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One Way to Improve AI for the Knowledge Worker

One Way to Improve AI for the Knowledge Worker

May 26, 2026 Thom Dempsey

This past week, Meta laid off 8,000 employees as part of a sweeping restructuring toward AI — cutting roles in some areas while simultaneously moving 7,000 workers into new AI-focused positions. ClickUp, a Work Management platform, laid off 22% of its staff, also citing AI, but in a slightly different way. In short, these companies are doing the same thing (reducing staff) while pointing to AI as the catalyst. It’s easy to see why Knowledge Workers are becoming increasingly anxious. And while we have no desire to fan the flames, the news headlines are doing that for us. So what do you do?

First, we all need to have a healthy dose of skepticism around job security. Again, I don’t want to create any fear — but I do think we, as humans, can’t be naive here. The 40-year-old job with a pension is long gone. If you can’t show your value, you need to find a way, or you may get caught in a sweeping layoff. And strangely, the answer to finding that way is with AI.

What’s interesting about ClickUp’s layoffs is that while the CEO laid off 22% of his staff, he also introduced $1M US salary bands for those who prove 100x impact with AI agents. Now, one eyebrow should be firmly planted on your forehead for this one. If Zeb Evans has the money to pay at that level, why let go of people who could potentially unlock even more impact? There’s a good measure of calling BS on this — but the story is more nuanced than it first appears. Evans isn’t just offering a retention bonus; he’s making a structural bet that the nature of the work itself has fundamentally changed. ClickUp now runs roughly 3,000 internal AI agents across its departments — a 3:1 ratio of agents to employees. His argument is that he doesn’t need more people doing the old work; he needs fewer people doing entirely different work. Whether that holds up is another question. The proof will be in ClickUp’s product velocity and whether their best people stick around. Only time will tell.

However, what’s really interesting about all of this is that many CEOs, while pointing to AI as the reason to reduce headcount, also openly admit they don’t know how to generate real value — or revenue — with it. And the data backs this up. According to IBM’s CEO study, only 25% of AI initiatives have delivered expected ROI, and just 16% have scaled enterprise-wide. A PwC survey of more than 4,400 CEOs across 95 countries found that 56% report seeing neither higher revenues nor lower costs from their AI investments. More than half. These CEOs know they need to leverage AI to stay competitive, but the path to meaningful returns remains unclear for most. That uncertainty, paradoxically, is actually a window of opportunity for the knowledge worker who figures it out before their CEO does. That person becomes very hard to let go of.

So, here’s what you can do. Pick up the book Artificial Organizations and follow the path laid out in Chapter 3, which offers a practical framework for using AI as a genuine work partner rather than just a productivity shortcut. Use AI to help you produce a better product for you and your company. There is no guarantee that you’ll be safe when the next CEO pulls a Benioff. But if you can produce a better product, a better experience, and lead the way on your team in integrating AI into proving value at your company, then you are not on the expense side of the equation — you’re on the value side. And that’s where you want to be.

References and Resources

Meta slashes 8,000 jobs as it pivots towards AI; type: Article

ClickUp cuts 22% workforce as CEO Zeb Evans pushes AI-first strategy; type: Article

Salesforce’s CEO Called AI Layoff Blame a “Lazy Way Out” (And His Own Numbers Tell a Complicated Story); type: Article

IBM CEO Study: Only 25% of AI initiatives deliver expected ROI; type: Article/Research

PwC 29th Global CEO Survey: 56% see no revenue gains or cost reductions from AI; type: Article/Research


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AI: We Need a New Magic Word

AI: We Need a New Magic Word

February 26, 2026 Thom Dempsey

When I was growing up, I loved Pee-wee’s Playhouse. Every episode had a “magic word,” and whenever someone said it, everyone had to scream like crazy. It was ridiculous.

That’s what AI feels like right now.

For the past few years, AI has been the magic word. It’s everywhere. Everyone’s talking about it. Everyone’s an expert. And we’re all expected to react — loudly. Everyday. It’s exhausting.

