It's somehow really counter-intuitive and uncomfortable to challenge someone's honesty openly, maybe?

For example, I can be relatively rude and direct (without meaning to be about half the time), but when someone tells me a story that strikes me as unlikely or heavily embellished, I feel really uncomfortable challenging the story, because it's tantamount to saying "you're lying".

In the situations where I was 'conned', in hindsight I could have probably found ways to test the person involved surreptitiously. It just didn't enter my mind to do so. But openly challenging them just felt wrong to me, and it still does, because if you're wrong you just accused someone of lying.

So these days I make a game out of finding ways to surreptitiously test the people around me. I often forget how useful that approach is (trust, but test), and I guess your comment reminded me to apply it more.

Whether its a good plan to challenge someone's honesty actually has nothing to do with whether or not that person is lying, even if I have certainty and evidence. The question is: what is the best thing I can do for my life? If my accountant lies to me, I will call the police. But if someone turns out to not be skilled as claimed? It depends on context.

It doesn't advance my life to tear down someone else; the best thing I can do is try to build my own understanding and take action. My approach is to be curious, actively listen, and ask clarifying questions. This can be as simple as saying "tell me more about that." Once I have enough information and context, I can judge claims and ideas directly.

It's not about tearing down someone else, it's about assessing the validity of someone's statements.

I might have presented it as more suspicious/antagonistic than I meant. My actual approach is pretty much as you describe in your last paragraph.

Basically, my approach to 'new humans' is the biblical adage: "be as shrewd as snakes and as innocent as doves", because I do believe, as in the biblical context, that good people are sheep among wolves. I try to be a good sheep, but I know for a fact that I can't handle wolves without being clever.

So far it works pretty well for me, but I've found it difficult sometimes to explain how I try to be both a sheep but shrewd, calculation but not shrewd or manipulative.

That said I’ve witnessed plenty of cringeworthy moments watching members of the MIT community deal with guest speakers during Q&A.

In corporate environments that I've experienced, the otherwise very argumentative developers would never actually challenge Employee No. 9610 in their basic skills. There's a formal distance in every interaction, pros and cons.

But in the few startup environments (<15 people) the culture was much closer, and there's no way that they would not have been 'caught' very early on, probably even in the first interview.

Even the nicest manager and teammates in the world don't have to proactively call someone out on being incompetent if every sprint their tickets are going unfinished, etc. And with the tooling, it's an automatic paper trail.

I think everyone is going to get a lot quieter, as you don't know who's listening.

You can’t realistically look at engineering culture and say wow here’s a sympathetic bunch who stay quiet when they see something wrong. Just read what industry leaders Richard Stallmen or Linus Torvalds write.