In each “CEO Perspectives,” we explore the work and life experiences of an individual leader. Through these stories, we hope to bring to light strategies and advice other nonprofit leaders can use to guide them in their daily work and their lives as social sector leaders.

This “Perspectives” features a conversation between former Bridgespan Executive Search Partner Kathleen Yazbak and President Dan Cardinali of Communities in Schools (CIS). CIS is a nationwide network of passionate professionals working in public schools to surround students with a community of support and empowering them to stay in school and achieve in life. Dan’s commitment to this mission began in 1999, when he joined the organization as vice president of field operations. Soon thereafter he was promoted to executive vice president and then became CIS’s president in 2004.

Today, CIS has 190 affiliates in 25 states and DC, and currently serves 1.35 million students, having doubled the number of students served since 2000. Under Dan’s leadership, CIS has engaged in a network-wide strategic planning process, sought continual improvement through the measurement and evaluation of its programs, and established a voice in the national education debate. His work and the organization’s have been widely recognized, and in May 2011, Dan was appointed by President Barack Obama to the Presidential Advisory Commission on Educational Excellence for Hispanics.

Kathleen Yazbak: How did you find out about the opportunity with CIS?

Dan Cardinali: It was pure happenstance. I was volunteering at the Organization of American States, and the husband of the then-executive director of CIS connected me to CIS. I had never worked in public education in America before.

What had been your experience up until then, and how did it influence your being hired by CIS?

Cardinali: The job was to engage a large stakeholder environment and manage conflict between the network and the national office. Things were so polarized at CIS at the time.

So, really, I was hired less for my management experience and more for my training as a community organizer and long history of working with disenfranchised populations.

In my Jesuit education, I had developed a real love for social philosophy and how it relates to political environments and informs social change. The rigorous academics and rigorous experiential learning approach of the Jesuits made me feel at home while working in Mexico earlier in my career, where I was a community organizer working with a squatter community to secure land rights, running water, and education. Those years of working and living among poor people helped me build an understanding of the need to directly alleviate the devastation of poverty while working to improve the systems that perpetuated these dehumanizing circumstances.

I think that balance of having developed analytical tools and diagnostic capacity to understand a community’s zeitgeist helped me land the job.

You had spent five years working in field operations before being promoted to president. How difficult—or easy—was the transition?

Cardinali: It didn’t seem difficult because it was based purely on the nature of my relationship with Bill [Milliken, founder of CIS]. We had―and have―shared values, though expressed differently and arrived at differently, but we had clarity about the same things. We share similar experiences rooted in working with poor people, with respect, and within a religious context. Bill is brilliant, and we agree on the tension of managing direct service work and aiming for systemic change. And I was “green” to the national nonprofit scene—I was a community organizer who had spent the majority of his young adult life in and out of Mexico, so I wasn’t threatening.

How do you approach adding senior leaders to your team?

Cardinali: My job isn’t to be “in front” of my senior colleagues; we engage jointly in developing and executing strategy, and I use a “managing partner” framework as my leadership style. I find that clear and distinct frameworks of what success looks like are freeing to people. We at CIS are very metrics driven. Personal values and ambitions need to align with what we’re trying to achieve, and I’m constantly driving toward that. I’d rather rein in someone phenomenal than need to motivate someone.

I approach building a team from the perspective of partnership. I look for senior leaders who are highly skilled and experienced in their core areas. My goal is to create a bold, coherent, and aligned strategic vision for impact and then unleash the leadership team to do their best work and to work together to execute against that vision. With clear goals and yearly benchmarks the team has clarity.

I hire people who will make their own professional success. They need to be self-directed and creative. The hard part of my job is keeping people within the parameters. I’d rather let two people problem solve than jump in and resolve it for them but will if we reach an impasse.

How do you go about hiring for someone that will fit within your “managing partner” framework?

Cardinali: Over time, I have come to believe in “biographical interviews.” Before candidates get to me there has been a filter on competencies. So for me, it’s most important to find out who they are and what they believe is most important. There are a lot of well-trained people out there, but they won’t all succeed here.

