Dealing With Uncertainty: From the Crucible of Anxiety to the Chalice of Change — LESSONS IN LEADERSHIP

Dear Reader:

Last year I published two posts dealing with uncertainty. I have continued to reflect on the events that prompted the posts. I want to share with you some further insights into the challenge of handling complexity at times of crisis, and in particular what they tell me about leadership. My contemplation helped me uncover additional aspects about the leadership capacity within us, and stimulated a continuing search for what makes good leadership and how to develop it. It also made me realize how little I know, and how much help I need to better understand this topic. It has led me to recast my previous posts and focus on the question of teaching ourselves – and others – to be better leaders.

I will be using this article as the basis for a workshop I am leading on May 19, 2017 at the International Association of Management, Spirituality and Religion Conference at the University of Arkansas. The essence of my theme at that workshop is how to discover and unlock the leadership capacity inside all of us.

I very much seek and welcome any ideas, critique, suggestions and insights that you may have on this important topic.

First, a reminder: What makes us entrepreneurs is our consuming drive to bring new products to market to fulfill perceived needs. What makes us entrepreneurial leaders is our capacity to embrace the unknown and guide our organizations in times of difficulty and uncertainty. To be in the midst of this action, either as a driver or contributor, has been my joy for many years, and this joy continues as I serve on Boards and teach. The most difficult element then and now, as I dwell in uncertainty, is to find the right time and best way to act, so as to help shift uncertain situations toward greater clarity and positive resolution. I have come to recognize that nothing helps sharpen one’s capacity as much as living through a difficult experience.

A Situation that Challenged Me — Both Professionally and Personally

One of the companies for which I served as a Board member had reached an impasse. We were making substantial progress in a breakthrough healthcare technology, and were the first to engage in clinical trials. Some of our most recent results were awe inspiring. Yet we were frustrated by the financial market forces making it difficult to continue to finance development of the much-needed medical breakthroughs we were targeting. At the Board’s request, the CEO was asked to consider alternatives. The options were disconcerting: narrowing the research focus; reducing expenses, with consequent layoffs; realigning the ranks of executives to better correspond to a down-sized operation; mounting one more aggressive effort to attract financial resources in a very hostile fund-raising environment. The CEO’s recommendation was to double-down on the most advanced project and discontinue all others, which would significantly reduce the company’s expenses. The focus was to be driven by the COO, who had helped develop the options and was running the R&D. It was a sound recommendation that the Board accepted.

This recommendation was not unexpected, and is certainly not unusual in entrepreneurial ventures as they pioneer new technology. I had faced these same choices in the companies I had founded and grown. So I thought that with my long experience as an entrepreneur, I was well equipped to handle these complex issues as a Board member. As it turns out, I did have the right intuition about what to do, but in retrospect, I failed in several aspects of the execution. And this is where my learning begins.

The selected scenario required a realignment of the executive ranks to better correspond to a down-sized operation. The CEO counseled a measured approach. The Board felt that action needed to be taken immediately, which necessitated a drastically slimmed-down organization from top to bottom. In the course of the deliberations, I saw a clear – and to me obvious – path to reconcile the CEO’s desire for a measured transition and the Board’s sense that immediate drastic action was needed: Ask the CEO to become Chair of the Board and promote the COO to the top executive position. Not rocket science. But the sense of urgency in the moment and the severity of the timeline did not give much breathing room for the “of course” considerations that so often come only in retrospect. To me, “my” solution had all the correct ingredients: It would signal a smooth transition to the outside world; it would allow for a harmonious transfer of power and realignment while implementing the difficult step of reducing and focusing the organization. There was, for me, one more factor, which on the one hand, compounded my personal thought process, and on the other, opened up potential pathways to help resolve the crisis. The CEO had become a personal and very close friend of mine, and he trusted me. Unraveling and appreciating this additional personal pressure on me was to come later. At the time, I simply “knew” what had to be done.

The Board decided to implement the immediate change. They agreed to my suggested approach regarding the CEO. Because of my close personal relationship with the CEO, I volunteered to join the Board Chair in conveying the decision. I just could not do otherwise, unpleasant as the news would be that the Board wanted to accelerate something the CEO thought should be done in a more systematic manner. I was feeling the emotions that everyone was experiencing and, in particular, anticipating the CEO’s likely emotional dilemma. I was not about to leave this tough job to someone else.

The subsequent series of one-to-one meetings with the CEO and the COO – who had to agree to take over immediately from the person who had hired him in the first place – are hard to describe or even for me to revisit. I would not wish this experience on anyone. And here is the hardest part of the story (as if the rest was not hard enough): To my disappointment, in the end the Board and the CEO could not agree on the steps forward, in spite of my recommendation to put in place the smooth executive transition that I had envisioned. The CEO left the company. I had failed, and this weighed heavily on me.

In retrospect, I was obviously not fully aware of the enormity of the inner forces that were acting on me as I participated in these intense deliberations. I could intimately feel the disappointment of the scientists and physicians who had tirelessly dedicated a significant portion of their lives and careers to driving this important, next-generation technology forward. I could intimately feel the struggle of my friend, the CEO who had staked his life on pursuing the goals of this company in which he deeply believed and to which he had dedicated over fifteen years of his life. I also sensed the forces acting on the other Board members as they wrestled to make the best decision possible under very unpleasant circumstances and a tightening timeline.

To make matters even worse, shortly after we took these streamlining and tightening actions and the CEO had left, we received reports from our clinical trials that while the impact of our treatment was still significant, the level of progress of our study patients had slowed — something we could not immediately explain and had never before observed. We could see ways to determine the cause and implement adjustments, but in our current financial circumstances this was impossible. On top of the trauma of the staff reductions inherent in narrowing the operation’s focus and of the change in leadership, our team was now faced with clinical results that would significantly extend the timeline to commercial implementation and render the company’s survival much more perilous.

