Pre-Mortem
Imagine your plan has already failed. What went wrong?
A pre-mortem is an exercise you do before committing to a plan. You imagine it has already failed and work out why, while there is still time to change it.
“What could go wrong?” usually gets vague answers, because nobody wants to doubt a plan they like. “It’s a year from now and this didn’t work out. What happened?” makes the reasons much easier to name.
Pick the most likely reasons and change the plan for those. It’s the Inversion Principle applied to a single plan.