Collaboration Over Competition: The Key to Embracing Diversity
June 26, 2025
Start Here
July 2, 2025Dr. Noam Wasserman
Based on a workshop given at the CoJDS Think Tank in July 2025
On June 13, I had a thought during davening. I had said these words so many times over the years, but in light of the news about Israel’s attack on Iran the night before, I had a new insight. I was saying the three “שומר” phrases with extra feeling. I began, …שומר ישראל שמור שארית ישראל ואל יאבד ישראל. Hashem is the שומר ישראל, the guardian of the Jewish People, and we had just seen that the night before. But under what conditions? I realized that the next two lines give us the formula. …שומר גוי אחד שמור שארית עם אחד ואל יאבד גוי אחד. Hashem protects us when we are united, when we are “one nation.” And also, …שומר גוי קדוש שמור שארית עם קדוש ואל יאבד גוי קדוש. We’re protected by Hashem when we act as a holy nation.
This is not just something that is true for the Jewish Nation as a whole, but it seems particularly relevant to the work of the Consortium of Jewish Day Schools, which brings together schools of all types to enhance Jewish education and create the next generation of our גוי קדוש.
The Entrepreneurial Mindset and Failure
I would like to discuss how we may import some of the practices from the business world into Jewish day school leadership. Specifically, what can startups tell us about school leadership?
I entered school leadership from the world of academia and startups, having spent 25 years researching startups, governance, and team dynamics. Having applied those lessons to the schools whose boards I have chaired and then to the Sy Syms School of Business at Yeshiva University, where I was dean for six years, I am starting to apply these mindsets and practices to day schools. Additionally, over the years, as I’ve reflected on the insights gained from my research, I have come to realize that many of my thoughts have been shaped by our mesorah, the millennia of wisdom found in the Gemara, the meforshim, the machshava, and other sources.
Rather than simply importing business practices into the world of school leadership, I prefer to think of my approach as “Torah U’Business,” combining Torah and business. Let’s explore how we might benefit from combining the two. As we head into the next school year, I hope to leave you with some practical ideas with which you can experiment.
Let’s start off with the happy topic of failure. Most people have probably heard that entrepreneurship is associated with a high failure rate, yet people continue to try. The entrepreneurial mindset – that leads people to try, fail, and try again – offers valuable lessons in resilience and growth that can be applied to other domains. We could certainly learn what to do from such people, but even more importantly, can we also learn what not to do? Failure feels terrible, sparking a natural reaction of “woe is me”. Founders would give anything to avoid it! And schools are in a “can’t fail” position. Yet, without knowing the causes of failure, it can be hard to avoid.
In my research, I’ve looked at the fundamental questions: Why do startups fail, and why do people pursue them despite the risks? I had been in the startup world for five years, and as I entered the PhD program at Harvard, I sought to find the answers to these questions. This led to years of research, studying data from 20,000 founders. A key starting point was a pivotal 1989 paper by Dr. Bill Sahlman that examined venture capitalists, who are investors who back only 1% of the business opportunities they see. You would expect that with that level of discernment, they would almost never make bad investments, but that’s not true. His paper asked why these failures happened and offered some very interesting observations. 35% of failures stemmed from issues you might expect, like cash flow crises or a poor fit between the product and its market.
However, there was one far bigger reason that overshadowed all the rest of them in terms of why startups with the greatest potential were coming crashing down to the ground. It was only one line in the paper and one number in a table, but it leapt out at me from the paper. When I saw it, it said to me, “This is where we have to look in terms of being able to increase our chances of success.”
65% of the reasons for failure were the people problems. The frictions between the founders, the tensions between them and the other people they hired to complement them as they were growing, or as they had holes that had to be filled. It was the בין אדם לחבירו that was bringing down even the best of these startups.
And so, this is what set off 20 years’ worth of my research, to be able to understand: What are the early people decisions that founders make that go awry? What are the ways in which the teams can do better? We have natural instincts about with whom to found a company and about how to architect the team. But those natural instincts can actually be counterproductive, heightening risks for the team rather than helping it. How should we think differently about those natural instincts?
As Steve Jobs, the cofounder of Apple, said: “Follow your heart, but check it with your head.” In the spirit of “סוף מעשה במחשבה תחילה,” how can we understand where we need to put a little more thought into a decision before making it?