A Message of Significance

These events led to many sleepless nights for me. Now that the CEO had left, the questions that continued to haunt me were: Had I done everything I could? What was going on inside me, as I struggled with these forces? How was I handling the unraveling of a company I had supported for so many years? How was I coping with the deep disappointment of a very good friend and a threat to a friendship I cherished?

As I was wrestling with these challenges, my friend Bob Quinn, Professor at the University of Michigan Ross School of Business, posted a brief article in his blog entitled “An Elusive Leadership Skill.” [1] It prompted, in me, a cascade of ideas and reflections about leadership, all centered on the issue of coping with uncertainty in situations as complex as the one I was facing. I found two phrases in Bob’s post particularly thought-provoking:

  • Leaders “pursue their purpose by stepping into the crucible of anxiety,” and
  • Leaders “communicate the simplicity from the other side of complexity.”

The first phrase introduces the very descriptive and appropriate metaphor of a crucible: a container that can withstand severe conditions, usually high temperatures, which is often employed to conduct chemical reactions under harsh conditions. As I consider some of the most difficult leadership situations I have dealt with, many of which have involved personnel issues, I can picture stepping into such a crucible and standing there with a great “churn” in the pit of my stomach – and the sensation of being overwhelmed and even torn apart by the process.

The second phrase is derived from the wisdom of the early 20th century jurist Oliver Wendell Holmes who, in essence, said that he cares little about the simplicity on this side of complexity, but gives much value to the simplicity found on the other side of complexity. He is actually reported to have said it even more dramatically: “I wouldn’t give a fig for the simplicity on this side of complexity; I would give my life for the simplicity on the far side of complexity.”

Bob’s post could not have come at a more appropriate time, as it so aptly characterized my state of mind at that moment. I knew I had to remain immersed in the crucible. If I were to act without my full emotional engagement and instead simply ponder the elements of the situation dispassionately, I would be making decisions from the simplicity on this side of complexity — comfortable but irresponsible. I could also, at that point, have just resigned from the Board and left the issue behind — in effect, finding the simplicity for me, without much further regard for the complexity with which the company was dealing.

This put into focus a harsh reality of life: If we are to be players in an important mission, we have to endure the churn of the crucible and hope a new understanding crystalizes – or not step into it at all. There is no halfway measure: Full exposure is needed to appreciate the totality of a problem and do justice to our commitments with integrity and honor.

Full immersion is, of course, the lot of the CEO. It comes with the office. As members of the Board, our immersion should be no less intense, but we are granted a different vantage point and perspective, whence comes the value of our role. But just like a CEO, we need to be willing to absorb the anxiety of immersion and thus be open to learning in real time. And, perhaps most importantly, we must be able to overcome two elements that may easily mislead us: our egos and our prejudices. In the heat of the chemical reaction, we may not even notice these reactive agents.

In this situation, my ego pestered me to find a solution in short order, consistent with my image of being a seasoned executive. Meanwhile, my “better nature” struggled to find a path that would allow us to resolve the situation without damaging the dignity of the key players, in particular the CEO. As I pondered these issues, and at moments felt the natural urge to “escape the situation,” something became clear through the insights of Bob Quinn’s post: While we are compelled to dwell in the cauldron of uncertainty, our equally important task is to find a way to get to the other side of the combustion so that we can discern the essence of the quandary and gain clarity. We need to find the simplicity on the other side of the complexity. Yet it also became clear to me that while I needed to step out of the furnace, I had to do it without detachment. I still owned the situation! I had to maintain my link to the complexity but not be overwhelmed by it. I was not just an observer; I continued to be a protagonist. The admonitions that some were giving me to “be objective” or “be professional” totally missed the point.

No. I was not going to quit the Board. The only viable alternative for me was to fully continue in the complexity: to continue to be totally immersed in the subsequent deluge of facts and unknowns, of pressures and opinions, of perceptions and vested interests, and of major disappointments.

Converting the Crucible

When, in the heat of the Board deliberations, I suggested elevating the CEO to Chair I took a chance. I had not talked to the sitting Chair who had led the Board well for a long time. The Board was about to commit to a decision, there was no time for procrastinate. Many alternatives where considered; none of them sat well with me. I could have let the direction of the discussion continue and “go with the flow.” But I deeply felt the “rightness” of my approach, and had a deep, irresistible urge to express it. I was in what Bob Quinn calls “the state of authentic engagement.”[2] I spoke forcefully. It resonated with the other Board members. And I became the purveyor of the difficult news.

As I walked out of the Board room to fulfill my task one of the Board members, who is not known to be very “touchy feely,” turned to me and said: “Ric, I love you.” I do not believe he was talking about me per-se. He was talking about me as the carrier of the sense of the group at that moment. It was the leadership moment. It transcended me, it responded to the spoken and unspoken needs of everyone. I was just a conduit.

Many individual meetings followed. I was engaged, yet my head and heart were not totally clear. I was deeply immersed in the cauldron and feeling the constant heat of the reaction. I had trouble sleeping. At times, I was unable to think clearly. I was suffering. And it was compounded by the fact that the CEO then left and we were facing the disappointing clinical results. Something needed to change within me, if I was to continue to be a positive contributor to the company.

The change occurred one morning, several weeks later and deeply influenced by my reflections regarding the crucible of anxiety: In my daily meditation, I suddenly moved the crucible from the interior of my gut to just in front of me. While this sounds illusory, it was very real to me. In a moment of incredible clarity, I was able to “see” all the elements churning in the crucible of anxiety in sharp focus, and actual shift them out of my tense interior.

