Questions and Quests

Are we asking the right questions?

Mar 23, 2023

Dear friend,

Starting this week, I’m shifting my publishing cadence to Thursdays. This allows me to write higher quality work, since I find I have more creative energy earlier in the week. I have a few updates I’m excited for over the next month, and soon some more projects to share. For now, I hope you notice an improved quality as I continue to love writing these.

Questions guide our quests

Sometimes a question gets stuck in your head and refuses to let go. Those questions guide an inquiry that refuses to let you out of it’s grip, turning into an obsession for an hour, a day, a lifetime.

If you have kids, you know this phenomenon all too well. The constant “why daddy” of my four year old daughter, or my son’s never ending barrage of questions about the Mandalorian universe. Much like the idea in What Do You Do With an Idea, a good question may hide from you for a time, but it never really leaves you.

Some questions stick to our minds at the surface. They lodge in the gray folds of our brains where they stay long enough to bug us and maybe our friends; eventually they move on though. Other questions can change the entire course of your life. And the biggest questions, those that have struck thinkers since the early days of man, demand a commitment few of us have ever been asked to give. Like marriage or religious conversion, they hold our minds, grip our attention, own our aspirations until we beg them to leave our poor, ravaged bodies. Even then, we may not be free.

All that to say, I think questions matter a lot. I think they matter so much that we should teach ourselves how to ask better questions.

The first time I really understood how a big question could change someone’s life was when I joined the Navy. I was only a few years out of college, still awe struck by the raw displays of naval power. Surrounded by hundreds of precision weapons and a handful of airplanes and ships, I understood how this power was designed to make our enemies ask themselves “Do I really want to do this?”

As the days passed into night, hundreds of miles from the nearest ship and even further from the nearest land, we’d find our way up to the crow’s nest. A gray steel patio off the ship’s tower, the crow’s nest was our respite after a long day of heavy work. Green newbies and seasoned leaders alike, we’d convene after the last planes had landed and the last reports were filed, swapping stories and submitting to the wonder of the night.

Everywhere for miles the stars shone so bright they looked like a thousand diamonds thrown across a blue blanket. The sticky sweet air would blow past our skin, holding on just enough to warm our skin a degree or two. The smell of the air mixed with the sweet smell of cigars — Cuban or Honduran, and the lightly glowing ring of tobacco burning in our cigars was the only lights below the heavens till the ends of the earth. The stories would continue long after the buzz had faded, long after the saltwater breeze had turned to a chill, and long after the devil himself had retired.

I remember the stories. They’d grip me with laughter and with wonder. Every senior leader that would share a smoke and a tale with us always blessed us with their story of why they’d joined. Every leader I admired had the same story.

DCAG (the senior fighter pilot in the air wing) loved to tell his origin story that started as a 17-year-old kid. His girlfriend at the time wanted to see Top Gun in theaters. His eyes would stare off into the distance, no longer with us on the crow’s nest, as he remembered his blond-haired, blue-eyed girlfriend, and how she cut the date short because he had ignored her the entire movie. His hands involuntarily traced every dogfight as Maverick fought MiGs, played volleyball, and got the girl. He remembered more about the screen than he did about her. And I get the impression she was beautiful.

He ended the relationship, applied to the Naval Academy, and the rest was history.

I listened to that story hundreds of times that year. I compared my own ambition to the chiseled jaws and sweeping hair (or sometimes shining head) of the leaders I admired the most. I loved their childlike joy when they had flown that day. I wondered if I had the gravitas in me to own a room like them. Most of all, I looked forward to the story at the end of a long night.

By the twentieth time, I could guess most of the story. But I always knew the ending. I anticipated the moment their eyes returned to the night, when they’d fix their gaze away from the sky and onto my eyes. Whether they’d seen Tom Cruise once or twenty times, they’d all share how he’d sparked a question that captured them. I could ask the question a split second before they would.

“I asked myself, could I do that? I’m still finding out”

As an aside, the craziest fighter pilot I ever met and the most like Maverick in real life was an Israeli Colonel I went through Navy Test Pilot School with. Ironically, he had never seen Top Gun before. He told us of sitting in an air conditioned cubicle taking his entrance exam, wondering what his future was going to be. I imagine him seeing afterburners on the page. I smile thinking that he told the recruiters he was turning down his engineering position to fly airplanes. He’d regale me with stories of flying F-15s and F-16s with multiple combat missions. I always suspected his stories stretched the truth; I never dared to ask. That was one question that wasn’t worth risking.

He would close down the officer’s club most nights. The man was like an artist at the stick of a plane.

In A More Beautiful Question, Warren Berger breaks great questions into Why, What If, and How stages.

Why questions are all about seeing and understanding.

To ask good Why questions:

Pause
Challenge assumptions (including our own)
Use inquiry to gain a deeper understanding of the situation
Question the questions we’re asking
Take ownership of a particular question (become obsessed with it)
Be comfortable not knowing

What If questions are all expanding possibilities

Good What If questions (or what the business world calls brainstorming) rely on:

combinatorial thinking, or the ability to combine ideas that don’t normally go together
smart recombinations, or finding novel connections between old ideas
Acquired knowledge about the problem from diverse viewpoints
state of inattention, or when you’re not focused on a question. This is why our best ideas come in the shower

How questions are where you converge on an idea and give form to it

How questions are the domain of prototypes. They involve incremental progress with lots of failures. If we want to get to an answer, we have to go from Why and What If to How.

A More Beautiful Question is a business book, and you may not be interested in business. But maybe, like me, you’re interested in the questions that capture our attention. We don’t choose our obsessions. But I believe our questions let us guide that inquiry into areas that light up our soul.

Academic researchers are taught how to frame really good research questions – the null hypothesis, refutability, and the like – but the rest of us are left to figure it out on our own. As more people discuss the importance of questions, I think we can all learn how to inquire better. Whether it’s the new skill to work with an AI system or the means to find your next path, questions are having a heyday.

But I can’t shake the feeling we’re asking the wrong questions. That we’re only really scratching the surface, and we risk being held by a paper tiger. What are we missing?

Until next week, have an intentionally curious week,

Latham

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