We’re going to take a look at some of the things that I discovered in my research on startups, but also how we can understand the בין אדם לחבירו and even the בין אדם לעצמו. What’s going on in our own heads that then affects how we interact with the rest of the people on the team?
Team Dynamics: Questions to Ask Yourself
To set a baseline, let’s consider four key team dynamics. Try to think about your teams as you answer these questions.
- Difficult Conversations: Is your team skilled at handling tough discussions? There is a natural human inclination to avoid having difficult conversations. And yet, by avoiding them, not tackling the elephant in the room, that elephant grows and tramples everything else. Often, it’s even tougher down the road to tackle the issues that were avoided in the beginning.
- Accountability: Is your team able to hold each other accountable? Accountability is often missing, even though it’s clearly important.
- Decision Making: Is it clear and unambiguous who makes key decisions for your team? Ambiguity about decision making leads to confusion, frustration, and, often, inaction.
- Role Clarity: Are the roles and responsibilities of the team members crystal clear? Lack of clarity leads to people stepping on others’ toes and important balls getting dropped.
How important do you think it is for teams to be good in these four areas? How many teams actually are high performing with all of them? There are natural human inclinations that lead to these things going awry. Despite knowing these are important, we don’t have the tools to ensure that we’re going to get better at them.
Let’s take a tour through some of the tools and explore a mindset that we can develop around these issues of team dynamics. We’ll start with the mindset and follow it up with five tools that I’ve found to be very valuable in terms of my teams and the things I’ve been able to architect. These practical strategies address these challenges and are applicable to both your team and your board.
Mindset: Accepting Criticism – עזר כנגדו
Does it feel good when you have a performance review and you get some critical feedback? No! Criticism often triggers a defensive reaction, and we’re loath to receive or even give it. Criticism is a common cause of failure, either when teams break apart or when the fear of criticism prevents problems from being addressed.
If we look at the founding team of the world, we can find a model for criticism that is very helpful. The Torah refers to בין אדם לחבירו, the relationship Adam and Chava were supposed to have, in a two-word encapsulation: עזר כנגדו. The word עזר means “helper” while כנגדו means someone in “opposition”, and so the meforshim try to explain how these two contradictory descriptors come together to describe the relationship.
Rash, quoting .יבמות דף סג, says that it will be עזר (help) if you merit it, but כנגדו (opposition) if not. In fact, Rashi even describes the opposition as להלחם, to fight. Getting the כנגדו is להלחם. Rashi is describing our natural recoil from pushback. If you’re fortunate, your spouse will serve to help you achieve what you want in life; but if you’re not, your spouse will stand in opposition to you.
However, the Netziv offers a different, prescriptive view: he explains that we have to see the כנגדו as the עזר. The best relationships are with someone who is willing to do something that no one else is willing to do: have the difficult conversations about where we can improve and where we can reach our potential more fully. The כנגדו, opposition, is the best עזר, help. In this view, instead of being fearful of and hurt by criticism, we should say, “Thank you for highlighting that very useful way I can reach more of my potential.”
I think .בבא מציעא דף פד is one of the most packed and insightful pages in ש”ס. It relates the story of רבי יוחנן and ריש לקיש, how they met and became chavrusas, and then we read of ריש לקיש’s demise. Afterward, רבי יוחנן was inconsolable, and ר’ אלעזר בן פדת was appointed to be רבי יוחנן’s new chavrusa. It didn’t go well. ר’ אלעזר supported everything רבי יוחנן said. רבי יוחנן complained vehemently about that, saying that ריש לקיש had always challenged him with “24 darts” and that that was key to his intellectual development. רבי יוחנן recognized that the כנגדו was the factor that pushed him to greatness. ר’ אלעזר avoided criticism, like Rashi’s view, and he couldn’t adjust to the כנגדו mindset that רבי יוחנן craved, and as the Netziv advocates. (It’s fascinating to note that Rashi’s explanation of עזר כנגדו is taken from a statement in .יבמות דף סג… by, yes, ר’ אלעזר בן פדת!)
