How To Prepare For Your Executive Coaching Call (With Me)

Your first coaching session may have you feeling excited and nervous. Excited about what’s possible and the changes you will make. Nervous about not knowing exactly what to expect, and what will be required of you. I’ve been there myself and know what it feels like.

If this is our first time connecting for an executive preview session, or if we are about to start a coaching program, or if you are just curious about this work — there are 21 ways you can prepare to get the most out of your investment.

What I’m sharing with you below is specific to how I approach our work, presented in no particular order.


Coaching is like riding a bicycle

I can tell you all about how to ride a bicycle – to move your feet, to balance, to keep your eyes up – but until you actually experience what it feels like to ride, it won’t make any real sense. Coaching is similar – I can tell you about the benefits, the results, the tools, and the client stories – but it won’t make real sense until you experience it for yourself. Instead of talking about it, let’s set up a call and see what kind of difference we can create for you.

Investing in yourself

This kind of engagement is for people who are ready to own their authentic place in the world, perform at their best, and make an impact with their work. To make transformational change, or to significantly improve your performance requires commitment and investment in yourself. Most clients invest $10,000 or more over the course of our work together, on top of the time for our calls, and the implementation of the insights we discover.

You have to do the work

Much like fitness — I can’t do the hard work for you, eat healthy for you, or exercise for you. You have to do the work, and there has to be a reason powerful enough that will keep you going when you face obstacles and setbacks. My role is to help you discover that reason, the future you want to create, and support you along the way.

I am in your corner

Studies show that more than 50% of CEOs experience loneliness, and 60% of those also find their performance suffers as a result. What I found is that high-performing leaders often don’t have a support structure they can lean on. They can’t share their true thoughts and feelings with their employees, their team, their peers, friends and quite often – their spouses. Our work creates a safe container where you can be truly yourself, and work through your challenges without judgement. I am in your corner.

Coaching and therapy

While there is overlap between coaching and therapy, the simplest explanation I came across is that therapy tends to deal with healing the past, while coaching deals with creating the future, from the present. Each is powerful in its own way, and you may want to leverage both. Sometimes, in coaching sessions, we’ll dig into your past to discover the roots of your behaviour or worldview today.

The thing is rarely the thing

Rarely have I had a client who came to our work with the “real” challenge. Most often, there is a challenge behind the challenge — the real reason that led them to seek out support. Sometimes it’s conscious and often it’s not. That’s where our work takes a transformative turn. You might think that your team is underperforming, and they should just do better — and we might discover that you’re the cause of the dysfunction. A couple of years ago, I worked with an extremely successful entrepreneur who had communication issues with her team, and we uncovered that the real challenge was her relationship with her life partner. If there is a reason behind the reason, I will help you reveal it.

What got you here, won’t get you there

You may have heard that statement before, and I found it to be true. What got you to this point in your life and career — your childhood, schools you attended, friends you made, lessons you learned, experiences you had, positions you had, teams you led — often create an invisible ceiling that’s exactly what’s holding you back. Our work shines a light on your current worldview, behaviour, and the impact of both on your success. We then make purposeful changes to help you unlock the next level of your authentic performance.

This is a 200% relationship 

I remember reading this the first time and thinking it was a silly statement. After working with dozens of leaders, it started making sense. A coaching relationship requires both of us to be fully present and fully invested. That’s how I show up to our calls, and I hope you do as well. The best results occur when you show up at 100%, and I show up at 100%. When we come to the work from that perspective, we can create transformational results.

Insights and action

You’ll find that you will often discover an insight. A new perspective that shifts the way you look at the world. Sometimes they’re mind-blowing (“Wait, I am responsible for how our COO treats their team?”), and sometimes they’re subtle (looking at client meetings like a game of golf was a recent one). One single, powerful insight can change your professional trajectory. And… an insight alone isn’t enough. We need to put it into action to create the results you’re seeking. It becomes a cycle of insight > action > insight > action > insight > action. That is what actually gets you to an intentional, created future.

Allow things to simmer

Sometimes there is a question, or an idea, or an insight that doesn’t occur to you until days, or weeks after the call. Sometimes you might feel like nothing happened in a session, and you may wonder if it’s working. Let things simmer. Tumble them over in your mind. Reflect on the conversation. Journal on it. Notice what thoughts or feelings you might have. How do those serve you? Where else do they show up? YOU can create incredible value out of any session if you choose to.

Sometimes all you need is one 

I’ve had a number of calls where the client was complete in one conversation. Something shifted, they got what they needed, and went off on their way. I don’t put any pressure on you to work with me. You may only need one call, and that’s perfect.

