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dive deep illustration -greenOver twenty-five years ago, before we used the word coaching, I started doing work with CEOs in one-on-one settings. That is what we called it, with a slight variation, one-to-ones. During the hundreds of hours I spent sitting across from the CEO ‘s in their offices, I began to get a feel for what the power, limits and process of coaching entailed. There were no coaching books to read back then, but organizational development professionals and the fields of leadership and counseling informed me on the listening and evocative/provocative methods for adding value to the CEO, their leadership and their personal and organizational lives.

I had many an adventure in those settings. I still do. And I imagine most coaches do as well, at whatever level we are coaching. Our profession leads to breakthroughs in awareness for our clients, as well as unplanned mishaps, laughs, and insight. And, most of all, hopefully, it leads to re-covered or dis-covered layers of their humanity and potential that these leaders need for moving ahead.

Here is just a bit of guidance garnered from what is now well into the thousands of hours of one-on-one and group settings, and from teaching coaching skills to about 1000 professionals on their way to coaching certification over the last 12 years. It is guidance for the internal coaches, and the external coaches who work with them, and I am pleased to be making a small contribution to a book that is broad in its scope and relieves me of needing to be comprehensive.

The guidance:

  • go deep and facilitate the transformational
  • play your hunches, or intuition, with skill
  • understand the psychological dimensions of this human process called coaching


Go deep

Not all coaching issues need deep coaching, the kind that leads to transformational outcomes.  But almost all coaching issues are not very far away from the deeper issues that do require deep coaching. This chart is one way to think of it.

Presenting Issue Possible Deeper Affiliated Issues Possible Deepest Affiliated Issues
Time Management Not seeing the role clearly Being a compulsive doer. Not being able to handle ambiguity. Not enough work on values.
Conflict with a peer Not having a broad enough perspective Having to win and competing : or overly compliant
Unsupportive boss Not approaching the boss well Not fully responsible for self, or rejecting authority, or never having learned the lessons that come with a poor boss
No time for exercise Committing to too many goals Not understanding the reality of limits

Books have been written about all the columns above, best-selling books. Working with Difficult People and  Getting Things Done are just two titles of very popular seminar and book genres (I have taught them and read them)  that locate the issues in column one and two and help people treat the symptoms with rigor.

Coaches need to address the symptoms in column one with our best listening and solution-based coaching. Small and immediate wins build momentum and serve the client. Column two is where the work of deeper coaching begins and column three is where it can end, more often than not, if the coach has the depth to not be satisfied by shallow or even moderate victories. In column three we are coaching the client on mental/emotional models, and blind spots, the ones that help the client renew their outlook and refresh their life-long habits.

So we keep two agendas as coaches, the immediate hot stuff, and the deeper slow-burn stuff. By bringing into play column three we are working with shadow material—parts of ourselves of which we are the most unaware– where the re-capturing of what has been lost in the process of growing adapted to society’s norms takes place. It is here that we work for the deepest of transformations. All the columns provide good work and column three is where my best adventures have been as a coach: like my physician leader who took his natural political prowess and combined it with some self-disclosure and vulnerability, or my manufacturing President who overcame his cloying inner voice, the one he called Igor, that eroded his confidence.

Billy Joel, pop artists and little known executive coach, wrote this in his song” In the Middle of the Night,”

I must be searching for something, taken out of my soul,
Something I’d never lose, something somebody stole

Like all poets, he is giving, in a few words, an image that is universal. He is singing about  soul parts that are lost in the process of living life. Many  successful executives  have only a dim idea that all humans pay a price for growing up to be “successful,” including themselves. But when they get 360 feedback that they are deeply failing in some aspects of leadership, they often wake up and decide it is time to expand . They don’t really know how they are doing and that their shadow is showing until they get the 360 feedback, and coaching can be the means to recapture what was stolen from their souls.

