Dedicated to Building Shared Understanding of Wicked Problems

The Power of a Good Question

by Mark Mateski on December 22, 2008

Asking the right question at the right time can help avert disaster. In fact, one could characterize red teaming and alternative analysis as the practice of posing and answering contrarian questions—questions such as “How could our adversary circumvent our defenses?” or “What flaws in our new product line might we have overlooked?”

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While the implicit approach of watching and doing does work in many cases, it is possible to build the skill more explicitly and systematically. Of the many resources available, I focus on one here: dialogue mapping. Specifically, I discuss the art of framing good questions within the dialogue mapping approach. While dialogue mapping can fill a book (see Jeff Conklin’s Dialogue Mapping), the question-framing portion of the approach is worthwhile as a standalone framework.

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