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Small-Scale Question Sunday for August 16, 2026

Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?

This is your opportunity to ask questions. No question too simple or too silly.

Culture war topics are accepted, and proposals for a better intro post are appreciated.

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The hard part is getting that across to them for budget approval. You can’t frame it as an expense. If you say you’re putting in a request for an $800k investment to upgrade the backend because we’re currently carrying a $2.3 million risk that’s expected to grow with our current rate of expansion, that’s something they’ll understand.

One useful application of LLMs could be translating tech concerns to C-suitese...

I’m not normally a fan of the suits, but I recognize it’s less them I dislike than it is the C-suite culture in general. I realize their jobs are hard and the good ones suffer for the publicity the bad ones get. Techies can be just as stubborn as anyone else can be, but what’s true for them is also the rub that lawyers have gotten for a long time. TrustedSec has done a lot of pentesting work for major corp’s out there, but in the pre-negotiation phase one frustration they’ve dealt with a lot is that “lawyers don’t know how to do anything other than lawyer;” which is to say they don’t understand the tech side of things. Well. Techies often don’t understand the business and economic side of the equation either.

If you speak tech to the balance sheet, they may understand what you’re saying but at no point do they understand why what you’re saying is relevant. The hardest part in talking to them is to get them to understand that you pay regardless. You don’t want your business to get vandalized? You’re going to pay higher corporate taxes for police. You want good public infrastructure? You’re going to pay a cost for that. And consumers don’t want to pay either. We know how to secure systems a lot better. It costs money… And nobody wants to pay for it. Do you want to pay 2x for all your stuff? Not really. But maybe you have to to reach the objective you need.