We find a successful incident of עזר כנגדו in the Gemara in .ברכות דף י, which describes the different reactions of רבי מאיר and his wife, ברוריא, to some hooligans in the neighborhood who were causing trouble. רבי מאיר wanted to pray for them to die. ברוריא suggested that he was mis-reading a pasuk: it didn’t say that sinners should end, but that sinning should end. She said that he should be praying for the sinners’ repentance rather than their demise. To his great credit, רבי מאיר accepted her כנגדו pushback. He saw she was correct; he davened for Hashem to have them be חוזר בתשובה, and they were.
This mindset applies beyond Torah. In my course, “Founder’s Dilemmas”, in the MBA program at Harvard Business School, we examined founders and their relationships through the lens of עזר כנגדו. Based in part on that concept, one of my students, Jessica Alter, actually founded a company called Co-Founder Dating, which focuses on helping co-founders determine whether they have what it takes to be compatible. In a prominent blog post, Jessica wrote that one of the critical skills for founders to have is “the ability to fight well”, how to develop a כנגדו dynamic that will become an עזר to everyone on the team. We have many examples of this within the entrepreneurial sector.
It also applies beyond business, to our personal relationships. Another one of my “Founder’s Dilemmas” students came to me and said, “Noam, I’m never going to be a founder.” I began to apologize for convincing him to take the wrong course, but he stopped me and told me that while he’s never going to be a founder, my course was saving his marriage. This was a surprise to hear, especially in the MBA program, after more than a decade of studying founders, writing papers about founders, and naming the course “Founder’s Dilemmas”. Even my almost-finished book was named for founders! I asked him, “Tell me more, David. What does this have to do with marriage?” I understood that what he was going to tell me was my כנגדו, from which I can learn more.
He told me, “I’m a newlywed. We are struggling right now with how to make decisions together, rather than being independent from each other. How do we define roles within our marriage? How are we able to fight productively?” He explained that he began importing a bunch of these lessons from founders into the challenges they were having within their couplehood and found that there was a lot of application. He grabbed me by the lapels and said, “Noam, you are too narrow-minded. You think that you’re only studying founders, but this applies to all areas of life.” He gave an example: Early on, they were looking for equality within the team. He would cook one day, and she would do the cleaning, and then they would swap the next day. The problem that they were having was that every other day, the food was burnt, and the floor was dirty. And so, instead of the fisticuffs he was having with his wife, they decided to adopt something they had seen in the founding teams: playing to their strengths. They decided not to be so fascinated with that equal division and instead tried to map what we have to do to the things we are best at.
And that’s when I began to appreciate the בין אדם לחבירו lessons that we can apply in all sorts of directions, including within our teams and in all of the most cherished relationships, whether professional or personal. These are fundamentals that run counter to many of our natural inclinations, so they take work.
Another example of this is found in research by Dr. Richard Hackman about “grumpy orchestras”. What kind of orchestras play well together, make beautiful music? The ones where everything is all nice and smooth (“like Kumbaya”) or the ones where there’s a little bit of tension or conflict within them? And he actually found that the grumpy orchestras played a little better. The ones who were able to bring up issues and push each other to greater heights were the ones helping each other to improve. They made better music.
And in a radically different arena, I recently saw a picture of the Harrison twins. They are star bodybuilders and they credit each other. I just love the image of pushing each other; the כנגדו that jumps out from this image. When asked, why did they get to the heights of the profession? They pointed to the כנגדו of being able to push each other to greater heights.
These are some of the examples of being able to see it as a helping hand when you receive criticism, when you get that pushback. We have to retrain ourselves, we have to build our כנגדו muscles, individually, בין אדם לעצמו, and then also within the team.
At Ramaz, I began to introduce this mindset to my senior team, encouraging them to be my כנגדו and highlight my blind spots. Our summer off-site retreat included chavrusa learning on Rashi and Netziv’s interpretations of עזר כנגדו to foster this culture. It also came up in the office. I prepared a document and showed it to the Ramaz CFO. She said it looks great. But I challenged her, “Give me at least one way to improve it. Give me the כנגדו.” And she gave me an important improvement I could make. I incorporated it, and she was able to see that we’re serious about this.
We need to be able to invite it in, not just wait for it, but within your team, be able to foster it. We must build this “כנגדו muscle” individually and as teams, actively soliciting pushback.
