The Learning Leader: Orchestrating Organizational and Personal Change
B. Elka Abrahamson
B. Elka Abrahamson is President of the Wexner Foundation.
Credit: Kurt Hoffman
Who is Invited to Lead?
In 1972, I was a counselor-in-training at Herzl Camp in Webster, Wisconsin. If you also found your Jewish essence, your neshama, your soulfulness, at camp, this memory might resonate. One steamy midwestern August afternoon, a charismatic and beloved senior staff person tapped me on the shoulder and directed me to teach the camp song to a dining hall filled with new campers. In that moment, I was assigned a mighty important leadership challenge with no time to weigh my options. A few minutes later, I sprang into action and taught the beloved camp rouser.
Later that evening, the senior staff member who had allowed me no time to process his invitation explained that he had not wanted to give me the chance to say no. Looking back, it is no surprise that he saw in me what I failed to see in myself. This was a time and place where summer camp leaders were loud, funny, and charismatic men, and I needed help seeing myself in this coveted role. Fortunately, I met the moment. While there is a longer conversation to be had about pushing an unsuspecting adolescent into leadership, being given permission to lead has proven to be a crucible life moment for me.
Leadership by invitation is not unusual, neither decades ago at summer camp nor today across the landscape of our many Jewish organizations. We keep an eye out for those in our communities who have the “it factor,” individuals in possession of a sometimes undefinable “know it when we see it” quality of leadership that mixes measures of poise, magnetism, confidence, and an uncanny ability to connect with everyone. Though we frequently do, it is a mistake to confuse leadership with charisma, which is a complex, double-edged quality that can be deployed for the common good or for personal gain. It is a mistake to rely only on instinct, to look only for the “it” to identify who should assume leadership positions in Jewish life.
Leadership is not the ability of one person to release energy or generate enthusiasm in front of a crowd but quite the opposite. Leadership is better characterized as the capacity of one person to carefully consider and understand how to thoughtfully unleash the potential of others. It is not the province of the loudest or funniest or even the smartest person in the front of the room. Leaders intentionally and sensitively bring out the best in others around the room. It is not about being seen; it is about sacred seeing.
In this exploration of leadership, I consider the ability to successfully manage transformational change, a core feature of effective leadership, within a community or organization. I identify key skills, reliable frameworks, and dependable practices for those exercising leadership in the Jewish community, with the hope that these ideas will provide some guidance in the tireless pursuit of rising to meet our considerable challenges. Central to successful leadership is ongoing study of the field itself, rigorous practice of acquired skills, meaningful feedback, and a trustworthy cadre of truth-telling peers.
Leaders Understand the Challenge of Change
During my first year serving as a congregational rabbi, I quickly realized that the kiddush was set up in a most inefficient manner. I sketched a new arrangement and casually asked the custodian to rearrange the tables. It never occurred to me this might be controversial. Not a wise move. I caused tremendous upheaval for a longtime and beloved shul donor who, I later discovered, routinely set up the kiddush tables every Friday morning together with a circle of loyal volunteers, including her husband prior to his death. In rearranging the tables, I had unintentionally disrupted significant personal connections for a small chevreh of shul members. Speaking with me following my blunder, the agitated group unpacked their resistance: Didn’t you know about this weekly gathering? Nobody told you about us? Didn’t you see or hear our weekly coming and going? We could have managed the rearranging had we discussed your solution together. They reminded me first, that we all want to be noticed, and second, that we cling to the status quo to a surprising extent and for private reasons.
Moving the kiddush tables proved to be another defining moment in my leadership development, one that I only fully understood when, a few years later, I first encountered Ronald Heifetz and Marty Linsky’s model of adaptive leadership in their book, Leadership on the Line (2002). Heifetz and Linsky argue that exercising transformative leadership is the art of delivering loss at a rate a community can absorb. In their view, leadership is fundamentally about orchestrating change, and change, whether delivered in small or large increments, is difficult. We are all creatures of habit. We hold on to things as they are because they represent predictability or memory or control in a world of constant unpredictability.
As a people, we love and rely on religious ritual and custom, the building blocks of our rich and value-infused Jewish life. Predictability is embedded in Jewish practice. It is a source of comfort and purpose, and it is a link to our ancestors. But our general reliance on rituals and customs leads us to imbue our organizational traditions and practices with a permanence they do not necessarily deserve: the annual gala; the art on the walls; the structure of membership dues; the titles we give our leaders; the melody we have always used for Adon Olam (mine is the right one). We grow an attachment to our bricks and buildings. We are even fiercely loyal to our prior leaders and can interpret as disrespectful or dismissive departures from what once was.
