Driving Complex Decisions
garrettdbates.com
garrettdbates.com
It really helps to front-load the controversial questions. That way, if the team/organization/leadership gets mired down in that discussion, it's (1) determining constraints to reduce your search space early, and (2) it isn't setting false expectations about how long the decision will take because the design work hasn't even started!
One thing I miss about working in a startup is that you didn't have that many stakeholders to go through, so there wasn't nearly as much communication/stakeholder overhead to work through.