Up The Creek With a Paddle

From Legal Management The Journal of the Association of Legal Administrators Edward M. Gurowitz, Ph.D.


Terry Keyes, the new Chief Administrative Officer of Fithian, Berman, de Haas and Sinclair, was stumped. For most of its hundred-year history the firm had shown modest but substantial annual growth in all the measures that count – client load, revenue, profit – but over the past several years all of these, but particularly the rate at which their client population was growing, had gradually begun to decline. After trying everything they could think of to turn the situation around, the partners in the firm brought Terry in as CAO with a mandate that was nicely phrased and worked out, but that amounted to “Do Something!”

That was two years ago. During that time, as Terry’s semi-annual performance reviews attested, she had done an outstanding job of putting in up-to-date management systems, updated the firm’s hopelessly antiquated information systems, shifted client feedback about the firm’s service from luke-warm to downright effusive, and put the firm in the first rank of employment desirability for the City’s law school graduates. All of this slowed the decline but did not stop it, and while some of the older, more conservative partners felt that this was sufficient, Terry was under increasing pressure from the younger partners to turn it around. An MBA from a leading business school and ten years of experience managing businesses and professional organizations had brought Terry to where she was today– at age 35 she was one of the youngest people in her position anywhere – but told her nothing about how to do what was being demanded of her. The question keeping her up nights was some version of “after you’ve done everything you know how to do, everything you can think of to do, everything anyone tell you to do, what do you do?”

Actually, nothing Terry has done in her life has prepared her for what she is now facing. Terry is very well educated and trained in management, but what is called for at FBdeH&S is something else. What is called for is leadership.

Authors, theorists, generals, politicians and even lawyers have offered many models of leadership, each model viewing leadership through the lens of each writer’s interests and expertise, yet leadership in organizations, particularly in professional and service organizations, remains, like Justice ________‘s definition of obscenity, something we can’t define but we know it when we see it.

To begin with, we should define the dilemma that Terry is facing. Terry is trained and experienced in management. We define management as skillfully dealing with what is (and has been) in an organization or business. That is, management consists of knowing the facts, including the facts about the past, and dealing with those facts effectively to deliver on business goals and outcomes. What Terry needs is leadership. In contrast to management, leadership deals with what is not yet. Said another way, management is definitive or descriptive, leadership is creative or generative.

The purpose of this article is not to argue that leadership is better than management or that we should be leaders and not managers. A well-run organization, in our view, is one that has available to it the power of leadership – to create futures into which to live and the power of management – to maintain, stabilize, and leverage what is happening in the present and experiences gained from the past. For maximum power and leverage in the present, an organization has to have a past that provides learnings on which to build and a future that provides incentives into which to grow.

Some years ago a noted economist did a study that proposed to determine what makes people happy. He summarized the study thus: If you study two hypothetical families today, one (A) with an annual income of $45,000 and the other (B) with an annual income of $75,000, and Family A knows that next year their income will be $55,000, while Family B knows that next year their income will be $65,000, which family will be happier? The answer, of course, is Family A, because happiness is a function not of one’s current or past circumstances but of the future into which one is living.

We would argue that the same is true for organizations and for the people in them. This means that, even in an organization that is not in decline, that is successful and growing, the source of the organization’s continuing success and its people’s satisfaction will be determined by the future (if any) that the organization’s leadership has created. In organizations we call this future the organization’s vision; the creation, existence, and promulgation of this vision is the job of leadership.

Management is past-based

Given management’s concern with the present and the past, a large part of the job of management is description. Description deals with the world by means of a particular process: to observe and then to represent accurately what was seen. First, one gathers all the facts it is possible to gather about whatever is the concern at hand. Then one attempts to turn the data from these observations into information, i.e., to accurately describe, define, explain and to reach an understanding, all done from the supposedly superior perspective of hindsight. One sees and reports on what is in view when looking backwards from after the event. Taken to its conclusion this process results in formulae or prescriptions that will supposedly ensure the organization’s ability to repeat what was done (if it was desirable) or to ensure the organization’s ability to prevent that repetition (if it was not). Thus the orientation of management is always toward the past, and its aim is to preserve stability either by minimizing disturbance or by stabilizing benefits.

