Taking on a software project can be a difficult task. We have recently published an article on this topic, to help customers know what they should be asking, in order to intelligently compare different software developer offers on the table. In a nutshell, we would say that you should approach this as any piece of work that you have done, for any project you may have undertaken. Ask who will be doing what. Find out what their processes are, how they define deliverables, and how they monitor performance against Key Performance Indicators). But most importantly, focus on what you want. Explain what it is, and ask them what it is they need to know. Confidence is great, but find the company that will ask you the most questions. The more they ask you, the more they are showing that they know what the project pitfalls are, and they are indicating they are already working to avoid those. And remember: It is completely OK for you not to know the ins and outs of IT. It is your software provider's job to adjust to you, and explain what goes where and why.