Rooted habits in an organization can trip up leaders who fail to fully comprehend the unique challenges of leading change. Still, meaningful change is essential to ongoing renewal, to creative possibilities, to imagining what could be, and, most of all, to expanding our strength and reach. The possibility of change lies at the heart of the most sacred day of the year, Yom Kippur, and new visions yet to be realized live in the hearts of transformative leaders.
Adaptive leadership requires those exercising leadership to recognize that resistance to change is expected and understandable, a step in the change process. Our stiff necks, our own ancient resistance syndrome, go back generations. The questions leaders need to ask are: How do we know when to take decisive action, and are we clear on the steps? How do we attain the wisdom and the sensitivity to know when generating discomfort is necessary, and when is it not worth it? What if we are certain a change must happen for our institutions to grow? With experience and reflective practice, discernment becomes clearer, the change process more effective.
I was once invited to speak freely, or “unplugged,” with the search committee of a major Jewish institution seeking its next president. The search committee was engaged in a clever exercise bringing senior organizational leaders with no interest in the position to articulate how an effective new hire might advance this legacy organization. I embraced the opportunity to imaginatively put forward changes unencumbered by commitments! To my surprise, the search committee pushed back and put up barriers to my suggestions, both the trivial and the radical. Though they sought concrete ideas for significant transformation, they met any new ideas with resistance even within the context of a thought exercise.
And yet, CEOs, directors, and presidents are rarely, if ever, hired with a charge to maintain the status quo. Most of us, like the members of that search committee, genuinely want to embrace change. It is only when somebody moves your kiddush tables that the heat rises, and you find yourself resisting. Adaptive leaders develop the ability to use the rising temperature, even to turn up the heat, in a change process by being thoughtful about how high it can rise, how much simmering is possible before reactions boil over and out of control. In the adaptive leadership framework, this is called the art of calibrating disequilibrium in the room. In practical terms, calibrating disequilibrium means that the one exercising leadership must articulate or gather from others clear and compelling cases for change and then turn them over to the community for conversations. An agile leader facilitates the process of generating a zone of productive discomfort as may be necessary to transform the enterprise.
Too many of us who assume leadership positions avoid discomfort, anxious that our own people, those who regard us as caring, accepting, and embracing, will turn on us. Productive discomfort is essential for meaningful change and in that zone, constituents we care about may be frustrated or angry. This is the art of leadership, balancing risk and reward, heat and calm, in transformational work.
The Talmud tells an ancient tale about leaders moving furniture that illustrates the great benefit that is possible when we dare to make purposeful change:
It was taught: On that [day that they removed Rabban Gamliel from his position and appointed Rabbi Elazar ben Azarya in his place, there was also a fundamental change in the general approach of the study hall as] they dismissed the guard at the door and permission was granted to the students to enter. (Berakhot 28a)
In this story, Rabbi Elazar ben Azarya takes on leadership of the study hall after Rabban Gamliel is removed, and he exercises leadership with a new approach. Dismissing the guard at the door, Elazar ben Azarya allows anyone to enter rather than using selective criteria to choose suitable students. So successful was this change, the text tells us, that 400 (or even 700) benches were added to the beit midrash to accommodate the new students. Elazar ben Azarya’s leadership instincts proved right.
When Elazar ben Azarya opened the beit midrash doors, he was surely aware of the existing organizational norms gleaned from his earlier experiences there. He was able to diagnose and understand communal needs. Only then did he enact his own vision, opting for inclusivity by inviting a diversity of voices to interpret the tradition. He used his prior knowledge to make a transformative decision about the future of the community he would lead. It seems he understood the adaptive challenge.
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Leaders Identify Adaptive Challenges
In his book Fall in Love with the Problem and Not the Solution (2023), inventor Uri Levine notes that, in our hurried organizations, those in well-placed leadership positions often surface solutions before the problem itself has been fully defined. We push programs, projects, or initiatives forward without an exhaustive consideration of the specific “thing” we are trying to solve. Effective change leaders diagnose challenges with a focus on adaptive change, and they do not confuse adaptive changes with technical ones.
