Hah, funny to see Peter's take on this. I always ask these three basic questions:
- What general approach will you take to this project?
- When do you expect to have it completed?
- Is there anything that I can clarify?
The basic reason for #1 is that it gives me a quick overview of how well several contractors understand my needs (about 70% of the time there's a fundamental misunderstanding which avoids a lot of hassle later on). Here's what I look for:
"From what I understand of the requirements, you're looking for a application that returns the user's proximity to a database of craft breweries that accept MasterCard based on your API data. This sounds pretty straightforward. First, I'll evaluate the API protocol to connect it with data storage in your application. Then, I'll use geolocation data from the phone to create an array of distance within 100 kilometers and display up to 20 of the lowest available entries. From there, I'll post the searches to the search history. Let me know if that sounds good to you, or if you have other ideas for how we could make this happen. I'm open to different approaches. I would advise you to consider one small suggestion though - detecting whether GPS is turned on at the point of search and prompting the user to turn it on."
That demonstrates both know-how and flexibility.