The art of understanding, part I: How to understand everything about a person

Without pushing them to a pulp

If you want to understand someone, the first step is to stop trying.

A few months ago, an aspiring coach asked me, “But how do I understand everything about a person?” Letting out a heavy sigh, his face showed what he didn’t say: I’ve tried everything, and it’s not working.

Normally, I might not have even noticed the question. But the frustration, the exhaustion, the utter mystery of it all—I recognized it clearly. I had been there myself.

I knew what he was hoping for too. “If I can just find the perfect question, the right strategy, if I can just engineer, construct, orchestrate, then I’ll get them to open up.”

My answer to him in that moment? “The more space you give them, the quicker it goes.”

It rolled out like a reflex—because of what coaching has taught me: understanding someone deeply isn’t about extracting every last bit of data—it’s about making room for them to step forward and reveal what’s there.

And it’s not just a coaching thing. Anytime you’re trying to really get someone—whether it’s a friend, a partner, or a client—the more you push, the more they will pull away.

Drilling for answers

I’ve always had a need to understand how things work, but especially when it comes to people, there’s no manual—no recipe you can follow to figure them out. Before I was trained as a coach, I thought the way to go was to ask more, press harder, and push until I got the answers I was looking for.

I wasn’t exactly waterboarding people, but I was definitely making conversations way more intense than they needed to be.

Not only was I a not-so-pleasant conversation partner, but I never got what I actually wanted either. Even if I got my answers, they never added up to something satisfying because I wasn’t listening, just drilling for something deeper and ignoring what was already there.

Well into my coach training, my mentor coaches would try to tell me, “If you’re too busy interrogating, you won’t hear what they’re really saying.” But I couldn’t see another way yet. More questioning still felt like the key to deeper understanding.

Then I started seeing glimpses of something different. First in others—watching my teachers demonstrate real coaching—then in my own training sessions.

When I stopped filling every silence, people started thinking out loud, showing me what was on their mind without any effort on my part.

Before coach training, a conversation would go something like this:

Me: “How’s work going?”
Other person: “Ugh, it’s just frustrating. I’ve had such a busy week.”
Me: “What is frustrating? Like, are you overwhelmed or does the work just suck? Did something happen?”
Other person: “I don’t know, it’s just everything.”
Me: “But something is getting to you. Is it your boss? The workload? Are you bored there?”
Other person: (Sighing) “I mean… I don’t know. Never mind.”

What I started experimenting with during my training would sound more like this:

Me: “How’s work going?”
Friend: “Ugh, it’s just frustrating. I’ve had such a busy week.”
Me: (Pausing)
Friend: “…I don’t even know where to start.”
Me: (Reflecting) “Sounds like it’s more than just a busy week.”
Friend: “Yeah. It’s this feeling that… no matter what I do, I don’t feel like I’m making progress.”

When this started to shift for me—stepping back more and providing space—people would automatically start filling that silence with insights I never would’ve imagined to probe for.

It felt a little like magic sometimes, but I kept slipping back into my old habits.

You’d think that doing less would be easier. But it was the hardest part.

The art of stepping back

“When we train coaches in AOA, there is a single core skill we spend months and months teaching. That skill is Listening. It’s simple, but not easy. Most of it involves learning how to get yourself out of the way.” — Joe Hudson

Eventually, the glimpses won me over.

I saw how, by taking a breath, relaxing my grip on the conversation, and simply being there, we got to the heart of things more quickly and effortlessly. It was like creating an invisible vacuum that people instinctively filled with details, insights, and revelations.

For the first time, I wasn’t just blindly charging ahead, obsessively piecing things together—I could actually get a feel for people without having to push them around.

It felt like a cheat code. And a relief. Because honestly, pushing like that was exhausting and had never felt good.

Finally, my need to understand was being satisfied in a way that trying to control it never could (and okay fine, it helped others too I guess…).

I see it everywhere now, especially in the helping professions—teachers, coaches, counselors. The pros understand that their best work happens when they get out of the way.

It’s why inspiring educators like Maria Montessori and Ken Robinson emphasize letting the child lead, not interfering, and paying attention rather than constantly directing.

It’s the same in conversations: when you stop pushing, people find their own way forward. And ironically, they end up revealing the things you wanted to know anyway—faster, more openly, and without the pressure that shuts down real understanding.

If you force it, you lose

But why does this work? And why does pushing for answers fail so consistently?

I think it’s wired into us. My brain feels like an always-on prediction machine, constantly scanning for patterns, for missing pieces, for answers—completing an unsolvable puzzle.

But people are not puzzles.

For a long time, I thought more effort meant clearer answers—that if I just kept asking, filling silences, and chasing down understanding, I’d finally get to the bottom of it.

But it was exactly what kept me from it.

Real understanding needs space to exist. Otherwise, you end up grasping at nothing. It’s a universal principle: the harder you push, the less you get.

I didn’t just learn this from coaching. I felt it, physically. In part 2 of this series, I’ll share how a slow-motion martial arts practice made this truth undeniable.