Is proactive AI coaching actually useful, or just creepy?

Curious what people here think about agents that watch your workspace and nudge you before you ask. Example (full disclosure, I'm involved with this one): Ren (tryren com) is basically a coaching sidekick for managers. You add it to the Slack/Teams channels you choose (never DMs), and it also picks up context from meetings and your calendar. Once a day, it sends you a short private brief based on what actually happened: who deserves credit they haven't gotten, which 1:1 keeps slipping, who's quietly taking on too much. Each of those becomes an item on your "Dial," a five-step scale from a light one-sentence mention up to a real conversation or a clear boundary. Ren suggests the lightest step that could work and drafts the message in your words. Nothing sends unless you send it, and nobody else sees the suggestions, not your boss or your company. The idea is that most managers don't skip these conversations because they don't care. They skip them because they never noticed the moment, or didn't know how to say it. A few things I keep going back and forth on: Would you want an agent pointing out conversations you should have, or would that feel like being managed by a bot? Is "only you see the suggestions" enough to make it not feel like surveillance? Where's the line between helpful nudge and annoying notification?