Coaching Others Will Make You a Better Leader and Human

by | Blog, Executive Coaching, Leadership Development, Team Coaching

Coaching Others, and That Unique Relationship, Will Make You a Better Leader and Human

How to Coach Others

The activity of coaching, for me, is like a relationship meditation. Those who’ve received coaching at any level will find great benefit. However, what most people don’t realize is the coach also finds great benefit and value. Not all practitioners will agree with me, but a coaching relationship is not one way or merely a service to be delivered. For the past 20 years, I’ve coached thousands of people, in each one of those interactions was a relationship that was important to me. While I may never communicate with most of those people again after our professionally prescribed time together, they had an impact on me. This is because it required me to put all my energy into them and  from them to put all their energy into me. While not a traditional relationship, a powerful one nonetheless.

Suspending Judgement

I fundamentally believe that every individual has so much to offer and so much to access. They want to be better than their current iteration. That, to me, is beautiful. When we both get to a place of psychological safety, we can dig into what’s really going on. From here we can discover a future plan, behavior, or improvement that they want to make and get real about it. It is a powerful transformation to watch. What really makes the difference in this unique relationship is the perspective that abandons judgments and biases that we may bring to the relationship. In the style of coaching I practice, I go into every conversation fully believing that the person I am coaching is creative, resourceful, and whole. This means that I’m suspending any preconceived judgments that others may hold or that I may hold. I can now ask powerful questions without fear and hold up the mirror to the person with a certain level of courage.

Previous Relationships

This is difficult to do with whom we have a very good relationship. For example, if I have to give feedback to somebody and it’s my preconceived notion that they are not creative enough to solve their own problem, or resourceful enough to find what they need to solve that problem, or that they’re incapable of solving that problem, I might hold back because I’ve already given up on them. In a coaching relationship, even as I may hold human biases and opinions, I totally suspend these beliefs and completely show up believing in the other person’s capability to find resolution to challenges and fully capable for owning their success. The client feels that. They feel your trust and belief in them.

Think of someone you consider as a great friend, a soulmate, someone that you fully and openly confide in, and them in you. The reason why you are great friends and soulmates is because there’s no judgment between you. If your great friend makes a mistake, do you avoid talking to them about it? Do you judge them for these mistakes? No, you don’t. You suspend these judgments because you know their soul and you also know their intentions were probably not bad or you have empathy for the mistake they made. You listen to them carefully. You don’t make judgments. You trust their capabilities to move along and help them as best you can. In this scenario you likely felt very good about them confiding in you. That’s how it feels to be a true coach.

Coaching Setup

Sitting with another human being, with a total focus on listening deeply, suspending all judgment that you may have, and truly connecting with others in a state of flow is deeply rewarding. I can almost compare it to a state of mindfulness where you allow your entire purpose to be focused. While in that state of focus, all your own troubles and challenges seem to melt away. Throughout my professional career I’ve had anxieties, crises of confidence, and confusion about decisions. But that all clears away when I can be in total open care for someone else. When a coaching session ends that state stays with me. It’s an exercise in empathy that allows you to sense another’s feelings in a positive way. With all this in mind, a great coach and client relationship is predicated on how the coach engages the client.

Coaching Elements

The process of coaching someone involves many moving parts, but we can break it down into three main elements: Safety, Listening, and Asking Powerful Questions. These the most important elements to consider when figuring out how a coach should engage you as the client.


The word safety in this regard can mean many things to many different people. However, I use it to mean creating an environment where the person you are working with can freely discuss things without thinking there are consequences for their honesty or openness. No one is going to tell their boss or their subordinates they have a competency challenge or they are unsure of themselves in a given situation.

Leaders and successful people will not open up and speak freely if they don’t feel safe. If there is any doubt that what they say could be reported back to their bosses, you won’t even get to the starting line. They need to believe you are there to listen and what they say gets locked away in your mental vault. I like to help disarm clients by telling them, “we are all coping. I do not know anyone that is not challenged with something in their life, if not in this immediate moment, it’s coming”. For clients to know and believe that we’re all just coping and trying to figure it out is a powerful thing. It is a moment for them to relax and release what they have to say. In the moment, it’s reminder that the human condition is more complex than just getting a project done.


As a coach, 90% of your time will be focused on listening. If you receive any formal coaching training, you will learn that the act of listening is a deeper process than just listening to the words the other person is saying. For me, in my coaching process/philosophy, there are three levels of listening. Level 1 is where we listen to what is happening in the moment, the story a person is telling you. In Level 2, you are listening for values and contradictions. Finally, Level 3 is the place where you listen to your intuition about a situation, a person, or a room.

