You just finished briefing your boss on the latest proposal. You and your team spent hours hashing over details. You ensured you presented the big picture, highlighting critical points for understanding. You ask for questions and find your boss has plenty. You wonder where you went wrong. The truth is you did a great job. Your boss understands the importance of asking critical questions about everything in the organization. The knows to verify things that appear to be one thing to ensure they are not something else. With experience, the boss learned the right questions to ask related to a host of issues and situations.

Using questions to stimulate discussion and analysis has been called the Socratic Methodⁱ. The questions focus on learning information in areas of interest for the questioner. Quality answers are supported by proof in the form of an accepted fact, expectations based on analysis, data from test results, or another accepted proof. Challenging proof and conclusions occur next in the Socratic Method.

Socratic questions that stimulate discussion and analysis may include:

– What is the risk related to that decision?

– How do we reduce the risk?

– What proof exists to demonstrate risk reduction?

– What impact will the decision have on … ?

– How does the organization deal with that impact?

– What other ideas did you explore and why were they not presented?

– What is the most important consideration and why?

– Are there examples of following a course from history; if so, what happened and why?

– What are your measures of success and how did you determine those measures?

– What are the costs in terms of money, influence, credibility, etc.?

These are only ten possible questions inspiring critical discussions and analysis issues or topics. They are a starting point. Use critical thinking questions to test your theories before presenting an idea to others. Ask someone to challenge your assessments with the Socratic Method. The more you practice, the better your assessments. Your ability improves by responding to challenging questions asked by others.

Experienced leaders develop core questions used in every analysis. Core questions stand the test of uncovering important information repeatedly. Experienced leaders develop questions for particular situations. Sometimes they are developed as the situation unfolds or come from preconfigured questions developed for different situations.

Whether you are developing a course of action to market a new product, or deciding where to go on your next vacation, learning to ask the right questions helps you make better decisions. Questions that challenge conventional thinking allow decision makers to identify alternative courses of action and determine if they would be effective. Allowing others to challenge your conclusions with Socratic questioning improves your logical thinking. As you step into your next leadership position, or prepare a briefing for the boss, take time to think about questions to uncover the best solution to any situation.

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