Your OOO is the most-read thing you write. Why’s it so boring?

Welcome to Prompt, Tinker, Innovate—my AI playground. Most weeks, we’re talking tools, workflows, and time-savers. But this time? We're getting personal.

The holidays are around the corner. Your inbox is about to get stuffed with auto-replies that say absolutely nothing. “I will be out of office with limited access to email.” Snooze. This week, we’re flipping that. You’ll use AI to write an Out of Office (OOO) message that proves even your auto-replies have personality—and quietly reinforces your brand while you’re off the clock.

This week’s playground: Write an OOO message that reflects your personal brand

Most auto-replies are wasted space. But they don’t have to be.

Your OOO might be the most-read thing you write all year. Hundreds of clients, colleagues, and leads will see it. So why phone it in?

A great OOO only needs to do one thing:

Set expectations—when you’re out, when you’re back, how often you’ll check email (if at all), and who to reach out to if something can’t wait.

But a fun OOO can also give you three extra wins:

1. It reminds people you’re an actual person.

   A hint of personality keeps you from sounding like a policy update.

2. It leaves a small, memorable impression.

   People notice when something isn’t bland. Some even reply to say so.

3. It reinforces what you’re known for.

   Humor, clarity, sharp thinking—whatever your “thing” is, this is an easy place to let it peek through.

I've had people reply to my auto-replies just to say they loved them. That’s the kind of low-effort, high-impact connection you want.

My approach: Give your work a personality.

Part of my personal brand is built around helping team build their own AI Teammates. Because that is my thing, I write OOOs where my AI tools are part of the story.

Sometimes they are working hard so I don't have to; sometimes they are "resting" (i.e., turned off).

Here are a few excerpts from my archive:

• The "Working Trip" (Malaysia & India):"My own AI teammates are coming with me—they’ll be handling navigation, translation, politely reminding me to hydrate, and maybe even making a few friends while we’re out helping others build theirs."

• The "Real Vacation" (South Korea):"Normally I give my AI teammates the time off too, but not this time... They'll be working full-time on navigation, translation, and making sure I know exactly what I’m eating before I commit to it."

• The "Family Chaos" (East Coast):"As always, the AI tools are resting peacefully—unbothered by family dynamics, casserole debates, or small talk about traffic. Lucky them."

My hook is AI. Your hook might be your spreadsheets, your camera, your code, or your sketchbook. Whatever makes your day job distinct—give it a cameo.

Your AI experiment: Try this prompt

👉 Time to tinker: Copy and paste this prompt into ChatGPT, Claude, or Gemini, filling in all of the [blanks] with your information.

📝 Prompt: "Act as a creative copywriter with a witty, approachable, and professional tone. I need to write an Out of Office (OOO) email auto-response for my upcoming time off. The email should be functional but memorable. It should set expectations, but also humorously mention [your hook—project, tool, update, or sidekick] in a way that that reflects the vibe of my absence.

Context:

1. I will return on: [insert date]

2. My backup contact for urgent needs: [your response]

3. Where I am going/What I am doing: [your response: e.g. skiing in Aspen, visiting in-laws, staycation with new puppy]

4. Will I be checking email? [your response: e.g. nope, sporadically, emergencies only]

5. The vibe: [your response: e.g. chaotic family fun, avoiding screens, unplugged and asleep]

Please give me 3 variations: Option 1: Lighthearted and witty. Option 2: Professional but with a creative twist regarding my 'hook'. Option 3: Short, punchy, and humorous.

Ensure the reference to my 'hook' reinforces my expertise but keeps the tone light."

💡Pro tips: Stretch your prompt like this

Got your first version? Great. Now use these add-ons to test new angles:

• “Give me a version that’s even more playful.”

• “Now try one that sounds like it was written by a robot trying to be human.”

• “Make it feel like I’m off on a secret mission.”

• “Rewrite it so it sounds like the to-do list is plotting against me.”

• “Now rewrite it in 140 characters, like an old-school tweet.”

Small changes in prompt = big changes in vibe.

What did you discover?

The holidays are for recharging—but that doesn’t mean your personal brand has to go quiet. Set up an OOO that keeps your voice in the room, even when you're out of it.

Share your favorite below and use it for your Thanksgiving break (for those celebrating in the US) or an upcoming holiday for everyone else.

Until next time—keep tinkering, keep prompting, and enjoy the time off.

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