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How to Ask Simple Questions


Two months back, I wrote about asking simple questions. I explained what simple questions are and why they are important. I shared how simple questions are an often-overlooked gem, which, when employed, act as sparks, igniting the flame of curiosity. I also shared how it is through the art of asking simple questions that we unlock a profound depth of understanding and insight, untangling the intricate webs of elaborate inquiries that we often find ourselves in. This article is a follow-up to my previous article — Asking Simple Questions — and I will focus on how to ask simple questions, or as Clay Christensen puts it, how to ask good questions.

“Without a good question, a good answer has no place to go.”Clay Christensen


I agree with this quote because I think it is so true. Rarely are good questions complex. Yet, for a long time, I thought good questions were these complex, elaborate, and profound questions that once asked, just unlocks everything and provides great answers. I could not decipher what it meant to ask good questions. I heard leaders talk about asking good questions, but I did not truly understand what it meant. Good questions are simple questions that layer on each other to gather insights, creating a compound effect.


Yet, this definition of good questions took me a while to understand. Even though good questions are simple questions, I feel more pressure to ask good questions than to ask simple questions. When I focus on asking good questions, I put the burden of generating the question on me. I am obsessed about the outcome. There is ego involved. It is all about me. My brain starts spinning as it tries to figure out what good questions to ask. There is the need for certainty that the question I ask will be a good question that will unlock everything and provide great answers. And while I am deep in thought trying to come up with a good question, the meeting or event is over. Time’s up! Someone else has asked a simple question followed by another simple question, and, voila! insights are uncovered. When I ask simple questions, I feel the burden of the question is less on me and more focused on understanding and learning. I don’t know if this has ever happened to anyone else, but it is my perspective. This is perhaps more psychology than logic. 


This article is a follow-up to my previous article — Asking Simple Questions — and I will focus on how to ask simple questions, or as Clay Christensen puts it, how to ask good questions. 


In the realm of leadership, design thinking, innovation, and strategy, the ability to ask simple questions is a potent tool. Simple questions possess the power to unlock complex solutions, foster creativity, and drive meaningful change. Whether you are leading a team, navigating challenges, or charting a course for innovation, mastering the art of inquiry via asking simple questions is essential. Here is how you can leverage the art of asking simple questions to fuel strategic leadership, discovery, and innovation.


  1. Start with Purpose:Effectively asking simple questions begins with a clear understanding of your purpose. Before diving into inquiries, articulate your goals and desired outcomes. Are you seeking to understand a problem, generate ideas, or challenge assumptions? Align your questions with your objectives to ensure relevance and impact. This is critical. For example, conducting user research requires asking questions. But far more important than the questions asked is understanding why you want to ask those questions — what is the goal of the research? The same applies to driving an innovation session or hackathon. The questions to ask and the structure of a brainstorming session are different from the structure of an idea validation session. During a brainstorming session, all ideas are welcomed. The goal of a brainstorming session is to push the boundaries of possibilities. Asking simple questions or prompts such as “And what else?” allows others to layer on each other’s ideas to achieve the goal. Whereas, during a validation session, you are more likely to probe deeper into ideas and ask prompts like “What would have to be true” about this idea or that idea. The purpose of the validation session is to critically examine strategic possibilities that are desirable, feasible, and viable. The purpose of both sessions during the ideate stage is different. The questions are different, yet they are simple.


Lately, I have been reading books on negotiation, psychology, and leadership. I am reading a book — The Coaching Habit by Michael Bugay Stanier — given to me by one of my MBA professors (shout out to professor Nouman) at Rotman School of Management, University of Toronto. The goal of the book is not to teach and provide advice but rather to coach, to tell less, and ask more. Because according to the book, our advice is not as good as we think it is. The Coaching Habit explains seven different questions to ask to kick-start your coaching: the kick-start question (so what is on your mind?), AWE question (and what else?), focus question (so what is the real challenge here for you?), foundation question (what do you want?), lazy question (how can I help?), strategic question (if you are saying yes to this, what are you saying no to?), and learning question (what was most useful to you?). What is striking about these seven questions is that they are all simple questions.


  1.   Embrace Curiosity:Curiosity is the fuel for innovation. Approaching every situation with an open mind and a thirst for knowledge can encourage us and others to explore new perspectives, challenge conventional wisdom, and seek deeper insights. To cultivate a culture of curiosity within our team or organization that will stimulate creativity and drive innovation, ask simple questions from a curiosity perspective to understand a problem not provide a solution, to gain more perspective about a situation not state your perspective, and to understand assumptions not critique assumptions. Solutions come later. Asking simple questions from a curiosity perspective sets the foundation for understanding and alignment before problem-solving. It’s the same reason why the empathize phase comes first in the design thinking and strategy formulation process. Simple questions that reframe “why questions” to “what or how questions” such as “What made you ask this question?” instead of “Why are you asking this question?” can foster more insight and make the other person less defensive in response.


