By Matteo Cassese. I help brilliant overthinkers lead.
Leadership coaching is one to one work on your problems as a leader. The coach asks, you find your own answer. Nothing is taught. You find your own path, and I share my experience only when it saves you time. The work is about future action. If it were focused on healing past wounds it would be therapy.
Someone told you to get a leadership coach. What would you be paying for?
I stumbled into coaching. I never thought I would be a coach. My clients taught me how to coach them and it has been the most wonderful professional discovery of my career. Today, I am proud of defining myself as a coach, a sparring partner to extraordinary individuals who wish to accomplish the extraordinary.
Leadership coaching in one paragraph
Leadership coaching is the work of finding the gap between the leader you are today and the leader you wish to become. What is the gap? That’s where the coach lives. I shed light on the gaps, and then we figure out whether this is a gap we want to fill or a gap we need to avoid. It’s like one of those holes in Super Mario: do we need to jump longer to avoid the hole, or do we need to fill the gap with new knowledge, with new techniques? Coaching works because you get interaction, you get validation, you get feedback. The principles you find are yours. This is the kind of work I do in leadership development coaching, one to one.
Leadership coaching is not training, mentoring or therapy
Training teaches you a skill you did not have. Mentoring hands you a path someone else already walked. Therapy looks for the reasons you are the way you are.
To arrive at a mindset change you don’t need new skills. You don’t need new information. You need realizations.
A mentor will tell you what to do, and a coach will ask you what needs to be done. In leadership coaching the coach wants to know what’s your way of doing things. A mentor, rightfully so, has a path: do this, do this, do this, and then you become a great leader. I have a good sixth sense for what people are ready to hear and what they need to figure out for themselves. So I will switch to mentoring, or anchor to one of my own experiences, when you are perfectly fine hearing the answer and figuring it out by yourself would be a waste of time.
Coaching is about action and therapy is about reflection. I’m not so interested in the roots, in the causes. That is the job for psychotherapists, a profession I respect enormously. My interest is in breakthroughs: trying things out and seeing if they change the way you see your board, your meetings, the people on your team and yourself. I send a lot of clients to therapy if they haven’t done therapy. It helps them figure out who they are, and then they can figure out what they want.
On this topic you can also read what does a business coach do.
What happens in a leadership coaching session
In a leadership coaching session I never know what I’m going to ask you next until you finish talking. Even though I have a path in my mind, I let your answers influence that path. I’m really listening. I’m very curious. I have no preconceived idea. I’m a baby with eyes wide open, and when you give me the answer, at the very least I ask: what do you mean by that? Your answer sparks another question, and we follow these trails.
We spend a little bit of time on the problem, and we try to understand what the confines of the problem are. Then we try to find the ways out. The decisions, ideas and experiments that are born out of this process are yours to implement in between our sessions.
I’m your coach, but I’m also another teammate of yours. We don’t work on theory, or on how you should do it. We work on: how do we solve this? I’ll be your sounding board, your support, your partner and your coach. I don’t think it’s useful for anybody to have an expert on the mountain who tells them how it’s done.
When leadership coaching is the wrong answer
When I go to my personal trainer, I don’t need to motivate myself, because I have him telling me one, two, three, and I don’t want to disappoint him, so there is a delegation. It works in personal training because I just need to move this weight from here to here. It doesn’t work in coaching. There is a tendency to say, okay, I have a coaching session with Matteo, click, okay, Matteo, what do we do today? That is the opposite of effectiveness for me. A good coaching process is: I have these 15 problems. Okay, we can work on that.
Leadership coaching is the wrong answer when:
- You want the answer handed to you. A mentor will do that better than I will.
- You expect the session to do the work for you. The work is yours, in between the sessions.
- The problem is in your past. Then therapy comes first.
- You want someone to decide for you. That is consulting, and I stopped doing consulting work in 2019.
What leadership coaching costs and how long it takes
Is it worth it? Compared to the training market, coaching will be more expensive. Leadership coaching starts with an intro call: tell me where you want to go, and I’ll tell you how we get there. Monthly coaching starts from 1,000 EUR a month: two 60-minute calls a month, unlimited emails and messages in between the calls, one to one, online. The full pricing is on the leadership coaching page.
How long does it take? Coaching can vary in length. Typically people work with me for a year on leadership coaching.
Questions leaders ask about leadership coaching
Is leadership coaching the same as executive coaching?
It’s the same work.
Who is leadership coaching for?
Leadership coaching is for founders and executives who walk in saying: these things are going all wrong, I’m feeling this way. I help you figure out what you want and how to get it.
How is leadership coaching different from consulting?
I worked as a consultant for seven, eight years, and in my experience no client appreciates the work of a consultant. They only appreciate the work they do themselves. More in what does a business coach do.
Does leadership coaching work?
It does. I am especially good at creating a space for you to feel safe and open up about the real cause of the problems affecting you as a leader. This vulnerable space allows us to cover enormous amounts of ground in very little time.
Is it online or in person?
Online, one to one or in-person. Up to you. Between the calls you write to me whenever something happened in a meeting. I’m always curious about getting updates in between calls and meetings.
Before you book anything, take the free leverage assessment. Three minutes, and you arrive at the intro call knowing what to put on the table first.
What you should do next
Discover what’s holding you back from the inside out. Understand where you naturally have leverage and where it eludes you.
Take the free founder mindset course.
Tell me where you want to go. I’ll tell you how we get there.
About Matteo Cassese
Business coach, keynote speaker, and mythmaker, Matteo helps leaders thrive in chaos and conflict. Twenty years across tech, film and consulting, seven of them at Warner Bros., founding-team at Netflix Italy, and advisory work for Sony, LinkedIn and Heineken. His unique perspective as a queer nerd passionate about mythology and technology creates a safe space for leaders to be vulnerable and reach their full potential. Read more about Matteo.
