The real challenge is attention management. Switching gears from an execution orientation (knocking off tasks) to a careful thinking orientation is hard. The hardest aspect of deep work (for people used to a structured form of productivity) is immersion in the task/topic without a concrete plan of "how" to tackle it. (The necessary immersion is what makes "deep" a good metaphor) Every such session is a risky investment where you don't know what you'll come up with. Unless you believe it's a risk worth taking, trying too hard to de-risk endeavors will rob you of opportunities for deep work.

Deep work involves situated thinking -- thinking while doing, making use of feedback.

OTOH, the structured approach biases towards separating the two closely knit parts into "planning" and "action" -- so much so that in our organizations the two are done by different people/teams!

Drucker said that a decision has been made only when it's clear what the actions are. Correspondingly, deep work is required to the extent that the analysis can't be front loaded in that manner.