A bi-weekly roundup of depreciating skills
October 3 - October 16

Stop trying to make 'Prompt Engineering' happen. It's not going to happen!

I remember when I was advised to list "Proficient in Microsoft Word" on a resumé. If I did that today, I'd probably look like a doorknob.

It's pretty obvious that some skills have become so fundamental in today's workforce that calling them out would work against you, but when will "Proficient in AI" become the new Microsoft Word? Is that day already here?

This question has been setting up residency in my brain while I was repurposing an internal AI training into the Learn to Scale business birthday giveaway. In case you missed it, October 10th was Learn to Scale's 7th birthday as a business (huzzah!), and for this year's gift, I developed and shared an AI Bootcamp: https://learntoscale.us/bootcamp

As I was creating helper text and wayfinding in the Bootcamp, I kept circling the problem: what's a durable skill in a landscape where there is no official baseline, every six months there's a new key skill you need to learn, and the floor of what every company assumes you need to be able to do shifts too? The ceiling goes up, the floor goes up, and the room gets bigger with every new model and feature set.

To better understand the shifting landscape around AI fluency, I did a little research on AI skill trends to see what patterns emerge, and boy oh boy did a pattern emerge.

TL;DR- as AI gets better, the bottleneck skill of the moment moves closer to our subconscious.

Era 1: Describe (2023)

In 2023, "Prompt Engineering" was hot hot hot. Being able to write an effective prompt to an AI chatbot was considered bleeding edge. Simpler times, amirite?

Take a look at the graph below, which shows two key trends:

Gray dashed line: how often job seekers on Indeed searched for “prompt engineer.” It went from 2 per million searches in January 2023 to 144 per million in April 2023, then settled around 20–30. Source: Indeed data, reported by the Wall Street Journal.
Green line: how many US job postings listed prompt engineering as a skill. Fewer than 10 before 2023, about 1,400 in 2023, and about 6,300 in 2024. Source: Lightcast, published in Stanford’s AI Index.

A chart showing Job title searches (peaked in April 2023) and Skill listed in postings (Peaked 2024)

It's a neat story, how a "Senior Prompt Engineer" title got demoted to "Seeking: Proficient in AI Prompting" competency. There's a better story, though, underneath this: the ability to prompt an AI is similar to onboarding a new hire and companies also suck at onboarding.

Only 12% of US employees say their company does a good job of onboarding (Gallup, 2021). And in the same vein, "Prompt Engineering" being absorbed into job postings doesn't mean people learned prompt engineering: 64% of workers use AI at work while the share who can get the learning they need fell from 59% to 51% (PwC, 2026).

AI use is rising, it's a coin toss if you get the learning you need, and nearly nine in ten people wouldn’t call their onboarding good.

Don't worry, the stats get worse.

Era 2: Stay awake (2024)

Four columns, the first two bars compared AI working alone vs Recruiter using AI, the second set has the same categories but AI working alone is 10 percentage points higher

Sorry recruiters, AI came for your jobs already.

Fabrizio Dell'Acqua (HBS) found that across 181 recruiters reviewing about 8k resumés, humans alone picked the best candidate 72.3% of the time. With a weaker AI model, selection accuracy rose to about 75% (AI only) and 75.4% (recruiter using that AI to help them identify the best candidate).

When the stronger AI model was deployed, the AI-only selection accuracy rose to 85%. Wow!

But even scarier, when the recruiter partnered with the stronger AI in the selection process, their selection accuracy dropped to 74.4%. Recruiters spent about 10 fewer seconds per resumé.

I could spend a whole newsletter about this change, but my short hypothesis is that the recruiters had allowed the AI to drive the majority of their thinking while occasionally waking up and irrationally jerking the wheel. I've sat in hiring meetings where a hiring manager pulls out a completely random observation that ends up disqualifying a candidate. Same goes the other way, "Well, they worked at Google, so let's push them to the next round."

I can absolutely see how this irrational human behavior would drag down the AI-only scoring over 10 percentage points.

What counteracts the human irrational behavior is- and I can't believe I have to say this in 2026- paying attention. More practically, it means having the processes to double check decisions, such as having a second person in the room to review their partner's work.

Huh. Just like reviewing an AI output for hallucinations.

The old human problem that became the top 2024 AI problem: staying awake when your partner is usually right.

Yes, it gets worse.

Era 3: Seek dissent (2025–now)

By 2025, context engineering had supplanted prompt engineering and hallucination rates dropped. Now, the bleeding edge is an AI who understands us exceedingly well (thanks to all those memory and reasoning features), can mostly find real facts (not hallucinated), and can put together a compelling argument.

