I cannot answer this question because I miss the context and I have no clue what kind of product we are talking about here.
Generally speaking I would learn about the product, think about were it might fail, think of ways to find those problems and think of ways to explore the product to find unknown risks. This is the same approach as I described in question 1:
- Missions for your testing
- Product analysis
- Oracles & information sources
- Quality characteristics
- Context: project environment
- Test strategies