CEOs: Here's How to Not Screw Up Your AI Memo
A field guide to saying the hard thing without sounding like a monster.
Dear valued employee,
I would like to share important news about the future of our company. As you know, we are living through a period of unprecedented technological transformation. Your leadership believes that artificial intelligence (AI) represents a tremendous opportunity. With AI, we can move faster, do more with less, and win in exciting new ways. We are uniquely positioned to capture the upside of this generational...
Have you received one of these tone-deaf CEO AI memos? If so, I’m sorry. If you haven’t, I’m also sorry, because you probably will.

But this is really a story for the CEOs that may be reading this: You don’t have to suck this badly. You can write the “AI memo” more honestly. It won’t kill you.
AI Memo Worst Practices
Before we examine some best practices for the AI memo, let’s look at examples of things not to do. They are easy to find. The AI memo is an established genre that stretches from AI’s breathless introduction to today’s Fortune 500 CEO pronouncements:
Do not threaten your employees. “We will need fewer people doing some of the jobs that are being done today.” (Andy Jassy, Amazon CEO)
Do not turn a pep talk into a fire alarm. “AI is coming for your jobs.” (Micha Kaufman, Fiverr CEO)
Do not refer to people as line items or “lower-value human capital” when describing the impacts of AI. (Bill Winters, Standard Chartered CEO)
Try not to invent a new underclass and then throw the employees you’re axing into it: “AI is coming for measurers.” From an op-ed that gleefully starts, “Two weeks ago I laid off more than 20% of my workforce.” (Matthew Prince, Cloudflare CEO)
Don’t introduce AI as a performance metric. “Starting with the next performance review... we will also ask how frequently does each person default to AI.” (Kaz Nejatian, Opendoor CEO)
Don’t imply that your employees’ current skills have always been inadequate. “[AI adoption turns] work that once took hours into tasks done in minutes.” (Jane Fraser, Citigroup CEO)
And don’t cheerlead a technology your audience is terrified of. Read the room! (Eric Schmidt, former Google CEO)
The CEOs guilty of these memos and op-eds are not dumb and their analyses on AI’s impact are not necessarily wrong. That’s not the problem. The problem is manners. Old-fashioned, didn’t-your-mother-teach-you manners.
But I get it. A workforce is a resource, and CEOs answer to shareholders. That audience needs to see how a company is pushing forward, competing, optimizing, exploiting new technology, yada yada. One way to send that message is to write to the employee, but not really for the employee.
I propose a better way.
AI Panic with a Smidge of Empathy
CEOs: When you’re writing to your employees, write to only them. You can write a separate letter to your shareholders. It’s two different audiences, and they need two different things. Employees need clarity and empathy. Investors need confidence and market-appropriate aggression. These are not the same memo.
What that in mind...
Address the only topic that really matters. Every employee wants to know one thing: Am I next? If you don’t cover this at first, nothing else lands. Paying rent is way more important than “velocity.”
Write to the most frightened person in the room. Bad AI memos are written with a subtextual wink to the AI-excited early adopter. That’s a fraction of your workforce. The rest need something different.
Give people something to do. Action quells anxiety. Even small steps. Link to training materials, things to read, forums for questions.
Encourage screw-ups. Did you get everything right about AI from the start? No. So don’t expect your terrified employees to become expert overnight. Tell them that you will not penalize them for experimenting and learning.
Do you want loyalty? (This is a real question. You may not. You may be trying to encourage employees to resign so you don’t have to re-train them or lay them off. But let’s assume for the moment that’s not the kind of CEO you are.) If so, tell your people: We will help you build skills that you can take with you, not just use here.
Think of the AI memo not as a declaration but an introduction, as of a new hire to an existing team. It’s awkward but necessary. You cannot engineer away the inevitable halting first steps. People have to establish their own relationships.
The AI memo is hard to tackle because AI is disruptive and some of those jobs really aren’t coming back. But you can be honest without being a dick. Tell the truth, treat people like people, and resist the urge to make your investors feel better at your employees’ expense. It’s actually not complicated. It’s just difficult.
This story is part of the Caller Calls Back project, in which I examine the intersection of technology and etiquette. For editorial consulting, visit me at Catchphrase Publishing.