My early morning meditation ritual is a very spiritual time. Everyday, I take twenty minutes of very private time to sit still, quiet my mind, and attempt to move beyond the noises and pressures that crowd my thinking and my psyche (including those that are conspiring to tighten my gut.) Once in a while, this practice allows me to reach a state of deep peace, which carries with it an empathy and caring for everything and everyone, near and far. That is just what I needed, in the current state of affairs, and suddenly, instead of a crucible, I found myself holding a different sort of receptacle in my arms, which contained all the churning elements. But it was now in front of me where I could see it, rather than ominously lurking inside me. Importantly, this vessel felt amicable, not antagonistic. I felt love (yes, love) pouring into it, and a strange new ability to attend to each part of the mix – people and situations – in a warm and caring way. This experience startled me: I had converted the crucible of anxiety into a chalice of change.

The moment was unbelievably liberating. My ego dissolved and I became focused only on the highest good. My purpose as a member of the Board clarified and became not just another job, but a sacred task. My fear turned into confidence, and the chalice enabled me to finally employ all of my leadership tools more effectively: my analytical capabilities, my sense of purpose and passion, my moral compass and my spiritual anchors. This would not have occurred had I not been practicing my daily mediation.

I use the word “chalice” advisedly. The crucible burns with intolerant heat, while the chalice refreshes and rejuvenates, bringing transformation when we drink from it. To me, the chalice connotes a vessel that purifies, transmuting the elements and giving us an ability to see the process with greater clarity.

The moment I embraced the chalice I was transformed. I had a much firmer view of the dynamic whole, and sensed the simplicity on the other side of complexity. Most importantly, I found the strength to be fully present while confronting the conflicts with gentleness. I recognized the best in each actor, and I felt that no matter what I had to do, I could perform my duties with respect for each party. And part of that feeling of compassion was toward myself.

This came as the Board made the wrenching decision to liquidate the company. Several of the other Board members chose to leave. I chose to continue. The chalice transformation made it clear to me that I had to see the situation through to the finish, regardless how painful it was to disassemble a company with which I had been associated for a dozen years. My goal, together with two other Board members, was to implement the wind-down in a manner that safeguarded the dignity of the employees who had worked so tirelessly in the pursuit of our dream of a medical breakthrough and, equally important, to find a home for the technology that would ensure the continued pursuit of the possibilities of a treatment that might save the lives of our children and grandchildren. I also dedicated myself to rebuilding my friendship with the CEO, which had been deeply frayed by the events that had unfolded. I could not have done this had I not converted the crucible into a chalice.

A Crucial Conversion Ingredient

I believe that this flow through complexity to simplicity has deep spiritual significance. It is therefore not surprising that the insight of the conversion from crucible to chalice came to me during meditation. It also indicates that there is a much deeper aspect of this that could have implications for our leadership – and life – journeys: our ability to hold opposites without feeling threatened.

A special passage from Father Richard Rohr’s book Eager to Love keeps coming back to me in this context[3]:

Paradox held and overcome is the beginning of training in non-dual thinking or contemplation, as opposed to paradox denied, which forces us to choose only one part of any mysterious truth. Such a choice will be false because we usually choose the one that serves our small purposes.”

This suggests that avoiding our “smaller purposes” becomes crucial when we need to transform the crucible to a chalice. This is also true when we face many of our leadership challenges. In my classes and in my book, I speak of the necessity for leaders to continuously move from the specific to the general, from the narrow to the broad. As leaders, we absorb the broad uncertainty of our venture so that others on the team can focus on more specific aspects of the mission, which they are often much more qualified to tackle. I liken this to our breath: When we breathe in, we expand our horizon, taking in the 360-degree vista. We are alert to opportunities and threats without blocking them with our prejudices and small purposes. Yet we cannot just breathe in; to survive we must also breathe out. When we do, we transmit energy, passion, direction and focus. It is a continuous flow. In the breathing-in phase, we must hold opposites. We need to be able to encompass paradox. We need the capacity to fully entertain conflicting positions. And we need to fully understand contrasting positions from those who advise us.

The Leadership Voice

To sense the “simplicity on the other side of complexity” is not enough. Our task is to permit our leadership capacity to manifest. We must therefore unshackle it. The transformation from crucible to chalice is a step in this “coming out” effort. I propose that true leadership springs from an inner well that sustains an inner flame. It is a delicate flame, protected by a lifetime of defense mechanisms that develop as we cope with our personal experience of living. To allow an opening in this armor without damaging the inner layers is subtle and delicate, yet that is the required effort.

The place that I am talking about is difficult to describe. A wonderful passage from Thomas Merton perhaps does so best[4].

“Again, that expression, le point vierge, comes in here. At the center of our being is a point of nothingness which is untouched by sin and illusion, a point of pure truth, a point or spark which belongs entirely to God, which is never at our disposal, from which God disposes of our lives, which is inaccessible to the fantasies of our own mind or the brutalities of our own will. This little point of nothingness and of absolute poverty is the pure glory of God written in us, as our poverty, as our indigence, as our sonship. It is like a pure diamond blazing with the invisible light of heaven. It is in everybody, and if we could see it, we would see these billions of points of light coming together in the face and blaze of a sun that makes all darkness and cruelty of life vanish completely. I have no program for this seeing. It is only given. But the gate of heaven is everywhere.”

And, of course, the beauty in this is that as our leadership voice springs from a point of light linked to all lights, it speaks directly to the light in other individuals. They feel it. They do not have to go through the intellect to sense it fully: It is expressed from that deeper place. It prompts even the hardest of us to say, “I love you.”

An Opportunity for Reflection and Deep Learning

Bob Quinn, in his book Deep Change: Discovering the Leader Within,[5] looks at leadership not as behaviors and techniques, but as a “state of being.” As a guide and teacher, I echo Bob’s thoughts. The capacity for leadership is in all of us. As Bob’s book title suggests, we just have to discover it.

