How Should I Start A Coaching Conversation?

By Toku

Every coaching conversation that ever was had to start somewhere. Whether it was a life-altering session that changed the course of human history or the worst conversation any coach has ever had, all conversations have to start.

So how in the hell are you supposed to figure how to start it?

When I was a new coach, I loved being in the mix of a powerful conversation. I could feel my clients getting insights and new understandings, I could feel the next question on my lips, but at times starting a coaching session felt a little like starting a make-out session. Polite but awkward conversation, tentative advances and subtle cues, and a fair degree of uncertainty and self-consciousness.

Once I got some experience under my belt I noticed that my OPENs started coming from a different place. I would ask the same question again and wait for a response. And while the question got things started, I felt a little like the husband in a stagnant old marriage taking my boxers off for our tried-and-true Sunday night ‘whoopie-making’ session.

Which is why whenever I think about the question of how to start a coaching session I try to think about what can make a coaching session both simple and direct, but also powerful and unique. Which is why in my OPENs I always try to include three key elements:

  1. Rapport: Before you are coach and client, you are person and person (unless of course you are coaching an alien, in which case you are person and xorlax). So first be a person; ask them how they are, share a little about yourself. This shouldn’t be very much of the conversation and notice the tendency to stay here too long. But building rapport is essential—especially if this is a new client or your first conversation.

    While you may abhor small talk, these social pleasantries get a lot done in a short period of time.
  • Comfort. Since we know how to answer social questions, we feel more at ease and can dust off the rust of our conversational mind.
  • Connection. We use these simple questions and curiosities to connect with lots of people so there is a nice neutral groove that helps us get connected quickly.
  • Transition. These rapport-building questions can stand as a transition from whatever was before into the space of a conversation.
  1. Context: Once you’ve gotten that out of the way you need to set some context. If this is the first time you’ve coached someone you can do this by creating a set of simple agreements. The ones I’ve used for a long time are:
  • Anything is possible. In your regular life there are rules about what’s possible; for the next hour can we suspend those rules?
  • Radical honesty. In most of life we aren’t honest because it’s dangerous, so let’s agree to be honest with one another—you about what’s really going on, and me about what I really see.
  • I do deep work, but you control the depth. Some coaches coach on the surface, but I love to work on the physics that dictate your world, so I’ll go as deep as you want and you can always say, “Hey, can we go deeper here,” or “Hey, can we slow down.”
  • 200% responsibility. In most of life we take 50% responsibility, and then if the other person doesn’t meet us we drop to 40% responsibility or lower. In this conversation you’ll agree to get what you want even if I ask the dumbest questions in the world. And I’ll agree to treat you like your life changing breakthrough is a question away even if you show up incredibly resistant.

These agreements—which I’ve adapted and adopted from conversations I’ve had with Christina Berkley, Rich Litvin, and more—are powerful because they set a simple but impactful context for coaching. They set a context of possibility, depth, honesty, and responsibility. Without expressing these contexts it’s very likely that my clients and I will default to a context of fear, doubt, protection, and safe betting.

Of course I don’t use agreements for every conversation, but I do make sure that we have a powerful context, either an existing context from previous coaching or one created in the moment.

  1. Presence / Awe: Michael Neil offers a simple model of coaching in two steps: (1) Show up, and (2) Respond to what shows up. And even though this model is incredibly simple it’s also powerful because in many ways nothing is more powerful in the opening of a conversation than to be really present with our clients.

For most of our lives people aren’t really present with us. They are self-conscious, distracted, and set on their own agenda. So just being willing to be really present with your clients is a deeply powerful gift. Developing this ability through meditation and concentration practices can help but you also have to deploy that ability for it to be effective.

Often new and even experienced coaches are so worried about doing a good job that they forget to deploy their presence with their clients. Which is why many great coaches start sessions with deep breathing or a mini-meditation as a way to get both themselves and their clients really present with one another.

Even more so, masterful coaches actually generate a palpable space of awe around their coaching. Some do it with their deep presence and their being, some using the environment of the coaching experience, and some using meditations, incantations, or agreements that evoke a sense of awe for the entire session.

In some way the goals of all three of these elements are the same. The same as in any ritual that shifts us from our everyday life to something different, more magical.

I remember recently on a trip to San Francisco a friend and myself stepped inside a cathedral we were walking by. And almost immediately something changed. The air inside was still. People talked quietly or whispered to one another. The light coming through the stained glass shaped the energy into one of mystery and magic. The arches and height of the ceiling spoke to the work, planning, and craft that went into creating this building.

The creators of cathedrals understood well that in creating a sanctuary they needed to offer an experience that asked humans to step out of the mundane and into the divine. And that’s what you’re doing when you start a coaching conversation.

You meet your clients at the entrance of the temple in the midst of their human lives, you walk with them through the arches and doors as they move from the ordinary to the extraordinary and then you sit with them quietly as they are drawn into the chamber of divinity and have their inner selves prepared and quieted to be touched by something beyond themselves.

So if you want to start your coaching sessions powerfully you must learn the simple but powerful process of crafting a powerful OPEN, and learn how to use these powerful elements so that you know what you’re doing and at the same time it still feels like you’re doing it for the first time.

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