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4 Ways to Tell If Your Spiritual Questions Are Good Ones

4 Ways to Tell If Your Spiritual Questions Are Good Ones

“Well, now, that’s a silly question.”

And with that, my new homeless friend was off with a breathless destruction of my cheerfully naïve, “How are you?” I hadn’t expected a philosophical discourse in return, but that was precisely what Alan gave me.

“That is a question that cannot be answered. What is man, how is man, where is man going? You fancy yourself a philosopher?” (He did not wait for an answer to this.) “Well, these are questions that philosophers have been asking for millennia, and no one has found an answer. So the next time you come over here, do your homework and ask about the history of Epiphany or what we should do with the monarchy.” 

Not only had Alan established himself as one of the most intelligent homeless people I’ve ever had the pleasure of talking to, but he had reminded me of a key lesson: There are, in fact, silly questions.

“No stupid questions” is the cliché that sanctifies every effort, that emboldens even the most timid to put their questions to the world. And inasmuch as it signals a welcome to questioning, that’s OK.

But as Alan clearly reminded me, even those who write books on the practice of questioning still have something to learn. And in a generation that is so proud of itself for being open to questions, we would do well to make sure that the questions we’re asking are actually good ones.

Over the past decade, I’ve spent a good deal of time reflecting on the questions I ask and how to ask them better. Through undergraduate discussion classes, leading small groups, advising, moderating public discussions and more, I keep coming back to four criteria to help evaluate which questions to pursue and which to leave behind. 

1. Context

Learning to question well demands seeing how our questions fit the context before us. Contrary to the objection of my friend Alan, “How are you?” is a perfectly fine inquiry upon meeting someone. It’s pleasant and open-ended, so as to not be threatening.

Yes, it may be too cursory, a token offering that doesn’t convey sincere interest. But when sincerely asked, the question signals an open invitation for conversation.

Yet sometimes, people make inquiries that simply don’t fit the context or timing. One of the most hilariously egregious examples I can remember was at a mixer upon just arriving at Oxford as an undergraduate. A good friend and I were introducing ourselves to a particularly energetic girl, who turned to my friend and said, “And what are your deepest hopes and dreams?”

I turned away and tried to contain my laughter while my friend graciously responded, “That is way too invasive a question for someone that you’ve just met. That’s like a 10 on the intimacy scale, and we’re at about a 1.5.” It was beautiful. And awkward. And hilarious.  

Knowing the time and place where a question belongs is a more difficult skill than it seems. But it’s critically important. A good question asked at the wrong time or in the wrong spot in a conversation may not move people the way that it should. 

2. Intention

Questions are a form our love takes in the world. When we inquire, we seek something out—we do something that entangles not only our minds, but our hearts. And if our questions are not aimed toward understanding or toward the good of ourselves or another, then we engage in a practice that potentially does unwitting harm. 

Take the expert in the law whose question launches the parable of the Good Samaritan in Luke 10:25-37. Luke suggests he started his inquiries to test Jesus. His only interest was in exposing Jesus, not understanding Him. It wasn’t so much an inquiry as an inquisition. 

As a question, it wasn’t neutral—in part because no meaningful question can be neutral. As something that we do as humans and expressions of our loves and desires, our questions either conform us to the pattern we have in Christ or draw us further away. 

Knowing people’s intentions when they pose questions is difficult. But it’s not impossible. Having spent (literally) thousands of hours listening to people ask questions, it’s easier to tell when someone is genuinely inquiring and when they’re only posturing. What starts in earnestness can quickly erode into an attempt to hold all the attention.  

3. Form

“It’s the heart that counts” is a cliche that needs to be questioned, and badly. Because in discerning good questions from bad, the form matters, too.

Consider the first question in Scripture: “Did God actually say, ‘You shall not eat of any tree in the garden’?” The serpent’s inquiry is a poison pill, designed to erode Adam and Eve’s confidence in the gracious providence of God. But that is discernible in the form of the question itself. 

For one, the question introduces uncertainty about God’s command.“Did God really say?” Not content with a single assault, though, the question opens up multiple fronts.

The name the serpent uses for God drives a wedge between Adam and Eve and their Creator. To that point God had been YHWH, the “Lord God,” the one who is near to His people and will remain faithful to them. But the serpent switches to the more generic name Elohim, replacing the intimate, gracious authoritarianism of the Lord God with a more distant conception of deity akin to the “man upstairs.” The change moves Adam and Eve into foreign and less friendly territory. 

And then there is the most obvious fault in the serpent’s question: God did not actually say, “You shall not eat of any tree in the garden.” He did not say that at all. The quotation is a misquotation, a bit of bad scholarship.  

Our words establish contexts, even when they are packaged as questions. And those contexts establish a range of possibilities for response and for action. Questioning well demands no less than being attentive to the forms of our inquiries. 

4. Depth

This is the most nebulous of the criteria, the one I am not sure I can explain. Good questions take us somewhere—they draw our attention to facets of the world we hadn’t noticed or considered.

Most of the time, our lives stay on the surface of things—which is where they belong. We don’t try to look deeper because we have things to get done. But good questions make us pause and attend to the world a little more closely. They make the familiar seem wholly strange and new, like we’ve never seen or understood it before. 

Questioning well is an art that takes practice. And as my friend Alan underscored for me, there is no end to the need for improvement. But so we should expect.  For the glorious message of the Gospel is that we are freed to question badly, but are sanctified to question well. 

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