Executives are worried

Hello again my friend,

With all this talk of AI, there's a huge wave of dread among those of us who are not executives.

Individual contributors. Managers. Even some directors. All of us have cause to see AI as a very sharp double-edged sword. A huge boost for some, but for others, it outright takes their job.

Roughly 30,000 people at Oracle were recently laid off. But it feels messed up because the company is doing well financially. Its owner (who I've written about before) is literally one of the top 6 richest men in the world.

And yet there's something nobody's talking about. The executives? They're fine. They're always fine. But will they stay that way for long?

That got me thinking. What actually makes someone an executive? Not the job description stuff. Not "sets the vision" and "aligns stakeholders." The real thing. What is it about these people that keeps them in the room when everyone else gets the email at 6am saying their role's been eliminated?

What’s to stop AI from wiping them out, and replacing them with younger, cheaper, twenty-something year olds that have time and energy to give?

I've been sitting with this for a while. The idea of an “executive” has fundamentally changed, because of AI.

Let's lock in.

For decades, being an executive meant one thing above all else: you knew more than everyone else.

You'd spent 25 years in the industry. You'd seen three recessions. You knew every client, every competitor, every landmine. That knowledge was your moat. It's why companies paid you the big bucks and gave you the corner office. Because you could walk in and say “at my last place, we did this, and it worked, so let’s do it here.” and it would work.

It made sense. Information was hard to get. Analysis took time. If you wanted a competitive landscape, someone had to spend a week building it. If you wanted to understand a market, you needed years of pattern recognition that couldn't be shortcut.

That was the deal. Time in the seat + knowledge + power (which I’ll cover) = executive.

AI changed the equation.

The 25 years of pattern recognition? A motivated person with Claude or ChatGPT can get a version of that in an afternoon. Not a perfect version. But a good enough version. Good enough to be dangerous.

Need a competitive analysis? Minutes, not weeks. Need to understand a new market? Hours, not years. Need to review financials, build a strategy doc, analyze customer data? The tools are right there. For $20-$100 a month.

I wrote about this in my piece on the future of work, the person who "knew everything" used to be unfireable. Now? If that knowledge is all they've got, they're in trouble. When everyone has access to the same information, the information stops being the differentiator.

So what's left?

I've been paying close attention to the executives I respect, and the ones I don't. And the gap between them has almost nothing to do with knowledge, skill, or even experience.

It comes down to a short list. And honestly, most of it sounds simple until you try to do it consistently.

Is your communication confident, or does it flounder?

This is table stakes now. When everything is async, Slack messages, Loom videos, written updates, your communication is your leadership in a very practical sense.

There's no body language to supplement a wishy-washy message. No hallway follow-up to clarify what you actually meant. If your written communication reads as uncertain, people downstream don't just lose confidence in the decision. They hedge their own work. It creates ripple effects across an entire team where nobody really knows what’s going on, because that initial message didn’t make it cut and dry.

The exec who can write "we're doing X, here's why, here's what I need from you" in four lines and make it land? That person is operating at a fundamentally different level than someone who writes three paragraphs of caveats.

The caveats and hedging are always a sign that someone spent too much time justifying to their boss, their team, and the PR vultures. But that’s the issue. Leaders may be available to answer questions, but if there’s no need to justify, they don’t.

Can you stick to a vision and just push, push, push?

Having a vision is easy.

The hard part is holding that vision steady when the board pushes back. When the quarter looks rough. When your best engineer quits. When a competitor launches something that makes everyone panic.

The exec's job isn't to have the vision. It's to be the person who refuses to let go of it when everyone else is ready to pivot to the shiny thing. That's not intelligence. That's stubbornness channeled productively. That’s why so many great companies recognize who they are, what made them successful in the first place, and protect it.

Are you willing to be the "bad" person?

This might be the single most important one. And it feels so counter-intuitive. My younger colleagues and friends love to talk about how their CEO is “that bitch,” and while it’s crude, it makes a point.

Making the call that pisses people off but is correct. Killing the project that the team loves but isn't working. Saying no to the CEO's pet idea. Letting go of someone who's well-liked but underperforming.

Most people will do anything to avoid that discomfort. They'll delay. They'll delegate the hard conversation. They'll create a committee to "evaluate options" instead of just making the call.

The person who can say "this is what we're doing, I know you disagree, and I own the outcome,” and do it in a way where people think I don't love this, but I respect that they made the call, and I respect them. That person is an executive regardless of their title.

Is there a sense of urgency to what you do?

There's a specific energy that real operators have. Not panic. Not performative hustle.

Just a constant low-level impatience with things not being done yet. A bias toward "let's ship it Tuesday" instead of "let's discuss it next sprint." It’s easy to give everyone the afternoon and leave it to later. That’s why it’s such an important part of leadership.

