Oct. 18, 2026

A couple days ago, I offered a challenge: Try to identify whether a given passage was written by me or by Claude.

To be fair, maybe I set this up in a way that made it too obvious which was which? After all, I just instructed Claude to write a brief post on a career development topic, and then I copy/pasted the output verbatim.

There are a variety of ways to make AI-generated text sound more human, but I didn’t attempt any of them.

But isn’t this the version of AI text that we’re being flooded with all day every day?

• I see countless LinkedIn posts that are, at best, lightly edited by a human.
• I sit through slide presentations where all of the content, as well as most of the trainer’s script, are clearly AI-generated.
• I watch YouTube videos where the speakers use all the characteristic tells in their speech, revealing who really wrote the script they’re following.

If you want to claim that people can or can’t spot that, then that’s the kind of test you need to run.

Regardless, let’s try a more advanced version of the test.

I’m going to use a very basic humanizing technique: I’m going to instruct Claude to write in a way that sounds like a human.

(There are more sophisticated ways to do this, but this alone results in a dramatic improvement in my eyes.)

Okay, the topic is getting passed over for a promotion (a true story in the human version). This time, each passage is somewhat longer.

Who wrote which?

PASSAGE 1

I got passed over for a promotion in 2019. Honestly, I was annoyed for about a month.

I’d been there four years. My projects shipped on time, my reviews were solid, and I’d more or less decided the role was mine. Then it went to someone else, and I spent a few weeks doing that thing where you replay every meeting in your head and build a case against everyone involved.

Eventually I asked my manager for feedback. I expected something about my skills. Instead she said, “You’re great at your own work. But I’ve never seen you help anyone else get theirs across the finish line.”

Ouch. But fair.

I wanted to argue, and I couldn’t, because I knew she was right. I’d been so heads-down on my own list that I treated every request from a coworker as an interruption. Someone would ask a question, I’d answer it as fast as possible, and I’d go right back to my screen.

So I started doing small things. Nothing dramatic. Reviewing a coworker’s slides at 4:55 on a Friday. Answering the “dumb” questions from new hires without sighing (okay, sometimes sighing). Staying on a call an extra ten minutes to help someone debug something that had nothing to do with my goals.

It felt a little fake at first, like I was doing it for the wrong reasons. For the first couple of months, I probably was. But somewhere along the way it stopped feeling like a strategy and started feeling like how I worked. Turns out helping people is more fun than guarding your calendar.

Nobody noticed at first. Nobody sent a message saying “hey, nice job being nice.”

About a year later, a role opened up, the same one I’d wanted before. Three different people recommended me for it, and I hadn’t asked any of them. One was a new hire I’d helped during her first week. I didn’t even know she’d said anything until my manager mentioned it.

I got the job.

I still think I deserved the promotion the first time around, at least on paper. But I’m glad I didn’t get it. I wasn’t ready to lead anyone, and I wouldn’t have known why.

Moral of the story: stay mad for a month, then go be useful.

PASSAGE 2

I was once passed over for a promotion, despite being the most senior member of my team and being recommended by the person exiting the position. They brought in an outside hire who had a more advanced degree than me but zero experience in our technical area.

Part of it was probably the credentials. But I think the bigger part was something that happened during the interview…

They asked, “Tell us why you’re the best person for this job.”

I replied, “I can’t tell you that, because I don’t know if I’m the best person for this job. I don’t know the other applicants or their qualifications. If there’s someone who’s a better fit for this position than me, then you should hire them.”

(In case you haven’t picked up on this, I can be a bit too literal and black-and-white in my thinking at times.)

When the CEO told me I didn’t get the job, they also said, “I wanted you to tell me that you are the absolute best person for the job and why. You have to make us feel confident in the decision.”

Again, I said, “But you shouldn’t hire me if there is someone more qualified for the role…”

In this case, rather than responding to the real prompt (in essence, “Argue why you’d be a great fit for the job”), I perseverated on why I viewed the literal question as unanswerable.

A few months later, the new supervisor was gone. I won’t say anything else about that.

When I interviewed for the position again, it was a very brief conversation, and I said something like this: “There is no one on this planet more qualified for this position than me. No other person understands the nature of our work or our clients as well as I do. I’ve built many of our systems, and I know how to run every single one of them.” Et cetera. Something along those lines.

I got the job.

I don’t know what the career advice is here. I don’t advocate for shameless self-promotion or exaggeration, not even to get a job you really want. (I only said true things in my rant during the second interview.)

I still stand behind my original response on technical grounds, but now I realize how uncharitable my interpretation of the question was. I was being obtuse, almost intentionally missing the point.

Maybe that’s the advice: In any conversation, we should seek to respond not necessarily to the literal question posed but rather to the heart of what the person really means. In retrospect, I guess that’s just basic human empathy.