Distinguishing the difference between these two types of change is essential and not always obvious. Technical problems, while not necessarily easy, are solved with existing expertise. Adaptive challenges are far more complicated precisely because they will require people to change behaviors and habits. They are complex and ambiguous problems that interrupt familiar patterns and require a fundamental shift in mindset and assumptions. They require new learning. An easy illustration of the difference between technical and adaptive challenges can be drawn from a familiar case, the dreaded day when adult children determine an aging parent can no longer drive safely. The technical solution, the known and readily available one, is to take away the keys. The larger and far more difficult adaptive challenge is to support a parent facing a crushing loss of control, possible isolation, and even anger over who makes decisions for them as they relinquish independence.
Here are some brief examples drawn from the Jewish communal landscape that illustrate the differences between adaptive and technical solutions:
We want members of our community to integrate Jewish learning into their lives meaningfully and authentically. The technical solutions emerge quickly: send weekly or daily texts with manageable questions and digestible commentaries. The adaptive challenge is far more complicated: How to move people to genuinely weave Torah learning into their lives?
When neighboring synagogues consider a merger, members are quick to resist owing to technical issues including parking lots, endowments, and dedicated stained glass windows. Conversation centers on budgets, staffing concerns, and where we will sit in a new sanctuary, especially on the high holidays. The patience required to craft a compelling case for collaboration crumbles when a list of technical hurdles and unquestionably tough losses overwhelm what should be an adaptive conversation.
Such a process should begin, as Levine recommends, by embracing and fully diagnosing the problem and then, unencumbered by excuses, imagining how a merged enterprise might strengthen the Jewish community, might better educate children and adults, might offer a diverse menu of worship options, or better serve individuals and families with pastoral needs. These can then evolve into motivating and not paralyzing conversations.
The generational divide in the way diaspora Jews relate to Israel that has come into sharp and often painful focus over the last year has been met with a variety of understandably rapid responses. Technical solutions have included improved Israel PR, promoting a wave of new influencers, billboards, TikTok snippets, easy-read brochures with quick Israeli history lessons, and attempts to influence social media algorithms to feature positive content about the state. Adaptive solutions to this issue are not going to be such clear-cut quick fixes. They are complex, and require time, new thinking, and a significant shift in how we all approach this challenge. There will be some (should I say more?) disequilibrium. It will require shared, heated, and open conversations to come to a new and full understanding of the challenge, and ultimately to uncover a set of long-term solutions.
Legacy organizations are battleships, sturdy and stable, requiring a long time to change directions. Smaller institutions and start-ups, in contrast, are motorboats, speedy and easy to maneuver. The metaphor illustrates why an increasing number of entrepreneurial leaders envy (or choose to work in) the start-up world. But it is also useful in considering adaptive strategies for incubating fresh, wildly imaginative ideas within a large organization’s existing infrastructure. What if innovators literally moved in? Technical excuses can shut down these conversations, as issues become quickly knotted up in questions of insurance, heating bills, competition, strangers in the building, rent, and others you can imagine.
Credit: Kurt Hoffman
An adaptive conversation, in contrast, will focus on what opening the doors of legacy organizations as incubator/shared/co-working spaces could look and feel like for the future of our community. It could be exciting and energizing but will require changes in fundamental attitudes toward ownership/membership, even toward the very nature of what it means to be a community. The same is true for the smaller startups that often turn down invitations to share existing legacy space fearing loss of independence, assumptions about reputational erosion, and the sometimes-stubborn priority to “go it alone.”
Effective adaptive leaders tinker courageously with grand possibilities even if those around them prefer to pursue the probable or safe over the intractable. Effective leaders take time for “what if” conversations even when there are risks involved in saying them aloud. No changes can be made if they are not spoken about or if they are only contemplated and vetoed in private. Transparency, when possible, is a leadership strength even when it leads to frustration or hesitation. This is the messiness of change leadership: holding the tension thoughtfully and regarding it as part of organizational (and personal) growth rather than preventing it at all costs, thus rendering the communities we lead (and our own visions) static.
Change leaders must artfully guide those in these conversations past resistance and toward the transformative possibility waiting around the next corner. This is a skill that must be honed. It requires practice, constant self-coaching, and feedback from trusted allies.
