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Worst possible question

As explained in Architecture Modernization: Socio-technical alignment of software, strategy, and structure

A worst possible question asks people to imagine an intentionally undesirable outcome or option in order to encourage unconventional thinking.

A worst possible question invites people to answer in the opposite direction from what they expect. In a listening discussion, that permission can open up more creative thinking. Answers may reveal that the organization is already doing something participants consider harmful, or uncover an unlikely idea worth refining. section 4.3.3

Invert the opportunity question

Ask: “What is the worst possible business opportunity that this organization could go all in on?” Look for both uncomfortable descriptions of current choices and surprising ideas with potential. section 4.3.3

How Architecture Modernization: Socio-technical alignment of software, strategy, and structure covers it

How deep it goes
Defines the prompt type and its purposes, but gives no step-by-step procedure.
Examples
Asks participants to imagine the worst possible business opportunity for their organization.
What you can do after
Practice/perform an inverted prompt to spot existing problems or find unlikely ideas worth refining.
How it connects
Connects structured discussions with creative thinking and business opportunity exploration.

This explainer was generated by Manning's knowledge graph from the text of Architecture Modernization: Socio-technical alignment of software, strategy, and structure. The section links point to the parts of the book it draws on.