Vulnerable Questions: A Tool For Deeper Connection

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This week is Canadian Thanksgiving which makes it an apt time to discuss Israeli psychologist Daniel Kahneman’s “What You See Is All There Is” theory. 

Kahneman and his best friend, Amos Tversky, won the Nobel Prize in Economics in 2002 for their work in behavioral economics. “What You See is All There Is” says our brains are wired to believe that the information we have is all the relevant information there is. 

While I’ve never celebrated Canadian Thanksgiving, I am an American Thanksgiving celebrant and I want you to imagine a big table filled with all your favorite holiday dishes. 

Your job is to consume as much food as possible and maximize your happiness. So you dig right in, filling your plate with sweet potato yams, turkey, gravy, buttery mashed potatoes, skip the green beans and corn, add a little extra butter to the rolls, and before you know it, you’re stuffed. 

You’re maximally happy – this is a good thing if you’re an economist or glutton– until grandma comes out of the kitchen with her famous apple crumble. 

How could you have forgotten the apple crumble! 

You were the victim of what Kahneman describes as “overconfidence.” When your mind makes decisions, it deals primarily with Known Knowns, the food already on the table. And your mind routinely mistakes to consider Known Unknowns, like the apple crumble. It also fails to recognize Unknown Unknowns like when your uncle’s new girlfriend brings out her homemade cheesecake, your favorite dessert. 

What’s so incredible about Kahneman’s work is the breadth of its application. Everywhere you look, you can find examples of human “overconfidence” derived from the bias we overlay onto the things we know. And the gaping hole of information we haven’t considered.

Most of us humans have outsourced our need to know more to two professions: scientists and theologians. 

In our current environment, scientists describe and categorize the Known Knowns and they ask more meaningful and pointed questions about the Known Unknowns to broaden humanity’s knowledge base. The theologians ask questions to take the last step and provide myth and story to bring order to the Unknownable.

Science and religion are two sides to the same sense-making coin. And this structure has been incredibly productive; increasing humanities well-being for more than two centuries.

But on the individual level, which is Kahneman’s field, we routinely fail to ask questions about the Known Unknowns and fail to recognize that there are even Unknown Unknowns. 

We stuff ourselves with Known Knowns. 

Our overconfidence bias streamlines our perception of the world. It eliminates all the choices that are not on the table. Our minds navigate with what we think is a global map of weak resolution, when in reality, our map isn’t global, but is hyper-local – what we are most familiar with. We rarely gain enough awareness to ask the questions about what is beyond our myopic map. 

Now let’s presume our Thanksgiving Day table is an analogy for relationships. We overstuff ourselves with what we know we like, and most crucially, what we know other people like: only the most popular dishes are on the table. Sometimes referred to as Turkey Day, Thanksgiving Day tables lack variety.

The same is true of most of our conversations and our relationships. They lack variety; they are stuffed with tryptophan turkey.

Just like asking questions will unfurl Unkown Unkowns and draw better maps, it also invigorates relationships. 

For the last few months, I’ve been experimenting with questions in a way that I’ve never done before. 

During conversations, I continuously sit with a question to myself: “What is the most vulnerable question I could ask at this moment? What is the question that I really want to ask but I’m holding back because I fear it might put the relationship at risk?”

When a friend, whose business is struggling, explained his creative juices were leading him towards productive procrastination, a risky question I asked unlocked a new insight, restored his productivity, and our relationship has strengthened. 

You could say that I’ve been living in “the question.” 

Or you could say that I’ve become aware of the fear that holds me back from sharing my perspective. 

And while a question might not be an arrow-like point of view, clear in its aim and direction, a question has the perspective of a flood light, diffuse but still with an aim. It’s an aim with many possibilities and many answers. 

In the world of relationships, I find asking questions requires vulnerability much like sharing a personal  story. 

The key benefit to me is that vulnerable questions keep me from managing relationships – trying to control everything so that the relationship is “successful.” Instead of trying relentlessly to fit in, garner approval, and maintain control, vulnerable questions allow me to follow my wonder and map new territory in the relationship.

Wonder and vulnerability seem interconnected. 

A question will pop into my head during a conversation: I wonder about something the person said; I have an inkling that something doesn’t quite add up; I don’t see everything is perfectly logical. 

And before that curiosity can even get a breath, I fill in the blanks with a story of my own or an assumption on what the person must have meant to say. I quickly judge and condemn the thought. I tell myself, “You can’t ask that, it’s too risky.” 

So I swallow the question. Or reformulate it with all sorts of perfunctory caveats to water it down into its most palatable form. I turn my wonder into management. 

I am managing the other person's emotions.

I tell myself I don’t want them to get upset. What I really want is to avoid the feelings I will feel when that person gets upset. I don’t fear their reaction nearly as much as I fear my own discomfort that arises from their reaction. 

And this is how we become Canadian Thanksgiving stuffed managers. 

We manage everything. We stick to what we see, to the information that we have, to the stories that we connect to everything that is on the table. And we forget to ask about grandma’s apple crumble or about a surprise cheesecake. 

We totally miss out on the connection and love on the other side of vulnerable questions. 

In relationships, everything you want is on the other side of being seen. It’s on the other side of asking vulnerable questions. It’s on the other side of sharing from the heart. It’s on the other side of you being your authentic self. 

Vulnerable questions are my new favorite tool for increased connection and love.

If you want to move forward, you can’t move forward without being vulnerable. You can’t move forward without other people. Everybody needs help in moving forward. Failure, weakness, vulnerability, it’s like a connector. It connects us to the world because what you’re doing is giving out this signal to the world, ‘I need you because I can’t do this by myself.’ - Dr. Phil Stutz, Stutz (2022)

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Dave Shepherd

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