Make it aweful first
I often find solutions in the opposite. What would make this experience awful? Once you know that, you know what to focus on.
One technique: imagine you’re in the future and the project has failed. Ask why. Suddenly it’s easy to see what might cause failure. Now you can solve for those.
In workshops I ask: what would be the worst way to solve this? It’s a structured exercise. Surfaces what to avoid.
Most people aren’t used to thinking in opposites. Some wear the “Devil’s Advocate” hat, but that’s unstructured. They can say whatever they want.
This is guided Devil’s Advocate. That’s why it works.