From your experience, what are a few simple, high-level questions you ask to see the feasibility of a new feature request before moving into more technical aspects?

Generally the question that I like to ask is: “How will the proposed solution make things faster, better, more cost effective?”

What and how big is the intended audience?
What problem is it solving for them?
How many would use this solution for free?
How many would pay for it?

What does it impact - additional growth, user acquisition, user retention/adoption, reduce user dissent, revenue, cost reduction
Is it a common scenarios or a corner case
If corner case, what is the damage with and without the feature
Does this align to roadmap and strategy or conflict with existing or future builds
Is the competitor building it and what uniqueness does it bring to product