The Art of Asking Questions

Often, people around us don't share what could benefit us, including their valuable insights and unique perspectives and we don't ask. When we remain unaware of what others truly think, feel, and know, we make poorer decisions, stay stuck in unsatisfying situations, and miss opportunities for learning and connection.


Conversely, when we tap into this hidden wealth of insights, we can forge deeper, more meaningful relationships and unlock new levels of learning and growth. This post outlines a five-step approach to discovering what others truly think and feel.


Step 1: Cultivate Curiosity

We all have our own narratives about our lives and the people in them. We get caught up in judgment, resentment, and anxiety, so convinced of our own perspective that we don't become curious about others' viewpoints.


Cultivating curiosity means breaking out of these certainty traps. We tend to default to certainty instead of curiosity due to a combination of cognitive biases and social conditioning. It's a survival mechanism: We can't possibly process all the information we're exposed to daily, so our minds automatically filter and select a small range of that information to make decisions and take action.


Next time you find yourself feeling certain, try injecting more curiosity into your thinking. What information about this person or situation might you be overlooking? What challenges might the other person be facing that you're not aware of?


Step 2: Create a Safe Environment

Decades of research by Harvard Business School professor Amy Edmondson and others have shown that for people to speak up, they need to feel safe doing so. In other words, they need to genuinely believe that you won't judge, shame, or punish them for sharing openly with you. This is especially important when interacting across lines of difference, such as age, race, or gender, which can amplify the risks (real or perceived) of speaking honestly.


The key is to make it as safe, easy, and appealing as possible for them to speak honestly. If in past interactions you have reacted negatively or judgmentally, you need to work to create a safer environment moving forward. Even if you haven't, it's likely that the other person has at some point experienced shame or punishment for speaking honestly and thus feels unsafe on some level. While they might feel they "should" feel safe with you, it's more effective to take extra steps to ensure they actually do feel safe. Better safe than sorry, right?


Step 3: Ask Good Questions

With the foundation set, it's time to start asking questions. Unfortunately, most adults ask far fewer questions than they should, and the ones they do ask are often motivated by something other than learning and understanding. Yes/no questions ("Don't you agree?") or those that put people on the defensive ("What were you thinking?") produce no valuable information and can actually stop conversations.


In contrast, good questions help you learn from the other person. They signal genuine interest, reflecting a true intent to learn from and understand the other person not to make a point or influence or fix them. They invite honesty by being clear and direct, with no hidden agenda. Good questions tap into the other person's story to surface the underlying meanings, reasons, emotions, and experiences.


Step 4: Listen to Learn

The way we listen affects how much we learn and how well we connect with others. But while 96% of people consider themselves good listeners, research shows that we hear (and retain) only a fraction of what people are actually telling us. It's easy to feel like you're listening when what you're really doing is waiting quietly until it's your turn to respond or scanning the other person's words for openings and ammunition you can use to defend yourself or refute their argument.


Whenever you find yourself doing this, ask yourself the question: What could I learn from this person? Then let that intention guide your listening. Your main goal is to understand what the other person is trying to communicate to you. Focus on freeing up your attention to listen for different levels of meaning, putting everything else, including your best counterpoints, on hold.


Step 5: Reflect and Reconnect

Finally, you need to process what you heard in a way that allows you to truly learn and grow from it. To do this, ask yourself these three questions: (1) How might what I heard change my perspective on the situation? (2) What steps can I take based on what I've heard? (3) How might what I heard challenge my deeper beliefs, assumptions, or ways of being?


After thinking it over, explain what you learned and your next steps. This final step significantly shapes the future of your relationship with that person. When someone has taken the risk of sharing their honest thoughts or feelings with you, they need to know that it was worthwhile. If you don't reconnect, it can leave the other person feeling ignored or worse, used. However, when you take the time to share what you've learned, you open the door to deeper connection and ongoing learning that benefits both of you.



Used together, these steps are nothing short of a superpower one that anyone can use to transform their relationships and unlock exceptional learning and growth in every aspect of their life. In the upcoming articles, we'll delve deeper into why people hold back and each step of the Ask Approach.

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