The challenge for us as teachers is to figure out how we can help others (and ourselves) with this discovery; what we can do to “free” ourselves to capture that capacity; what state of mind allows us to manifest it in the right moment. How do we train for it? How do we coach it?

Two words in Father Rohr’s quote are noteworthy, as he refers to paradox: “held” and “denied.” What are we constantly denying as we face situations? What makes us deny? Does therein lie the secret ingredient — the catalyst for a crucible to chalice transformation? How do we train to hold paradox?

Here are some recommended steps for making the most of the opportunity when we come face-to-face with uncertainty:

  • Recognize the complexity.
  • Know that our job as leader is to fully enter the crucible of anxiety.
  • Acknowledge that it will be uncomfortable.
  • Commit to remain in the crucible as long as you need to, resisting the temptations of “easy” solutions.
  • Allow the transformation of the crucible into a chalice (by the deep reflection and contemplation that allows a mindset change and converts the problem into a sacred task rather than a burden) thereby gaining the peace that enables the discernment needed to help you arrive at the eventual decision or action.
  • Then, step to the other side of complexity with the simplicity offered by clarity.
  • Act only when you have reached the simplicity on the other side of the complexity.
  • Enact your decision with conviction, confidence and respect. Capture the leadership moment. Speak from your “center.”

Consider the times when you have felt the crucible emerge. Were you able to transform it into a chalice, even if you may not have characterized it as such at the time? What did you learn from this? Examine how you might improve such situations and how, in the future, this might help you in better leading your organizations or teams.

And perhaps even more broadly: Might the crucible-to-chalice model help you in resolving your own personal affairs?



[2] Bob Quinn Post June 24, 2016

[3] Richard Rohr, Eager to Love: The Alternative Way of Francis of Assisi ( Cincinnati, OH: Franciscan Media, 2014)

[4] From Merton’s Conjectures of a Guilty Bystander, quoted in Lawrence S Cunningham, Thomas Merton: Spiritual Master, Essential Writings (Mahwah, NJ: Paulist Press 1992) p 146

[5] Robert E Quinn Deep Change: Discover the Leader Within (San Francisco: Jossey-Bass 1996


Dear Reader:

I write my blogs sporadically. Triggered by particular events or situations with which I am deeply involved, I find myself prompted to write because of the acute nature of the matter. This post, however, is different. The subject has been lingering inside me for a long time. It rarely rises to the acute level, but rather I feel it as a dull “chronic” discomfort in situations when I sense a problem, but the stimulus is not strong enough to incite me to act. And then I bemoan the fact that I did not act in time. It’s like an ache telling me I should go and see the doctor… Yet I don’t go, figuring that trying to describe it would be too amorphous and thus embarrassing. Of course most of the time, it dissipates and life goes on just fine. But sometimes it does not.

The subject? Maximizing the effectiveness of a Board of Directors. I have been involved with Boards for almost half a century, and I attribute much of my entrepreneurial success to the extraordinary nature of the Boards I have been privileged to build and serve under as CEO. As I reflect on what worked so well, a few factors are evident:

  1. Each member of my Boards has been a superb professional.
  2. Members have joined my Boards because they believed in the company mission and trusted the executives.
  3. They did not do it for money, yet felt respectfully compensated for their efforts.
  4. They respected the other Board members, enjoyed their company, and did not hesitate to express their opinions while listening to the opinions and positions of their colleagues.

At the same time, I recognize that the Board of Directors is often comprised of strange bedfellows, which can be awkward. Meetings are few and far between, often months apart; some of these meetings are by phone; in-person meetings are even more infrequent. Members may know each other outside of the Board, but most likely do not see each other very often. They may live in different parts of the country or the world. To say they are a team is sometimes a stretch. To make them a team is possible but takes concerted effort. Yet Board members have a weighty responsibility: to monitor the company’s performance on behalf of the shareholders and ensure that execution meets expectations. To do so, one of their most important responsibilities is to hire and monitor the performance of the CEO. Yet for their deliberations and decisions, they depend on information that is provided by the CEO – who is, most likely, also a member of the Board. This places the CEO in a strange position: being a part of a group from which he or she may be excluded, when certain decisions are taken behind closed doors.

Most of the time this works very well. In addition to the caliber of the Board members, two critical factors facilitate good results:

  1. An active effort on the part of the CEO to work with the Board, by communicating often, managing the information flow and making key executives available for complementary discussions; and
  2. The skill, sensitivity and impact of the Board Chair.

It is the Chair on whom I want to focus in this article. I have been privileged to act as Chair on many Boards, as well as to serve as a Board member under many different Chairs. As I think back to the most critical growth periods of my companies, I attribute part of our success to my discipline in taking time to check in on all Board members frequently, to keep the information flow current, to never allow for any surprises, and to ensure that views are expressed and heard even in the most pressured moments. The times when I did not do well as Chair occurred when I fell into a few traps, which I describe below as typical “Syndromes.”

While many shortcomings can manifest themselves during the normal course of Board business, many manifest during Board meetings. The challenge is that Board meetings can be highly “charged” by the very nature of the participants, their inherent intensity and the import of their role. To work best, Board meetings require members – in particular the Chair – to be very aware of and present to emerging dynamics. When the tenor begins to crescendo, a good Chair senses this and redirects the energy before a discharge occurs. If, on the other hand, the Chair is affected, in whole or in part, by any of the Syndromes outlined below, things may rapidly take a course that is unanticipated or unintended.

