Yesterday, I joined Dapple AI’s AI Outlook 2026, and it was genuinely one of the more insightful conversations I’ve heard recently, not because it hyped the future, but because it grounded it.

Here’s the biggest takeaway I can’t stop thinking about:

The people getting “left behind” by AI aren’t human operators. They’re operators who are resisting change.

That distinction matters!

What’s emerging isn’t a future where AI replaces thoughtful, capable operators, it’s one where operators who learn how to work with AI gain leverage, clarity, and speed… and those who refuse to engage quietly lose relevance.

And yes, starting IS intimidating.

New tools, new language, new ways of thinking about work. That discomfort is real. But tell me this honestly, when has anything worth doing ever been easy?

You want to get in shape? The beginning is brutal. You don’t know the movements, everything feels awkward, and progress is slooooow. But once you learn the fundamentals, you grow, physically and mentally. 💪

AI works the same way!

At first, it’s clunky. You don’t know what to ask. You don’t trust the output. It feels like more work, not less. But once you understand the basics (how to prompt, how to validate, how to integrate it into your workflows) your capacity expands.

Not because AI is “doing your job,” but because it’s removing friction so you can do the real work:

🔮 That’s the future for operators.

Not louder productivity, not chasing every new tool, but quietly building fluency, and compounding it.

Here’s a simple, real-world way I’m seeing EAs and Chiefs of Staff use AI well, without over-engineering anything.

Scenario:
Your exec comes out of a packed day of meetings and asks,

Instead of manually combing through notes, Slack threads, and calendar invites, an operator will:

What changed here isn’t effort, it’s leverage.

The operator didn’t “automate themselves out of a job.” They moved up the stack, from note-taker to decision curator.

If you’re intimidated by AI, don’t start by trying to automate everything.

Start here:

Use AI as a first draft, not a final answer.

Your value isn’t the summary, it’s knowing what matters, what’s missing, and what your exec needs to see first.

That judgment is still very human.

I’ll be honest for a second, I was confused at first too.

People throw around words like AI, agents, automation… and suddenly it feels like everyone else got a manual you missed.

So here’s the simplest way to think about it.

AI is like a super fast helper.

It can:

It does not think for you.
It does not know what’s important unless you tell it.

An AI agent is just AI with instructions.

Imagine you’re explaining a task to a babysitter or a new helper:

You say:

An AI agent is the same thing, you’re just writing it down instead of saying it out loud.

Because no one explains it like this.

They make it sound:

In reality, if you can explain a task to another human, you can explain it to AI.

AI is good at:

AI is not good at:

That’s still your job (and your value).

AI helps you start faster.

You still:

Think of AI as a helper, not a replacement.

If it feels confusing at first, that’s normal.
Everything useful feels confusing before it clicks.

We’ll keep breaking it down, slowly, simply, and without the tech jargon.

You don’t need to “learn AI.” You just need to try one tiny thing.

Grab one of these:

Nothing new, np prep.

Any AI tool you already have access to works.

Paste the text in and type this:

That’s it.

Now add one more sentence:

You just gave AI a job. 👏 Congrats, that’s an agent (even if we’re not calling it that yet).

Quick gut check:

Fix it, adjust it, use it or delete it.

Either way, you practiced (Kudos to you).

You just:

If this felt awkward or underwhelming, good. That means you’re at the beginning, not behind. Five minutes today beats “I’ll learn this later” every time.

We’ll build from here, slowly, simply, and together ☕🖤

Quick update — our next Office Hours with Molly Medvecky, founder of EA Enneagram, has been moved to March 4th. Apologies for the schedule change, and thank you for your flexibility.

We’re still excited to welcome Molly for a live session on the Enneagram and how it actually shows up at work, from communication styles and stress responses to boundaries and day-to-day dynamics for EAs and operators.

If you’ve ever thought “I know my type, now what?” — this one’s for you.

New details below:

🗓️ March 4th at 12pm ET
🌐 Free & virtual
⏰ 45 minutes
💬 Cameras optional; coffee mandatory-ish (tea still welcome)

We’d love for you to join us for this free session, it’s practical, approachable, and designed to help you understand yourself (and the people you work with) a little better.

Still thinking this through? Same.

We’re talking about it inside The Inner Office, our free Slack community for operators who want to compare notes and get unstuck faster.

For anyone who’s decided: I’m learning the tool, not arguing with the future.

Follow our Spotify playlist for inspo! 🎧