That was clear from the response to my post last week about AI (you can read it here). The exhaustion and overwhelm are real.

So instead of adding to it, here’s one thing worth focusing on:

Read Why Human Connection Is Your Ultimate AI-Era Advantage by Carrie Varoquiers in Forbes.

Why? Because it centers on something we can actually control.

While AI handles the rote and repetitive, we can double down on what humans do best: connect, collaborate, innovate, and care. The opportunity isn’t to do more. It’s to do more of what only we can do, and that is to connect.

And that’s not exhausting. It’s energizing.

References and Resources

Here’s a short video from Pee Wee’s Playhouse


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Does a Bridge Decide to Collapse?

Does a Bridge Decide to Collapse?

February 19, 2026 Thom Dempsey

To start, I am not an AI expert.

But I’m going to attempt to answer a deceptively simple question:

What is AI?

Yes, you can Google it.
You can ask Claude or ChatGPT.

You’ll get a clean, technical definition.

That’s not what I’m interested in.

Instead, I want to explore the answers people actually mean when they say “AI.”

Because AI isn’t easy to box in or define.
It’s a projection. A fear. A promise. A belief system.

So what is AI?

  • AI is the god of everything.
  • AI is utopia.
  • AI is the apocalypse.
  • AI will take my job.
  • AI is the imagination of a few tech billionaires.
  • AI is inevitable.
  • AI is biased and racist.
  • AI is proliferating faster than its implications can be understood — or regulated.
  • AI is an opportunity for humanity.

Over the next few weeks, I’ll explore each of these definitions (some I agree with and some I do not, but their consideration is important).

Because each one reveals less about AI — and more about us — the creators and regulators of AI.

AI is already embedded in our daily lives. It recommends what we watch, flags fraud, screens resumes, generates images, and predicts behavior. It creates pressure to learn, adapt, keep up, and not be left behind. And not just for humans but for companies.

So when we ask, “What is AI?” we’re also asking:

  • What is it this time?
  • Who benefits?
  • Who is harmed?
  • Who decides?

Recently, I had the opportunity to hear Timnit Gebru speak. She opened with the same question:

What is AI?

Her answer?

“I don’t know.”

And I loved that.

Here is someone widely recognized as an expert — formerly co-lead of the Ethical AI team at Google — who began not with certainty, but with humility.

She co-authored research that outlines the risks of large language models, including bias, racism, environmental costs, and the amplification of harmful content. She was later forced out of Google after raising those concerns.  Following her departure, Dr. Gebru founded the Distributed AI Research Institute (DAIR), an independent organization for AI research.

While tech-billionaires like Elon Musk or Sam Altman often speak about AI with sweeping confidence, Gebru began with doubt.

And maybe that’s the most honest starting point.

Before we define it, perhaps we need to ask:

Who gets to define it? Why should we be a little skeptical of that answer?

Because, regardless of its definition or intentions, AI was created by humans.

A bridge doesn’t decide to collapse.

  • If AI is racist, it was trained that way by humans– without consideration of inflammatory source data
  • If it self-replicates, then someone built it without consideration of the implications of AI building AI without human involvement (a very real scenario for Alibaba and Meta)
  • If it causes harm, then humans designed, deployed, or failed to regulate it.

A bridge doesn’t decide to collapse.

And AI does not decide to exist.

It is a human construct.

Which is why the definition of AI should not be exclusively owned by those who are also accountable for its consequences.


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Too Much Information – One Idea to Manage the Noise

Too Much Information – One Idea to Manage the Noise

January 19, 2026 Thom Dempsey

I’m overwhelmed.

There is so much coming at us, and so many methods for that information to reach us. At work, it could be Teams, Slack, Email, Cell, a CRM, or a work management platform; at home, it’s called the internet. The endless Internet. And our children, partners, pets, politics, and, well, just life.

