Upskilling: Chasing the Impossible for Most People
March 17, 2026
Another dinobaby post. No AI unless it is an image. This dinobaby is not Grandma Moses, just Grandpa Arnold.
The idea that one can take a group of 100 white collar workers and upskill them to “do” AI strikes me as a little crazy. For a short time, I taught a class at Duquesne University, did a one year tour in a program set up from youth offenders, and for some reason I still don’t understand served as a director of a special program at Northern Illinois University for special admission students. I learned that upskilling at each of these levels was difficult. The Duquesne experience made clear to me that bright people who had chosen a profession in the Catholic church were not “into” learning some new methods. My work with young people made clear that upskilling a person with traditional instructional methods was a waste of time. Therefore, when I hear about upskilling white collar professionals to learn about AI and then use AI to perform some job functions, I think a dose of reality may be needed.
A good example of this fanciful thinking appears in “The AI Cost-Cutting Fallacy: Why Doing More with Less is Breaking Engineering Teams.” The premise is now a trope. AI will make workers more productive. The Harvard Business Review explains that AI usage causes some workers to experience stress. The estimable HBR management wizards call this condition “brain fry.”
A 45 year old professional utility rate statistical analyst waits for a local train. He has been terminated because he insists that smart software cannot perform the requisite mathematical analyses required to determine probable power demand of a new data center coming online in three months. His superior wants to use the optimistic, hallucinated outputs from the firm’s new AI system. He knows he will be RIFed because AI does not have the know how our hero has gained over his 20 year career. Thanks, Venice.ai. Good enough.
“The AI Cost-Cutting” article states:
In late 2024 and throughout 2025, a dangerous narrative took hold in boardrooms across the tech industry. The logic seemed seductive in its simplicity: if AI tools like GitHub Copilot, Cursor, or Windsurf can help a developer write code 20% to 50% faster, then surely a company can reduce its engineering headcount by a similar margin while maintaining the same output. This “spreadsheet logic” has led to a wave of premature optimizations, where leadership teams view AI licenses as a direct substitute for human talent. The expectation is straightforward: buy the tools, cut the bottom 5–20% of the workforce, and watch margins improve. However, this approach fundamentally misunderstands the nature of software engineering. It confuses typing speed with problem-solving.
I agree.
The article then grinds through MBA jargon to make clear that efficiency has a downside: Degradation, not improvement. The conclusion of the write up, however, veers into the upskilling craziness. The article states:
Your domain experts are more valuable than ever. AI can write syntax, but only your people understand business logic. Train them to master Horizon 1 tools to prepare for Horizon 2.
Horizon 1 and Horizon 2 are MBA speak for producing needed software faster and then pushing to get smart software to do the “work.” How does one move “domain experts” along this yellow brick road?
Easy. Upskill.
I want to point out:
- People who don’t “upskill” are essentially watching the train depart from the station. Most will not be on the train. A local to the local unemployment office is definitely a possibility.
- People who won’t “upskill” are waiting for the pink slip to arrive via email or a quick Zoom meeting. Resistance means termination.
- Training programs that don’t output appropriately upskilled individuals will be chasing new contracts or waiting for a local to the local unemployment office.
- The leadership who pitch, manage, and have to report to an upskilled board of directors will be in a precarious position. Failure is bad for one’s business career.
The larger question is, “Why do people believe that upskilling adults who may have their sense of self anchored in a particular bucket of knowledge, systems, and methods is going to work?”
Upskilling won’t just as modern education is not cranking out large numbers of high performing graduates. Isn’t upskilling just a stopping point on a road that requires off loading and on loading the people needed to make the business work in the smart software centric organization?
Stephen E Arnold, March 17, 2026
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