The mandate from above is clear, just get it done! Avoid everything that's in the way: all advice, all expertise, all discovery efforts that detract from hitting the Date™!
What these organizations don't realize is that all software change can be modeled as three components: Value, Filler and Chaos. Chaos destroys Value and Filler is just functionality that nobody wants. When date pressure is applied to software projects, the work needed to remove Chaos is subtly placed on the chopping block. Work like error handling, clear logging, chaos & load testing and other quality work is quietly deferred in favor of hitting the Date™.
Finding value is the result of enabling individual and group-level discovery attempts. It's not the result of everyone following one leader's gut.
What just happened is a new software product/feature was created that no customer wanted. This happens way too often. In fact, most hyper important software projects that must be done by date certain or else, have deep flaws that cause some variation of this phenomenon, flaws that include:
Not wanted - Company specified a solution to a problem that customers don't actually have
No Rarity - Company is pursuing an iKnockoff of existing products. The market already has two scaled competitors with working solutions, customers naturally spend budget on products that are already successful to avoid risk
Incorrect Packaging - Customers need a website, but the company created an iOS app instead
Incorrect Pricing - Customers need SaaS pricing, but the company created a shrink wrapped, on-premise solution with CapEx and maintenance agreements instead
My own time in a Silicon Valley startup has proved this much to be true; planning doesn’t make for better software. In fact today our design systems team doesn’t have sprints, we don’t have tickets or a daily standup. Each day we come to work, figure out what’s the most important thing that we could be doing, and then we—gasp!—actually do it.
Watching so many other teams slowly flail about whilst they plan for quarter 3.2 of subplan A, whilst our team produces more work in a week than they all do combined in a quarter has been shocking to me.
After four years of working in a large startup, I know what I always assumed was true: you don’t need a plan to make a beautiful thing. You really don’t. In fact, there’s a point where overplanning can be a signal of inexperience and fear and bullshit. The scrum board and the sprints and the inane meetings each and every day are not how you build another Super Mario 64.
Instead all you have to do is hire smart people, trust them to do their best work, and then get the hell out of their way.