Sometimes, you want to give your cleaner specific instructions, or maybe even a list of them, without coming across as too demanding or annoying. If you know what I'm talking about, then rest assured - there is absolutely no reason to feel awkward about making sure the service meets your needs. In fact, real professionals will welcome your instructions and often, they will be the ones asking you questions in order to better serve you.
For recurring Standard Cleaning service, we have found that clients like to provide their cleaning professional with a list of instructions. After a cleaning or two, the pro usually won't need the list anymore but they can snap a photo of it just in case. If you want to add any instructions to the list, always be open and communicative with your professional as they want you to be satisfied with their service. Cleaning professionals care deeply about client satisfaction, because they know that their current and future work opportunities depend on it.
While it is perfectly okay to tell your cleaner what you want at any time, I would advise against shadowing them along every step of the cleaning process. In order for your professional to give you their best effort, you want them to feel at ease; shadowing them could signal that you don't trust them or you doubt their expertise. Of course, you would not hire a cleaner if either of those two assumptions were true, but that is how the cleaning professional might perceive the situation.
In a Deep Cleaning, your requests might be more exhaustive since it is a more intensive cleaning. I would suggest writing a clear list of your instructions and handing that to your cleaning pro(s). You should always check to see what your cleaning pro has said about their Deep Cleaning offering in order to ensure it lines up with your needs. If it does not, then you should let your pro know in order to avoid any misunderstanding,
So, the short answer is that you should never feel awkward about telling your cleaning professional what you want done, but you should let them do what they do best once they have heard your requests.