I look at
- Manual and repetitive processes
- Administrative workload
- Existing software and systems
- Spreadsheets, documents and email-based workflows
- Data and information flows
- Integration opportunities
- Bottlenecks and duplication
- Reporting processes
- Customer and internal communication
- AI opportunities
- Automation opportunities
- Technical feasibility
- Existing SaaS options
- Open-source solutions
- Whether custom development is justified
- Potential system migrations or replacements