I am human and I often waver between healthy skepticism and optimism about LLMs. I try to test claims, question demos and be honest about what breaks. And, I am also too quick to judge work I do not understand.

My biggest learning from the mobile and social era of technology is that it’s easy to (mis)attribute foresight to people working on cutting edge technology. I remember being close to the technology and really understanding its fortes and foibles. However, that knowledge never translated to additional insight into areas where the tool was deployed: journalism, medicine, law, education, biology, art, or government.

For work, I often thought about how a tool might influence a field, especially as a consuting technologist in my early days. However, one thing that I had to keep relearning was knowing the tool does not automatically translate to understanding the field it enters.

I have made that mistake in many ways. I looked at the final thing someone produces and assumed I understood the work behind it. An article. A memo. A contract. A lesson plan. A diagnosis. A press release. A piece of software. The classic: If you “just” change $small-thing, it’ll be all good.

The hidden work behind the artifact was always hard to see and never obvious. I never appreciated that until actually talking to the people involved and growing older (and hopefully wiser).

A software engineer doesn’t just produce code that runs once. Similarly, a journalist does not just type sentences; a lawyer does not just summarize documents; a doctor does not just match symptoms to conditions; a teacher does not just explain a topic.

Most fields involve decisions, expertise and nuance. And of course there’s waste, internal politics, habit, personal and personnel flaws. The trick is knowing and differentiating why some wastage is justified because experts hit the failure mode that an outsider has not imagined yet.

To me, this is the biggest concern with LLMs. LLMs make the outside view more seductive because they are really good at producing artifacts.

They can write a press release. They can generate a functional app. They can summarize a contract. They can draft an article. They can make a lesson plan. They can make mostly functional software.

That is impressive.

It also woos us into a bad conclusion: if the output is easy to imitate, maybe the field was easier than we thought.

I am noticing this pattern in the AI industry.

Source: Eric Jorgenson on Twitter

A journalist vibe codes an app and wonders how LLMs are going to revolutionize software engineering.

A biologist asks an LLM for a press release and wonders how much communications work really requires.

A software engineer watches an LLM summarize legal text and decides that lawyers are toast.

I am not poking fun. It’s human to fall into this trap and underestimate the taste, maintenance, sourcing, accountability, timing, and the small decisions that separate acceptable work from good work and the judgement that separates good work from the great.

I still want and support skepticism especially when it’s mixed with optimistic gumption. To the note of wastage above, some experts do hide behind complexity. Some fields protect bad norms. Some institutions deserve hard questions. Some work will be changed by LLMs in ways insiders do not want to admit. Blindspots are eveywhere.

Yet, I want my skepticism to start with curiosity, especially when I am outside my field. I strive to start with: “What do they know that I cannot see yet?”

That question slows me down. It makes me ask why the work is shaped the way it is. It makes me more careful about calling something obsolete because I can now imitate one visible part of it.

Permit me to wax nostalgic about the early internet.

The early internet gave me access to people who explained problems and solutions. Forums, blogs, mailing lists, early Twitter, random personal sites. People wrote down what they knew. They (usually)answered questions from strangers sans snark.

That internet was never innocent. There was plenty of ego, cruelty and bad faith. I am not asking you to be polyannish. But, a lot of the culture I valued and luckily got to see was built around being useful.

Over time, too much of online life shifted toward performance: Mock a weak claim; get rewarded. Write take down posts and earn kudos. I can admit that there is a morbid entertainment factor to it. I know I’ve rewarded such “hot takes” with both attention and support.

However, I feel like we’ve taken that to its fanatical end. For whatever reason, today, slow explanations are branded boring; tarning anyone asking a sincere question as naive. We also reward these performances with attention, which is the new currency everyone’s seeking.

Let me repeat, I am not immune to this pull of judging.

A brief aside on judgement: A judgement means that one can stop thinking about it. It means I’ve reached a conclusion. My brain can move on to another thing after a satisfying sharp line. It’s the easy thing to do. And of course it’s natural to want to do easy things.

So, I mustn’t forget cynicism has its own gullibility. It mistakes the least impressed person in the room for being the most right, instead of considering them the least generous.

It might just be me getting old. I do not want to confuse those two again.

The people I trust most are rarely the fastest to dismiss. They are the people who make the room smarter. They ask good questions. They give context. They can be blunt without being cruel. They know how to say, “I do not know enough yet, help me understand…”

I am lucky to have found people like that in past places of work and in life. I found them in the parts of early Twitter that still felt generous.

They remain endlessly positive, hard to impress, direct and their criticism is pointed toward improving the work. They take care to not humiliate the person doing the work.

That distinction matters to me.

Today, I trust intelligence less on its own. Intelligence sans benevolence is a weapon. It overreaaches without humility. Intelligence often underappreciates the hidden human work.

So, I think helpfulness is the better signal.

By helpfulness, I don’t mean politeness or niceness, which are more avoidant traits (trust me, I know). By helpfulness, I mean the habit of leaving things a little better than you found them.

A meeting for a decision is a great example to help explain this more. Imagine someone just presented an argument for a key decision with some staholders in a room. And you think they missed a nuance that would help the room come to a decision.

You will carefully choose your framing of the explanation. For example: you might say. I think Rob made an excellent presentation of the argument for us to come to a decison. Points x, y and z suggest this important nuance that will help us understand the tradeoffs of this decision. Thanks for highlighting them, Rob.

The framing goes a long way to explain the nuance but passes the recognition to the person rather than call out your own helpfulness / intelligence. This is particularly important in high power dyamics situation.

Or in the cae of 1:1s, it may mean naming a weak argument, or suggesting to someone they might be moving too fast.

In group settings, it might mean asking questions that help with shared understanding of the context.

It definitely means: refusing to reward a cruel joke even when the room enjoys it and standing up for thr person who’s feeling the humiliation.

So, repair, clarity, better work, kindness.

That is who I want around me. This is who I aim to be.

I observe most interactions with this lens now.

How do they talk about someone who’s not in the room? Are they careful / careless?

How do they react when corrected? Do they become curious or defensive?

How do they manage a situation when they have the higher power dynamic? Do they explain kindly?

How do they wield power? Resposibly or do they get entitled?

When they observe cruelty amongst peers? Do they join / cut it out?

No one is perfect. I am certainly not and have had to learn through my own mistakes. I still vividly remember my power trip after being elected the school leader of the kindergarten through fifth graders. That’s a story for another time.

My point is that patterns are observable and so is someone learning and improving. What people reward, excuse, and do when nobody (important) is watching tells a LOT about the person.

I want to surround myself with people who are curious, build, are skeptical without sneering, and making people small. All of this leads to making it easier to tell the truth.

That is what I’ve best appreciated in my favorite professional cultures. It’s easy to say, “I am wrong,” “I don’t know,” and hear “This is good, and this part still needs more work.” It’s what I practice in my own mentoring.

Making admissions costly, causing people to posture, harden, pretend - those are places I want to avoid. Rewarding contempt is a certain path to misery.

Hence I naturally gravitate towards people who are and make me more honest, more curious, and more useful. If this resonates with you, I’d like to get to know you better. Connect with me. On twitter, mastodon, threads, linkedin or email.