Questioning my questions

On my renewed respect for precise articulation

“It is better to know some of the questions than all of the answers.” — James Thurber

“To be able to ask a question clearly is two-thirds of the way to getting it answered.” — John Ruskin

“Judge a man by his questions rather than by his answers”  — Voltaire

Alright, alright, I get it. Questions are important, jeez.

And naturally I agree, how could I not, with the bright minds above.

I think about, work on, and I’m even trained in asking questions. And I thought I was pretty much on top of my question game. But apparently not always.

Mediocre

I’m part of a monthly ‘conversation crew’ called the Da Vinci Café. Basically a bunch of highly curious, broadly interested, and intellectually inclined folks who get together on Zoom to talk about deep stuff.

Since it’s still in its experimental phase, the format differs each session but usually, to get things going, someone presents a question as a starting point for further discussion. This leads to a couple of responses and gets the ball rolling. The discussion then continues in a big group, in breakouts, or both.

This time, I presented a question to the group.

As soon as people began to respond and discuss, it started to dawn on me, these responses were different than I had expected. They were taking this discussion into an entirely different direction as I had intended with the question.

Had I not been clear?

No, I had not.

They were actually responding to my question quite carefully, accurately, and thoroughly. I realized quickly that they had heard me correctly but I had just posed an extremely mediocre question.

Mediocre in terms of articulation. It was unspecific and broadly interpretable I now clearly saw. Looking back at my own question I realized that if it had been posed to me, I would have probably ‘misinterpreted’ it myself.

After my initial question, the discussion went on for more than half an hour and although it was still very interesting, I felt unsatisfied. Not because I didn’t ‘get my answer’, these meandering conversations are not meant to be straightforward and I quite enjoy that, but because I had thought that I was a better questioneer than I apparently was.

Professional

The first question we ask in a conversation matters.

It drives how a conversation starts and the possible direction it takes, at least in the first instance. It sets the tone.

In coaching conversations this is especially true. Depending on the type of coaching, we might want something that sets the scene, states some boundaries, and clears the way for a constructive conversation. I’m always tinkering with my ‘first questions’.

There’s a big difference between ‘How are you?’ and ‘What have you been working on this past month?’

Since we’re having the session for a specific purpose, ‘How are you?’ is often unhelpful and can waste valuable session time. It’s casting too wide of a net. People can go into last weekend’s festivities just as easily as their most private mental challenge, or anything in between.

I’m not saying people shouldn’t ever say ‘How are you?’ , I’m just clarifying how broadly these questions can be interpreted and how ultimately unruly they can be.

I realized in the café that it might be worthwhile to rein in and refine my questions outside of coaching as well.

Airtight

After writing last week about my struggles with posing good affirmations, I was pretty confident that questions were not something I had to look into.

I’m good at questions. I’m a naturally curious person and enjoy asking them. I was trained to make them powerful as a coach, I think about them a lot, plus, I’ve been asking questions all my life.

But the humbling experience in the café put them back into focus big time. Especially their phrasing.

There’s a level of specificity to questions that can make them sharper and less broadly interpretable. If the question is vague or broad, chances are higher that people interpret them in their own way. Especially in a space, like the café, where this type of open interpretation is fostered and encouraged. And what sounds like a good question in my mind, isn’t always that clear when spoken out loud, especially to a group.

It made me refocus my aim and energy back on questions. And mainly, how to articulate strong, ideally ‘airtight’ (as narrowly interpretable as possible) questions.

Damage control

Language is limited. Even if we’re constructing our sentences extremely carefully, still, we never quite know how they’re going to land in another person’s world.

Everything is open for interpretation.

And obviously there’s no way to make a question completely airtight. We simply can’t. Even if we manage to express what we really mean (which is already difficult and nearly impossible), even then, the interpretability is always going to be broad because language is symbolic, imprecise, and personal.

What we can do though is to deploy some damage control. Making it the least broadly interpretable as we possibly can before we ask it. Add qualifiers and caveats, or even context to the main question.

And after we’ve asked it and we’ve learned the general response, refine it once more. As I will do with mine.

So what would I do if I had a time machine and could go back into the same session and ask the question again?

After having come up with an organic, curious, and engaging question, I would simply take a beat and purely look at the articulation of the question. Go through it and question the question itself. How could this be interpreted? What could I add or subtract that would make it clearer, pointier, and narrower?

Now, sadly, I don’t have a time machine yet. But who knows, I might ask the cafe for a rematch.