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CEOs and Key Executives, If you don't have an Executive Coach, You Are Flying Blind

When pilots get instrument rated they put a physical hood or visor with a blocked view on their heads obstructing the forward and horizon vision. These pilots are to fly the plane with only view the instruments and messaging with ground control radio. While pilots may be able to look at instruments (like their dashboard) to assist, having assistance from ground control is vital if they are to land safely or navigate away from weather reported from other pilots. Similarly, many CEOs seem to unwittingly fly by vision only, and when forced to operate at a higher level when their are greater risks and unseasonable business weather, they are forced to fly by instrument only (using their dashboards, key performance indicators, and levers of business). Yet if they use only these instruments and do not have support of ground control, they risk great peril to their companies. This is where the executive coach comes in... they are literally the ground control providing assistance and narrative that is not visible to the executive while flying their business.


Since the beginning of recorded time, kings, leaders, and what we would call executives have sought counsel, guidance, and mentoring from coaches, advisors, and mentors. One of the earliest coaches in recorded history, Socrates, believed that individuals learn best when they have personal ownership of a situation and take responsibility for the outcome. The tool or catalyst most cited for the success of Socrates coaching method was his deep-rooted questioning method. When broken into its basic parts, Socrates coaching method had six basic question threads:

  1. Asking clarifying questions, striving to understand basic concepts. ...

  2. Probing underlying assumptions. ...

  3. Probing rationale, reasons, and exploring physical evidence. ...

  4. Questioning viewpoints and perspectives. ...

  5. Probing implications and consequences of alternatives. ...

  6. And in the end, questioning the questions themselves.

As an executive coach, this last point is most interesting to me as frequently the opening question perplexing the one being coached turns out not to be the best question at all. A coach using the Socratic method will often invite the one being coached to reframe or rewrite the opening question after the initial conversational discovery yields a fact pattern, assumptions, and events that add color to the analysis. Hence Socrates’ great credit to the coaching industry is to relay that frequently the problem lies not in our answers, but in our questions. If you ask the wrong question… and answer the opening question without sufficient discovery for underlying issues, answering the opening question without mindfulness of the situation can lead to poor outcomes. The University of Nebraska has an informative article covering this type of coaching method; Socratic Questioning.

However a great coach is more than just an AI autobot of hard questions. A great coach has the ability to partner with the one being coached to help transform a series of events, situations, assumptions, and considering the character of the individual being coached… and through artful reframing, encouragement, and motivational conversation the coach helps one being coached can raise their level of performance much higher than if there had been no coaching. In this light, the discernment and emotional intelligence of the coach is vital to understand and appreciate the nuance of situations, settings, and human experiences.

Consider for a moment one of my favorite illustrations of the role and power of a great coach in the historical recreation of “The King’s Speech,” The coach (in this story is a speech therapist) who works with the King to overcome the King’s speech-impediment, self-doubt, confidence, to deliver an authentic speech in his own style that honors the King’s own authenticity. Notice in the story that the coach (himself a practiced speaker and orator) does not give the speech himself, his role is to help “the King” to deliver the King’s speech helping the sovereign reach his greatest potential. The relationship between the King and the coach is challenging, the coach asks much and its not always pretty, however over time their relationship builds, trust increases, that in the end, the professional relationship becomes so strong that the King invites the coach to take a seat in the royal family’s box at events. There is much to learn from this story for executive coaches and the ones being coached.

In modern history, sports performance coaching has taken a leading role in shaping what a coach brings to the game. The quotes below from great sports coaches are equally applicable to executive coaching today. Consider the following sage advice:

“The interesting thing about coaching is that you have to trouble the comfortable, and comfort the troubled.” Ric Charlesworth, Hockey

“One of the things you realize with a lot of high achievers: You have to figure out a way to make things their idea.” Hank Haney, legendary golf instructor and coach to Tiger Woods (2004–2010).

“To be as good as it can be, a team has to buy into what you as the coach are doing. They have to feel you’re a part of them and they’re a part of you.” Bobby Knight, Basketball.

“Winning is not a sometime thing; it’s an all-time thing. You don’t win once in a while, you don’t do things right once in a while, you do them right all the time. Winning is habit. Unfortunately, so is losing.” Vince Lombardi, American Football

“A common mistake among those who work in sport is spending a disproportional amount of time on “x’s and o’s” as compared to time spent learning about people. Mike Krzyzewski, Basketball

“It’s what you learn, after you know it all, that counts.” John Wooden, Basketball

If you like these sports-focused coaching questions, you can find many more at: Coaching Quotes from the Best Sports Coaches

Whether in ruling kingdoms, sports or the executive suite, coaching can be of great value if the coached individual or team actually listens, ponders, practices, and puts into place the key principles explored in the coaching session(s). Tiger Woods benefited from coaches at various developmental stages of his game and the coaches rotated in and out when skills were mastered or new techniques were required. Michael Jordan had coaches and you can read at UNC the notes his coach gave him to work on in college, and in the pro’s Jordan working with Phil Jackson Woods continued to benefit from great coaching; indeed, few greats have made it to the pinnacles of their careers without coaches.

Turning to the role of executive coaching. Many have written on the topic of what executive coaches can do for you. I like an article written by Zak Slayback (2017) wherein he writes in ‘Startup,” What Can Coaches Do for You? about the subtle differences between mentors, advisors, and coaches. In his article, Zak wrote, “The goal of the coach is to facilitate learning, focus, and results. Coaches are trained in the strategies for achieving the results specific to their domain of coaching. Although they may not have experience generating the results you are looking for in themselves, they should have experience generating these results in other people or organizations.”

