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In design thinking the first stage often revolves around gaining an empathic understanding of the problem we're trying to solve for our users. With something like a physical product or an app you can physically observe the user with it in their natural environments or you can set up a user test environment and observe them. But with something like an Ecommerce website I am running into a bit of a mental wall regarding how to begin empathizing with my customers pain points and needs.

Initially upon thinking about it I don't feel like going to a cubical with my customer and watching them complete a purchase will be much more valuable quantitatively than watching the recorded funnels in my testing software. Qualitatively it does provide the benefit of getting to define the why, but I have a hard time defining benefits outside of that. Could someone enlighten me on additional benefits or methods at this stage?

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This is a famous illustration by Designit that I really love. The main benefit of qualitative methods is not just the why, it's the whole discovery phase. After running some depth interviews with the shoppers you are likely to come away with lots of insights. These insights then give you specific hypotheses to test using your quantitative methods, instead of staring blankly at the stats and trying to find meaning in the data, or wondering how to interpret unusual trends. You might find that their decision process is different from what you thought, that they perceive the pages differently, or that they behave in a way you didn't expect. Much of this might also show in the numbers once you know you need to look for it, but without this context it's much more difficult to spot.

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It is a good idea, to start to categorize your main types of customers. Try to make some personas. Use demographics, culture, education, technology knowldege, etc.

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