The point about how the expected decision timeline is often a small part of the total decision timeline really resonates with me. Often (in my big tech experience) we say we can get a design done in a week, and then we spend three more weeks running the design up and down the leadership chain and through stakeholders elsewhere in the company, at which point you're three weeks past the date everyone expected and you finally have a plan.

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.

I like the saying - weeks of coding can save us hours of planning.

Not bad ... now i did reflexively cough at the implied need to get something, anything outside there - sounds political for show - but ok i get it. Thanks for the post!