It depends; there are no easy answers to this. There are a number of initiatives that a company should undertake, including
disaster recovery, business continuity planning, Sarbanes-Oxley (SOX)
compliance and data security -- these are all exercises that force you to examine your data. The retention of data is based on the value of the data to the company and related legal implications or compliance requirements. Many companies are spending a lot of money on these exercises, and it would be wise to add the consideration of retention to any data management initiative.
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Of course, there are practical limits on what you can do. A file server or email server can be quite challenging when we have terabytes of unstructured data, so it may be impossible to evaluate every single file. Many companies adopt a global approach and archive large quantities of data. But, even when a company has trouble looking at older data, strong policies are needed for record creation going forward. You may not be able to fix what happened in the past, but it's still important to make corrections so that you don't keep repeating the same mistakes. Don't push off the problem.
Listen to the Unstructured data FAQ audiocast.
Go to the beginning of the Unstructured Data FAQ Guide.