Going Deep Enough

At the start of 2016, I made a commitment to myself. I wanted this year to lead to a significantly higher income than 2015. Not by simply working more, but by becoming more effective at the conversations that actually created clients.

By this point, I was having real breakthroughs with my coaching clients. I could help someone see how their thinking in the moment was creating their stress rather than their circumstances. I could guide them to their own insights without needing to give advice. The rapport I built created psychological safety, and that safety allowed people to open up and shift.

But in my enrolment conversations, I could feel there was room for me to be more effective. Some calls flowed easily, while others never quite clicked. Yes, I was having warm, friendly conversations. People generally liked me and enjoyed talking with me. But more often than I wanted, nothing happened. The conversation would end without any clarity about moving forward professionally, and without a strong desire on their part to continue the work. Looking back, friendliness had become a way of keeping some conversations at surface level. The connection was pleasant, but it wasn’t deep enough to open the door to real change.

When I brought this to Steve Chandler, he wasn’t baffled or surprised. Instead, he pointed me in a simple yet uncomfortable direction. He said the conversation had to go deep enough for something to shift in the other person. As Steve would put it, the needle has to move. Something has to alter inside them to the point where they naturally ask, “How do we keep this going?”

That made a lot of sense. And almost immediately, my internal dialogue kicked in: Great. I need to go deeper. But how do I actually do that?

Steve seemed to read my mind and suggested a way of setting the context that changed how I approached these conversations. I could say something like, “If you were a client, there are a few questions I might ask you. Are you open to that?” Almost everyone said yes. That simple permission shifted the tone from casual, friendly conversation to something more intentional.

One of the first questions he suggested was, “Why haven’t you achieved this yet?”

Asked with genuine curiosity, this question revealed far more than people expected. It helped uncover what the real obstacle was. When someone told me they wanted to get control of their business, for example, the issue was rarely that they didn’t know what to do or what the next step was. The same was often true with health or relationship goals. This question helped them see that the struggle wasn’t about information or discipline. It was about how they were relating to their thinking.

What I noticed was that I didn’t need to resolve everything in one conversation. If we needed more time, we could always schedule another call. As Steve had said, I would get better over time at finding the heart of the issue. There was no pressure to get it “right.” That was a relief. I’d been operating as if I needed to nail it perfectly every time.

Another question Steve suggested was, “Why do you want this?”

That question turned out to be surprisingly powerful. Very few people had ever been asked why they wanted the thing they were chasing. They knew what they wanted, but often took for granted what they believed it would give them. Peace. Satisfaction. Approval. A sense of arrival. Exploring this either strengthened their desire by uncovering what really mattered to them, or revealed that their assumptions about the goal were flawed. From there, we could explore a more direct path to what they truly wanted. Some people call this the goal behind the goal.

All of this pointed to one central shift for me: slowing down.

I didn’t need to be more persuasive. I needed to be more present. I could take my time in enrolment conversations. I could deepen rapport not by being friendly, but by being a coach. By asking meaningful questions. By sharing my own struggles and journey when it was relevant. By staying genuinely curious about how this person experienced their world.

My role became clearer. I wasn’t there to perform as an expert in the Three Principles. I was there to become a student of the person in front of me. The questions weren’t a script. They were part of a way of listening more deeply, a toolkit for truly serving the conversation.

And when I slowed down enough, something else began to happen. The conversations started to change. People didn’t just feel understood, they felt something shift inside them. They experienced the impact of coaching in the conversation itself. And when that happened, the question of working together no longer felt awkward or forced.

It became natural.


Photo taken in January 2016!

With love and appreciation,
Ankush Jain
Coach and Author of Sweet Sharing – Rediscovering the REAL You

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