The “Strongest Voice” Syndrome

A situation that appears in particular at Board meetings is something that all Chairs face: the Board member with the strong voice and the quick mind (especially financial), who can overwhelm a meeting and reduce the opportunity for considered deliberation, often by dint of his or her brilliance and eloquence. In doing so, such a strong voice may rob the Board of the great value of hearing different viewpoints and shared experiences. I learned this the hard way with some very vocal Board members in the early years of my entrepreneurial journey. But I also learned that if managed properly, such a situation can end with very positive results. One case that is strikingly vivid in my mind was when my young and small pharmaceutical company considered buying a large manufacturing plant in North Carolina. It contained a very sophisticated sterile manufacturing facility, something that was outside of our expertise. One Board member stated flat out that such a move would be crazy. His voice seemed particularly relevant because the facility had been built under his watch when he was CEO of the seller, a large drug company. You can imagine the weight of such an opinion. Fortunately, we were able to navigate the discussion to an examination of what it would take to make such an acquisition possible and prudent (in addition to the need for sizable funding which, at that point, we did not have.) In the end – and that end was 10 months later – we did make the acquisition and it catapulted our firm to be the largest outsourcing manufacturer of drugs in the Americas.

The “Founder” Syndrome

Being a company Founder is one of the greatest joys of the entrepreneur, especially if the enterprise grows. As I advise many Founders, a critical part of success (as it certainly was for me) is building superb Boards. Ideally, the Board is truly a strong, independent voice that enriches the leadership, guides and mentors the entrepreneur, and ensures that the business avoids mistakes that waste time and money. For this to be the case, an active, free and candid dialogue at the Board level is paramount. We must be careful not to overwhelm the Board with our “Founder’s aura,” which can be limiting. We tend to be so focused on our passionate vision that our capacity to listen may be affected. Selective hearing is a common ailment. We Founders need to constantly remind ourselves to clear our ear canals.

The “I am Still the Boss” Syndrome

This happened to me several times, and is related to the Founder-Chair issue described above. I founded a company of which I was CEO for many years. Eventually, I transitioned to Chair when we brought in a new CEO more capable of further growing the company. My shortcoming as Chair was due to the presence, often inadvertent, of my fingerprints on the everyday running of the business. I had given up the CEO title, but never fully let go. And the new CEO could feel it, as could the employees. Without meaning to, I was exerting an influence over the company that did not allow the new CEO to fully gain the leadership needed to propel the company to new levels. And I never appreciated that because of my lingering presence the incoming CEO – who I had recruited and felt very positive about – never entered the full covenant needed for him to be an effective entrepreneurial leader. A few years later, he found “a better offer” and resigned, giving us a very “generous” three-week notice. When I asked him how he could leave the company hanging at such a critical time, he simply said, “Well, what’s the problem? You’re still here.” That told the whole story.

The “Confusion between Executive and Non-Executive Chair” Syndrome

There are circumstances when companies need to have an Executive Chair as well as a CEO. This might occur during a transition period when a President is promoted to CEO or when a new leader is transitioned into the company from outside. In general, the Executive Chair holds some of the responsibilities of the CEO, and spends much more time on the company’s business than an ordinary Chair would or should do. The responsibilities of the Executive Chair often include some operations, whereas a non-executive Chair’s do not. The problem occurs when a Chair acts as if he or she is Executive Chair – often without even noticing it. In the process, the Chair will disenfranchise the CEO, eroding some of the CEO’s initiative, and not allow the CEO to fully become the organization’s leader. This is a very inefficient situation. While I may have good intuition and the best intentions, as Chair I may suggest initiatives to the CEO. Only when such initiatives are wholly “owned” by the CEO do they stand a chance of being successfully implemented. Implementation is not our job as Chair, although our demeanor may raise expectations to the contrary.

The “Clinical” Syndrome

As Chair, we are tasked with many key activities on behalf of the Board. They include being the key interface between the Company and the CEO in negotiating the employment agreement, coordinating performance assessments, reviewing compensation, or the much more difficult task of negotiating the exit of a CEO who is being replaced. As with so many complex negotiations, personal feelings may make the task more difficult. In those situations, some of us tend to take a more clinical approach and keep it impersonal. This may work well to get the best “terms” but, in the end, is not likely to yield a win-win outcome. Hiring, performance reviews and the rare need for separation are very sensitive and personal events for all involved. Showing the warmth of our humanity in these times is essential for a good outcome. As Chair, we need to remember this. Yes, we represent the Board, which is a somewhat impersonal “body,” yet it is an entity comprised of individuals. Part of our task is to carry this humanity to the discussion, regardless of whether being “detached” might seem the more expedient approach.

The “Overbearing” Syndrome

Let’s face it: Those of us in CEO or Chair positions are, by definition, individuals with strong personalities and, often, high adrenaline levels. We are passionate about what we are doing, and approach every task with gusto and exuberance. As we grow in our leadership journey one of our most important learnings is how to “tune” this enormous energy to be appropriate for different situations. Some of us are not very aware of the “long shadow” our personas cast. Sometimes, our hugs (while meant with a genuine and caring intent) can be too tight. I have both embodied this myself and seen it in others. The challenge is how to be fully present to this dynamic, especially in the Chair-to-CEO relationship. If our inclination is to get too involved, we need to recognize when we are stealing some of the breathing space from our CEO, and pull back.


The net of this post: If you are Chair, take the time to examine whether there are any aspects of these syndromes that ail you. If the answer is “Yes,” talk to fellow Board members or the CEO about your concerns, and recruit these colleagues to monitor you and help you become a better Chair. Further, I propose that neither the Chair nor the CEO are the most effective monitors of their own performance – or for that matter of the Board as a whole. These are tasks best relegated to a skilled external resource whose objectivity and professionalism inform their insights. So consider engaging an outsider for a regular 360 review of your performance as Chair and the effectiveness of your Board. While this may be time consuming and add expense, it is an extremely valuable investment that can make the difference between a good Board and an excellent Board. I have found such 360 reviews by an outside professional to offer some of my own best opportunities for personal growth. It also does wonders in “lubricating” the dialogue among Board members.




