Outsmarting AI?
Workplace challenges from the new tech are going to be enormous. Are firm leaders up to it?
By Jonathan Dahl, Chief Content Officer
November 24, 2025
“This conversation can serve no purpose anymore.”
—HAL 9000 computer, “2001: A Space Odyssey”
I swear, I really wanted ChatGPT to write this column. And I think I gave it a pretty detailed and helpful prompt, even asking politely if it needed any more information. But its attempts at composing the text just didn’t come out right. I did share an example of my writing with it, but how was ChatGPT supposed to know that I’d never use phrases like “the transformation feels less like a revolution and more like a quiet unease” or “performative adoption is everywhere”? It just sounded—how can I (or ChatGPT) put this? Artificial.
I’m sure the technology will get a lot better, and at a mind-blowing pace. But the mounting evidence suggests that, at least for the foreseeable future, the warnings about AI wiping out the vast majority of jobs for humans have been overblown. In my view, the real issue about AI isn’t job replacement, it’s job disruption—more specifically, disruption in the workplace. Unlike anything we’ve ever seen before.
Most experts agree that while AI can’t fully take over most jobs, it can lop off a good chunk of almost anyone’s role by writing their emails, proposing strategies, and doing incredible research in a matter of seconds. Now that workers can have maybe 20 percent to 30 percent of their time (or more) given back to them, how in the world will companies manage that? We’re talking about millions upon millions of workers. Even the most highly motivated employee might not know how to productively use all that extra time. Can companies (or even AI) ever hope to track how each and every worker spends their day? Would they (or their workers) ever want them to?
And I’m just scratching the surface of all the workplace disruptions, way beyond the privacy and accuracy issues that make headlines today. Which AI tool is best to work with? I call it “the AI dating game”—the tools we pair ourselves with will matter enormously as the tech becomes more specific and useful. Then there’s the matter of firms keeping employees up to speed on all of AI’s constant improvements. We’ve never seen a tech change so fast. And the other day, I noticed two people had skipped a meeting and dispatched their AI agents to take notes in their places. Is that OK? Only a blink of an eye ago, in our This Week in Leadership newsletter we raised the question of whether or not employees should disclose their use of AI, out of fear of losing their job. Now that seems ridiculous—of course you need to be working with it, if you want to keep your job.
I think it’s this workplace implementation that is going to give firms fits for a long time, and I doubt even AI will have all the answers. Indeed, it’s going to take some special smarts to handle this right, with firm leaders doing a lot of redesigning jobs, developing new workflows, and elevating workplace training. In short, this will need to be a conversation with a purpose.
