plus AI.” You know your family. You know your kitchen. The AI knows how long a twenty pound turkey takes. Together, you get a better plan than either one would produce alone.
You don’t need special commands, either. If you can explain it to a neighbor, you can explain it to AI.
Job 1: The Thanksgiving Meal
Prompt With Detail
The secret to a good prompt is detail. Don’t type “give me a Thanksgiving menu.” Tell it what you know.
Copy this and change the details:
I’m hosting 12 people for Thanksgiving. Two are vegetarian and one is gluten free. I have one oven and a four-burner stove. Dinner is at 4:00 PM. Build me a menu, a shopping list organized by store section, and a cooking schedule that works backward from 4:00 PM.
Iterate Until It Fits
The first answer is a draft, not a decision. So push back. Here are a few follow-ups that work:
My oven only fits the turkey. Move two sides to the stovetop or make them the day before.
Cut the grocery bill by $30 without losing a dish.
Rework the schedule so I’m out of the kitchen by 2:30 PM.
It will rework the plan as many times as you ask, and it never gets tired of you.
Execute or It Doesn’t Count
This is where most people stop, and it’s the only step that matters. Print the schedule. Tape it to the fridge. Send the shopping list to your phone. A plan that stays in the chat window is just a nice conversation.
Job 2: Holiday Travel
Travel is where AI for the holidays really earns its keep, because travel is mostly logistics.
Copy this and change the details:
We’re driving six hours on the Wednesday before Thanksgiving with two kids, ages 8 and 11. Build a packing list for cold, rainy weather. Plan two stops with food and bathrooms. Give me a backup plan if we hit heavy traffic, and five car activities that don’t involve a screen.
One Caution on Live Information
AI can be wrong about anything that changes by the minute. That includes flight times, prices, and road closures. Therefore, use AI to build the plan, and check the live details at the source. The airline’s app knows your gate. The chatbot is guessing.
Job 3: The Gift List
Here’s the trick with gifts. Describe the person, not the product.
Copy this and change the details:
My dad is 70. He loves fishing, hates clutter, and already owns every tool ever made. My budget is $50. Give me ten gift ideas and tell me why each one fits him.
Then iterate. He already owns three tackle boxes. Try again.
You’ll get better ideas in two minutes than in two hours of scrolling. And if someone on your list keeps saying they need to figure out this AI thing, I happen to know a book.
A Few More Jobs Worth Handing Off
- The toast: “Help me write a 60-second Thanksgiving toast. Here are three things I’m grateful for this year.”
- The seating chart: “Seat 12 people at two tables. Keep these two apart. Put the kids near the kitchen.”
- The budget: “Here’s my gift list and what I plan to spend. Total it and tell me where I’m over.”
It can draft a seating chart that keeps the peace. It cannot stop your uncle from bringing up politics. The technology isn’t there yet.
The Serious Part: Holiday Scams Have AI Too
Everything above is available to criminals too, and the holidays are their busy season. The FBI warns shoppers every year about fake stores and orders that never arrive.
Now add fake voices. The Federal Trade Commission has warned that a scammer needs only a short audio clip, often pulled from social media, to copy the voice of someone you love.
This isn’t about being afraid of the technology. It’s about using it with your eyes open. I work in federal and defense IT, where we assume someone is always trying to get in. You can borrow that mindset for the holidays with four rules.
Rule 1: Don’t Click the Link
If you get a text about a package or a deal, close it and type the store’s address yourself. Also, a brand new website with prices at half of everyone else’s is not a bargain. It’s bait.
Rule 2: Set a Family Code Word
If you get a call that sounds like your kid or your grandkid, in trouble and needing money right now, ask for the code word. If they can’t give it, hang up and call them back on the number you know.
Pick something nobody could guess from your Facebook page. Not the dog’s name.
Rule 3: Nobody Legitimate Wants Gift Cards
Not the IRS. Not the power company. Not your grandson. Anyone who asks to be paid in gift cards, wire transfers, or cryptocurrency is telling you who they are. Use a credit card instead, because it gives you a way to fight a bad charge.
Rule 4: Watch What You Feed the AI
In my world, we’re careful about what data goes into any tool. You should be too. No Social Security numbers. No card numbers. No medical records. The prompts in this post work fine without any of that.
If you do get hit, call your bank first. Then report it at ic3.gov and ReportFraud.ftc.gov.
Your Homework This Weekend
Two things.
Pick one holiday job and hand it to AI. The meal, the trip, or the gift list. Run all three steps: prompt, iterate, execute.
At dinner tonight, pick your family code word. It takes thirty seconds, and it could save someone you love a lot of money and a lot of heartache.
If you want to go further with AI at work, I’ve written about AI strategy beyond the hype and how to score whether your AI tools are paying off.
AI won’t cook the turkey. But it can take almost everything else off your plate.
Lead. Learn. Lift.
I walked through these prompts on Working Out CxO on GTV FOX 5 Plus. Practical AI for the Rest of Us is available at practicalaibook.ai. It makes a pretty good gift.