Over the last several years, while working with my students, I have developed a series of descriptors that profile the entrepreneur. They are based on my experience as a life-long creator of new ventures. Like all “lists,” this is an abbreviated articulation of what is a complex and multi-faceted whole. Yet it serves to highlight some elements of what all entrepreneurs need to consider, as we strive to become better leaders.

My list is split into three domains of the entrepreneurial character: Inner, Outer and Core. I am not attempting to be comprehensive; I mainly want to trigger an active conversation that deepens our understanding of what makes an entrepreneur. Here is the short list:

INNER: -Passionate -Positive -Risk Tolerant -Big Thinker -Visionary
OUTER: -Articulate -Clear -Enthusiastic -Inspiring -Nimble
CORE: -Consistent -Authentic -Persevering -Discerning -Grounded

Clearly, many other characteristics might be added. Here are a few that have been suggested in my class discussions: Salvager (I like this one!), Dreamer, Realist, Courageous, Charismatic, Tough, Resilient, Self-confident, Good Self-esteem, Integrity. I am sure that you can think of others, and I welcome any ideas. My main aim is to take these characteristics and examine what I call the three key habits that an entrepreneur needs to master if he or she is to become a good leader: To Balance, To Breathe and To Trust.


This may seem to be the easiest of the three, but yet is so often forgotten. The main reasons we entrepreneurs tend to neglect balance are:

1. We do not know ourselves well enough to identify our strengths and shortcomings (or if we do, we are unable to admit them, which amounts to the same thing), and

2. We are impatient. Often, for us, it is so much easier to just plow ahead, figuring that by the time we tell others what we want to do and how we want it done, we might as well do it ourselves. Yet the key to growing a venture is to engage others in the journey, and then deploy all constituents in the optimal way to reach our goal. To do this, we need to find balance, starting with ourselves.

Let’s take another look at the list of domains above, and consider where we sit in the optimist-realist scale. When I ask my students, most identify themselves as optimists. While that is fine (since a non-optimistic entrepreneur will find it hard to gain a following), we have to be very careful not to overlook the criticality of realists in our midst. In my book Letters to a Young Entrepreneur, I mention a number of instances in which having hard realists around me balanced my rose-colored glasses and saved our company.

Perhaps of more immediate relevance to all of us is the balance between leading and managing. For most of my entrepreneurial career, I never really tackled that question. I just did what I thought needed to be done, often resulting in micromanagement, and thus often limiting the creativity and contribution of others. Later, as an “entrepreneur emeritus” and teacher, my course preparation led me to a classic Harvard paper on the subject: John P. Kotter, What Leaders Really Do, HBR December 2001. I urge you to read it. It captures, in a wonderful way, a vital topic. I summarize Mr. Kotter’s concepts as follows:

Where a leader points, a manager plans.
Where a leader aligns, a manager organizes.
Where a leader inspires, a manager problem-solves.
Where a leader produces change, a manager produces predictability.

What each of us should examine is our propensity to lead or to manage. There is no value judgment in this question. Both are essential. The key lies in matching our skill with the need: achieving balance!


As we grow in responsibility, whether in our own entrepreneurial ventures or in our roles within larger organizations, we expand the breadth of the topics that fall within our purview. We gain an increasingly broad sense of the task at hand, and we take on an increasing span of responsibility and accountability. In Letters, I introduce the concept that a leader’s main job is to absorb uncertainty (Chapter 3.) Presumably, as leaders by definition we have a more comprehensive view of the venture than do others – or at least we should have. Think of what we do when we drive a car: as we approach a sharp curve, our eye is (or should be) ahead of the curve. This makes for better and smoother steering. Also, as we “see” more of the road, we feel more secure in our steering. In the concept of “absorbing uncertainty,” a leader takes on the larger burden, so that others on the team can focus on more defined parts of the task.

To do the leadership job right, we need to encompass as much of the “scenery” as possible. I equate this with taking a deeper breath, as we spread our arms (and our awareness) to a broader horizon. This also requires us to look to the very edges of our field of vision – for threats and opportunities that may be less obvious.

This is the breathing in part.

However, we also need to breathe out, exhaling our breath in a purposeful manner to help our team gain focus and direction. As we breathe out, we point the way.

And this is the toughest part, at least for me: we need to breathe in and breathe out, continuously. My tendency is to dwell in one mode or the other – spending too much time either scanning the horizon or burrowing toward the completion of a particular project. To keep our venture healthy and alive, as leaders, we must sustain a constant flow between the two: breathing in and breathing out.


Both in breathing in to absorb uncertainty and breathing out to provide focus, a key ingredient is the mutual trust between our venture companions and ourselves. That requires us to be vulnerable, so that people can truly feel the genuineness of our commitment. And it requires that others “surrender” their reservations and have faith. That faith is critical. Without it, what we do is just mechanical and lacks the directional vector — the deeper purpose that is so important in providing energy to move toward our goals, whether we are leading or following. In Letters, I speak of trust packets as the vehicles in the exchange of commitments between leader and team member. I also speak of commitment as a mutual covenant, not policed by an outside document or a quality control officer. It is an internal act, upheld only and solely by our inner character.

This trust factor is the essence of the core within each of us. It raises the very fundamental question: can one learn to trust? Look at the adjectives I chose for the Core group above: Consistent, Authentic, Discerning, Persevering, Grounded. Are these innate? Or can they be trained?

The reason that this is an important issue in my course is my desire to leave my students with the tools to expand their leadership capacity. So I ask them to examine all the characteristics outlined at the beginning of this article (Inner, Outer, Core), in terms of whether they are shareable, learnable or innate — a topic of very rich and important dialogue, which touches on all three of the vital habits considered in this article: Balance, Breathing and Trust.

