How Asking Powerful Questions Can Lead to Strategic Outcomes

Key Takeaways: 

  • Leaders who ask questions and listen intently can realize enhanced learning and growth — along with improved organizational results.
  • As leaders become more familiar with a questioning approach, they can practice becoming more skilled at applying different types of questions to improve employee engagement, enhance innovation and achieve greater clarity on strategic direction.

Teachers are likely familiar with Bloom’s Taxonomy and its structured approach to asking questions in order to help students learn by remembering, understanding, applying, analyzing, evaluating and creating.[1] However, rarely does one find a college syllabus or corporate training outline focused on teaching leaders how to ask questions to improve results.

Thankfully, this does not mean that sufficient literature is lacking, and a review of several informative pieces indicates that leaders can study, practice and learn to ask questions in meaningful ways to achieve better individual, organizational and strategic results.

Harvard Business School professors Allison Wood Brooks and Leslie K. John have examined the power of questions. Resurfacing previous research, Brooks and John highlight the power of conversations to achieve both “information exchange (learning) and impression management (liking)” and highlight findings that reveal the asking of questions in those conversations achieves higher levels of both for leaders and employees alike.

Highlighting the impact on employee engagement, they point to findings that reflect conversations where the subject was asked genuine questions with a chance to provide meaningful responses led to a higher level of harmony between the conversationalists.[2]

Author Michael Bungay Stanier also finds higher levels of employee engagement in situations where the leader asks questions instead of directing. In his book The Coaching Habit, Stanier outlines research which finds that asking simple questions like “What’s on your mind?” along with “And what else?” as well as “What’s the real challenge here for you?” and “How can I help?” provide respondents the chance to reflect and unlock answers that they might not have contemplated otherwise.

This engagement not only provides better solutions, but also allows the respondent to feel listened to and respected.[3]

The power of asking good questions can also provide greater overall organizational growth, fueling innovation and providing greater exploration in the charting of strategic vision. In his book, A More Beautiful Question, author Warren Berger outlines a, “Why/What if/How” approach to questioning that unlocks greater creativity and innovative thought.

Starting with ‘why’ questions, leaders can lead their organizations to more clearly frame the problem or challenge at hand as they explore why a situation exists, why no one has figured out how to solve it yet and why the organization should invest more time in thinking about it.

Once the problem is framed, leaders patiently guide the exploration of possible solutions by asking ‘what if?’ questions. Berger finds that asking ‘what if’ questions serve as “…seeds of innovation,” allowing expanded creativity and different approaches to how the challenge might be overcome.

Finally, asking ‘how’ questions like “How do I decide which of my ideas is the one I’ll pursue?” and “How do I begin to test that idea?” provide the launch point from innovative ideas to reality.[4]

Leaders can ask powerful questions during strategic planning as well. Instead of employing a traditional approach to brainstorming specific goals and objectives, Strategic Doing authors Edward Morrison, et. al. encourage a more envisioning approach. By asking, ‘what might’ questions, strategic planners naturally open their minds by eliminating biases and barriers.

Once settled upon, the planning can continue in an open-ended manner by answering more specifically, “What could we do? What should we do?” and finally “What will we do?”.[5]

Learning to ask questions and listening more intently is only one step in a leader’s journey. Leaders need to continue practicing and learning to ask open-ended questions in an appropriate tone while encouraging follow-up in order to achieve the most valuable input from their followers and maximize professional growth and organizational results.




[1] Anderson, L.W., & Kratwohl, D.R. (Eds.). (2001). A taxonomy for learning, teaching and assessing: A revision of Bloom’s Taxonomy of educational outcomes: Complete edition, New York: Longman.


[3] Bungay-Stanier, M. (2016). The Coaching Habit – Say Less, Ask More & Change the Way You Lead Forever. Box of Crayons Press.

[4] Berger, W. (2014). A More Beautiful Question – The Power of Inquiry to Spark Breakthrough Ideas. Bloomsbury Publishing, Plc.

[5] Morrison, E., Hutcheson, S., (2019). Strategic Doing: Ten Skills for Agile Leadership. John Wiley & Sons, Inc.


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