Help a beginner out
There will be users with varying levels of expertise using your software, raging from beginners to experts. Most beginners will become intermediate users and few will become experts. Focus most of your time, resources and interaction on intermediates.
Beginners will quickly become intermediates, otherwise they will find another activity or product that allows let them do so. To help new users to quickly migrate to the next level provide some instructions, imagine them as being really smart but super busy. The initial help must go away once it is no longer needed. Nobody keeps the training wheels on the bike once they know how to ride it.
Sales, marketing and management will demo the product to customers, partners, who are not familiar with the product. This leads them to have a skew view of the user community leading to request such things as wizards or things like Clippy.
About Expert Users
Experts are few in numbers and high on impact compared to the other groups. They will ask for powerful features, can handle added complexity and want shortcuts to everything. Keep them happy but focus on the next group.
Perpetual intermediates need access to tools, they do not need scope and purpose. Tooltips state function making them perfect for this group. This is the group actually reads documentation. Intermediate users will stick to the same set of tools and functionality and will rarely venture out to try obscure features. Make this set of tools easy to find and remember. Given that they make the bulk of your user community, take care of them.
This post was inspired by David Alfonso.