The deep column three coaching is soul retrieval work. On the surface come the problems of difficult employees and the too demanding job. Below the surface is where the work is. Start where the clients are. Do the work that needs to be done. This book has many ideas on how to do just that. And in the process, help them get more whole and recapture the original possibility of themselves. This is what makes leaders more effective.

Play Your Hunches

As coaches we are required to learn the science of coaching and practice it as an art. When we discipline ourselves to learn the science we can then free ourselves up to play our hunches, use our intuition and do what is needed in the moment. What will happen can be inside or outside our models and even our understanding at the time it happens.  It can be what has to happen in the unique moment of this client in this situation with you, the only coach that could be there at this time. This conversation has never happened in the universe before this and will never happen again.

Let me illustrate with one of my adventures. This is not an internal coach example, but the hunch part is the that applies to all coaching.   A few years ago, I was called into a large non-profit organization where the CEO and COO had grown at odds with each other.

My worst/best moment with a narcissistic boss:

The Context:  I am brought in by a non-profit board to coach the COO.  I start with a series of interviews with board members and the VPs. The COO is in deep trouble with his CEO and the interviews reveal he is not preforming in a few important areas. They also reveal that the CEO is notoriously dictatorial, while being quite the visionary. He’s been in charge for 20 years.

In my first joint meeting with the two of them, having created some rapport with the CEO during the interview about his COO, the CEO declares to me and my COO client: “I’ve told my VP team how un-motivating it is for me that I, for the first time, am not going to receive a bonus from the board because of our poor performance.  That just can’t happen!”

I hear what he says and feel a deep reaction inside me of shock and disbelief. He has hundreds of people on staff working for low wages, the recession has kicked in and job losses in his organization have started to happen. Many staff are at this organization, a non-profit, to serve its greater mission and the community. And this CEO, known for a bit of ostentation with his wealth, is moaning about his bonus all over the management team.  I quickly assess that this could be my last conversation in this organization, that the board also respected me, and I respond.  “Do you realize how un-motivating it is for your staff to hear about your bonus?  These people care about the mission of the organization and the community that they serve and to have you talk about your bonus is absolutely un-motivating and it says the wrong things about you as a leader.  So I highly recommend that you never say that again and keep your bonus discussion to the board.”

The CEO looked at me and did a double take, like he did not expect this comment, and so he could not take it in. So I said it again, pulling no punches. He gets it this time. “Oh, yeah, I see your point,” he says, only a bit sheepishly, and nods. We get back to the COO discussion, the purpose of our meeting.

45 days later, the CEO tells me how great the COO was doing.  Five months later the COO was gone, making an elegant exit, (there was no longer enough money to pay those two big salaries).  And the CEO told me how much he appreciated me leveling with him on the bonus discussion.  In this case, I had taken a big risk within a client setting with the boss of the client, one of the sponsors of the coaching. I went with my feelings and my hunch from years of work in organizations that informed me about the rift that so often happens between C-suite concerns and the reality of the front line.

The uber-strong reaction I had to the CEO—basically, a “quit-whining” directive– happened to work well on that day with that client.  I have never been tempted before or after this conversation to say anything as strong and challenging to my client’s boss with so little rapport in place. I am not sure it would work again. And yes, of course I was protecting the COO, my client, from having to put up with this kind of crud from his leader. I could be criticized, for doing so. There is more to the story that would make it too long. My main motive, more of an impulse and hunch, was to be a mirror for this CEO and provide strong feedback.

My point is a simpleone. Use your intuition and play your hunches. I am not sure why I did what I did that day but it worked, or that it was necessary, but I do believe it was was good for my client and his boss. Coaching can go outside the models we have all studied and can be real and value added in ways that only that moment call for. Trust yourself to be in the moment and do the right thing, assuming you have worked on yourself enough to trust your hunches. Discipline allows you to make hunches, remember.

Finally, forgive yourself when you are wrong with a hunch. If this conversation would have blown up on me I would still have a lesson, wouldn’t I?  And expect some failures. I have had clients that definitely needed deeper change work as leaders and I could not figure out a way to facilitate that change, try as I might.

