Problem

Focus on the problem you are trying to solve, not solutions. Ask questions until you determine the root problem. Also, what business goals are you trying to achieve?

Stakeholders

Whose opinion will influence the direction of the project?

Working Team

Who are the people working directly with you on this project?

Timeframe

When is this needed / desired? Any constraints or dependencies?

End Users

Who are the people that actually will use the solution? Outline typical use cases and map out different user roles.

Risks

Assume that one year from now, this project has failed spectacularly. Write a summary explaining the reasons why the project was unsuccessful.

Research

Ask for analytics that would inform design decisions based on context.

What documentation sources exist?

Screenshots / existing system access