I spent a few years running knowledge management at a 150-person company. Our job was making sure people actually understood our company's products, rather than just saying they did. We had ample training resources, gave quizzes, encouraged questions, even had a bot in Slack they could tag when they weren't sure about something. Still there was never any indication that people didn't understand things. That is, not until employees made costly mistakes.

That experience (plus a separate one where I tried to raise concerns through HR and couldn't get an honest conversation) is what led to HushAsk: anonymous Slack routing with cryptographic identity protection.