In all of these discussions with my students, something has bothered me: the prevalence of the designation “innate.” It implies that we either have “it” or we do not. It implies finality. Core is, by its nature, deeply internal — you cannot have others “cover for you.” If you do not have it, you are “done-in.”

I have begun to take a different view. I have come to believe that everyone of us has the capacity for integrity, honesty and authenticity. Each of us has a deeply seated spark of goodness. But as we fend off the challenges of living, we tend to develop coping mechanisms that “shield” this spark of light. We grow a “shell” around our spark — a shell of varying thickness, depending on our own personal life journey. Our task in learning to be good leaders and, for that matter, happy people, is to learn to shed — or at least crack — this shell, so that the inner spark can shine through. As others see our light, it becomes easier for them to trust us to lead our entrepreneurial ventures to success.


On October 5, 2011 Steve Jobs died. When hearing the news I was deeply saddened. Tears came to my eyes, even though I had never met the man. So what caused this emotional response? What touched me to impart such a sense of loss? It was clearly not the loss of a personal relationship, nor the news of a sudden, unexpected tragedy that befell a fellow human being. So what thoughts triggered my sadness? In the end it boils down to the close connection between a person and a product. I love my MacBook Air, my iPhone, my iPad. I also love my Audi, my Bose sound system, my sailboat – yet I cannot imagine “grieving” for their progenitors. And yet I grieve for the person I associate with the Apple products that I cherish.

So I immediately dove into Isaacson’s biography of Steve. I wanted to get closer to the man behind my emotional response. And I came out quite troubled.

I knew something of Steve’s life, of course. It could not be helped having lived in Silicon Valley for the last four decades. In fact, the more I read the more I was struck by how closely “our” paths had touched: my children went to the same middle school and high school as Steve, though a few years later. My professional life as an entrepreneur was impacted by some of the same people that influenced Steve:  Regis McKenna, who in the 70s spent many days with me and my partner Jim Cusumano, musing over how to position our company in what was then a brand new concept; Larry Sonsini, our company’s attorney since the early 80s; Tommy Davis Jr., whose venture firm was an early investor in Apple and also our lead investor in the early 80s. Steve and I even had an affinity for the same little Ryokan in Kyoto — the Tawaraya Inn — one of my favorite spots when I did business in Japan in the 1970s and 1980s. But the Steve who emerged from Isaacson’s book is a very different Steve from my image at that moment when I grieved for his passing. The Steve that emerged raises many questions in my entrepreneurial mind.

First, I want to list the things that I admire, which certainly fit with my idea of what makes a good entrepreneur:

  • His uncompromising belief in quality – inside out
  • His insistence that product comes first, not profit
  • His attitude to never be afraid of cannibalizing your own products; if you do not, someone else will
  • His attitude to leapfrog when you find yourself behind, not just catch up – or give up
  • His belief in cross-skill teams and the intimate participation of all departments — design, hardware, software, content — very anti-silo.
  • His insistence on focusing the company on a few key products
  • His uncanny ability to sense what the market needed well before the market knew it (I love his reference to Henry Ford, who said, — “If I asked customers what they wanted, they would have told me, a faster horse!”)
  • His keen sense of pricing of the “consumer” products he created, displayed as early as the illegal “blue box” that he and Steve Wozniak built to make long distance calls for free
  • His sense of aesthetics and simplicity – epitomized for me in the MacBook Air
  • His passionate pursuit of a product vision
  • His stubborn perseverance

Now to the troubling part: his behavior toward others. The picture that emerges from Isaacson’s book is of a person who seems to care only about his immediate agenda, and “used” everyone around him to achieve his goals. Even if only some of what we read is true, it portrays someone who has very little concern for the humanity and dignity of others, unless they serve his purpose. This bothers me deeply: I think it is the wrong template for a good entrepreneur.  In particular, something that really troubles me: he is reported to first dismiss people’s ideas and then resurface them later, without attribution. For me, this is totally unacceptable in a good leader. In this and other examples, he appears to disregard what most of us consider basic standards of behavior in a civilized society –what arrogance!

In my book I write:

“The tension between hubris and humility is one of the most serious personal dilemmas faced by the entrepreneur. Hubris, the point at which self-confidence turns into conceit, can be a trap in which we lose our bearings, with destructive consequences not just for ourselves but also for many others. To keep in balance we need to maintain a spiritual anchor and manifest that core in our moral and ethical behavior.”

I am not sure Steve Jobs ever had any bearings. His own family, when commenting on why he was so “mean” to others, is reported to have said that ““he lacked the filter.” Certainly not a very Zen-like balance. As Isaacson said: “Unfortunately, his Zen training never produced in him a Zen-like calm or inner serenity.”

And yet this complex person was able to tune so directly into the essence of products that we could not imagine before they were in front of us, but once we touched them we would say “of course, we knew it all along!”  This single mindedness raises some powerful questions:

  • Are all extraordinary people so focused that they cannot relate to those around them in any way but the one that serves their focus? Mozart was a genius who left an indelible legacy. From what I gather, he also was not a very nice person, and had the habit of deriding those around him with a vast superiority complex. Perhaps that is not surprising. Mozart was a young genius who was never allowed to grow up in a normal way. Did Jobs have a normal childhood? He was certainly precocious:  at 13 he called Bill Hewlett and landed a summer job! Is it surprising that he never lost the child within–the good, the bad, the immature?
  • Was the price of “strewn bodies” worth the gain of these delightful products that so many of us cherish?
  • Is ruthlessness a desirable trait in the service of a product vision? Isaacson: “The nasty edge to his personality was not necessary. It hindered him more than it helped him. But it did, at times, serve a purpose.”
  • Jobs was described by many of his co-workers as having a  “distorted reality.” To what extent did this serve the purpose of achieving the seemingly impossible? (I should listen to myself; I suspect some of my colleagues thought I had a distorted reality as I drove our companies to uncharted territory…)
  • How safe is it, in the long run, to have a CEO who does not believe that the rules apply to him? Many companies eventually collapse from this belief, as some have in the last decade…

