The art of understanding, part III: When to speak

Try, train, trust

“But how do I know when to speak?”

It was a question all of us had asked out loud at some point, but even when we didn’t, it was always hanging in the air during those early months of coach training.

Not what to say, but when. That’s what we were all wrestling with.

When to reflect, when to pause, when to ask a question, when to hold back, and when to do something else entirely. It was all a complete mystery to us.

We were brand new to this kind of communicating. We were a bunch of nervous novices, trying too hard to get it right.

Before our training had started, we were used to doing what everyone does in conversation: say something, ask something, keep the conversation moving.

But coaching wasn’t about driving the conversation, as we learned. It was about understanding the person in front of you and it required a totally different, way less pushy way of communicating.

For many of us, this shift from doing to being felt like the pendulum had swung too far the other way. We felt like butterflies just out of the cocoon, our wings still soft, not quite ready to fly. Suddenly, we didn’t know what to ‘do’ anymore.

The theory was clear enough: give space, listen, trust them to lead. But the actual implementation of that lesson was less obvious. It all felt awkward and unnatural.

The question we all had was: If I’m not doing anything, what exactly am I doing here?

We hadn’t yet realized that this ‘non-doing’ wasn’t just passively sitting silent. It was being actively present, just without needing the conversation to go anywhere.

Performing presence

Understanding isn't something you can force.

But even if you’ve stopped pushing the conversation forward, you might still find yourself counting the seconds of silence, rehearsing your next question instead of actually listening.

Don’t worry. That’s normal. We have active brains, and they won’t stop churning out thoughts, questions, and all kinds of interesting things that we would much rather share, than keep to ourselves.

I watched a whole classroom of aspiring coaches (including myself) make this same mistake: when we finally stopped pushing in our conversations, we still hadn’t fully let go.

Whether consciously or subconsciously, we were still waiting for the moment we could steer again, just presenting ourselves more stealthily. We were still clinging to the idea that understanding is something you manufacture.

We liked to think we were being more present, because we had followed the instructions.

But really we were just performing. Still strategizing, still managing, still trying to get it right. Just more quietly…

Letting go of that required something else entirely.

The alternative

So if understanding is not about driving the conversation, what does it take?

Trust.

Trusting the other person to know how to lead and share what’s relevant, yes. But even more importantly, trust in yourself.

That you don’t have to keep scanning the moment. That you’ll notice what matters, when it matters. That you don’t need to steer or push to make something happen.

This can’t be performed, so appearing quiet while internally prepping your next move won’t do it. While trusting yourself like this does look quiet from the outside, on the inside, it’s alert, connected, and fully there.

It’s not pushing, but it’s not disappearing either. It’s staying with them, close enough to feel what’s happening.

You know those conversations where you feel completely seen? The best listeners you’ve ever met aren’t silent because they’re waiting their turn or don’t know when to speak.

They're silent because they trust themselves enough to listen. And they trust the conversation to take care of itself.

And when they do speak, it’s like they’ve plucked something essential from everything you said, and handed it back to you without any agenda.

Like this:

The best listeners: “Hey, how are you?”

You: “Yeah, I’m okay. Just busy. Very busy at work I guess. It's good. Work, life, the usual.”

The best listeners: “Sounds like work isn't as energizing as it used to be.”

You: “Wow, that’s exactly… wow, yes! I haven’t felt challenged at work in a while actually.”

That kind of engaged presence? That’s what trusting yourself and the conversation looks like.

And it’s something you can train.

Training trust

I didn’t trust myself at all when I first started coach training. Like a newborn deer, I was shaky on my legs, unsure, and bracing for disaster every time a silence stretched too long.

I say training but it was actually more like undoing everything I thought I had to do in conversations.

We didn’t do this by studying techniques, reading books, or ingesting a lot of information.

We practiced.

Again and again. Listening, reflecting, holding silence. Missing the moment. Slipping into old habits. Trying again.

Not to ‘get it right,’ but to stop trying so hard.

To relax the grip. To stop managing and start following.

Like a jazz musician practicing scales, not to plan every note in advance but to forget all that and just improvise to the music when it’s there.

Understanding someone doesn’t come from performing the right move at the right time, or grabbing the right technique for the right situation. It comes from allowing yourself to respond freely and authentically, because you were actually listening.

It feels liberating to step into any conversation (no matter the stakes) and know that you can just be there. With them. As yourself.

As opposed to training muscles, trust isn’t something you build by pushing harder. It’s trained by letting go.

Not so you can say the perfect thing at the perfect time, but so you don’t need to.

What it looks like

I’ve learned to embrace the kind of trust that true understanding actually comes from. In myself, in the moment, in the conversation.

I’m not pushing, I’m not disappearing, and I’m not performing.

I’m staying with someone. Long enough to really hear them. And trusting that that’s enough.

It doesn’t look like effort.

But it takes everything I’ve trained for.