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How Asking 'Why?' Completely Changes the Game

The one key, simple step toward resolving a conflict is asking, “why?” I know it sounds too simple to actually be useful, but it works because it is so simple. Asking why helps you stand in the other person’s shoes and truly understand the Thought Models they are having that are motivating their side of the conflict. It only works if you have done your work first to understand and feel comfortable about your own perspective. Ask yourself “why” first, and make sure you like your reason for continuing the conversation. You know you have your work first if you are open and willing to say your opinion, you understand what the best outcome looks like for you, and you are more committed to the best outcome than to being right.

One of the strangest things about the results of asking “why” to another person is that you always discover that there is something reasonable, something you can have compassion for, about the other person’s perspective. If you have tried asking “why” and have not found something you can have compassion for from the other side’s perspective, you just have not asked “why?” enough times. Even if you still know the other person’s perspective is wrong, asking “why?” creates space for you to have compassion and understanding and help the other person walk toward your perspective.

It is like two people are standing on top of their own mountains, in their own mountain fortresses of being right, shouting at each other. When one person asks “why?” it is her coming out of her mountain fortress and taking a step down the mountain to understand where the other person is coming from. From there, she can walk with the other person toward a shared understanding. It takes strength and security in your own perspective to be willing to ask “why?” without people pleasing or pretending to agree with something you don’t. In the process of asking why, truly all you need to do is genuinely understand something reasonable about the other person’s perspective. You can absolutely continue to believe the other person is wrong, but until you understand the thoughts behind what the other person is saying, you can’t truly know what you are disagreeing with.

Put your argument on pause and just listen, even though it is hard and you believe the other person is the one who needs to listen to you. If there is space and the person you are talking with is willing to answer, get permission from them to ask questions and ask “why?” five times or ten times. This is the hardest part of truly being curious – stepping out of your own argument. Do not try to explain your perspective until the other person asks or you offer and get consent to do so. Explaining your position is not helpful, understanding the other person’s perspective is. You lose the Why Game if you try to explain your position before you can accurately reflect the other person’s position. However many times it takes for you to find something that seems genuinely reasonable to you, ask “why” until you find that thing. Usually, we all agree on core points of safety, security, feeding our families, and caring about the people who are important to us. We disagree about how to do that, and our disagreements are genuine, so I am not encouraging you to pretend you agree where you don’t. I am only offering this tool as a starting point.

When we ask why and try genuinely to understand, we can see our mountain from the other person’s perspective. We can stand in their shoes, even if we decide those shoes are not a good fit for us in the long run. When we can discover the thoughts behind her actions, we are in a better place to help her understand why those thoughts are not serving her, if that is indeed the case.

Often, asking “why?” sounds disingenuous to us because we expect other people to have the same thoughts as us. What I have found since I have started working on these resolution processes is that we all have incredibly different thoughts and reasoning behind what we do. I often preface my questions to clients by saying, “I am not pretending to be dumb, or trying to make a point, but I genuinely want to make sure I understand why. I’ve discovered in my work with people that if I make an assumption about a particular person’s reasoning, I will often get it wrong.” The purpose of asking “why” is to genuinely understand and stop making assumptions. It is not to play dumb so that we can trap someone else in thinking errors. Until you can genuinely, openly ask “why?” you know you have your own work to do in questioning your own thoughts and shifting power dynamics to understand that you have power in the situation.

Again, you need to be confident in your own power in the situation, and have worked on your own thoughts and like the reason for your perspective first, before you ask a person you’re in conflict with why they are acting the way they are. This is a tool for someone who is in a power position in a conflict situation, not for someone who feels disadvantaged. When we feel powerless, we often see other people’s perspectives and accept them above our own. Criticizing and diminishing our own perspective is generally more destructive and likely to lead to conflict than failing to understand another person’s perspective.


This is a selection from The Inclusive Leader's Guide to Healthy Workplace Culture. For a free copy of the book, visit Or you can purchase online via Amazon.

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