Getting a special hotel room can make or break a trip, so here are five questions you should ask to be sure you get the best room possible — or maybe even an upgrade.

The key is to get the front desk clerk involved in choosing the best room for you and not letting the hotel booking system choose it for you. You do that by making specific requests at the check in counter such as:

Does this room have good wi-fi reception?
Thankfully more and more hotels are offering in-room wi-fi for free. But in a world where you frequently “get what you pay for”, a free connection could also mean weak or spotty reception. Since wi-fi is broadcast via wireless routers located in hotel corridors, rooms closest to the routers get the best reception. Front desk staffers usually know which rooms get the most complaints about poor wi-fi reception, so they’ll actively search for a room they know gets a strong signal.

Can I get a newly renovated room or one with a great view, a corner room, or a quiet room?
Simply asking for any of the above gets the hotel clerk involved in choosing your room. Since these features don’t usually affect the room rate, by asking, you are likely to get the best room for the price.

Is there an adjoining room?
Noisy neighbours can distract you if you’re working, taking business calls or meeting with clients in your room. This is also an important request if you are a light sleeper. If peace and quiet is important to you, ask the clerk for a non-adjoining room (one without interior doors leading to an adjacent room).

Does this room have a large, well-lit desk and chair?
Some hotels have desks in every room that are suitable for working. Some don’t. By letting the clerk know that you plan to work in your room, you are more likely to get a larger or better room set aside for business travellers — maybe even one on a special club or concierge level reserved for elite level members of hotel loyalty programmes or those on specially negotiated corporate rates.

How much could I pay for an upgrade to a bigger/better room or suite?
Most hotel desk clerks are weary of guests asking for something for nothing. But by offering to pay slightly more than your reserved rate, you could end up with a much better room. The amount will vary based on how busy the hotel is, and how many higher tier rooms are available. You’ll never know how much it will cost to get an upgrade unless you ask… so ask! You might be surprised.

Have you ever talked your way into an upgrade? How did it go for you? Please leave your advice on our Facebook page.

Chris McGinnis is the business travel columnist for BBC Travel