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In general, for "skill challenges" players should be telling the GM whatever they intend to do, and then the GM can advise what is the proper skill to do so. There will be other more experienced players that will tell you what skill they are trying to use though.
For example, in said alcoholic's woman's case, a player can say "is there anything wrong with her? Does she look in good health?" and then you can say "Well, a heal check may reveal more. Give me a skill check".
The second type of player will say "So, can I use heal to see if anything is wrong with her?" and so on.
One final way to do it is you think the skill check represents a character noticing something out of the ordinary spontaneously, you can roll their heal check secretly, and if anyone at the table makes the check, you add to the woman's description. "She looks like an old lady. Greg and Xanathul, you two only notice some bags under her eyes and a bit of an odor."
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Another thing you can do, assuming you have checked out the players' character sheets before the game (and made notes) would be to call for a D20 roll. Then, you can add the character's bonus to the roll, without telling the player what he was rolling for.
I actually use this technique quite a bit. I'll call out for a D20 roll, for example, for a Perception check to notice certain things, or perhaps a Knowledge check. I don't tell the players what they are rolling for (and sometimes, I've called for the roll before they are actually in the room they would be seeing something, sometimes it is just a roll for no real reason!)
On the suggestion of a friend, I downloaded the GameMechanics Initiative cards. I'll have the players fill these out, and additionally list all of their knowledge skills, with bonuses. I also usually do a quick once over on their character sheets, just so that I know what to expect, but also to pull things like the Heal skill bonus, if I know it will come into play.
Putting all this together has helped me out quite a bit. Since I have stopped using a screen for PFS play, this lets me be a little sneaky! You can even use a player's roll for the stealthing rogues that another players is rolling to perceive!
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Sometimes these are passive checks that don't require a player to ask about it at all.
If someone would noticably appear as if "something is off" because of their health when the character looks at them, a heal check is immediately called for regardless of whether the player asks about anything. The character can just "tell" (or not, on a bad roll).
Perception and maybe Knowledge are the most common passive checks, but it works here with Heal as well.
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That might be a symptom of not wanting to release the wrong information prematurely, but it's something GMs should teach themselves to avoid.
There's an enormous amount of information in the scenarios that the scenario doesn't tell the GM to tell the players ever, and you need to hand out as much of it to them whenever you can to improve the quality of the game.
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Thanks for the advice guys, in all fairness it would be a little out there to expect them to roll some of this stuff out of the blue. What I was worried about was that they'd feel that I'm pushing them rather than letting them take the lead and in retrospect I doubt they'd actually feel this way given the unlikely nature of them guessing what to roll and when.
Do it and get a feel for if they seem like they don't enjoy being asked; they may not. Outright ask them after the game if you want to get some feedback about another way you could have done the same thing.
Ask them if they'd prefer the way you did it earlier, or this new way which you had considered doing it?