Start with workflows, not tools
List important tasks: issuing an invoice, finding a record, tracking an order. Identify the people, applications and data required for each one. A usability issue may point to an information flow problem rather than a missing piece of software.
Make dependencies visible
Map exchanges between tools. Record the source of truth for each data type, duplicate entry and manual operations. Include access, backup and recovery constraints. A simple map that users can verify is more useful than a complex diagram nobody maintains.
Turn findings into decisions
Assess issues by business impact, frequency and correction cost. Separate quick improvements from structural change. Assign an owner, success criterion and review point to each recommendation. A useful assessment produces a decision sequence, not a shopping list.