• AI Weekly
  • Posts
  • Are CEO's a Thing of The Past? We Dive into It 🤖💼

Are CEO's a Thing of The Past? We Dive into It 🤖💼

Could artificial intelligence replace your boss?

Author

Joshua Clear
April 06, 2025

In partnership with

You’ve heard the hype. It’s time for results.

After two years of siloed experiments, proofs of concept that fail to scale, and disappointing ROI, most enterprises are stuck. AI isn't transforming their organizations — it’s adding complexity, friction, and frustration.

But Writer customers are seeing positive impact across their companies. Our end-to-end approach is delivering adoption and ROI at scale. Now, we’re applying that same platform and technology to build agentic AI that actually works for every enterprise.

This isn’t just another hype train that overpromises and underdelivers.
It’s the AI you’ve been waiting for — and it’s going to change the way enterprises operate. Be among the first to see end-to-end agentic AI in action. Join us for a live product release on April 10 at 2pm ET (11am PT).

Can't make it live? No worries — register anyway and we'll send you the recording!

Could AI Take Your CEO's Corner Office? Not So Fast.

Hey there, savvy reader! Let's talk about an AI development that's percolating through C-suites everywhere: Could artificial intelligence replace the boss in the fancy office?

A few years back when ChatGPT started shaking things up, we were all worried about AI coming for designers, programmers, and drivers. Now, The Hustle has posed a more audacious question: Could AI replace the highest-paid employees in the corporate world—the CEOs themselves?

The Numbers Make a Compelling Case

Let's talk cold, hard facts first:

  • CEOs earn about 290 times more than their average employee (talk about wage gaps!)

  • A stunning 49% of CEOs themselves believe AI could automate most or all of their duties

  • Many CEO tasks involve data analysis, performance tracking, and analytics-based decisions—all AI sweet spots

So... Can AI Run the Show?

To find out, The Hustle had Claude AI roleplay as CEO for three struggling companies—Southwest Airlines, Starbucks, and Nike. The results? Let's just say it was part corporate buzzword bingo, part genuine strategy, and a surprising dash of humanity.

For Southwest Airlines: While the human CEO implemented layoffs and scrapped beloved policies like open seating, AI-CEO suggested:

  • No layoffs (early retirements instead)

  • Keeping open seating for most but adding premium assigned seats

  • Doubling down on the popular two free bags policy

For Starbucks: As the human CEO jets around on private planes while laying off workers, AI-CEO proposed:

  • Fair treatment of employees and good-faith union negotiations

  • Reducing employee workloads to improve customer connections

  • Moving closer to headquarters to cut commuting costs (no private jets here!)

For Nike: After some initially vague suggestions, AI-CEO recommended:

  • Returning to Nike's risk-taking design roots

  • Leveraging running clubs and cultural tastemakers

  • But waffled on crucial decisions like layoffs (indecisiveness—not a great CEO trait)

The Verdict: AI as Sidekick, Not CEO

While our silicon friend showed some strategic chops, it also revealed critical limitations:

  1. Emotional intelligence gap—it can't truly inspire employees or navigate complex investor relations

  2. Data bias risks—AI is only as good as what it's trained on

  3. Indecisiveness—AI Platforms (Think Claude/ChatGPT) often revised answers after follow-up questions (a career-ending trait in the C-suite)

Bottom Line

For now, it looks like AI won't be stealing the corner office, but it might be sitting in the adjacent cubicle. As Phoebe Moore from Essex Business School aptly put it: "While you may not require the same number of leaders, you will still need leadership."

The future likely involves AI augmenting CEOs rather than replacing them—handling data analysis, automating repetitive tasks, and providing unbiased recommendations. But when it comes to rallying the troops or making tough calls with conviction? Humans still have the edge.

What do you think—would you trust an AI to run your company? Hit reply and let us know!

Need another caffeine boost to process all this? We've got you covered. Check out tomorrow's newsletter for our breakdown of companies actually using AI in their executive decision-making process.

Reply

or to participate.