First, imagine this scenario. You and your candidate go out to Starbucks for coffee to discuss your project. Only before doing so, you grab someone from the line just after they get their coffee. Yes, I mean someone "off the street" who you have never met and has never met you. You ask them to join you and your candidate. The three of you sit down and you sip your coffee and introduce yourselves to each other. Let's say that random gal from the line is Mary and your candidate is Jim.
You look at your candidate (Jim) and say: "Jim, please explain to Mary what we do in our business."
That's it. At that point you clam up. You resist the temptation to jump in and clarify things. You do not necessarily expect Jim to have all the nuances of your business down pat. But before you commit to working with him, you do need to know that he knows enough about what you do to recognize how information technology can bring the most value to your company.
Now having thought through how that conversation would go, and what Jim would have to say that you would be satisfied with, start to put together a package of material. Remember, this material is aimed at a tech person to make sure they understand enough about your business to be able to recognize what from their range of expertise would bring value. Once you have that material, you are now ready to set that appointment for Starbucks. Make sure you email it to them along with the calendar invite. Also make sure they know they are expected to review and discuss it at your meeting.
When you do get together you're probably not going to grab that random gal from the line (although it would be really interesting to see how that would play out!). Either way, your first question should be something like this: "What do you think about my business?"
This is purposefully a very vague and open-ended question. Do not ask him or her: "Do you understand my business?" That is a "yes/no" question. Start vague and open ended. Here is what you want and do not want to hear.
You do not want to hear about their mastery of technology right out of the gate. You do not want to hear about their last project or that really cool feature they came up with. The really talented tech people know this (or should know it). You want to hear them grasping for a way to articulate what you do. If they seem a little uncomfortable, that is actually a very good sign. They are uncomfortable because their work requires a deep level of mastery of technology. It also requires a deep level of mastery of your business. If they are grasping - even if awkwardly - for a way to explain your business it means they: 1) already know their technology; and 2) realize they need to know your business. That is the kind of person you want to work with.
The person you absolutely want to avoid is the super-senior, smartest-guy-in-the-room tech guru who is all wrapped in with impressing his peers with how cutting edge he is. These pocket-protector types are more into getting the propeller on their beanie spinning faster than the geek next to them. Your business will be forgotten in the breeze all those propeller beanies generate.
Your small business really requires that the money you put into IT gets you the right solution the first time. A careful evaluation of the tech person/people you work with will go a long way.