There are also other interesting articles that explore the ROI of coaching such as an article titled, Return on Investement from Using Executive Coaching — Smart Moves Inc. In this article, the author found a 5.7x annual ROI on coaching. To me, this seems to be a low-bar for success and what I would deem the minimum level of expectation. In my own executive coaching, I strive to achieve a much higher level of success; over a 3–5 year horizon, I seek to obtain a 3x increase in the company revenue, EBIDTA, profitability, or another key measure as determined by the client. And I have much enjoyed helping leaders get the most from their opportunities as many have met or exceeded this goal having coached multiple INC 500 awardee companies and their executives. The growth goal is only one example of a goal that executive coaches help the coached deliver. Working with larger companies, sometimes the goal is to visualize a new future for a company, division, or technology, and these are worthy goals as well. Whatever the goal that is developed together for the coaching experience, the goal becomes one of the overarching theme of our coaching work together.

Another insightful article on executive coaching was written by Diane Coutu and Carol Kauffman that was published in HBR (Jan 2009) titled: What Can Coaches Do for You? This article is interesting to me because it was research based on the outcomes from 140 interviews with executive coaches and five subject matter experts on coaching. They interviewed some of the highest paid coaches (with some charging as much as $3,500 per hour), which begs the question is executive coaching worth it?

Contu and Kauffman write that… “Ten years ago [1999], most companies engaged a coach to help fix toxic behavior at the top. Today, most coaching is about developing the capabilities of high-potential performers. As a result of this broader mission, there’s a lot more fuzziness around such issues as how coaches define the scope of engagements, how they measure and report on progress, and the credentials a company should use to select a coach.”

Importantly, before engaging a coach, one must consider what is the role of the coach. Consider the following illustration. Coaching borrows from both consulting and therapy, but to be successful, coaching is neither therapy nor consulting.


In 2019, “Coaching is partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential;” this is the definition of coaching by the International Coaches Federation (ICF). Under this definition, a coach need not have mastery themselves in a given topic in order to inspire an individual to greater performance. Rather a great coach needs curiosity, discernment, wonderment, and the ability to engage and ‘partner’ with the one being coached by means of thought-provoking and creative process to achieve greater understanding, awareness, goal setting, accountability, and performance.

Interestingly, in this modern definition of coaching, a coach’s prior knowledge of a topic can be a stumbling block to coaching success. Knowing something, or thinking we know something, can cause temporary blindness like jumping to conclusions too quickly. Whereas a coach’s state of ‘not knowing’ can lead to a coaching journey with deeper levels of active listening, questioning, wonderment, pondering, and understanding of the individual being coached. Asking great questions is a hallmark of top executive coaches.

Nonetheless, prior experience of a subject is frequently valued by executives when seeking mentor-like executive coaching from been-there, done-that prior executives who are now coaching in their field. This type of ‘executive coaching’ is a combination of pure coaching and ‘consultative’ styled coaching; wherein the coach is sought for their past experience and they frequently draw on past experiences and learnings to help the ones they are coaching avoid the pitfalls, stumbling blocks, and guide them on a surer path of growth and success.

Great coaches that I have observed have discernment and a keen sense of wonderment in the individual being coached, and the subject matter being coached. Further, great coaches have the ability to ask great questions that can set a mind on fire with imagination, or trigger great quests and journeys. When I was an CEO early in my career, my own executive coach helped me by how he questioned me with gut-wrenching questions… like ‘so how is this working for you?’ When it was clearly obvious that things were not working, and the question led me to a deep discussion and discovery on how I might ponder, consider, and address a particular issue. And asked these hard questions session after session, I would usually shake my head, grin, take ownership for my role in my own non-performance, and get to work on fixing the key issue that I had ignored or was too blind to see.

Over the years, I have come to value hard questions and believe that a great question can lead an executive to more powerful understanding and action than any lesson plan or checklist I might recommend at the end of a coaching session.

So what are some reasons people come to me for executive coaching today…

  • To get help organizations and executives get ‘un-stuck.’

  • To call out the ‘elephants in the room’ that others are too afraid to see or deal with.

  • To help executives question their answers. Frequently in companies, nobody dares question the leader and a coach that can speak the truth with discernment and wisdom to a client is a valuable ally in business and life.

  • To speak the hidden or silent truths to executives that other executives dare not speak.

  • To help companies assess and repair culture and rid companies of toxic behaviors.

  • To help executives visualize next steps, role play, and explore options before making concrete decisions.

  • To help the executive or company transition to the next step, stage, or transition.

  • To develop a confidential friendship and bond with someone who will speak the truth,

  • Yes, during the conversation of coaching we often deal with hiring, firing, development, growth, sales, markets, forecasts, people, contracts, development, people issues, capital issues, technology, M&A, legal issues, and all sorts of issues impacting the workplace and lives of executives.

  • However, at our highest purposes, coaching is partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential

Summing up, executive coaching is vitally important. Yet coaching is not for everyone. Ben Franklin said poignantly, ‘experience is a dear teacher; and fools will learn by no other.’ Some people are not coachable and must learn through their own school of hard-knocks and challenging life experiences.

To be most effective, executive coaching requires that the individual coached embody a high degree coachability (i.e., humility), curiosity, lifetime learning, desire to improve, and the discipline to put practice the method until competency is achieved with muscle memory.

Not everyone can do this, and as I coach I want to work with only those that are coachable, teachable and have a desire to get better at whatever it is they are doing. For in the words of a wonderful coach I have met and admired, the most important things a CEO will ever learn, are those things they learn after they think they have learned everything. I love executive coaching and helping my clients (the executives and their companies) achieve their highest purpose and find more enjoyment and fulfillment in the journey.

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