When selling big-ticket items and sizable contracts, there will come a time in the process that you must speak with your contact's boss. It's simple math: Your contact, no matter how much he reassures you, is not really the contract-signing decision maker. This means that you have to speak to the real decision maker, or risk your contact presenting your product/service/solution. As that person is not an expert in your company or solution, nor is he or she a professional sales person, perhaps you should try to keep your role as sales person and the contact should take the role as matchmaker.
My best recommendation is to avoid any potential awkward moment by thinking in terms of a road map. The one I use is a simple one-page document, which lays out for you and the contact the natural steps that are followed, based upon your experience, in the selling/buying process.
This should be relatively simple. It can be done in a single page on which you have laid out the steps in your process and then what happens at each step. The "what happens" involves exchanging information, meeting people and deciding whether to continue.
What is important to recognize is that this road map gives you a shared understanding of the course of events in the buying process. It also allows you to confirm in the first meeting that your contact is willing to follow this process. Here's how you use it:
Step 1 -- Present the map
Once you have secured interest from your contact, present the map. Remember, this is a simple, one page document that just lays out the normal course of events. You don't need to go through it line by line, just the general approach.
Step 2 -- At each interaction with your contact, refer to the map.
The map is what keeps you aligned with your contact and forecasts the next step. By referring to the document at each step, you are creating a path that everyone understands. If there is a delay at a step, your reference to the map becomes about getting the necessary information or people connection to complete the step in order to take the next step.
Step 3 -- Always declare the prospect's version of "why."
Sales people who use this tool successfully don't waste their time explaining to the buyer why our company wants to follow this map. Instead, the sales person can explain specifically why the prospects that follow this process get more complete answers, detailed recommendations and more value from the process.
My personal experience is that this tool works best when the focus is on providing clarity in the decision-making process. Telling the prospect that by following the process you are able to bring more information, people and clarity to the proposal is usually motivating enough, (if they are seriously interested), to get your contact to provide the right people and information -- including his or her boss.