Let me define a term.

Asinine Legality: When an overly strict legal interpretation creates a situation that is asinine by any amount of common sense, and has huge potential negatives that are unaccounted for because of a fixation on surface-level legality or process formality.

Asinine Legality comes up from time to time, and I’ve noticed a few instances recently. Asinine Legality typically grows as organizations scale, so it needs to be actively combated.

One of the reasons for a lot of the silliness in government organizations is Asinine Legality. Legal risks are higher in government, and there often isn’t much penalty for getting nothing done, so many people just operate without questioning some insanely asinine systems that stem from Asinine Legality. And the people in government who do put their neck on the line to get shit done in spite of it are absolute heroes.

Let me give an example. In the wake of the WindBorne <> United incident, the NTSB asked us not to talk to the press and to stop posting on Twitter. I refused, pushed back, and had a phone call with someone from the NTSB. I told them that I simply could not agree to this, but instead wanted to understand what they specifically cared about so I could work to accommodate it. And what they wanted was reasonable: simply that we not share facts learned from the investigation itself until the report is out, not state any conclusions we have with confidence, and defer to their reports as the source of truth. All very reasonable. The Asinine Legality approach would have been not to question the initial request and just stop communicating about it, even when that led to asinine results, such as me looking highly weird and cagey when asked about the incident, and me being unable to transparently state what I believe to be true.

Asinine Legality typically occurs when someone who doesn’t understand the legal system treats it as a scary black box, and treats unknown legal risks as more important than known practical concerns. Asinine Legality is the reason that you don’t have a legal team run your company when you are trying to grow. A good lawyer should point out risks to you, keep you informed about what could happen, and then ultimately what you do next is a business decision that you make. This is most relevant for a CEO, but it’s actually relevant at every level of the company.

Technically, every time you send a message to anyone, you are taking legal risk. If you wanted to minimize legal risk, you should take zero actions ever. Of course, the result of that would be that you would be unable to perform your job, and you would be fired. So, you simply have to engage with legal risk in everything that you do, similarly to how you engage with motor vehicle fatality risk, and it’s part of your job to understand it and be smart about it.

The antidote to Asinine Legality is common sense and asking questions. Do not disregard legal risk. It’s very real. Just approach it with common sense, a desire to seek deeper understanding, and rational, calibrated risk tradeoffs. When something seems weird to you, and the justification is around ill-defined legality, become skeptical. Don’t just stop asking “why” when someone says “legal reason.” Keep asking why, and ask things like:

Final note: LLMs are awfully calibrated on the subject of Asinine Legality. Do not trust them for calibration here. They are often overly risk averse, but then, with certain prompting, they also might encourage very reckless behavior. They are a great source of knowledge and understanding, but the judgment is on you.