Toolset 1: Advice, Not Feedback
Here’s one simple insight that can help you make this transition. Social psychologist Adam Grant suggests reframing performance reviews as “advice conversations” rather than feedback. In his book, Hidden Potential: The Science of Achieving Greater Things, Grant writes, “Instead of seeking feedback, you’re better off asking for advice. Feedback tends to focus on how well you did last time. Advice shifts attention to how you can do better next time.”
Feedback focuses on past mistakes or successes, which can be hurtful, demotivating, or simply breed complacency. Advice, however, looks forward, offering constructive tips. Grant suggests asking, “What’s one thing I can do better?” This kind of language invites כנגדו in a productive way, easing teams into this mindset.
Toolset 2: Action Items Table
We have identified two primary barriers to accountability within teams. First, does everyone understand what they are supposed to be doing? And second, what is the implication if you don’t get it done?
If you’re looking to enhance accountability, here’s a simple tool to use at the end of meetings. An action items table captures the Action Item (what needs to be done), the Responsible Party (who is responsible for getting it done), the Due Date, and a fourth box for Status/Comments (such as updates from ongoing action items or barriers that are anticipated or have come up).
| Action Item | Responsible Party | Due Date | Status/Comments |
| Clean front entryway carpets before PTC | Facilities manager | March 22 | |
| Research and present options for new maintenance ticketing system | IT director | May 15 | |
| Prepare list of summer maintenance priorities | Facilities manager | Next meeting | We decided not to paint the gym last summer and do it this summer instead |
You hold your meeting following the agenda, but before you leave, fill out (or prefill) the Action Items Table. Then, share the table (e.g., via Google Docs) with team members, giving them a chance to correct or adjust deadlines. Then, you begin the next meeting by reviewing the table. If deadlines have been missed or barriers have been identified, the party responsible is accountable to explain what happened. This fosters accountability by clarifying tasks and sending the message that we care about tasks getting done, on time. I use this with direct reports and teams at Ramaz, from one-on-ones to senior management, ensuring everyone knows their responsibilities and commitments.
Toolset 3: Homophily Checklists
Another area of human dynamics is that we naturally gravitate toward people who are similar to ourselves. This is called homophily. This might seem positive, and we know people do this when looking for friends, but with teams, this can lead to problems. If team members are too alike, they will have redundant skills. For example, you can imagine that two guys who are founding a technology company will both be great at understanding and building the underlying software or hardware. But neither of them will be able to do the “company” part because they don’t know business. They have doubled down on a domain, which can also lead to unproductive conflict (both technical founders want to make the technical decisions!), while leaving a big hole in their capabilities.
You end up with a team that can do one thing very well, if they can manage to agree with each other, but fail in the other critical areas.
An example I used in my Harvard course is Pandora Radio, the online music company. The founder, Tim Westergren, a musician, initially discussed his idea for his company with a friend who was also a musician. Tim’s ideas, including developing an algorithm to predict what kind of music a listener would enjoy (what became the Music Genome project), required a strong knowledge of music, so it would have been only natural to start the company with other musicians (see checklist below).
Fortunately, Tim realized that such an approach would leave his team with gaping holes. He also needed someone with technical expertise, as the company was in the technology sector, and someone who could manage the business side of it.
The lesson from Pandora Music is to use a Homophily Checklist, where you create a list of the skills needed and put a checkmark if someone on the founding team has that expertise. You’re looking for every box to be checked, but only once! Someone should be able to carry the team in each critical area, and you shouldn’t have redundancies.
In schools, homophily can lead to teams with similar backgrounds, resulting in redundancies and gaps. School teams should take the time to develop their own checklist of required skills and roles within the school. This list can help when hiring new people, countering the instinct to hire those who may be fun to spend time with, but will not help close blind spots and weaknesses in the organization.
The same thing also applies to the boards of directors in our schools. Look at your board and see how similar or different the members are. Do you have a clear checklist of the capabilities you should have on your board? Are there any boxes that are double-checked or unchecked? If so, what is your game plan for being able to fix the problems introduced by that board profile?
Toolset 4: Need, Can, Want Framework
The fourth team dynamic above was role clarity: Is it crystal clear who is supposed to be doing what? When I joined the business school at YU, the top three leaders were great jacks of all trades who were able to do anything. They pitched in with whatever issue came up. Is that a good structure for a team? No! No one becomes an expert in their domain. No one knows who to send people to to take care of things and make them happen.
