Etiquette
Naming the thing
If there is one thing you want spoken to, name it plainly in the brief and say how you want it handled; hinting at it gets a clip that dances around it.
Guides on Etiquette: Being declined, Nothing exotic, Opening well
To get a judge to address a worry, name it once, plainly, and say how you want it handled - honestly, reassuringly, or with a brief acknowledgement. A judge can only respond to what is on the page, and a worry left implicit usually stays implicit in the clip that comes back.
Say the thing, once, plainly
Most requests that mention a worry do it sideways. "Just curious what you think, no pressure" is doing a lot of hedging around a sentence that actually means "I am anxious about one specific thing and want to hear about it." The hedging feels more revealing than it is: Gilovich, Savitsky and Medvec (1998) named this the illusion of transparency, the tendency to overestimate how far others can discern our internal states.
There is no version of this that requires elaborate framing. "I'd like you to speak directly to [the specific worry]" is a complete instruction, and it is the sentence that separates a clip that circles a topic from one that actually lands on it. Giving a judge one concrete specific to respond to is the general version of this advice; naming a worry is the highest-value instance of it, because it is the one thing you are least likely to say out loud without a prompt to write it down.
Judges are not mind readers, and being coy does not protect you from an answer you might not like - it just makes the answer less likely to arrive at all. A clip that was asked to dance around a subject will dance around it competently, which from the buyer's side looks exactly like a clip that missed the point. It is a different failure mode from a low automated score with no context attached, which at least states plainly what it measured; a dodged worry from a person states nothing at all.
Say how you want it handled, not just what
Naming the worry gets you a response. Saying how you want it handled gets you the right one. "Address it honestly" and "reassure me on it" and "just acknowledge it briefly and move on" are three different clips from the same starting material, and a judge asked to guess which one you meant will pick the safest option, which is often the least useful one.
This is the same logic behind why a register needs stating in one line rather than left to be inferred: the judge is good at delivering a register on request, not at guessing which one a hesitant brief was circling.
Where the line sits
There is a version of "worry" this does not cover. If what concerns you is really a health question - pain, function, a change you have noticed - that is outside what any judge can honestly answer, and a good one will say so and stop rather than perform an opinion they are not qualified to give. Judges avoid medical language for exactly this reason, and a worry of that shape belongs with a doctor, not a brief. The same applies when a worry about appearance has become consuming: the NHS describes body dysmorphic disorder as a condition where a person "spends a lot of time worrying about flaws in their appearance", flaws often unnoticeable to others, and says to see a GP if you think you might have it.
The same boundary sits underneath the difference between what a person and an automated model are each built to assess: neither is qualified to answer a medical question, and only one of them will tell you so unprompted. What a judge can do is respond to how something reads, feels, or presents, in the register you asked for, addressed to the worry you actually named rather than the one you danced around.
Making it easy to name
If you find the direct version hard to write, it helps to separate the worry from the request for a moment: what, specifically, do you want to hear addressed, and in what tone. Write those two things down first, then build the rest of the brief around them. It is a smaller ask than it feels like while you are avoiding it, and it is exactly the kind of specific that turns a generic request into a clip that is about you rather than about nobody in particular.
None of this needs a number attached to it either. If a measurement is somewhere underneath the worry, that is a separate and more precise question with its own method, and answering it first often removes the worry from the brief entirely rather than leaving it for the judge to guess at. Rate Cock's comparison of a person's read against an automated score is worth a look if you are still deciding which kind of answer actually addresses what is bothering you, because the two are built to answer different shapes of question.