The Hardest Part of a Proactive Assistant Is Knowing When Not to Speak

Almost everything written about proactive AI is about the generating half. How the system notices a pattern, how it phrases the insight, which model reads the calendar. That half is not the hard part. The hard part is the decision immediately after: having noticed something true, do you say it? A proactive assistant has an asymmetric cost function. Surfacing something useful earns a little trust. Interrupting at the wrong moment loses a great deal, and users do not give a second chance to a notification stream they have already learned to ignore. Once attention has been trained away from a channel, it does not come back. So the interesting engineering sits on the restraint side, and it is systematically the side that gets built last. I know that because on the first notification system I owned, I built it last. The design that does not work The common shape is: generate candidate insights, score them, and filter against a threshold. It fails in two specific ways. The threshold is a single scalar standing in for many unrelated reasons to stay quiet. "Not this person", "not at three in the morning", "not in the first week", "not again, they have dismissed this three times" and "not today, the budget is spent" are different rules with different owners and different failure modes. Compressing them into one number means none of them can be reasoned about, and tuning any one of them moves all the others. And nothing records why anything was suppressed. A threshold returns false. The suppression behaviour — the most important behaviour in the product — becomes the one part of the system that generates no data, and therefore the one part that cannot be improved. Two questions, two places The design I settled on in LILA separates the questions completely. Is this worth saying at all is a reasoning problem. It depends on the content, the evidence behind it, and whether the observation is one a product should be making. It has nothing to do with the time of day. Should it be s