Start by thinking in context. What I mean is that everything exists within a context. We operate this way intuitively in everyday life. For instance, when we typical Americans read the sports page of a newspaper or blog, we automatically know and expect certain figures of speech. It enhances our comprehension and enjoyment. But, when we read about other current events, we expect a different type of reporting. In other words, our expectations are tempered by our knowledge of what we are reading.
The same goes for design. But, it may not be as intuitive. We don't aways have the luxury to assume what the client and audience understands and expects — unless we are in-house employees. So, the best way to get the context is to ask the right questions.
The right questions help the client express what they assume may be the case. The right questions help us designers understand those assumptions, and enable us to even challenge them a bit. We do this to get to the nuggets of contextual thinking. Once we get into the world in which this design will exist, we can begin to make decisions that can make a nice looking design into an extremely effective design.
Photo courtesy mconnors of morgueFile.com