The common advice to ask 'why' five times can reinforce an incorrect initial framing of a problem, leading you to optimize the wrong thing. A more powerful approach is to first question the frame itself by asking, 'Is this the right thing to focus on?' before diving into causes.
A study of artists found the most creative ones didn't block off more time to think. Instead, they practiced 'reflection in action'—constantly mixing drawing with rethinking the problem. Reframing is not a separate, time-consuming first step, but a continuous habit integrated into the workflow in short intervals.
Systems are designed to reward visible, reactive work (a police officer writing tickets) over often-invisible prevention (an officer whose presence stops accidents). This creates a culture that values firefighting over fire prevention, misaligning incentives from true public safety or organizational health.
Expedia received 20 million support calls for itineraries because each department (marketing, tech, product) focused only on its own metrics. No single silo owned the cross-functional problem of preventing calls, so the problem festered despite its massive scale. True ownership must transcend departmental lines.
An executive who hated his boss reframed his problem from 'I need a new job' to 'My boss needs a new job.' He gave his boss's resume to a headhunter, who found the boss a new position. The executive was then promoted into the role, solving his problem without having to leave.
Rockford, Illinois, eliminated veteran homelessness not with broad policy, but by creating a real-time, name-by-name census of every homeless person. Stakeholders then coordinated on each individual case, which revealed the systemic leverage points needed for macro change. You can't help a million people until you understand how to help one.