An acquaintance is someone you know, but you don’t hang out with them socially, and if you ever did, it would only be as part of a large group of people.
Most of the time you’re with friends, things are fine—the awkward parts are the exception to the rule.
But that assumes that you can only be normal around someone you know well, which is not true.
The worst is when you meet someone for the first time and they try to squeeze your hand off while giving you this fake, plastered smile and it becomes this unspoken competition.
I’ve found that what works best for me is to simply not mind that things are awkward. If you post a comment below with a great question to ask, I will update the text list and PDF by removing my least-useful or most-lame question and make room for your awesome question. Oh man, I don?t see my self approaching to my could be client making him go through a round of 72 questions. That said, I have a questionnaire that I use in the SECOND step, where I’m actually collecting real data for a real job or at least real website RFP or SOW. I probably won’t use all of the questions from this list but it’s a great reference to start, big thanks! Hi Ben: There is a time for organized socks approach and there is a time for the random-socks-generator approach! Some good points here to jog your memory, but I need to agree with the people that say this list is too long… I would group them up and personally (despite the your resoning for having them in a random order) would probably put them into a logical order. Smaller clients on the other hand may be overwhelmed by the amount of questions and their possible implications.
Personally, I prefer not asking too many questions but rather listening to what the client has to say about his business in his own words. More often than not, these questions lead to interesting discussions and insights for the customer, especially because I’m dealing with a lot of start-ups. To increase your chances of having her say yes when you ask her out, you need to exhibit the characteristics that she wants.

When finding a girl that you feel like you want to ask out, watch out for the signs on how she reacts towards you.
It could be someone you went to high school with but were never friends with, someone who lived down the hall from you in college for a year, a friend of someone you know, or someone you work with or used to work with but you don’t know very well. Authentic is the enemy of awkwardness, and with acquaintances, the only two authentic options are #3 or, if you really do want to advance the relationship into friendship territory, #2. I started using a new barber last year, and I was pleasantly surprised when instead of making small talk or asking me questions about my life, he just started talking to me like I was his friend or involving me in his conversations with the other barber. Both people are typically so petrified by the awkward-potential that they end up acting insane. Even though unlike the former two categories, nothing real is at stake (other than your dignity), stranger interactions can provide some of the most awkward moments in life. The Inexplicable Sneeze Standoff is possibly the single most awkward part of my life, especially since I’m a Multiple Sneezer.
You should print this out and keep it handy during new client calls so that instead of doodling, you can oodle this list and free-associate questions in a purely right-brain manner. Categorized the questions, so they know what are you looking for, maybe they want to answer first the categories they know better and stay at the end with the more technical categories. Reduce the number of questions, you can do combos or include more stuff in just one question. But glancing at it during a call or composing an email might jog the ol’ noggin to ask this or that question.
I’d love to see this broken down into stuff you can realistically ask the client when you first make contact, however. You don't need to get decked out in a suit and tie to ask a girl out, but make sure your clothes are clean and well-fit, that you've brushed your teeth and are wearing deodorant. If you appear attractive to her before you ask her out, there will be a lot less pressure on you when you do work up the courage. Your right brain will dart around this list subconsciously and hopefully make connections between the random questions listed and what your client is actually saying on the phone.

Client was looking at those questions and by-the-look-on-her-face you could see that she was so boring. Will be using this for the next potential client meeting as reference, there were defiantly a few in here i didn’t think to ask up front. Of course, it depends on what kinds of clients you’re working for, but if they have their own marketing department that can answer all the questions up there, they will usually be briefing you in the way they are most comfortable with. Pay attention to what she is saying so that when she asks you something or stops talking, you can continue the conversation intelligently. Simply say "Hi" or "Hey." As the conversation moves forward you can give her a complement or ask her a question. I want to help you figure out what questions to ask, and not simply tell you questions I would ask.
But in listening, I sometimes (well, many times) forget to ask basic questions because I get so lost in this or that of what the client is talking about. This list of 72 questions is a list of questions you might ask 5 or 6 of in a given conversation, only to go back later and ask a few more later.
For instance, you see the client has an ugly logo – might be time to ask for a redesign since you are redoing the site and the logo is hopeless.
So I present below the best 72 questions to ask prospective web design clients, along with a PDF chart. So the best I can do is ask questions, and hope to cover as many show stoppers up front, and then come back in subsequent conversations to fill in the blank. This list of 72 questions is simply meant to stimulate that right-brain thinking to ask those questions and to ready your mind for that first call with a new client.

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