Leadership Fast and Slow

Jon A. Levisohn

What are the necessary or desirable dispositions or capacities for leaders of Jewish day schools? The list is long. A common refrain, heard particularly when a school is launching a search for a new leader, is that the head of a Jewish day school needs to be “God on a good day.” Or maybe even more than that. Whereas the Jewish tradition teaches that God is eternal and unchanging, day school leaders are often expected to be agents of positive change in their institutions.

In recent years, one of the most powerful frameworks for thinking about change has been “design thinking.” Often associated with the design firm IDEO and with the d.school at Stanford, design thinking is an approach to innovation or change, to creating something new to meet certain needs or solve certain problems. It has a distinctly Silicon Valley vibe. Design thinking is unsentimental about legacy institutions or processes. The criterion of success is whether the innovation solves the problems it is trying to solve, for those human beings whom it is trying to serve, rather than whether it meets some other predetermined standard for what a solution is supposed to look like or what a tool is supposed to do. 

Moreover, design thinking emphasizes creativity and intuition over rationality and analysis. This does not mean that design thinking ignores empirical realities. Quite the contrary. Typically, a design-thinking approach will begin with data collection, and will emphasize how important it is to understand the presenting problem clearly and precisely in order to develop appropriate solutions. But design thinking also recognizes that good ideas often flow from messy, unwieldy processes, and that we need to create spaces for those unwieldy processes if we want to generate new solutions.

So what does this have to do with Jewish day schools?

Design thinking is not just a matter of creating a better can opener or a better wallet. Design thinking is really a technology of change, including an approach to organizational change. Good leaders, then—including good leaders of Jewish day schools—are people who are equipped to lead design processes within their organization, helping those organizations adapt and flourish. 

This way of thinking about Jewish day school leadership is compelling, it seems to me, for the following three reasons. 

First, it’s non-technical. When we think about developing leaders within a design-thinking framework, we do not focus on training people in technical skills. Instead, we focus on cultivating capacities or dispositions that are decidedly non-technical: the ability to listen and observe carefully, in order to understand a problem fully; the capacity to generate creative ideas in non-judgmental fashion; the patience to deal with the uncertainty when accepted ways of doing things are challenged. These may be hard to cultivate, harder than technical skills. But that’s exactly what makes them so desirable. 

Second, this way of thinking about leadership is compelling because it’s solution-oriented and client-focused. We want our leaders to be positive people, focused on solutions rather than merely on problems. We want them to flexible and open-minded, more concerned about meeting the felt needs of human beings than about the correctness of their orthodoxies or even the preservation of their organizations. We want our leaders to be focused on what works, to be pragmatists rather than metaphysicians.

And third, this conception of leadership is compelling because it celebrates creativity over rationality. We want our CFO to be a model of rational analysis. But our CEO? We want that person to be interested in data, for sure, but data-wonkery is not enough. We want more from that person. We need a creative thinker, someone who can do more than just come up with a better delivery system—someone who can imagine a whole new framework. The CFO needs to follow the rules and make sure the information is correct. The CEO needs to tell us the story of ourselves. That capacity, that ability to tell us our story, has to be rooted in the facts, but it should never be limited to the facts. It has to inspire, ignite a spark in our own imagination. That’s why it requires the leader’s creativity, to imagine possibilities that are not currently obvious. 

Those are three strengths of the model, three ways that we might think about design thinking as a paradigm for Jewish day school leadership. This is all helpful to us, as we think about what we want leaders to be and to do. But there are also grounds for critique, and those critiques will help us think about Jewish day school leadership as well.

First, we noted that advocates for design thinking often emphasize its positive orientation, its focus on solutions rather than problems. But at the risk of stating the obvious, you cannot have a solution unless you first have identified a problem to be solved. In other words, those who embrace design thinking refuse to get locked into a negative discourse around problems, and instead find ways to pivot to a positive discourse that generates possible solutions to those problems. But this still assumes that what we see, when we look out at the world, is a field of problems.

I should note that this assumption—the assumption that the responsible thing to do, when looking at the world, is to identify the problems so that we can find the solutions—is not unique to design thinking. It is also closely associated with what is often called “strategic philanthropy,” the movement in the last decade or so away from reactive responses to requests for aid and towards a proactive articulation of problems in order to develop strategic approaches to solving them.

There are good reasons to adopt a strategic philanthropic position, just as there are good reasons to adopt a design-thinking approach. But in education, we know well that there is also a danger here. We know what happens when we frame children as problems to be solved, as “drop-outs” or “children-at-risk.” And the danger doesn’t go away just by focusing positively on the solution rather than negatively on the problem. No child in school wants to be “solved,” any more than they want to be pathologized in the first place. When we look out at a classroom, we don’t see problems sitting in front of us; we see people. We are not trying to solve anything; we are educating. 

This is not to say, of course, that there are no problems in educational spaces. Sometimes it is genuinely helpful to articulate a problem in order to work on a solution. But according to the old adage, if all you have is a hammer, then everything looks like a nail. We at least have to acknowledge the possibility that “solutions” are our hammer and “problems” are our nails. There are problems in education, and we ought to work on solutions. But the business of Jewish education is not about solving problems. 

