“Ai in the office is reportedly creating a flood of ‘workslop’ that takes longer to fix than do from scratch,” according to @Polymarket. In April, Sullivan & Cromwell were caught using Ai in a court filing, apologizing for “hallucinations.” But it’s going to get worse. In 2025, I witnessed two successful leaders outsource their own critical thinking to Ai.
I don’t buy into the fear that Ai will take jobs, or Ai will enslave humanity, but senior leader’s outsourcing their brain is genuinely terrifying .
I’ve worked with tech founders with half-billion dollar exits and executives at global brands on messaging, comms and PR. And I’m definitely not an Ai fear-monger. Quite the opposite—I believe Ai will spark massive opportunity and new jobs.
But it cannot be overstated: your most senior leaders are not immune to Ai workslop—that may be your most vulnerable.
My entire job is helping founders communicate to their audience in ways that make an impact. Clearly and consistently communicating who they are and how their company is unique to all internal and external stakeholders is tough work. It’s emotional, uncomfortable, and can be frustrating.
It’s not uncommon for CEOs or founders to want to bypass it for this reason.
Client A
In what had been standard process for Client A, I had met with a handful of company leaders, surveyed staff, spent hours with the founder and distilled the company’s entire brand message into simple, easy to understand language.
It’s always an incredible moment to clarify an entire brand into simple language everyone understands—the clarity and precision provides freedom. Usually for the fist time the larger team feels like they’re rowing together and focusing on the same objectives.
What we had developed brought tears to my eyes, but then something changed.
I started seeing irregular feedback. With a friendly nudge, the founder conceded he ran the messaging we developed over months, through an Ai tool.
His Ai had coached him to change the messaging approach, revising the entire document to something he liked better. Not wanting to give a reason to dig his heels in, I asked him to share it with me.
It had merged what we built as a team into other more common boiler-plate startup language, diluting the much-needed clarity his company needed. While I do understand the magnetic pull of familiarity—a constant battle—what surprised me was his willingness to overlook obvious and damaging mistakes.
In one sentence, the revised document claimed his company’s goal was to disrupt the very industry their key customer belonged to! Had that been published, he would have killed a mutlimillion dollar opportunity.
I figured that would put an end to it. But he doubled down. “Obviously it’s not perfect,” he said with a laugh.
The relationship he had with Ai was one where he trusted it implicitly. He was unbothered by its major hallucinations and errors.
This continued for another 30 days. His Ai tools were both all-knowing and easily forgiven. Finally I told him I was not a good fit for his organization.
I have no problem with founders using Ai for whatever projects they deem appropriate—it’s their money! But I do have a problem when Ai is used to undermine someone they chose to hire.
I chalked this experience up to stress, or simply that he didn’t like my work product and didn’t know how to tell me.
Then it happened to another founder. And this time it was far worse.
Exhibit B
After working with one client for nearly a year, it was clear the product they had been developing would simply need more funding to scale and funding they didn’t have. That’s when the founder decided he would pivot.
After seeing concrete success from our previous projects together, he told me I’d be a key asset in helping them pivot their messaging. A wise choice but this time with a twist.
For this new project, I’d not be working directly with him anymore, but his new Ai CMO.
The Ai CMO would tell me what to do every day and I’d simply execute the plans and strategies the Ai CMO told me to do. Shocked, I asked why he wouldn’t simply hire an entry-level person that could do the same thing. He shrugged it off.
He said my first task was to get up to speed on the organization by reading a short manifesto and long report he had created to outline the new focus.
The report was incredibly exhaustive and at least 50 pages long. As I began reading, I noticed the writing style wasn’t his at all. It was formulaic, vague, and just plain odd. I couldn’t make sense of it.
I finally asked if he used an Ai tool to create it and he said he had.
Before I could make heads or tails of what my next action step was, he emailed a new 100 page report I was also supposed to read. Then another. Then another. Then he said he’d be publishing these as books to generate buzz for his new pivot.
I finally tapped the breaks, and said asked for a reset. Irritated, he said all would be answered if I just read the reports. I told him our next step was to meet face to face and have a discussion on project scope and objectives.
He said he didn’t have the time and we both agreed this was no longer a good fit.
Conclusion: Ai provides speed and control.
I want to be crystal clear. These two individuals are wildly successful. Before investing in their new companies, neither had to work another day in their life. These are not “Gen Z interns” or lazy people. I consider them both to be quite brilliant.
But I think this problem is widespread.
I’ve witnessed founders online posting about Ai CMOs, Ai Chiefs of Staff, and generally preferring Ai workslop. Why? I’d guess because it’s non-oppositional and agreeable.
Some founders believe the core problem of scale is not having more people that think the same way they do. They grow frustrated when teams don’t immediately execute their ideas. But the tension of working with others they’re trying to avoid, is what made them successful.
Both founders had achieved earlier success with a co-founder that shared equal control of their companies but also provided resistance, keeping them in check. The tension from their co-founders wasn’t a bug, it was a feature.
I’ll summarize Yogi Berra, “I know I’m lost, but we’re making good time.”
Ai affirmation and quick execution feels like freedom, but when leaders ideas are put under tension, heat, and pressure that’s how great companies are forged.