Apple’s story is perhaps the extreme example of lessons we all should heed:

  • Apple seemed to be a very tense and competitive environment; one might even call it cut throat (certainly they cut the throat of those whom Steve considered to be “B” players.) Could they have succeeded with a more humane executive?
  • I cannot imagine building a company with an attitude that one day derides an idea as “junk” and the next day comes forth with the same idea as if it were that of the lead executive, not giving credit to the person who originally posed the idea. That is revolting to me. Yet, it was a pattern for Jobs. That people tolerated this is amazing. It calls for a re-definition of being genuine…
  • Toward the end of his life, Steve shared with Isaacson some final thoughts, including, “The reason Apple resonates with people is that there is a deep current of humanity in our inventions.” What was Steve’s definition of “humanity?” Did he really understand the concept? Or did he see only a small sliver of what makes us human?

In the end, Jobs was very lucky that he found people who would follow him in spite of his abrasive personality. And the rest of us enjoy reaping the fruits of his idiosyncrasies. I abide my tears upon hearing of his passing, even after reflecting on some of the less-than-commendable traits of this extraordinary and complex individual. I love my Apple products, and hope that they will keep coming, without loss of humanity either in their ultimate manifestation or in the process of their making.

A Brief Post-Script:

It is ironic that the company which inspired Jobs in his early years, Hewlett Packard, was founded and led by two individuals who were the antithesis of Steve. In fact, their management style became the template for many of us who became entrepreneurs: “The HP Way.” Also interesting: HP lost its bearings after its founders were gone. Ominous?


I do not know whether it is that I am getting old (a welcome fact) or soft (some may argue that on the human side I have always been) but I have been sensitive to touch lately. In my role as a member of the Board of Directors for several public companies and one academic center, I observe many chief executives and their senior teams. I marvel at the differences in how these accomplished individuals interact with their various constituents, particularly noticing those who are exercising leadership and those who are merely managing others. The difference can often be seen in how they connect: how they “touch.”

Two very concrete situations come to mind, involving two different organizations. In both of these cases, after reviewing presentations for an upcoming Board meeting, I shared by e-mail some brief observations with the CEO. One CEO immediately sent back a short note: “good comments, thank you.” I never heard back from the other. One touched me back; the other did not. Which case do you think made me feel better? Of course, there are many possible reasons why the second one did not respond. Too busy; never saw my e-mail; my observations not relevant. The latter was unlikely, since I did subsequently send the same comments to the Board Chair, and they were very positively received. But that is not the point. The point is that in one case there was closure of the interaction; none in the other. The first created an enrichment of the relationship; the second left a void. It was no big deal in the grand scheme of things, yet it was one of those subtle instances that to me differentiates good leadership.

Perhaps some CEOs think that we Board members do not need to be “touched.” After all, we are “accomplished individuals with extensive executive experience and a proven track record.” (This came from a Board Director job description.) Well, I have news for those CEOs: We are human too, vulnerable and uncertain at times, and with varying degrees of self-esteem, even if we all convey enormous self-confidence. We can all use – and often cherish – the feeling that we are needed and our contributions acknowledged and recognized. This is so even when (as has happened to me often) my suggestions, while not acknowledged, show up as actions later on. Yes, actions do speak louder than words, yet recognition still reinforces relationships.

The issue is, perhaps, aggravated by the prevalence of Internet communication. In my past career, I depended heavily on direct, in-person communication to fully convey meaning. I believe my colleagues felt my intentions as much as they understood them intellectually – tone of voice, body language, facial expression. And I could immediately gauge the level of understanding and connection in the exchange. Even silence in the conversation revealed enormous content. All those elements of effective dialogue are absent in e-mail communication, requiring us to be particularly mindful in the exchange. A word or two added to an e-mail can convey sentiment. The speed of the response can convey import. Cold as the electronic exchange medium may be, one can convey caring.

I believe it is essential to respond to all e-mails even with the briefest of acknowledgments. One of my favorite Board members, Ernie Mario, always impressed and touched me: he responded immediately to every communication, even if just with a short note. And one of my most treasured advisors, Larry Sonsini, always got back to me in less than 24 hours no matter where in the world he was. He made me feel that I mattered. But then Larry had this extraordinary capability to make me feel that I was the most important person in the world to him at that moment, no matter how busy he was.

We need to remember that so much of leadership is establishing and strengthening alliances. As leaders we are, after all, chartered with the task of sweeping others in our path to carry out the organization’s mission. We get others to join us, to the best of their abilities, in the pursuit of a goal. We seek ardor, not just execution. We seek added genius, not mere implementation. This requires continuous contact, acknowledgement, and appreciation of support. This touch, in the service of sustaining a vital connection, becomes even more important when the communication is largely electronic.

Granted, some of us need more touch than others, but I suggest that we all value it and, as leaders, must deliver it.

WELCOME TO A CONVERSATION about “Letters to a Young Entrepreneur”

In Letters to a Young Entrepreneur, I share some of the highlights of my entrepreneurial journey. On this website, I continue to offer reflections on my leadership experiences, and very much welcome your comments, critique and suggestions. Most importantly, I invite you to share your own experiences and insights, as well.

My hope is that through this dialogue we will all benefit from our common entrepreneurial adventure, and perhaps provide some new approaches to the challenges we all face as we embody our dreams.