That energy is contagious in a way that strategy decks aren't. People feel it and they either match it or they self-select out.

Those four are about how you move. But there's another layer that separates the executives people tolerate from the ones people actually follow.

Are you the type of person people respect?

Not "respect the role." Respect you.

If this person left the company tomorrow and started something new, would you take their call? Would you consider following them?

Most executives fail this test. People respect the title, not the human. And there's a massive difference between "I do what my VP says because they're my VP" and "I do what this person says because I've seen how they operate."

The first one is org chart compliance. The second one is actual leadership. AI can't generate that. Title can't generate that.

Can you make people want to actually do more?

Anyone can assign work.

The question is whether people come out of a conversation with you feeling like they want to go solve the problem, or like they just got handed a task.

The best leaders I've seen aren't just the ones giving big speeches. They're the ones who make a four-sentence Slack message that somehow makes you want to figure it out. Because you don't want to let them down specifically.

Do you actually care, or are you performing?

This is where most executives completely fall apart.

Corporate culture has trained a whole generation of leaders to perform caring. They say "how are you doing, really?" in 1:1s. They post about mental health on LinkedIn. They say "our people are our greatest asset" in all-hands meetings.

I still remember execs at my old workplaces that talked like that, and when the door was closed, they’d literally say “we have to fire all these people. And everyone can smell it when it’s bullshit.

People would honestly rather have a boss who's blunt and a little cold but consistent than one who does the caring theater and then lays off 20% of the team via a blog post about how hard it was for them personally. As much as people can see patterns in markets and industries, they can see patterns in people too.

There’s no substitute for being a good person, and now that AI is replacing so much of that executive moat, this is becoming more valuable. Would you rush to take a job with Larry Ellison after those Oracle layoffs if the pay was anything less than amazing?

Real caring in this context looks boring. Remembering that someone's kid was sick and asking about it without being prompted. Going to bat for someone's promotion behind closed doors when there's no audience. Letting people know you’re getting up to go get a drink and asking if anybody wants anything.

It's the stuff that doesn't scale and can't be performed. Which is exactly why it matters.

Here's what this all adds up to, and it's the part that might make some people uncomfortable.

The gap between a director and a VP, or a VP and a C-level, is often not about who's smarter or more capable. It's about who carries themselves like the person in charge. Who speaks with fewer words and more certainty. Who gets the benefit of the doubt, not just because they're right more often, but because they've built enough credibility that people follow them anyway.

I see a lot of cases where someone who's not an executive is just as capable. They just don't communicate as clearly. They don't have the "vibe."

And AI accelerates this. When anyone can produce executive-quality analysis, the analysis stops being the thing that separates people. What separates them is: do you walk into the room like you already belong there? Can you be a good coworker, and great person, who can be respected when you go into is work mode?

That's not "talent" in the traditional sense. It's closer to a combination of earned credibility, communication density, and the willingness to be the person who says "we're doing this" when everyone else is still hedging, or afraid of saying it because they might get shit on for it later if it goes wrong.

If you're reading this and you're not an executive, this is actually good news.

Because the old model was gate kept by time. You needed 20 years. You needed to "wait your turn." You needed grey hair and a Rolodex. Now, it’s gate kept by character and operating style.

All the note above in mind, let’s call it what it is in simple terms. Do people like and trust you? Or are you booking extra meetings and writing dozens of caveats to justify yourself, only to have people wonder what the plan actually is?

Some of it is personality. Some of it is learned through intensity, not duration. You can get a decade of leadership reps in three years at a fast-moving company.

And that's why a 25-year-old with a laptop can start a hyper-growth company using AI and outmaneuver companies led by "seasoned executives." Not because they're smarter (though that’s a piece of it). Because they have the qualities on this list without the bureaucratic drag. Clear communication. Urgency. Willingness to make hard calls. No committees. No "let's align with stakeholders." Just movement.

The experience premium is collapsing. The 55-year-old who’s coasting on "I've been in this industry for 30 years" is getting lapped by the 27-year-old who moves fast, communicates clearly, and isn't afraid to make the call.

And the response, "you don't have enough experience" sounds increasingly like cope when that 27-year-old is shipping faster and making decisions that are just as good.

The title of "executive" used to be about what you could do. The knowledge you had. The years you'd put in. The information advantage.

Now? AI has the knowledge. AI can help prioritize. AI can analyze, synthesize, and brief you in minutes.

One of the few things left is who you are when the title is stripped away.

Do people respect you? Can you move them? Do you actually care? Are you clear? Are you relentless? Will you make the hard call?

That's the new test. And it doesn't care how old you are or how long you've been doing this. Just ask the 30,000 people at Oracle who got that 6am email. The executives who sent it are still in the building. The questions are whether they deserve to be and if they’re next.

Thanks as always for reading.