An effective leader resists being pulled into the clunky path of technical stumbling blocks by removing themselves from the fray and taking what Heifetz and Linsky call a “balcony perspective.” This idea is rooted in the reality that those who exercise leadership are not immune from stubborn resistance to change, and they are not always able to keep out of tangled discussions, trivial debates, or personal attachment to a particular position. They can succumb to pressure and default to people-pleasing rather than pushing people to something new. At such moments, a leader is well served by moving away from the center of it all, where leaders often like to be situated, and traveling in their mind far above the noise to view what is really happening in the room. (In these moments, I sometimes physically move my chair slightly back from the table.)
Looking down from the balcony perspective, one can see the metaphorical “dance floor.” There, a leader can more thoughtfully identify patterns, take note of who is quiet and who is overly agitated. Spot the person who has taken over the conversation relying on authority gained from a title or history or stature. Notice who is marginalized despite their efforts to be heard. Returning to the crowded dance floor, a leader can now intervene more effectively, share studied observations, and gently reset the conversation as needed.
Leaders are Born and Made
Leadership requires persistent study to be maximally effective. Though I hesitate to draw on Moshe given the uniqueness of his stature in Jewish history, his ascendency to leading the Israelites is instructive. Consider Exodus 3:2, which describes his initial call in the form of an encounter with the Divine who appears from within an unconsumed flaming bush. The wandering shepherd possesses an exquisite curiosity that causes him to pause long enough to notice the strange sight; the spiritual awareness and patience necessary to be present for an unfolding encounter with the Holy One; and the humility needed to listen. His is a leadership awakening out of profound stillness. But be it the one who can capture the attention of a noisy crowd with volume and energy or the one who is captured by the sight of a Divine message alone in the wilderness, only a choice few leaders succeed solely based on instinct. Relying on born leaders is a shortsighted strategy.
Can leadership be taught? Or, as it is often posited, “Are leaders born or made?” The answer to both questions is yes, absolutely. What’s more, we cannot afford not to approach leadership as a serious subject of study. Replace the word leader with singer, and my point is better understood. Some are gifted from birth with musical talent that those who study a lifetime will never match. This is why I lipsync, “Don’t Rain on My Parade,” and leave the vocals to Barbra Streisand. But singing coaches know that incremental vocal improvement is attainable with new techniques, repeated voice exercises, and attentive practice, including ongoing integration of the learning into one’s singing. This is how a person can become a better singer.
Whatever innate ability a leader is born with, be it charisma or grit or resilience or creative genius or natural presence, effective leadership requires attentive and deliberate practice. Leadership skills should be pursued with a focus on specific improvements and according to articulated goals.
James MacGregor Burns, who is credited with developing the idea of transformational leadership, wisely distinguished management from leadership in his seminal 1978 book, Leadership. An overwhelming catalogue of titles published since then provides guidance on good habits to cultivate, bad habits to avoid, and everything in between. In short, one can study how to lead, and most leaders have a “leadership bible” to which they are loyal. Find the books and authors that speak to you and (the hard part) deliberately practice what they preach.
Beyond the books, find yourself a (critical) friend. Those serious about continued leadership learning take Proverbs 27:17 seriously: As iron sharpens iron, so one person sharpens the presence (literally, the face) of another. I appreciate the many dilemmas Jewish professional and volunteer leaders share on social media platforms seeking crowdsourced solutions. That said, nothing replaces the consistent processing of your leadership presence, communication, and personal case studies with a critical peer or mentor. Identify someone you trust to give you thoughtful and, when needed, sharp feedback on how you exercise leadership. Speaking personally, my own skills have been honed, and I have grown tremendously over many years, owing to fearless peers I rely on as truth-tellers and critics.
Brené Brown, in her book, Dare to Lead (2018), tells of asking one thousand leaders to identify the behaviors that draw positive recognition from team members. Asking for help emerges as key. It serves as a reminder that there is a difference between being called a leader and doing or exercising leadership. The distinction is significant. Stated simply, a leader is not something a person is, it is something a person does. It is a practice and not a position. The pursuit of leading requires rigor and the input of others even if your instincts are good, even if you have a high-powered title. Exercising leadership demands ongoing reflective practice, which is not a luxury, though it is too often regarded as one. Focusing on how one leads, asking for help in planned and spontaneous conversation, should be an authentic aspect of leading.
Yes, leadership can be taught, and learners, including rising leaders, volunteer leaders, and boards, benefit when encountering and wrestling with the same material.
