Granted I am a designer... usually I asked fellow designers about problems I am dealing with right now.

• How does your design process fit into the agile process at the start of a project?
• How do you implement user research/testing into your design process, If you do at all?
• What's your success or failures dealing with living style guides?
• What challenges do you face right now in your projects?
• How do you deal with the internal politics of the client when designing?
• What does your design/dev handoffs look like, what is the biggest issue with it?
• How do you currently document your discovery/research?
• How do you balance clients' wants vs devs capabilities when designing?
• How do you write your design-related JIRA tickets?
• Do you do visual QA on your projects after development?