When something breaks, many teams know something is wrong, but don’t know what to ask next. As systems grow more complex and AI accelerates change, this problem is only getting harder. This roundtable explores how teams can develop better instincts for questioning systems during incidents, and how data and AI can help. Christine will facilitate a discussion for technical teams to compare notes - individuals with experience with, or strong feelings about, AI SREs especially welcome. The conversation will explore shared challenges, the role of observability in providing essential context, and the questions that consistently help teams reach clarity and resolution faster.