Shaan Puri describes a tactic for finding the biggest risk in any plan: ask your team to name the one thing most likely to make it fail. This surfaces the core assumption hiding under initial enthusiasm, so you can build defenses against it early.
The Misery Loves Company tactic. At the beginning of any plan, everything seems achievable and everyone's optimistic. But it's one thing to ask somebody, what are the key risks in this? What is the most likely reason we would give that things went south? And this is a way to identify the core risk, the chief assumption, the riskiest proposition in your plan. What do you think is the number one reason it might go wrong? And then because you're identifying that upfront, you can now like work against that.
