Experiencing the Magic of the Organization: Making Boards Attractive

Phil de Toledo with Ilisa Cappell

An interview with Phil de Toledo

By Ilisa Cappell, Vice President for Leadership Development, Prizmah


IC: Research has shown that all too often, lay leaders lament their roles. They may say things like, “I drew the short stick, and that’s how I got stuck being board president” or “I had a checkbook and a pulse so that’s how I got put into the role.” They may be told, “I promise you won’t have to do anything, come sit on the board, we just need to fill the seat.” I know you have the opposite perspective, that it’s an honor and a source of pride to serve. Could you reflect on how we talk about lay leadership and what for you is that source of pride in the work?


PD: Serving on a board should provide a tremendous sense of pride that you are doing something good for the community. Community only works if individuals get involved, and being on a board is definitely a good way to be involved.


As far as the comments you have heard board members make, I wonder if that’s how people really feel or if it is just a little bit of a humbleness. When you do get selected for a board or leadership position, someone has identified you, and there’s a natural feeling of being self-conscious, of having been singled out. Maybe that’s the root of it: People should feel a little less self-conscious of having been selected for a leadership position and feel a little more pride.


If someone really doesn’t want to do it, then they are not going to say, “I got the short straw, what am I going to do?” They are just not going to do it. A more positive and constructive approach is for the person to think, “I can do this,” and “Wow, that’s kind of cool that I was selected.”


So it is a mindset. And maybe when you do it enough times you realize that it is something that you will enjoy doing. You wouldn’t be involved if you didn’t have some passion about the organization in the first place. And you should feel good about that. It takes work, time, effort and brainpower. It can be stressful. But at the end of the day, you are doing it for a good cause, or you shouldn’t be doing it.


It may sound a little self-deprecating when you say it, but downplaying your selection actually has a bigger negative impact because it makes it less interesting or inviting for the next person to serve. It would be better if you just said, “What an honor to be in this position.”


IC: How do we keep people’s emotions positive and their engagement high during their work on the board?


PD: When planning for a board meeting, it’s crucial to think about how you want board members to feel when they get back into their cars after the meeting. You want them to feel good that they were at that meeting. Notwithstanding the sacrifices they had to make to attend the meeting, including braving traffic, you want them to say to themselves, “I’m really glad I attended. I’m really glad I’m part of this organization.”


This takes planning. It is important that, in advance of the meeting, the chair and the organization’s executive consider how to

create a meeting where board members will feel good that they attended and that they are part of the organization. It can’t feel like drudgery. If it is, board members won’t stay engage or won’t stay on the board very long, and they will not have interest in taking a leadership position.


It’s a virtuous cycle—or its opposite.


Board meetings require focused attention by the board members and usually have a lot of reports, including a financial report, an investment committee report, a fundraising report, etc. But there also has to be enough sharing of the “magic” of the organization. In other words, sharing of the successes, how the organization is executing its mission and how it is impacting lives. In the case of a school, it’s usually the stories of the impact on the kids. These stories put board members in the right mindset. Ensuring that board meetings include the “why” and the “wow” of the organization reinforces and validates why the board members are dedicated to the organization and that it is doing good for the community.


IC: The theme of this issue of HaYidion is leading together. What you were just describing sounds like work that you did in partnership with the head of school. Could you identify some of the key ingredients that you feel contributed to that relationship being successful and the ways that you invested in that partnership?


PD: I’ve always approached any situation with a new working partner, whether it is in the nonprofit or the for-profit world, with a relationship discussion. Early on in our relationship, we talk about how we are going to work together and what are our preferred work and leadership styles. We discuss how we are going to deal with situations where we have differences of opinion. It is a lot easier to deal with these key elements of a working relationship, and setting the framework for how you will work together, at the beginning of a relationship than it is to address it in the heat of an issue.


I am always very clear upfront that we will be candid and transparent in all our communications. It is important to create a two-way street in which each partner feels comfortable and safe being open and honest. In theory, the head of school works for the board, and the board is represented by the chair. The relationship is hierarchical, which can be uncomfortable. In practice, you want the relationship to feel like a partnership, so it is important to establish a relationship of trust and openness from the beginning. If it ends up feeling like a hierarchical relationship, then something in the relationship has gone wrong and needs to be fixed.


It is important to create an environment where there is a safe flow of communication and information. If there are things that I, the board chair, can be doing better, the head of school needs to feel comfortable, and feel the obligation, to tell me. And vice versa. It is important that both parties agree to this expectation from the beginning.


IC: It strikes me that there are two elements at play here that seem so core to who you are. One is self-awareness, your ability to be reflective on your own. Your ability to say, these are the things I need to be successful. Here is what I am bringing. Here is how you might experience working with me, here is how I can best communicate, and your ability to receive and deliver feedback is one piece. The other thing is leadership awareness. You are coming into this really thinking about it from a design and teaching perspective. A lot of the things you are talking about are things you would hear from classroom teachers or professionals in the field, really talking about how would I lead a group of my peers.


For lay leaders now, coming into these roles, what is some advice that you feel they may benefit from, to help them grow in these areas that may help them lead their boards?


PD: Actually, the advice I would give is to the head of school. An important part of their job is to help the board chair learn their role; in many cases, this is the first leadership role for the new board chair. Heads of school are uniquely in a position to help the chair get educated about how to do their role effectively.


I’ve seen relationships between board chairs and heads that haven’t been very effective. In some cases, the chair thinks too much like “I’m the boss.” That’s never a good mindset. Or some heads of school think, “You’re just another board chair, and I’m going to stiff-arm you because I know what I’m doing and I don’t really need you.” The initial interactions of the head of school with the incoming chair can be very critical for setting the tone for a good working relationship during the chair’s term.


There has to be some vulnerability and some understanding by the head of school that they need to attract people to be board members and leaders and that, at the end of the day, these people are their customers, they are their donors, and all of them have the ability to make different decisions. So the head of school needs to create the environment where people will make the decision that they are going to support the school, to send their kids here, that they are going to want to be part of this community.


Board leaders need to keep an eye on the big picture even as they work in the weeds. Take the budget: If the focus is just on the numbers and not on the mission or how people are going to feel, the board is going to make one set of decisions. If the broader context of the what the organization is trying to accomplish is considered, the board may take a more nuanced view. The board needs to keep in mind that, yes, there is a business element but we are a school, we are not a for-profit business, and we need to keep the mission top of mind.


The people who work in a school are there because they have a passion for educating our children, for creating our society. Being an educator is not the highest compensated role, but it really does make a difference in the lives of the young people they educate. Boards need to be sensitive to that. The board’s constituency is not just the parents, it is the entire school; boards need to make sure the teachers feel valued and appreciated.


Supporting the head is a key role of the board chair. The chair needs to provide public support for the head where that is necessary as well as personal support. It can be a lonely job to be the CEO of an organization, and the chair may be one of the few outlets for the CEO. All of the problems come to the head of school; they have to deal with all the difficult issues that arise from all corners, let alone from a difficult board. All the more so if the head is managing the organization during a heightened time of stress, for example during Covid. The board chair’s attitude should be, “Thank God we have this head of school. We need to really support him or her, because they have a really tough job.”

Return to the issue home page:
HaYidion Leading Together
Leading Together
Spring 2021