Leadership is future-based

If leadership’s job is to create and implement futures, we should first of all define “futures.” In one sense, there is no need to create futures at all; after all, isn’t the future out there waiting for us to reach it? Intuitively this would seem to be so – we go to sleep at night and when we wake up, there it is: tomorrow! Used in this sense there is no need to create anything – all we need to do is wake up, and sooner or later we all do that. But what if the future did not have to be an extension of the past. Life abounds with examples of events that we call “turning points;” events that seem to create a break with the past and that, viewed in retrospect, seem to mark a break in reality – a defining moment, before which things “were” a certain way and after which things “were” just as definitely another way. In a world in which it was once absolutely true that the four-minute barrier could not be broken for the mile run, the sound barrier could not be broken for airplanes, and the gender barrier could not be broken in the best law firms, we have miles being run well under four minutes, supersonic passenger planes, and female partners and woman-led firms. Today it is just as true that the mile can be run in under four minutes, the sound barrier can be exceeded, and law firms can be gender-neutral as it was true that these things were not so as recently as forty years ago.

Just as our beliefs create our realities, organizations have their own “realities.” If you question that, think back to the first day you spent in your current organization. At some point after the paperwork was done, but before you had all your knickknacks out on your desk someone took you aside and gave you your introduction to “the way things are around here.” Since then you have had an intermittent but continuing tutorial in “the way things are around here,” and particularly the part of the program called “why that isn’t possible here, even if it might be possible elsewhere.” The outcome of this tutorial is an organization reality called “what is possible.”

You and I, as human beings, live our lives against many backgrounds, most or all of which go unnoticed. Barring accident or a trip to high altitudes, we pay no attention to the air we breathe. When we ask another person for a glass of water, we do not detail the request to ensure that what we get is cool or cold water, clean, not dirty or soapy, in a clean glass that is neither tiny nor huge, and handed to us for drinking purposes, not dumped on our head or in our lap. All of this is so “obvious” as to be not worth saying, and lives for us as an assumed background for the request. Another, less obvious background is a background called “what is possible.” We know our limits and we operate well inside those limits in what is called our “comfort zone.” Like a character in a fairy tale, however, if someone provides us with a pair of magic boots, we operate well beyond the limits of our reality of what is possible, certain all the while that the source of our new powers or abilities has nothing to do with us and everything to do with the magic boots. Unlike the fairy tale character, however, we almost never get the chance to lose the magic boots and to discover that the source of our breakthrough was in ourselves. Instead, we ascribe our performance to the organizational equivalent of magic boots – “we got lucky,” or “we were in the right place at the right time,” or “under the circumstances we had to produce or we would not survive, so the circumstances forced the result.”

We say that the magic boots, i.e., what allows for outstanding performance by individuals and organizations, is the creation and effective communication of futures that alter people’s reality of what is possible, and it is leadership’s job to create and communicate those futures.

The chart is based on leadership as we have observed and practiced it in business organizations. We see business leadership as falling into one or more of the following four models: expert, facilitator, mentor and co-generator. In Expert Leading, the leader imparts knowledge and information; success is judged more on the delivery of information and data than on any significant change in people’s behavior. In the case of Facilitator Leading, the leader acts as a helper committed to facilitating people’s progress; the focus is on the process through which people accomplish their goals. In Mentor Leading the leader trains, develops and promotes people who, in return, work on and forwards the mentor’s commitments. When a leader acts as a ‘steward’ in service of people’s commitments, Generative Leadership occurs.


In this schema, no type of leadership is superior to another. Each type of leadership produces different results and is therefore more useful in some contexts than in others. Expert Leadership is vital for beginners or newcomers to content-rich subjects. It is an expedient way of introducing the basic concepts of the organization at an intellectual level. The expert approach may be less useful in management, since in the manager/subordinate relationship expertise can look like being told what to do. While being told what to do by a benevolent superior may be helpful, it may also leave one with a sense that that superior doesn’t really appreciate their potential and thinks they can’t figure it out for themselves.

Facilitator Leadership helps teams and individuals to manage processes such as meetings more effectively. It can also help teams learn to question their mental models and to develop team learning capacity. Facilitator Leadership is less useful in a situation in which people need to invent a new solution that the facilitator has no idea of how to do. A potential pitfall of facilitation is that if the facilitator has a pre-determined outcome that she is trying to get people to, it can feel contrived or like a manipulation.