Level 1

Listening at Level 1 is where most people routinely listen to each other. This level of listening is self-focused. A great example of listening at Level 1 is if you are having a conversation with someone and they bring up a conflict they are having with a mutual connection and the you start asking questions to yourself in your head like ‘how does this affect my relationship with that person’ and then your mind drifts off to ‘was I supposed to pick up the kids today’ and then you may drift back to ‘what’s my next question, I don’t know what I am going to ask next’. Now you aren’t paying attention to that person. You are blankly staring back at them without being able to enrich the conversation. We can train ourselves out of this Level 1 listening. It’s akin to mindfulness, and with practice you can train yourself to keep from drifting.

Level 2

Level 2 of listening is where most coaches spend their time. This level is about consciously listening and focusing on word choice. During this level of listening, I am focused on how their words relate to a person’s values and any contradictions they may have. Here is where I get to hear what is at the root of the issue with which we are dealing and helps me move to Level 3.

Level 3

Listening at Level 3 is where you create a deeper connection. You can connect words to thoughts and feelings. In Level 3, your intuition kicks in and provides you with the ability to feel how this other person is feeling without their visual cues. Are they sad? Are they apprehensive? Are they afraid? Understanding these feelings helps guide the conversation and lead to the state of flow I mentioned earlier. When you ask powerful questions in level 3, you are curious and testing your “intuitive hits”. You might be wrong, but these provocative deep feeling questions can create space for exploring new ideas and directions. As a coach, like a great friend, you are courageous to ask the questions that other people won’t. As a coach, you must listen and trust your intuition.

Asking Powerful Questions

We’ve created a safe environment for the person we are coaching, and we’ve listened deeply and intently to them. As coaches, we haven’t really added any value yet. We’ve let our clients talk, vent, and ramble, but we haven’t actually helped them dig into their issues or allowed them to explore the issues. I believe that reasonable people come to reasonable conclusions. Asking clients powerful questions is where we help them do that.

What is a Powerful Question?

Powerful questions are always open-ended and never suggestive. A mentor or manager would ask ‘have you tried this’ or ‘what I would do is…’, but a coach is going to ask, ‘tell me about the things you’ve tried’ or ‘what kind of things can you try’. My team and I have pages and pages of questions we use at workshops and presentations to demonstrate the concept of asking powerful questions. However, these powerful questions shouldn’t be rehearsed so much as guided by the moment. These questions should come from a place of curiosity. Questions like, “I am curious about this…” or “I’m curious, you seem upset by this” or “tell me more about…”. This is why creating a state of flow is so important. Your powerful questions are born out of your connection with the person you are speaking with and from hearing who they are and what they are about.

Using Pause

A great example of this: one of my associates, she’s brilliant, will be coaching someone, and they will say something or make a comment, and she will casually say, “that’s fascinating” and pause. Her client will grab onto the idea that she found whatever was said fascinating and run with it. They will dive deeper into the issue or problem, all the while helping themselves reveal the true issue at hand.

Sometimes the best, most powerful question is no question at all, but rather a pause. Just as you may be sitting with a great friend and listening to them discuss a challenge, you both may just sit with it for a moment or two in silence. As a coach you are not an expert in your client, but a connected empathetic reflection of their feelings. Eventually your intuition will arise if theirs doesn’t. Asking questions is not performance art, it’s managing yourself and your client, providing the space for them to reflect and solve their own problem. If the time together is safe, you trust each other fully, it’s hard not to come to some productive conclusion.

Coaching Conclusions/Wrap Up

I’ve had over 200 hours of professional training, a terminal degree in organizational development, and over two decades of professional development to hone my skill and craft, but it is not that complicated. Yes, there are a few muscles that need to be practiced like creating safety, listening at Levels 2 and 3, as well as developing a sense of curiosity and real care. I think my greatest strength as a coach is that I know how to be a friend. I don’t think a good coaching relationship and the results born from that can be achieved by just following a few process steps. A good coaching relationship comes from two people who can connect, suspend all judgment, have confidence in each other, and be willing to open up about what the future looks like.

The more you work on these elements of coaching, the stronger your coaching relationships will grow. If we all practice coaching skills enough, we listen to each other more, and look for reasonable people to come to reasonable conclusions, we will not only solve our own challenges and create new direction for growth, will create better organizational cultures. If we extend these practices to our society, we will create a better world.

To learn more about how coaching can support you in your professional and personal development objectives contact us today.


About Sojourn

Sojourn Partners is a results-driven executive leadership coaching firm that empowers the professional workforce to think differently in order to realize the full return on investment in themselves and their companies. Professional leadership thinking and intervention, based on years of research and experience, place Sojourn Partners at the forefront in executive leadership coaching, organizational development, strategic planning and culture and climate change.


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