A curiosity-type question is different from an investigation-style question or a confirmation-style question. The goal of an investigative or confirmation-style question is to solve the problem, to poke holes until the suspect confesses or reveals his or her true intention, or to prompt the speaker to state the answer that we already know. Every question asked is less from a point of curiosity and more from a point of confirmation or investigation towards problem-solving and carefully steering the suspect toward the direction that we want them to go. People are less friendly and more defensive with investigative or confirmation style of asking questions.


Good questions come from trying to understand not trying to respond or reply. This can be challenging, especially when we are under pressure or put on the spot. But managing the pressure to come across as smart and positioning yourself to instead be curious, actually makes you seem smarter. It is one of those paradoxes of life. 


For example, during a change management session for an innovation project that I was leading at work, a leader asked me a question that deviated from the question that I was prepared for. This question was new, and at first thought, I wanted to jump in quickly and respond. My thought at the time was I must have an answer because having an answer meant I knew my stuff. Sure! But, a calmer voice from within told me that now may be a good time to ask the leader a question rather than reply with my standard answer. I wanted to understand why the leader was asking the question and what the leader wanted to achieve. So I asked, calmly: “What made you ask this question? I am curious, as I would like to know what you are trying to achieve and understand the situation, so I can properly answer your question.” Tone matters. The leader replied and told me the exact reason for asking the question. Turns out, the leader was right and the perspective shared made more sense. I changed my answer. 


  1. Keep it Simple:Steve Jobs once said, “Simple can be harder than complex: you have to work hard to get your thinking clean to make it simple . . . .” Complex problems often have simple solutions hidden beneath layers of complexity. And it is worth avoiding the temptation to overcomplicate our inquiries. Instead, we should strive for clarity and simplicity in our questions. One way to do that is to clarify meaning. Asking a simple question such as, “What do you mean by this?” can make the other person slow down to explain their meaning or perspective. This provides more background, context, and perspective for you to understand their pain point or perspective. 


To expand on this point, I would share a story from a design thinking podcast I listened to. The host of the podcast for this episode brought a guest speaker, who runs executive seminars. The guest speaker spoke about the importance of clarifying meaning. He went on to explain how clarifying meanings helped him improve the quality of service he provided for his executive seminars. What had happened was that the guest speaker noticed that during every executive seminar that he hosted, the attendees were busy taking notes instead of being fully engaged. And it bothered him. Curious about this, he decided to conduct some research. He followed up with a previous client, who had attended one of his seminars. And during the follow-up interview, he discovered that attendees of his executive seminar felt stressed about attending executive seminars paid by their organizations, as they were required to capture all the learnings to share the knowledge with their colleagues back at the office, who could not attended the seminar. By asking the client what he meant by stress, the guest speaker gained valuable insight into the pain points felt by the attendees of his executive seminars. This insight led him to hire a professional stenographer to take notes during his seminar to provide to everyone after the seminar. When the guest speaker shared this new offering with the attendees at his executive seminars, he noticed a collective sigh of relief as everyone put away their laptops and listened to him. This is the power of knowing how to ask simple questions by clarifying meanings. 


  1.   Challenge Assumptions:Uncovering hidden assumptions is critical for innovation and strategy. Challenge the status quo by asking questions that provoke reflection and critical thinking. Encourage yourself and others to question long-held beliefs, biases, and preconceptions. By challenging assumptions, we open the door to new possibilities and innovative solutions. Ask simple questions (such as, what made you choose this approach?) to clarify the underlying assumption. You could even challenge assumptions yet make it a dialogue by asking: What would have to be true for this idea to be viable?


A few callouts that can hinder or make your questions better: 


  1.   Iterate and iterate: Inquiry is an iterative process. Do not expect to find all the answers to a single question. Instead, embrace the journey of discovery and iteration. Ask follow-up questions to delve deeper into issues, refine your understanding, and explore alternative perspectives. 


  1. Trust matters. If trust is already broken, simple questions as instruments for uncovering complexity may be challenging to achieve as every question asked will seem more investigative or confirmatory rather than curious, heightening their defense even further.


  1. Tone and intent matter. Our tone is crucial to success. How we ask matters as much as what or when we ask. And the intent behind every question may seep out in our tone. There is power in listening. Model the behavior you want to see in others by asking thoughtful, simple questions and actively listening to the responses. Demonstrate your commitment to curiosity, innovation, and strategic thinking through your words and actions. By leading by example, you inspire others to follow suit and create a culture of inquiry and innovation that drives success.


In conclusion, asking simple questions is a powerful tool for strategic leadership, design thinking, innovation, and strategy. By embracing curiosity, fostering dialogue, seeking to understand assumptions, empowering others, and staying agile, you can leverage the simplicity of questions to unlock new possibilities, drive meaningful change, and achieve your strategic objectives. As leaders and innovators, let us harness the transformative power of asking simple questions to unlock the full potential of our organizations—it may be the key to unlocking your next great innovation.