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.