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How to ask better questions

The ability to ask better questions is crucial, particularly in our work as enablers of change. We often learn this skill on the job, unlike professionals in other fields, such as lawyers and psychologists, who receive formal training. By focusing on the types of questions we ask, we can better explore issues, uncover valuable information and understand the range of options available to us. 

Regular readers of our blog will know that we love the work of Chad Littlefield, and we often use his “We! Connect cards” in our activities, whether online or in-person. We’ve been reading the book “Ask powerful questions,” by Will Wise and Chad Littlefield in which they emphasise the importance of connecting with others through the art of questioning. We think their insights are useful for us as enablers of change! Powerful questions help us facilitate deeper connections, build trust, and encourage meaningful conversations. These questions aren’t just about gathering information but are designed to help us understand the emotions, values, and motivations of the people we work with.

For instance, the authors suggest that questions should be intentional, open-ended, and curious. Intentional questions are those that have a clear purpose and are asked with genuine interest. Open-ended questions encourage deeper exploration, avoiding simple yes or no answers. Curious questions show a willingness to learn and understand another person’s perspective. This approach aligns well with our work as enablers of change, as it encourages active listening.

The authors introduce the concept of the “Asking Powerful Questions Pyramid,” which offers a structured approach to facilitating discussions and helping a group to engage with the topic or issue. The pyramid consists of several layers, each representing a different type of question that deepens the conversation. Understanding and applying this pyramid can enhance our work as enablers of change, and help build trust.

At the base of the pyramid are intention questions. These questions establish the purpose and set the stage for the conversation. They help clarify what we want to achieve and why we are engaging in the discussion. For instance, when working with a group, we might ask, “What is the main goal of implementing this new farming technique?” or “What makes focusing on sustainable practices important?” These questions help create a shared understanding.

Moving up the pyramid, we encounter rapport questions. These questions aim to build trust and connection, creating a safe space for more open and honest discussion. They focus on personal experiences, values, and motivations. Examples include, “What inspired you to pursue this line of work?” or “Can you share a memorable success story from your farm?” Chad Littlefield talks about connection before content a lot and these questions help us achieve that.

Next are openness questions, which delve deeper into specific issues, challenges, and opportunities. These questions are more open-ended and curious, prompting people to explore underlying factors and potential solutions. For example, “What challenges have you faced with this new technology?” or “How do you see climate change impacting your farming practices in the next five years?” Openness questions help us understand the complexities of the situation and identify areas for innovation and improvement.

Towards the top of the pyramid are listening questions, which aim to uncover new insights and perspectives. These questions often involve some level of speculation and creative thinking, encouraging people to think outside the box. Examples include, “What is your greatest challenge at the moment?”, “What if you had unlimited resources to implement your ideas?” or “What other approaches might we consider to solve this problem?” Listening questions lead to a better understanding between all the parties involved.

At the top of the pyramid are empathy questions. These questions help us focus on others, and our worldview expands as a result. Empathy is having an understanding of the other person’s world, while maintaining an understanding of our own. Examples include, “What is it like for you to experience this?” or “Help me understand what you’re thinking about that” Empathy questions help us better understand how people are feeling about the situation and the possible future directions. 

In our work as enablers of change, applying the pyramid of questions can enhance our interactions with farmers and stakeholders. By starting with intention questions and progressively moving up the pyramid, we can build trust, explore issues in depth, uncover new ideas, and facilitate meaningful reflection. This structured approach ensures that our conversations are productive and enjoyable.

The pyramid encourages us to be intentional and mindful in our questioning. By consciously choosing the type of question that fits the context and desired outcome of the conversation, we can steer discussions in a way that reveals insights and allows deeper understanding. This approach aligns with the principles of effective communication and leadership, as it emphasises the importance of curiosity, empathy, and strategic thinking.

The pyramid might remind you of the ORID framework for questions and discussion which we’ve covered in a previous episode. Well, you’ve heard our thoughts, now we’d like to hear yours! Add a comment below the blog post and tell us about your experiences with asking better questions, including any tips and further ideas about it. Have you read the book, and if so, what did you think? We don’t want this to be just a one-way conversationjoin in by sharing your thoughts and ideas with us! 

Thanks folks for joining us on this Enablers of change episode. Remember to subscribe to our newsletter if you’d like to know when new episodes are available. And if you liked what you heard, please tell your friends so they too can join the conversation!


Wise, W., & Littlefield, C. (2017). Ask powerful questions: Create conversations that matter. We and Me Inc.

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Mal Cock
Mal Cock
11 days ago

Thanks again John and Denise.
Very important for good communication and decision making and an area I need to improve.

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