Instead, the business of Jewish education is about building a thriving Jewish community, creating an aspirational shared Jewish future, helping people lead good and meaningful lives. To reiterate, this point is not about optimism versus pessimism. I am not suggesting that we ignore the challenges. But we ought to notice the danger of pathologizing Jews and Jewish communities, simply because we’re locking into a mindset that says that we need to figure out the problems precisely so that we can be solution-oriented.

Second, I noted that design thinking is admirably attentive to the needs of human beings. The criterion of success for the product that is being designed is not elegance or efficiency or how many extra features it has, but whether it works for the person for whom it was designed. The criterion of success for any solution is whether it solves the problem that the client is facing.

But in nonprofit leadership, who exactly is the client? Sometimes, in direct service organizations, we can think about the clients as the people who are being directly served. If I’m working on homelessness, the client is the homeless population. I’ve got to keep their needs front and center. Many educational organizations are like this as well, at least in certain respects.

On the other hand, readers of HaYidion will surely remember the tagline used by RAVSAK, one of our legacy organizations: “Our client is the Jewish future.” The line was instructive, in effect functioning as a declaration of independence from short-term thinking. Relationships with day schools were not meant to be seen in transactional terms, as simply the provision of services for schools considered as clients. The thinking was bigger than that; it was focused on a longer-term horizon. Of course, it was also necessary to listen carefully to the schools in the network, to understand their needs. But if they only listened to the schools, only provided what the schools said they needed, they would not have been fulfilling their mission.

Consider, too, other kinds of institutions. What if I’m building an art museum? Or strengthening democracy? Or doing basic biological research? Then the client is not so clear. Those examples should serve to remind us that, even in schools, we may need to think more broadly about who the stakeholders are.

The third and final critique focuses on the ways in which design thinking is action-oriented. The design-thinking approach says, “Don’t just stand there, do something!” Try something. Adopt an experimental approach. Don’t be afraid to fail, and fail fast, and fail often. You’ll learn more from trying than you will from sitting on your hands while you worry about what to do. The claim is that leaders who are eager to try and fail, and who promote that attitude within their organizations, will be more successful than those who are focused on maintaining the status quo.

There is surely something valuable here. Very often, we do want action, experimentation, learning from experience rather than waiting for the perfect solution to magically appear. But not always. Sometimes, the right counsel is, “Don’t just do something, stand there.” Sometimes, we do not yet understand the situation correctly, we do not yet have enough information, and we have not yet figured out the right way of framing the problem. Sometimes, we need to let our current practice develop, we need to let it bake for a while, before moving on to the next thing. Sometimes, doing something—anything—because of this kind of action-orientation may well have a hidden cost down the road, in terms of institutional exhaustion and dissipation of focus.

In schools, for example, we sometimes see a frenetic embrace of every passing fad. Let’s try it out! Let’s see what happens! Why not? But when cooler heads prevail, we realize that the teachers are exhausted and do not have the time to learn from experiment A before we’ve moved on to B and C. In other kinds of nonprofit organizations in the Jewish world, too, we sometimes see an expectation that every new grant requires a brand-new initiative, a fresh innovation. Some funders seem to have a blind spot on this topic, never asking themselves what the cost might be to good and healthy organizations when the funders incentivize change over constancy. It sometimes seems that we take our best and most thoughtful practitioners and turn them into crazed hamsters on the spinning wheel of innovation. 

In these situations, we ought to be cultivating leadership not for action-orientation but for sustained focus, sobriety, maturity, systematic thinking, the ability to stay the course and invest for the long term even when there is pressure to try something new, to fail fast, to show quick results. In the design-thinking literature, data collection is typically a matter of a quick-and-dirty exploration of the needs of a particular target audience. Sometimes, that’s exactly the right approach. At other times, though, what we need is a slow-baking process of institutional learning, or of developing an intellectual infrastructure, over the course of several years. 

In his acclaimed best-seller Thinking Fast and Slow, psychologist Daniel Kahneman identified and explored the ways in which intuition and hasty judgment (what he called “System 1”) often leads to error. We focus on the wrong things, and are deceived by numerous cognitive “effects.” Our speed misleads. But this is not inevitable. We can act otherwise. We have a range of techniques for thinking slowly and carefully (“System 2”). When we do, we eliminate errors, bias and misjudgment. 

As we think about leadership for Jewish day schools, we ought to keep in mind leadership for calm and reflective deliberation, not just leadership for failing fast.

Leaders well-schooled in design thinking will be admirably attuned to the needs of real human beings, and will have the flexibility and creativity to develop new solutions rather than simply sticking with the status quo. These are important. We are rightfully critical of institutions that focus on their own preservation, rather than on serving genuine needs. But this is not enough for leadership. Something else is needed as well. Beyond facilitating the processes that generate solutions for present-day problems, leaders also have to have the capacity to think about the long term. They need to have the System 2 dispositions of calm and careful deliberation, of developing and executing a long-term plan. If they genuinely believe that their client is “the future,” they have to make decisions in advance of knowing what the future will bring—indeed, decisions that will create one future, a good and healthy future, among the many possible futures.

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HaYidion Leadership Dispositions Winter 2018
Leadership Dispositions
Winter 2018