The Paradox of Why

by Miki Kashtan

In an astonishing number of situations, knowing the “why” – why someone did what they did - is what helps us make meaning, be motivated, transform our assumptions, or open our hearts. At the same time, the “why” question – “why did you do that?” - is often the most difficult to hear, leading us to defensiveness and contraction. Both parts of this paradox have clear reasons (their own “why,” if you will). Once we know them, we can find ways to support ourselves and others in knowing the “why” that are less taxing for all.

Why “Why” Matters

For myself, understanding the “why” is the fundamental bridge between me and another. When I see another person’s action, decision, or choice, or hear their request of me, and I don’t know the “why” – either by being told, or by managing to imagine it effectively enough – a gap forms within me, made up of lack of understanding. The gap may be tiny and temporary, or it may be the beginning of growing and ongoing mistrust. This gap is likely bigger and lasts longer the less the other person’s movements align with my own preferences.

I have heard similar themes often enough to trust that in this particular way I am not that different from others. Just think of the last time someone didn’t show up at the time you expected them and you were irritated, then you found out the why and the irritation disappeared. Without knowing, we tend to fill in the gap of understanding by providing our own “why,” creating our own stories about what someone’s behavior means.

This is where our historical legacy can backfire. Only few of us, as far as I can tell, are truly able to live the assumption of innocence in its fullness. As a result, when we don’t like what someone else does, many of us are prone to coming up with explanations that dehumanize the other person: “She set me up to suffer because she is sadistic” or “He only did this for the sake of having more power” or “This decision came from left field; they don’t know how to plan anything.”

On the other hand, when we do hear the why, something changes magically. I’ve been in rooms where employees heard, for the first time, why a certain decision was made by a boss, and noticed the power of the shift that ensued. I’ve seen people receive a request and tense up only to relax into a comfortable “yes” when they understood why the request was made in the first place. It only works when the reason makes sense and allows us to see the emotional logic. Then we can plant ourselves in the shoes of the other person even if we disagree. This is a clear example of the immense power of empathy, and the distance we still, collectively, must walk to inhabit a spontaneously empathic response to life.


The “why” question is also another bridge: between me and a sense of meaning and purpose. This is often the internal “why” I direct at myself, which usually leads me to find the core needs that pull me along to do whatever I do. That self-understanding then provides the basis from which I can make my “why” available to another person, so that they can have the satisfaction of understanding.

Offering the “Why”

Although most of this piece is focusing on how to ask for the understanding we want, a big moral of this story is also to remember to tell others the “why” without waiting for them to ask. If I make a request, I want to remember to tell the other person why I made it. That both makes it easier for the person to find an authentic “yes” and to help me find other strategies to fulfill my needs if they are going to say “no.”

If I am in a position of leadership and I make a decision, I want to let people know why I made this decision in addition to telling them what the decision was. If I make a move, and especially if I imagine others won’t like it, I want to let them know why I am choosing to act in this way.

If you have to be a manager and you are reading this, I hope you will remember that the people you supervise will be far more willing to take on the responsibilities and carry out the tasks if they can understand the “why” – how do these tasks contribute to the whole and to you. I cannot overstate how important it is to people’s well being to be able to make those connections. They are not likely to ask for it, and, if they do, it will be harder for you to give it generously because of how it’s usually being asked.

Why Is Being Asked “Why” Hard?

Even though we want to know why, asking for it directly is not usually a reliable strategy to get a useful answer. The reason for this challenge is that we are so habituated to associate a “why” question with being reproached or shamed. Growing up, for example, being asked: “Why did you do that?” often comes with a stern look and frustrated tone. Whether or not the person who asked intended to frighten us, that is often the effect. Since, in addition, we rarely tell people why we ask “why” questions, the tendency to hear them as blame and accusation is reinforced.

Power differences only exacerbate this phenomenon. The person with more power is more likely to ask the “why” question of the person with less power, and more likely to be heard as blaming. The person with less power is not likely to ask the “why” question in the first place, usually because of fear, sometimes because of disconnection. Without consciously choosing otherwise, both remain separate, and susceptible to two-dimensional ways of seeing each other. 

Questions to Generate Understanding and Collaboration

Putting all these pieces together leads to the following conclusion: in order to maintain a flow of understanding and collaboration, we need to hear and say the “why” while finding other ways to ask for it. So far so simple, yet most people who have heard this insight from me tend to get stuck in this moment, not knowing what the alternatives are. This is why I am writing this piece: I want to support everyone who wants to be able to understand things better to know how to ask the questions that will get them the vital information: someone else’s inner experience of self-understanding.

The Why of Our Question

Given how important it is for all of us to understand the “why” of everything, the first thing I aim to remember when I want to ask a “why” question is to express my own “why” – the reason I am asking the question, where I am coming from, or what my purpose is. That can dramatically reduce the blame factor and increase trust. Here are some examples:

• To a boss: “I have been asked some questions about this policy from my staff, and I would like to have all the information necessary to answer their questions…”
• To a co-worker: “I am confused about how this is going to affect the project we are working on together; I want to ensure that we can collaborate effectively…”
• To a teenager: “I want to learn better how we can make agreements that work for both of us…”

In all these examples the “why” is provided in the form of expressing what I want that’s leading me to ask the question, and, some of the time, also how the information will help me with what I want to do. 

Focus on the Present and the Future

The past cannot be fixed; it can only be healed and learned from. This is why I make a concerted effort, when I am not happy with what someone did, to make it explicit that I am not angry about what happened, only trying to turn it into an opportunity for learning. The big trouble, for me, is just the awareness that I am about to ask a “why” question, and then the transformation of language happens almost by itself. Instead of the habitual “I want to know why you did what you did,” I remind myself that what was done has already happened. I might need to mourn it in order to have some acceptance. Whatever I do, in the end I cannot change the fact that what this person did is done. I can only focus on now and the future, and say so in so many words, such as: “I want to learn from what happened to support smoother operations in the future” 

What and How

Even when we explain where we are coming from and focus on the present and the future, for most people the word “why” itself it tainted, and no amount of explanation can undo that. This requires us to master the art of replacing the “why” question with a “what” or “how” question while continuing to aim for getting a “why” response! I still struggle with this myself, after some years of knowing about it, because I have never left behind the “why” phase from when I was three and four years old. I do notice the difference in effect when I do remember. In the examples above:

• To a boss: “I have been asked some questions about this policy from my staff, and I would like to have all the information necessary to answer their questions. Is there more you can tell me about what led to this new policy being adopted”
• To a co-worker: “I am confused about how this is going to affect the project we are working on together; I want to ensure that we can collaborate effectively. Can you tell me how you arrived at this conclusion?”
• To a teenager: “I want to learn better how we can make agreements that work for both of us. Do you know what keeps you from telling me before you leave that you want the freedom to come home whenever you like?”

Although there are no guarantees in life, as far as I can tell, when it comes to human relationships, I imagine that the above ways of ending the question are less likely to generate defensiveness, and more likely to contribute to collaboration. This is, essentially, what I hope to achieve when asking: to open up the possibility of mutual discovery and learning, for both of our benefit.

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