The longer I work in tech consulting, the more people start to rely on my choices in tough situations. And, the longer I do that, the more I tend to gravitate to a pair of questions: "why" and "why don't you not". Let me share a short anecdote about the second one. I recently worked in a team extending a tool for a customer; this tool abstracts the configuration of a complicated device to a more understandable level. For some expert-level situations, you sometimes need information (indices, etc) that is generated later in the process. A colleague asked my help with this feature; it seemed to required us to entangle UI code with configuration logic. Not being happy about this, I started wondering "why don't we not do this"?" Is there a way we can change the problem? We chose to remove the information from the UI, but make it more prominent in the generated configuration. Given the audience of this feature (expert users), there is no problem in making the user dig around in the generated configuration.
So, we all heard about the five whys; now add why don't you not to that list. Ask yourself, "what's the worst thing that could happen if we don't" and "how can we make this problem go away without solving it?"