At first your history taking skills will probably be rubbish, don't worry. I don't know if this is the same as what you're trying to express, but the one thing I found relatively mystifying when I first started the clinical years was exactly what questions I should be asking. Like it's all well and good to ask if somebody has chest pain, but how to clarify the nature of that chest pain (like what symptoms would point in one direction or another in terms of the aetiology) seemed like something I didn't feel I'd ever been taught either. Understanding the pathology and physiology of what is going on doesn't always equate to knowing what symptom to ask for or rule out.
You'll learn a lot of this stuff osmotically as you go through your clinical years and have to practice taking histories and getting feedback, and you'll also pick it up just by watching others on the wards or in clinics. Apart from that one other thing that can be helpful is to buy a book of OSCE scenarios with histories in, and if you practice them with friends you'll find you get better at asking specific questions, because the goal of those stations is that you should have extracted from the 'patient' everything in the history and used it to form an initial diagnosis. You should also get into your head the structure (ie PC, HPC, PMHx, PSHx, DHx, FHx, SHx, Examination) which it's useful to follow from the get go. It never lets you down!
The OHCM/S is actually a great resource when it comes to important questions to ask in histories because it specifically tells you things that would make you think of one diagnosis over another. It helps to start from that stand point and try to approach every history from the point of view of 'I am trying to find out what the diagnosis is and rule out other important alternative diagnoses' rather than the panic at the beginning of clinics which is just 'I am asking this person these questions because I must and I don't really know what I'm asking about'.