We've all heard that a customer who wants a 1/4" drill really wants a 1/4" hole. I'll take that further, and ask what he wants a hole for. Maybe, he wants to join two pieces of wood together in his kitchen. So I'd ask about what he's doing in the kitchen. He might tell me that he's installing this kitchen cabinet. You know where this is going. He starts asking for a cheap 1/4" drill and gets sold a kitchen remodelling job that he is happy to give a contractor because he really would rather be doing something else.
I have time and again gone in to a prospect who already had several quotes in hand, and walked away with work worth many times more than was originally quoted. However, I go in with the attitude that I have nothing to sell this customer. I find out what their concerns are, what they are looking for, what they have considered, and try to understand what their motivations are. If, for example, they just want a cheap roof so they can sell the place, I thank them for their time, and move on. They do not need the service that I can provide, so I don't try to change them.
On the other hand, we may find the customer is looking to change their roof after only six years. So, find out why they are not happy, and what their expectations are. At the same time, I also try to establish what the customer would want, in an ideal world. More often than not, I can give them some of that ideal world now. Of course, you have to be patient, and not "put on the rush". I have often taken three or four visits to a prospect to build up the trust and the rapport, and again to really understand what they want.
Now, let's sat that you go to an appointment, and notice that they have nice landscaping, the cars in the driveway are new and shiny, the customers themselves are well-dressed and coiffed. These people are just about screaming at you that appearance IS VERY IMPORTANT to them. So give them the premium products they want. Chances are that if they can afford to do the landscaping, they can afford to pay the premium for an attractive roof.
The real issue is not "Upselling", but pitching the right product for that customer. Not every prospect needs an upscale product, which by definition is a niche market. However, every product has a niche. You just have to recognize which niche your prospect falls into and propose the correct product for that niche. If you want to sell more "upscale" product, you have to find more "upscale" customers. To attract the "upscale" customer, you need to have marketing that catches their attention. Once you have their attention, they want to buy from an equal, so you need to present a personal "upscale" image.
I give courses to salesmen who work for roofing companies, and the hardest thing for salesmen to do is to un-learn the old sales techniques which are now stale and unproductive. The current market is not about selling product, but satisfying needs. Price starts as the number one item, and ends up being #4 or even #6, IF you are able to tap into the customer's real motivations. There is a very good market for "upscale" products, but you need to understand why people are prepared to pay for these, and then find more of these people!