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The Art of Asking

Five steps for unlocking learning and connection.

Key points

  • Too often, we fail to find out what the people around us really think, feel, and know.
  • Tapping into these unspoken insights can improve relationships and unlock learning and connection.
  • To discover what others think and feel, we have to learn how to ask the right questions, in the right ways.

Far more often than we realize, the people around us don’t tell us what would be most helpful for us to know, including their unique insights and original ideas—and we don’t ask. When we stay in the dark about what those around us really think, feel, and know, we make worse decisions, stay stuck in frustrating dynamics, and miss out on opportunities for learning and connection.

On the other hand, when we do tap into this goldmine of hidden insights, we can create deeper, more meaningful relationships and unlock new levels of learning and growth. This post outlines a five-step approach for discovering what those around you really think and feel.

Step 1: Choose Curiosity

Each of us is constantly telling ourselves stories about our own lives and the people in them. We get wrapped up in judgment and resentment and anxiety, so certain about our own perspective that we don’t get curious about what we might not be seeing.

Choosing curiosity is all about breaking out of these certainty loops. We tend to default to certainty instead of curiosity due to a combination of psychological biases and cultural conditioning. It’s a survival strategy: We can’t possibly process all the data we are exposed to every day, so our minds instinctively filter and select a small range of that information in order to make decisions and take action.

So the next time you catch 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 up against that you can’t see?

Step 2: Make It Safe

Decades of research by Harvard Business School professor Amy Edmondson and others has demonstrated that in order for people to speak up, they need to feel psychologically safe doing so. In other words, they need to really believe that you will not judge, shame, or punish them for sharing openly with you. This is all the more important if you are interacting across lines of difference, such as age, race, or gender, all of which can intensify the risks (real or perceived) of speaking candidly.

The key here is that it’s up to you 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 have to work extra hard to make it safe going forward. But even if you haven’t, it’s very likely that the other person at some point experienced shame or punishment for speaking honestly and still feels unsafe at some level. While it’s easy to feel like they “should” feel safe with you, it’s far more effective to take extra steps to ensure they actually are. Better safe than sorry, right?

Step 3: Pose Quality Questions

Foundation set, it’s time to start asking questions. Unfortunately, most adults ask far fewer questions than they should, and the ones they do are often motivated by a desire other than learning and understanding. Yes/no questions (“Don’t you agree?”) or those that put people on the defensive (“What were you thinking?”) do not produce any valuable information, and can actually shut down conversations.

By contrast, quality questions help you learn something from the other person. They signal true curiosity, reflecting a genuine intent to learn from and understand the other person—not to prove a point or influence or fix them. They invite honesty by being clear and direct, with no alternate agenda. Quality questions tap into the other person’s story to surface the underlying meanings, reasons, emotions, and experiences.

Step 4: Listen to Learn

How we listen determines how much we learn and how deeply we connect. But while 96% of people think of themselves as good listeners, research shows that we hear (and retain) only a sliver of what people are really 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 holes and ammunition you can use to defend yourself or rebuff their argument.

Whenever you catch yourself doing this, ask yourself the question: what could I learn from this person? and then allow that intention to guide your listening. Your only goal is to understand what the other person is trying to share with you. Everything else—yes, even your very best counterpoints—must take a seat in order to free up the attentional resources you need to listen for multiple levels of meaning simultaneously.

Step 5: Reflect and Reconnect

Lastly, you have to process what you heard in a way that really allows you to learn and grow from it. To do this, ask yourself these three questions: (1) How might what I heard revise my story about the situation? (2) Based on what I heard, what action steps can I take? (3) How might what I heard challenge my deeper worldviews, assumptions, or ways of being?

Once you’ve reflected, share what you’ve learned and what you plan to do next. This final step profoundly 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 want to know that it was worthwhile. If you don’t reconnect, it can leave the other person feeling unappreciated or worse, used. But when you take the time to share what you’ve learned, you open the door to deeper connection and ongoing learning that benefits you both.

Used together, these steps are nothing short of a superpower—one that anyone can use to transform their relationships and unlock unprecedented learning and growth in every area of their life. In the coming articles, we’ll delve deeper into the problem what people withhold and why, as well as each step of the Ask Approach.

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