Mentor Leading is highly valued in today’s business environment. When a senior member of an organization takes on the development of someone more junior, it is, initially at least, a win/win relationship. The junior person’s learning is focused around the real-world, realtime commitments of the mentor, as opposed to being focused around exercises in a class room. The person being mentored is exposed to the thinking of someone with more experience who is committed not only to the success of the project, but also to the person’s development. If the Mentor Leader is skillful, people’s ideas and thinking will make a real contribution to the project, while at the same time offering fertile ground for the Mentor to contribute. Mentor Leading often encounters a limitation when people have developed to the point that they are ready and eager to pursue their own commitments. At that point the relationship must transform or end. Generative Leading is a relatively rare and special relationship. It requires a leader who is willing to dedicate their work based solely on people’s commitments and is independent of the leader’s interests.

Generative Leadership develops people’s ability to create (bring things into being); it is most useful for the creation, initiation, and implementation of organizational agendas that are not mere extensions of what has gone before or of existing knowledge. For this reason, generative leadership is a useful model for developing an individual’s vision in the organization or a team’s shared vision. It is not useful when there is a “right” answer or approach that is known by someone.

How leadership can contribute to an organization:

  1. A leader has a unique vantage point in any engagement. To use a sports analogy, the players are on the field, the spectators are in the stand. Only the coach is on the sidelines, from which one can see the whole game, including all of the action on the field, while keeping in mind the game plan (or “vision”) overall. Thus a leader can see where mental models might be limiting thinking, choices and action.
  2. Regularly scheduled leadership conversations provide a system of continuity wherein people are motivated to work on whatever project, skill or behavior they are trying to make progress on, in part because they are accountable to someone outside of themselves. Leadership helps to create accountability.
  3. When leadership creates relationships across functions or divisions, individuals who would not normally work together develop a relationship and an understanding of one another’s work and challenges. Leadership facilitates an understanding of another perspective in the system and also increases communication and information exchange, thus leadership increases the ability of individuals to think in organizational terms.
  4. When a leadership sets up projects that people care deeply about, leadership reinforces and fosters an environment that supports people in living and working from a creative orientation, rather than a reactive orientation.

Since a great deal has been written about expert, facilitative and mentor leading, and less have been written about the generative dimension of leading, this article focuses on the latter. We have also chosen to focus on generative leadership because we see that as the rate of change increases, we find ourselves in uncharted territories more often than not. In these places, it is critical to be able to develop relationships centered around learning and creating together. Generative leadership is thus a powerful tool for developing generative partnerships in a constantly changing world.

How do I lead generatively?

Generative leadership is less about doing and more about being. While an expert leader focuses primarily on transmitting content and knowledge; a generative coach focuses on people’s commitments. The expert leader focuses on how articulate, knowledgeable and compelling she is; the generative leader focuses on listening and being.

The following are three key principles that inform generative leadership”

  • Be conscious of the questions that inform your listening. Are you listening from questions such as, “Where can I help them? Where are the holes in their thinking? What are they doing wrong?” While these questions may come from the best of intentions, they are organized more around the leader’s expertise and commitments than around people’s capabilities. A generative leader listens from questions such as, “What is possible out of this? What will this allow for? What does this open up? Who does this need to be communicated to?”
  • Believe in people. Be committed to their not only accomplishing their goals but also to their realizing their vision. This means being an unyielding, unreasonable stand for people’s success even when they become discouraged, and when it looks to any “reasonable” person like they should quit. Never question people’s commitment. Stand in the fact that they are committed, even when they forget.
  • Listen for workability. Nothing is ever wrong. There are no problems; only times when things stop working and reveal what is needed to have them work and for the project to move forward or even to take a quantum leap forward.

Terry’s account of one of the skills of generative leadership: listening. I have been working on peeling away the layers to being able to listen to people more deeply than ever. It is so incredible to get myself, my ego, the voices in my head out of the way to really hear what another person is saying. It requires constant diligence. The practice reminds me of the discipline of focusing on my breath as a form of meditation: my mind goes away, and then at some point I notice I have stopped focusing on my breath, so I bring my mind back. The mind goes away again, and again 1 minute, 10 minutes later, who knows how long it is: I notice it has gone away and I bring it back. Such is the case with listening: I go in and out of listening. And then notice I’m not. And bring myself back. Another part of focusing on listening is to notice the questions going through my head as I’m listening and to see if they are going to help me to listen in a way that empowers myself and the other or if the questions will disempower myself and/or the other. I’m becoming painfully aware of how much I miss through listening from judging and assessing questions. When I’m listening for the greatness of others, I develop great love for them.

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