For many people, this is not something that comes naturally (and as a consequence frequently means we are blinded by our prior perceptions, beliefs and experiences).
How can we make sure that we avoid this trap? How can we make sure that we do not subconsciously avoid the hard questions by replacing them by easier questions?
On the other hand, if good forecasters take take the "dragonfly eye" approach, and constantly say "On the other hand..." how do they actually weigh these different angles or finally come to a conclusion?