The Power of Recursive Questioning
Recursive questioning is an easy technique to apply when defining business challenges and designing solutions, although too often it is not used. Let's take a look at three frameworks and why those are effective.
While many frameworks exist, I prefer using these three because they apply to practically any challenge at any size organization:
Five Whys originated within Toyota to identify the root cause of a problem, and it works equally as well to understand the basis for a strategy or solution being proposed
"What business are you in?" asked five times is a classic exercise from Peter Drucker, which is helpful both in a strategic sense and to evaluate whether a tactic aligns with the organization's strategy
5Ws Framework are the who, what, where, when, and why that we learned in primary school; refer to this series for more details and an example
Note that a variation of Five Whys suggests using "what" and "how" instead of "why", as the latter can provoke defensive responses. Try both and see what works with your stakeholders.
As for when to stop, the first two offer a natural stopping point after asking the same question five times (if you take things literally).
However, the 5Ws Framework does not, so when do we stop asking questions?
Action items emerge to continue progress, whether it be to deliver something or gather more information for a subsequent discussion
Diminishing returns because answers are no longer contributing value
Stakeholder energy shifts to depleted or defensive, instead of inquisitive and collaborative
Why does recursive questioning work?
Exposes complexity associated with assumptions, processes, systems, and stakeholders
Follows how we learn as humans by triggering curiosity and incrementally building knowledge
Grounded in cognitive psychology because it forces us to use both intuitive and analytical thinking
Also, we've been doing for thousands of years, as it has ties to the Socratic method of open-ended questions.
TLDR: Use tactics like Five Whys, Drucker's "what business are you in", and 5Ws to guide meaningful discussions. Stop when you reach clarity or fatigue.