As an intel guy, this kind of thing is near and dear to my heart.
Red-teaming can be useful, but it's best when composed of outsiders who are less likely to share organizational mindsets. Structured analytical techniques are another option (ACH being the most famous) that can help people break out of their mindset and consider alternatives. The intel community uses a variety of methods, but of course it can't do that for everything given time and resource constraints. Training and experience count for a lot IMO as does a decent level of introspection.
It's an enduring problem to be sure and there are no easy or certain solutions.
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