A suggestion — knowing it may cost too much or take significant coding time.
I use Leo through the URL bar, center search box, “Ask,” and the Leo Button (which is still in the regular window).
From personal experience, I suggest adding a small guide — either before or after Leo’s answer — with text like:
“Ask more, perhaps in a casual manner, like talking to a friend, if more details are desired.”
I offer this because when I first started using AI, I had no idea this was possible. It opened a whole new world of searching. I realized I could ask question after question in a natural, conversational way.
Leo has spent hours helping me with terminal commands in copy/paste form — saving me days. I can’t express how much this has helped. There’s no comparison to a single, isolated question. The casual manner unlocked AI at another level — perfect for the curious, as one question can lead to another, and another.
So, a prompt like: “Ask your question in a casual, conversational way, like AI is your friend, if you need more help, detail, or just want to know more.”
Or a subtle line like:
“Ask more — talk to me like a friend”
— placed above or below the response — could guide users without cluttering the interface. 
My point? Highlight casual , more , help , and like a friend so users can’t miss it.