One way that I’ve found to sort through the noise is an app called Attrove. Every morning, Attrove, an AI Communication aggregator, reviews all my email, Slack, and calendar invites and writes up and records a 10-minute summary of everything I should be thinking about going into the day. It’s fantastic. It doesn’t replace taking notes or having a clear task list, but it does a great job of reviewing all the main comms channels. And because it’s AI, it treats all information equally, without favoring the sender or the number of exclamation points used. I do miss things without Attrove, and the $20/month is worth me avoiding too many dropped balls.

I’m curious what’s working for you to manage the noise?


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Did Someone Say AI?

Did Someone Say AI?

December 3, 2025 Thom Dempsey

To say that AI is everywhere would be an understatement. It’s fascinating to see how companies are leveraging the fear, excitement, and possibilities of AI to sell their product. One visit to San Francisco will prove this to be true. But on a human level, it’s equally clear that so many people are unsure what the hell AI is, really. Other than confusing. And a little scary. Thinking back to the proliferation of the internet and email addresses, AI feels very fast in comparison. So, what could you do? Well, you learn and evolve. Like you did with the Internet, or email addresses, or puberty. AI has massive potential, but there are so many “experts” on this topic that it’s common to buy into the fear—a common way to move products or services.

If you want to start to learn, pick up Mustafa Suleyman’s book on AI called The Coming Wave. It will help ground you and challenge you to find your own personal balance with AI. It’s daunting, yes. But if you can see one way to use AI to make you more productive, then you are learning. And evolving, and that’s all you can do right now, because AI is so ubiquitous.


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The Importance of Human Connection

The Importance of Human Connection

June 3, 2024 Thom Dempsey

As I wrote about recaptcha, a tool meant to differentiate between humans and AI, I realized that humans are not really in charge of so many things. The whole point of Recaptcha was to distinguish humans from AI but it has now been proven that AI is better at it than humans. Which is definitely sad for humanity but not the point I’m trying to make today. AI is now showing up in many forms and one alarming form (to me) is in team meetings. Instead of showing up, people will send an AI note-taker to take notes, summarize, and list next steps. Which has advantages. It’s efficient. But, what it can’t do is connect with other people on your team. What it can’t do is show up for someone who is presenting. What it can’t do is be human. That is not AI’s fault. That is ours if we choose to deprioritize human connection at work. If our meetings aren’t efficient enough, fix the meetings but keep the connection.

References and Resources

How AI finally won its war on CAPTCHA images by Dr Peter Bentley/BBC Science Focus; Type: Article

Bots Are Better at Solving CAPTCHAs Than Humans, Research Shows by Emily Price/PC Mag; Type: Article


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Not a Boomer Problem

Not a Boomer Problem

March 27, 2024 Thom Dempsey

AI is everywhere, and it’s affecting our jobs. It’s natural to worry about being replaced by a bot. The best action? Engage with AI to stay ahead. Here’s a simplified approach:

  1. Learn: Read up on AI. Start with articles or LinkedIn posts.
  2. Experiment: Try new AI tools. Familiarize yourself with different applications.
  3. Reach out if you want to know how I stay updated with AI.

Learning: AI isn’t leaving. Adapting is key.


Is AI a concern in your industry? Should it be? We’d love to hear from you.


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The Future of Childhood Arguments

The Future of Childhood Arguments

January 29, 2024 Thom Dempsey

This is ridiculous, I know. But how AI (Artificial Intelligence) will change our kids’ childhood experiences is terrifying and exciting to think about. The internet was one thing, and VR was an entirely different thing. But AI advancements in all areas of life are happening at lightning speed, and what that means for lived and worked experiences is, well, terrifying and exciting…and most certainly, unknown.

Learning: AI is changing (or about to change) everything – it’s probably best to learn as much as possible while we can.

References and Resources

The Coming Wave by Mustafa Suleyman; Type: Book


Does this resonate with you? How has AI changed your work and/or life? Or how do you see it changing your work and/or life? We’d love to hear from you.


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