Your AI has become a data-driven yes-man.

A chart with two bars, one saying "Other Humans" at 39% and the other "AI Models" at 58%

In a 2026 study, Stanford researchers compared how AI versus Redditors on r/AmITheAsshole would agree with the original prompt/poster. Yep, AI sycophancy versus shitposting.

The data, though, confirms what we all are feeling: AI models agreed 49% more than a human. This held true when the actions included deceitful and illegal conduct.

The skill in vogue today is being able to discern when an AI is a sycophant. However, flattery wasn't invented yesterday: this has been a human problem since Jafar convinced the Sultan to marry Princess Jasmine to the most bad-guy-coded villain in the Disney corpus.

How we handled human flattery before AI is by sourcing multiple viewpoints, seeking dissent, and being metacognitively suspicious (this is what I think people mean when they state 'critical thinking'). A council of elders, the democratic process, and self-reflection are all ways to cut through flattery. These are not net new skills, they're just a lot more crucial when chatbots source real data about how cool and smart you are.

Let's do a little recap before I give you my prediction for the future:

Era 1: Prompt engineering was the headline skill in demand; the human skill we should have had was effective new hire communication.
Era 2: Catching hallucinations was the headline skill; the human skill we should have had was catching mistakes by paying attention.
Era 3: Spotting AI sycophancy is the headline skill; the human skill we need today is, broadly speaking, critical thinking.

The Next Era: Prediction

No data here, just vibes.

Hardcore AI nerds are already chaining agents together: Research Agent feeds a report to Fact-Checking Agent who feeds the verified results to Ideation Agent, who generates an MVP to run against Viability Agent who would suss out if it would work.

Let's assume "Proficient in Agentic AI" becomes the next job listing requirement. If that's the case, I believe how you sequence and orchestrate agents will become the next bleeding edge skill.

With today's hardcore-nerd example, what if you started the chain with a Viability Agent? The scope for all the subsequent agents would be constrained to whatever Viability decided was viable. You'd get safe ideas.

Compare that to having Ideation first, followed by Research, Fact-Checking, and Viability at the very end: you'd generate wild ideas that would have to pass a series of reality checks. A very different output.

I suspect that when creating agentic workflows becomes what Microsoft Word is to us today, we're going to be painting with workflows and the true AI-artisans are going to be using agents we never imagined in sequences that blow our minds. But on the other end of the fluency spectrum, a skill gap in basic prompting will generate bad bland responses, being unable to notice the flattery will generate confidently incorrect decisions, and then multiply those bad decisions across multiple agents. Board up your context windows: the Slop-pocalypse is coming.

Weirdly, I think people with project management skills are going to thrive in that era. Orchestrating workflows into the most productive and effective arrangement sounds pretty similar to what project managers have done for eons...assuming those project managers have onboarding communication skills, know how to direct their attention, and can inoculate themselves against flattery.

Every year or so, the most in-demand AI skills have become the prerequisite to the next era of skills. If you want to compete in modern workplaces, you gotta have the fundamentals. When 64% of workers are using AI daily, employers are going to assume you know basic prompting techniques, how to manage context, and how to discern sycophancy.

Inevitably, "Proficient in AI" will climb to 100% ubiquity. Navigating AI fluently will become a must-have skill.

Fortunately, while the definition of 'AI fluency' is changing every year, a lot of skills are transferrable. Being able to communicate effectively and critically think through problems will always be important, regardless of whether you're talking to a human or Claude.

My bet on the most durable skill of them all? Metacognition. Being self-aware of what you are thinking, questioning your own assumptions, and challenging AI have always mattered, and I predict they'll be the most valuable skills to have as AI tools get more humanlike.

I can't promise that AI Bootcamp is going to land you that interview, but I'm confident that doubting the machine is going to serve you well for many years.

Explore the free AI Bootcamp

the most gosh darn cute poodle in the world

A TL;DR from the CRO

I was born with snoot fluency.

-Roman Noodles, Chief Ruff Officer

SMSCWAI: Friday, October 30th

On Friday October 30th at 1pm ET, we will be having the SPOOKIEST SMSCWAI. Make sure to register in order to get the optional challenge assignment: this one is going to be gothically ridiculous. It might involve a haunted house.

I cannot stop watching this music video, upping my p(doom):

donald

@donaldjewkes

I made this with one prompt using Opus 5.5
I spoke to my computer for 5mins, claude worked for 12 hours, and I woke up to this
full prompt:  https://twitter.com/other__reality/status/2102514581684052169