There is a tool for this that can also be used by people making career decisions, asking themselves, “Should I go into this field?” There are three questions to ask using this career tool: Is there a need in the world for this? Do I have the capabilities to serve this need (the “can”)? And do I want to do this – have the passion and drive to do it? We call this the “Need, Can, Want” tool.
Use this tool on the members of your team to help define roles:
| Need | Is there a real need for this role/task on the team? | |
| Can | Does the person have the necessary skills? | |
| Want | Are they passionate about this role? |
Where you can check all three Need, Can, and Want boxes, the decision is easy: do it! Often, though, one or even two boxes will be left unchecked, indicating that they may be in the wrong role (or might be heading into a suboptimal career). This helps define the lanes that everyone should be in. Who has the need, the can, and the want taken care of? That becomes the go-to person for that task. Within your school, it’s important that your team knows who it is, and then beyond the team, your parents, staff, and students should know whom to go to for what.
At Sy Syms, this process led to the creation of the “Whom to go to for what” sheet. We shifted from “jacks of all trades” to specialized roles. The sheet lists all of these issues for which people might need guidance, and lists the resources they can go to or the experts in it. This takes training, so that when a member of the team has a parent approach them about something, and their name isn’t listed for that issue, they tell them, “There’s a better person to deal with this for you, or someone who is empowered to make this decision for our school. Please go to that person.”
Doing this can also be a major culture booster, bringing transparency to everyone both inside and outside the team and helping solve the “you went to mom and got a no, so go to dad to try to get a yes” dynamic within the school. This is a way for your team and beyond to ensure that those lanes are clear, so that the expertise, need, can, and want are aligned, which will be beneficial to the team dynamic.
Thriving in the Head of School Hourglass
The head of school is often described as having one of the loneliest jobs in the world. Imagine an hourglass, with the board at the top and the school, including the families, students, and staff, below. The head of school is in that constricted spot in the middle, feeling pressure from both sides. The עזר כנגדו mindset and the toolset we’ve discussed can be used to thrive in the position, and the best thing about it is that it works both ways: downward to the school team and upward to the board.
Downward is more obvious. A leader can foster an atmosphere of עזר כנגדו, offering and being open to advice (not feedback), clarifying and assigning roles with need-can-want, avoiding homophily, and ensuring accountability with action item tables.
But this works upward, too. At Ramaz, half of the action items from my first executive committee meeting were assigned to board members. This advances the relationship between the head of school and the board, setting the tone that board members are there to add value. They find it even more rewarding if they’re not just listening to presentations, sitting on their hands, and not taking their phone calls, but putting their talents and kochos to productive use for the school.
And, of course, you have to foster your approach to כנגדו with the board, helping guide them in the ways they should push back on your ideas, and setting the expectation that you’ll be pushing back on theirs. We’ll get better by being able to discuss things openly. That’s the way to advance the mission of the school.
If we can adopt some of these best practices, we can become stronger in the lows and celebrate even more as we reach the highs of this wonderful ride. That’s where we can learn from other fields and incorporate elements from other domains. Hopefully, you and your team will be able to scale the heights and celebrate as you reach the top by seeing other ways in which we can adopt these tools. I found them invaluable. Try them out, pilot one of them, and see what kinds of things you might be able to learn and accomplish. These practices, grounded in Torah and business, can help your team scale new heights.
Dr. Noam Wasserman is the incoming Head of School for Yeshivat Ramaz (“The Ramaz School”). For the last six years, he has been the Dean of the Sy Syms School of Business at Yeshiva University. Before becoming Dean, Dr. Wasserman was a professor at Harvard Business School for 13 years, the founder of a center at USC, and a visiting professor at Stanford and Columbia. He has written two bestselling and award-winning books, The Founder’s Dilemmas and Life Is a Startup, and articles for the Wall Street Journal, Harvard Business Review, Fortune, and Inc. magazines, and others. He received undergraduate degrees from the Wharton School and the School of Engineering at the University of Pennsylvania, as well as three graduate degrees from Harvard: an MBA, an MA, and a PhD. He has worked as an entrepreneur, equity analyst, systems-integration consultant, and venture capitalist.