A word to describe an assistant who knows when to ask me for help on cases he is not familiar with?

I have an assistant who helps me deal with some daily works.

Currently, he deals with everything on his own. Apparently, there are cases he is not familiar with, but he never reports them to me. So I have to check all his results, which costs me a lot of time.

I hope that for cases he is familiar with, he could do it himself; but for the cases he is unfamiliar with, he should ask me for help, or mark those cases for me. So that I only need to check the cases he asked for help.

Finally, I want to say, this is actually a word choice problem in academic writing. We are designing a virtual assistant, and want a word to distinguish it from previous know-all assistants.

So what is the best word for the following blanks?

• You should be __ on this work.
• I want a __ assistant for this work.
• We design a virtual assistant that is __ comparing with existing ones.

I characterise the assistant you need as communicative. Being communicative is one of the qualities we most value in other people and we all agree that many mess ups occur because of lack of communication and one instance of that is what you are describing.

OxfordL defines at as meaning:

willing, eager, or able to talk or impart information.

Yourdictionary adds:

Giving information readily; forthcoming; Inclined to communicate readily; talkative.

Here is what a site writes about communication skills between boss and assistant:

If there is a breakdown in communication between you and your assistant, or if effective communication skills and practices were never established in the first place, everything can all fall apart. You may find yourself completing tasks you would normally delegate because you’re worried they won’t be done correctly...

And business2community asserts that:

Good communication is essential in any relationship but when your team is virtual it is crucial.