Learning How to Ask

Learning How to Ask

“You ask too many questions.”

I’ve heard that more than once in my life.

The first time was in school. My 5th grade English teacher, ironically named Mr. Ask, told me I asked too many questions.

Years later, I heard it again at our first pediatrician visit after our daughter Caroline was born. We were new parents. Everything felt important and uncertain, so we asked questions. A lot of them.

Each time, the doctor responded the same way:

“I refer you to the manual you received at the hospital.”

The manual, seven days old.

As if everything we needed to know was already written somewhere. As if the answers existed and our job was simply to find them.

Eventually, we left that practice.

When we requested our medical records, there was a note in the file:

“Parents ask too many questions.”

It felt like something out of Seinfeld, except the note was real.

For a long time, I carried that with me, quietly absorbing the idea that some people did not welcome questions.

Then, during this recent Passover, I found myself reflecting on something very different.

At the Seder, the youngest child asks the questions.

Not only is it accepted; it’s celebrated.

Then I thought more deeply about that tension, between curiosity and cynicism, and turned to the Four Sons: the wise, the wicked, the simple, and the one who does not know how to ask.

I realized I had been looking at them the wrong way.

I always wanted to be the wise son. The one who understands. The one who knows.

And if I’m honest, there were moments I drifted toward the wicked son too. Not because I believed what he believed, but because there’s something in all of us that wants to push, to challenge, to be seen.

But I never saw myself as the simple son.

When I moved to Miami two years ago, something shifted.

I started to notice not what I knew, but everything beyond it.

After sitting with that, I stopped aspiring to be the wise son and began to explore the simple one.

Not because he knows less, but because he leaves room for more.

This year, something shifted again.

In my work with AI, studying agentic systems through a course at the Harvard Data Science Institute, I began to see the same idea through a new lens.

The ancient conversation at the Seder table and the modern one in the classroom began to overlap.

Knowledge is no longer aspirational; it’s foundational.

In AI, the difference is no longer what the system knows, but how it is asked.

I noticed it more deeply when I began working with AI in a more intentional way.

Not just asking it questions, but building something with it.

I launched a small pilot, an agentic system to generate daily reflections for the Counting of the Omer.

I called it the MatzoAgent.

In my mind, I framed it through the Afikoman.

The middle piece of matzo we break, hide, and ask the children to find.

An ordinary piece of matzo, broken in half, becomes something more.

The youngest children, who ask the four questions, then search for the Afikoman.

And only when it is found can the Seder be completed.

That was the premise: that something hidden, in the archive, in the tradition, in ourselves, might be surfaced through the right question, asked daily, gently, over forty-nine days.

At first, I thought the power would come from the answers.

But that wasn’t what mattered.

What mattered was everything around the question: how it was framed, how it was guided, and how it was reviewed.

The system worked not because it was intelligent, but because it was directed.

Eighteen days in, a reader wrote to me.

She said she had spent the afternoon wandering through the site, unbeknownst to me, revisiting pieces she had read before and discovering others she had never seen.

She wasn’t writing about the daily reflection.

She was writing about everything the reflection had led her back to.

The system had not given her an answer; it had given her a doorway.

The question, once planted, kept working in her without me.

I began to realize something subtle.

AI wasn’t an authority. It was more like an ingredient.

Something to be used judiciously.

The value wasn’t in what it produced on its own, but in how I chose to bring it into the process.

The reader later put it back to me more clearly than I had put it to myself:

Even with AI, the work is the life. The AI is just how the question gets asked.

The difference between something generic and something meaningful often came down to a single thing:

The question.

The Afikoman: broken, hidden, waiting to be found.

I always enjoyed hiking with my daughters Caroline and Lucy. When they were younger, we told stories and riddles to pass the time.

One of our favorite riddles was the two men at a fork.

One always tells the truth. One always lies. You don’t know which is which.

Somewhere down one path, there is a treasure.

You can then ask one question.

After much discussion, and hiking, Caroline and Lucy discovered it:

“Which direction would the other man say leads to the treasure?”

And then you go the opposite way.

The path to the treasure is there.

But it only reveals itself through the question.

At the Seder, there is a son who does not know how to ask.

That’s how I always heard it.

But this year, I heard something else.

What if he does not know how to ask…yet?

Not because he can’t, but because he is considering which question is worth asking.

In the age of AI, questions come easily.

The harder part is knowing which ones are worth asking.

There’s a moment in Monty Python and the Holy Grail that I keep coming back to.

To cross the Bridge of Death, travelers must answer “questions three” correctly or be cast into the abyss.

The first travelers answer quickly.

They don’t pause. They don’t question the question, and they fall.

Then the final traveler, King Arthur, arrives and the question changes:

“What is the airspeed velocity of an unladen swallow?”

It sounds precise. Intelligent. Impossible.

A trick question.

Instead of answering, Arthur does something else.

He asks back:

“What do you mean, an African or European swallow?”

In that moment, everything shifts.

The Bridgekeeper is no longer the one asking.

He becomes the one being questioned.

He doesn’t know the answer, and he is cast into the abyss.

King Arthur’s instinct wasn’t to answer quickly, but to ask carefully.

And it saved his life.

Not by the answer he gave, but by the question he asked.

At the most basic level, AI rewards speed.

But at a deeper level, the level of agentic systems, the advantage belongs to something else entirely.

Not the fastest answer.

Not even the most knowledgeable one.

But the person who pauses long enough to examine the question, to refine it, to challenge it, and to understand what is really being asked, and what is not.

There is a moment with King Solomon that has always stayed with me.

Two women come before him, each claiming to be the mother of the same child.

There are no witnesses, no clear evidence, and no way to determine the truth through facts alone.

So King Solomon does something unexpected.

He calls for a sword and says that the child will be cut in half.

One of the women agrees, but the other cannot.

She steps forward and pleads, “Please, give the child to her. Just don’t harm him.”

The real mother doesn’t argue. She lets go.

The first traveler answered.

King Arthur asked.

King Solomon designed the question.

Each is a step deeper into the same practice.

King Solomon did not merely ask a question.

He designed the one that revealed the truth.

Maybe the wise son is no longer the aspiration, but the foundation.

Maybe the simple son reminds us to stay open.

Maybe the one who does not know how to ask is the one we’ve misunderstood all along.

Not because he doesn’t know…

but because he understands what it means to ask carefully.

We are surrounded by answers now.

But answers don’t change us.

Questions do.

The treasure is still there.

But it reveals itself not to the one who knows the most…

but to the one who knows how to ask.

If you could ask one question, what would it be?

Everything is known
But nothing opens without
The question we choose

Editorial note: The reader referenced in this essay reviewed the relevant passage and provided permission for publication.

Further Reading

For those who want to explore these ideas more deeply, I’ve included a few pieces that shaped this reflection:

A related essay I wrote on the simple son: Inspirations of Ignorance: Lessons from the Simple Son This essay also includes a photograph of the Four Sons from the Szyk Haggadah, a book my family has had since 1920. The illustration is by Arthur Szyk, whose work brings the Four Sons to life with remarkable depth and detail.