1. Ask questions. Always go to your client or stakeholders and ask relevant questions about the problems, issues, concerns, dislikes, and interests. You have to invest serious time knowing your users. This goes from asking how their day is to asking how filing for bankruptcy under Chapter 7 usually works.
2. Research. Even if your questions get answered by the prospective users of a specific technology project, you will have to do some additional research on your own. You have to understand the problem of your users. This exercise will improve your empathy towards the user, making it easier to create a better solution.
3. Constant communication. For any software development or document automation project, you will need to keep constant contact with the prospective users. Try to get feedback early on to make the necessary adjustments. There is nothing worst for a client than receiving a project that needs profound changes.
4. Avoid "legal" prose. As an attorney, I know we tend to use complex words or phrases in Latin. However, most of the time, the prospective user of the technology is not necessarily an attorney. Trying to make content understandable is critical for any project. It is not always fun to change the "traditional" legal language. However, we have to put our effort into it. That's why we have our designers, attorneys, and human-centered designers work together.
5. Test, test, and test. Always test any technology. This goes from focusing on a simple "typo" to something more complex of changing the user's workflow. For example, for a document automation project, testing could throw results that signal you need to improve how you frame questions or design the output documents.