Understand Psychology

Over the years coaching has stayed away from therapy, for good reasons. But that does not mean coaching can stay away from psychology. Leadership is all about psychology and human needs and inclinations, and coaching can be no different. This topic deserves several books, I imagine, and in this short space I will mention one of them. The Chair of Leadership Development at INSEAD, Manfred F.R. Kets de Vries, a psycho- analyst in the executive development field, wrote a book about coaching and therapy, entitled Coach and Couch: The Psychology of Making Better Leaders.

“… our unconscious plays a tremendous role in determining our actions, thoughts; fantasy’s, hopes and fears…  Moreover, the unconscious can hold executives as prisoners of their own past…The clinical paradigm can be described metaphorically as a way of exploring a person’s “inner-theater.” Behind the curtain we have a rich tragi-comedy playing out on our inner-stage with key actors representing the people we have loved, hated, feared and admired.  Early experiences are reenacted over and over again…Every executive and every employee brings their inner-theater with all its dramas and comedies to the work place.  Dysfunctional behavior arises when we try to keep the curtain closed.”

As an analyst who coaches executives, de Vries faces all the issues that most executive coaches face: workaholic patterns, narcissism, projections, questions of meaning. And de Vries, championing the term “therapeutically informed” coaching, argues that coaches without a knowledge of the unconscious are selling the work and their clients short. I could not agree more. My quest to get informed psychologically has lead me to Jungian psychology and Saybrook University. My first real mentor in coaching, Frederic Hudson of the Hudson Institute, saw the 40 year old version of me and advised me “to get more psychological.” I only dimly understood what he was driving at as he observed my too shallow  understanding of the workings of the psyche. Twenty plus years later, I get it, and I see many an aspiring coach who gets seduced by the presenting problem (column one remember) and missing the inner theatre where the action is.

The language of leadership development lends itself to psychological theories. Much leadership work uses narrative techniques, which allows and encourages work on memories, even those out of awareness. Leadership work reviews critical incidents–like mentors, bad bosses, and most importantly both failed and successful assignment—all of which carry both positive and negative emotional charges and mental models from the past into the leader’s present style.

The leadership field also uses somatic approaches like breathing and presence to get past the simple thoughts of shallow consciousness  to deeper layers of awareness. And it  uses metaphor (think Heifetz “getting on the balcony”,  as just one) which allows the entry into images and fantasy. And it explores espoused values versus lived values, so the neurotic splits between a will that intends something (espoused values) and the actual behavior (lived values) are ready material for coaches to explore. Psychological hang ups are often called, in corporate speak, blind spots or career de-railers, and such language makes the “inner theatre” of the leader available for the coach.

So what does “understand psychology” mean for us in the mainstream of coaching? Go back to school to study? Work with a therapist? Perhaps, but  that is not what I am really urging us to do. What I suggest are three things:

  • constantly work on your own awareness. Leave no stone unturned with every bit of anxiety, stressful communication, or repetitive behavior—including doing  too much work—that you experience. Get to its root. Journal about it. Work with a deep coach, a psychologically sophisticated coach, as a supervisor to work on Self.
  • don’t be fooled as a coach that what you are hearing the client present as the challenge or opportunity is the real challenge. What it is about It is never what it is about.  That is how my Jungian teacher James Hollis puts it. So go back to the first part of this essay on go deep. Column 3 is the psychological domain.
  • what you see is a compensation for what you don’t see. This is another Hollis phrase. This means to me, among other things, that our competent leader clients, looking and sounding very much on the outside like they have it together, have an inner theatre that is much different than what we all see. The narcissist is insecure, the control freak managers has an empowering side, the hard core politically inclined leader has an authentic vulnerability.


Have some great adventures, coaches. Be responsible and become worthy of your work and of your client. The privilege of coaching comes intertwined with a large amount of responsibility to work on yourself and see deeply into the human being who has entrusted you with a developmental conversation. Develop yourself continually.