Nobody needs coaching

Nobody NEEDS coaching. You are absolutely fine just the way you are, and you will get the results your current trajectory allows you to create. You can read books, take courses, or find a mentor who is further along than you are. There are lots of options available. Yet… some people WANT coaching. They WANT someone to walk with them, to be a stand for their own brilliance, to reflect who they really are, to remind them of their purpose when times are hard, to push and to challenge them, to support them through doubts, fears and questions, and to celebrate their success. They WANT to reach a new level of performance, success and impact — and they’re ready to make the necessary commitment. Unfortunately, I can’t want your success more than you do. That never works.

This is a workout

One of my mentors tells all of his clients to look at their sessions like a workout. It’s like going to the gym and working out with a trainer. They’ll push you, they’ll challenge you, they’ll support you and spot you on your last rep. Think of a coaching session as a workout. We’ll get in, do the work, dig deep, and with intent and consistency — craft the results you’re looking for. Come ready to work out.

We are friends off

A client I coached years ago told me “Man… for that hour, we were friends off!”. Ever since then, I set the same context for every coaching conversation. We’re not here to make you feel good or liked. You are not here to have a nice conversation and leave the same way you came in. I’m not here to be your friend. I AM here to serve you. Professionally. To tell you things other people won’t tell you. To reflect to you the impact of your thinking, feelings, and behaviour. To see the best parts of you, and challenge you to rise to that version of yourself.

Reserve time to reflect on the call

Timing coaching calls can be challenging. Sometimes they happen in the middle of your day, in between calls or meetings. Give yourself the gift of reflection. Strike while the iron is hot. Set aside 10, 15, or 20 minutes after our call to reflect on what worked for you, on your insights, and the actions you will take as a result. You will receive a post-session form to lock in your learning. While that form helps me keep track of our work, it’s meant for you to clarify your thinking.

Push back and shape the conversation

I will often check in with you during our session, to make sure we’re where we need to be. Sometimes I may notice something worth exploring and follow the thread in a specific direction. If that is not serving you, push back. You are an active participant in this process, and you get to shape the conversation so it serves you best.

Create the value

Just like the fitness analogy from earlier, I can not create value for you in these conversations. You have to take responsibility and create value for yourself. I will bring my coaching and consulting expertise, tools, frameworks, resources, connections, and experience. Come into the conversation with an open mind, and look for ways to create value out of the experience. How can you apply your insights in a way that creates generous ROI for you?

Please don’t try to be “good” or impress me

I remember holding back a lot when I hired my first coach. I wanted to impress them or have them not think less of me if I shared something vulnerable, or exposed a deeply held weakness. That only slowed us down, and I got less value from my investment. I invite you to not hold back. You don’t have to be “good” for me, you don’t have to impress me, you don’t owe me anything. There is zero judgement with whatever you bring to the table. If we are talking, I’m already impressed. Let’s put that aside and get to work.

Bring something real

If you want to get real value from our time together, bring a real challenge to the table. What’s keeping you up at night? What’s your greatest challenge right now? What’s the real issue you want to work on? What do you want to create next? Sometimes it takes a while to draw this out. The sooner we get to the real crux (or cruxes), the sooner you’ll generate meaningful results.

I’m not a fit for everyone

My coaching clients have transformed their lives, their teams, and their organizations. They’ve broken through glass ceilings, earned executive positions, and led companies through significant changes. Some have called me “the CEO whisperer” and said they should pay me double … AND … sometimes it just doesn’t click. I’ve had calls where we couldn’t create forward momentum, and I’ve had calls where all they wanted were simple tactical answers I didn’t have. It’s not always a match, and that’s perfectly fine – there are thousands of other coaches, consultants, books and courses to choose from.

Remedial and generative experiences

There are generally two modes for our work. Remedial — when we need to address a blind spot, a challenge, a performance or a communication issue. Think of this as clearing obstacles out of your way. The second mode is Generative — when we are exploring what’s next for you, the future you want to create, the bold new ideas you want to pursue, the next level of your performance and what it requires of you. This is where really exciting change can happen. Expanding what’s possible for you, and throttling up.

If that didn’t scare you off, we’ll get along just fine! If it did, you would have missed this awesome dad joke:

What did the ocean say to the beach?

Nothing, it just waved.

Are you interested in exploring how we might work together? Write to me. Tell me about what you want to create, what you want to change, what’s your greatest challenge? Let’s have a conversation.

If we are soon to have a call, know that I love this work and I am so looking forward to it!

– ernest

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