March 20, 2017
My first ever task writing software professionally was to make some small change to the Kaggle server. I spent a day or so following painstakingly moving down the call stack from the API endpoint to figure out which file I needed to make my changes in. I proudly showed my mentor the five line change I'd made. His response: "Oh, that file is actually automatically generated. Your changes are going to get wiped out during the build."
As that story demonstrates, communication has a lopsided loss function: If you tell me something I already know, you've wasted a moment of my time. But if you tell me something I didn't know, it can save me an almost unbounded amount of time. (It would have saved me a few hours had I asked for a fifteen minute overview of how the Kaggle servers worked before I tried to figure it out myself). So in theory, you should bias towards overcommunicating and insisting that others overcommunicate to you.
In practice, social considerations complicate this ideal. These stem primarily from the fact that we typically respect people with knowledge and experience. Explaining something suggests you believe the other person did not previously understand what you are explaining, and hence that you respected them slightly less than they'd previously thought.
In an ego-less world, perhaps it would be optimal to try explaining some topic if you thought the other party had less than a 90% chance of understanding, (where "90%" depends on how bad it would be for the person not to have that information compared to how long it would take to establish that the person did indeed understand). In the real world, though, the cutoff we set is typically much less than 90% because of the fear of offending the person we're talking to. The more offense we think the person would take--more precisely, the greater the negative impact on us due to offense the other party takes--the lower we set that threshold.
Similarly, it can be hard to ask people to overcommunicate to you. In doing so, you are suggesting that you aren't that knowledgeable, which can diminish their respect for you. I think this issue can affect powerful people especially hard, because often some of the legitimacy of their power comes from their image as being experienced or knowledgeable. ("How did she become CEO without understanding this simple thing?!")
So you can see how ego and the social value of knowledge can actually lead to less knowledge transfer.
Personally, my approach to handling this problem has been to... explain this issue to people I frequently interact with! I tell them explicitly, "communication has a lopsided loss-function, so I'll try explaining something to you even if I think you probably understand it; please don't take offense! Similarly, please tell me things even if you think I already understand them! I have a math background; I'm used to saying no to people who ask me if I know what numbers are."