A learning leader maintains a library of reliable books and a list of questions to be considered over and over:
Am I leading in a way that is consistent with my values?
Are my values aligned with those of my organization?
Does my organization have a shared leadership strategy? Are we in step with one another?
Do I see my team? Do I see my community?
Do I understand the ways conflict can be a source of creativity?
Am I comfortable with disrupting the status quo?
Do I orchestrate distress to the benefit and not the detriment of the community?
Am I meeting realistic self-care objectives?
Demands on organizational leaders are endless. Trusted colleagues and partners can be brought together in a leadership-learning circle. In that brave space, leadership strategies and the obstacles to pursuing them can be contemplated and resolved.
Brainstorming solutions to thick problems develops the leadership muscles of a staff team, especially if the senior leader is genuinely open to answers from anyone. Promoting leadership learning across an organization fosters connection and self-awareness and sparks elevated conversations. Maintaining one’s own best practices with consistent focus on deepening both the hard and soft skills of exercising leadership grows a leader’s confidence (not arrogance) and their comfort with discomfort. Ultimately, the one who exercises leadership can grow in courage and clarity of convictions, mighty forces in achieving stunning institutional changes that will fulfill the aspirations of a forward-thinking enterprise.
Brown underscores the value of vulnerability in much the same way our own tradition of mussar, the study of character building, values anavah, humility. A posture of vulnerability facilitates curiosity, a bedrock requirement for effective leaders. Curiosity often erodes with leadership experience. This is an ego trap to avoid.
Brown describes vulnerability as removing one’s armor which, ironically, makes us stronger in much the same way humility paves a clear path to discovery of so much we do not yet know, no matter how much we have achieved. “What do you think?” is another empowering question from which leaders can learn, while admitting “I do not know” can be an empowering answer. It is permission for everyone to contribute. Genuine curiosity is an invitation into a shared change journey, an opportunity for an entire community to learn and lead. Change is not linear by any means, and when opening the process, a leader must balance patience with urgency, an ongoing calibration for all who lead change.
Leaders Inspire
Defining reasonable timeframes and planning for absorbing losses is nearly unthinkable in a world of pandemics and horrific terror. Those exercising leadership today are exhausted by a cycle of instability, chaos, and even despair. We are flattened by forces far beyond our ability to control or understand.
While acknowledging these troubling times is important, a discussion of leadership would be incomplete without its more joyful dimensions. Those exercising transformative leadership, supporting individuals to become the best possible versions of themselves, and motivating communities to derive life-affirming meaning from Torah, even and especially in these times, must inspire with an infectious spirit of joy and optimism. Creativity is fueled by these attributes, and playfulness is a product of it. As can be said of tears, well-placed laughter is healing and even liberating. Leadership learning can be a stirring experience of self-discovery and personal growth. It is a serious business, this thing we call leadership, but uplifting when visions are realized, organizations transformed, or new entities emerge—and it measurably strengthens Jewish life.
Having described the experience of Moshe’s leadership call born in desert stillness, I conclude these reflections by shining a light on his sister Miriam’s leadership. In Exodus 15:20, once the children of Israel have crossed the sea to freedom, Miriam leads the women in dancing, timbrels in hand. We might be surprised that she possessed the presence of mind to schlep a timbrel during those pressure-packed minutes when the Israelites were escaping Pharoah’s pursuit. Recall there was no time even for the bread to rise!
Rashi’s explanation of this verse is instructive, offering a fitting exhortation to those who lead in distressing times. Miriam, he writes, was confident that redemption would be realized. Her tambourine, technically a percussion tool, was also a tangible symbol of her optimism. What a gifted leader. In literal fear and darkness, she transformed the tambourine into an instrument of hope when she danced in celebration of redemption after safe passage through the parted sea. The timbrels provided reassurance during our people’s monumental adaptive challenge. She prepared the women for an unlikely dance, urging them to pack, of all things, their tambourines. In doing so, they, too, were able to lead the people from trembling to dancing.
In this time of ongoing Volatility, Uncertainty, Complexity, and Ambiguity or VUCA, an acronym developed by leadership scholars Warren Bennis (On Becoming a Leader, 2009) and Burt Nanus, it is important to close with a note of gratitude, immense gratitude to all of you who are holding our communities in these days. You are turning VUCA into Vision, Understanding, Clarity, and Adaptability. You are leading us from fear and darkness to hope and joy.
