Thinking.........

.......beyond the restrictive confines the box can be both:
(a) positive - fostering creative leaps as in generating wild ideas (the conventional use of the term);
and
(b) negative - penetrating through to the "bottom of the box." This could result in a frank and insightful re-appraisal of a situation, oneself, the organization, etc.

On the other hand, the process of thinking "inside the box" need not be construed in a pejorative sense. It is crucial for accurately parsing and executing a variety of tasks, making decisions, analyzing data, and managing the progress of standard operating procedures, etc.
The phrase can be used as a shorthand way to describe speculation about what happens next in a multi-stage design thinking process.

Wonder if Euan, Abby, Marjorie and Niall think about such things..... my head hurts now but that may be due to the copious amounts of red wine I consumed last night..... bottled not boxed........ ;-P