Why I Ask Questions

Over the past several months, Chloe and I have been in conversation with clients, former clients, colleagues, and, in many ways, with our own past. These were not networking meetings. They felt more like an inquiry into a life. 

Across those conversations, and particularly during two recent evenings connected to Optimax, I heard something repeated back to me with surprising consistency: “What Bruce did was ask questions.”

Not strategies. Not answers. Questions.

I’ll admit, it unsettled me. I had always come prepared with stories. About what we built, what worked, what failed, and what it all might mean. I wanted to talk about the reality of things. That lives and organizations are not linear, clean, or predictable. That lives are human, meaning they are messy, contradictory, and often, unfinished.

But what people remembered wasn’t what I said. It was what I asked. For a moment, I wondered: Is that enough?

If a life’s work were reduced to a single line, would it be this: “He asked questions”?

And, as often happens, the question did its work. 

I had lived the alternative. There were times earlier in my career when I believed my value came from answers. I offered them freely, confidently, and often. And just as often, they went nowhere. Not because they were wrong, but because they were mine. Over time, working with leaders and groups, I began to understand something I had once missed:

People are rarely looking for answers. They are trying to find their own. And answers, especially borrowed ones, have a way of closing the very space discovery requires. So, I changed how I showed up. Or perhaps more accurately, I returned to the only way of showing up that ever really worked.

A good question does something an answer cannot. It opens. It disrupts. It reveals. It creates movement where certainty has settled too quickly. It allows people to see what they already know, but have not yet named or perhaps not yet allowed themselves to see.

This is why I am rarely interested in the first question on the table. I am interested in the one behind it. 

What is really going on here? What are we not saying? What must be true for this to make sense? 

These are not techniques. They are work. Rilke, the Austrian Poet, once advised: “Live the questions now.” And perhaps, that is the deeper truth underneath all of this.

I do not merely quote that idea; I try to practice it. I ask questions because I sense the world is often organized around inadequate answers, and because I have come to believe that a living question can be more transformative than a dead certainty. 

The questions are not a method I employ. They are the most authentic expression of who I am. My philosophy made audible, my cause made visible, and my way of staying awake.

So if I am to be known for anything, I find I am at peace with it being this: I ask questions. 

Not as a method, not as a performance, but as a way of staying awake to the moment, to the person in front of me, and to the reality we are trying to understand together. 

Which leaves you with the only question that really matters: What is the question you are not yet asking?