I now have some standard vectors of exploration. As I had said, my frame for looking at things is as a managing partner. I want to see that someone is self-directed, a team player, and can make good decisions about when to go it alone and when to check in with colleagues. My questions probe their life experiences, both successes and failures. We spend a lot of time together, and I’m deeply interested in how they think, learn, and process experiences and information. We talk about valuing “passionate professionalism” at CIS. Honestly, the professionalism is the easy part. Assessing whether a potential member of our senior management team is driven by the same passions that enliven CIS takes time, but it is well worth the effort.

What are your thoughts about your own succession?

Cardinali: I think every organization needs to think about it. I genuinely believe that if I leave CIS wouldn’t explode. Sure, who I am and my relationships are important, and things would slow down perhaps. But I believe that the way I’ve managed our team would enable them to keep the organization stable while the board determined who would be the next leader.

Your own role entails leading a network of 190 independent affiliates. How do you keep them connected to each other and CIS’s overall goals?

Cardinali: I engage people as peers. I recognize they are experts in what they do, and I’m providing context and glue for what we do collectively. My goal is to get individual affiliates to know what their impact is on the whole CIS movement. I have a similar frame of managing partner for CIS National vis-à-vis the CIS Network.

Often I’m on the road and focused on building relationships with leadership and front-line staff.  What I have discovered over the years is that local and even state leadership in our network don’t routinely think about the whole network; this makes sense since that is not part of their daily jobs.  However, each of them―every site coordinator, executive director, state director, and every one of the 4,500 CIS professionals―contributes to CIS’s identity, mission, and impact. I believe it is my job to link the individuals and organizations that make up our network and co-create with them a vision for achieving CIS’s mission. I do this by getting out to our affiliates, to the school sites, talking to leadership and front-line staff. I listen a lot and work to ensure that folks feel not only heard but understood. But I also work to link their work, their concerns, and their desires to the network as a whole. My goal, honestly, is for them to feel deep pride in belonging to the CIS network and feel that their work contributes uniquely to our success. I work hard on building our collective narrative.

How do you approach your own learning goals and professional development?

Cardinali: I’m not sure it’s scientific. My brother, who is a psychoanalyst, tells me I am constantly needing to know things. I am self-directed, and what prompts me to want to learn something new is that I’ll have a problem I’m trying to solve. It’s usually something more systems-level or strategic, and it gets me to my own growth. For example, I was grappling with the economic implications of our work beyond student outcomes. So I went out and asked people I trust and asked a lot of questions; I hopped on the web and found lots of information. Over time, I began to see patterns and insights that led me to sink my teeth into collaboration with a third-party expert in this field. 

I also went through the Casey Fellowship program, a wonderful and challenging 18-month professional development experience. The Casey Fellowship built both my skills and my intuition as a leader. Even in my work with Bridgespan Consulting and Bridgespan Executive Search, I was learning, and I’ve benefitted from the longevity of relationships with people who do different things than I do. Our senior team collaborated with Bridgespan to build a “theory of impact” while sharpening our data driven decision-making skills.

I also had specific things to learn. For example, when I first became president, my public speaking wasn’t as strong as I wanted it to be. I got formal help with a coach and I practiced a lot. With each opportunity, I was developing a body of work, testing things, and receiving feedback. I’ve improved over time.

Finally, I think my relationship with our board chair, Elaine Wynn, has had a lot of influence on my development as a leader. We often talk about what we’re trying to accomplish and who we are becoming as an organization. She’s amazingly wise and balanced and takes the time to work through challenges with me. I have learned a great deal from her.

What leadership tips would you offer to other social sector leaders?

Cardinali: The biggest one for me is to divide the soft from hard skills. My observation is that most folks lock into hard skill development because it’s easier: You set up your development plans, go to a workshop, etc. It’s easier to get into and diagnose and measure progress against. But that is the easier stuff.

It’s really the soft skills that hold people back, and that’s a dicier conversation that relies on the personal and the pastoral. It’s not a leader’s job to be a therapist, but it is a leader’s job to recognize that we are dealing with whole human beings and not just bundles of hard skill sets. The most effective leaders I know have put themselves on a continual process of self reflection and open willingness to confront the underdeveloped soft skills sets that are so critical to effective leadership. By being personally willing to do this hard work, good leaders become much more capable of supporting others’ leadership development while maintaining appropriate boundaries.

People will grow and change in a safe, trusted environment with well-managed boundaries. With one colleague, the tactical and execution nature of her work was solid, but she had trouble imagining herself in a leadership role. She’s remarkable: smart, strong, highly skilled. I’ve seen her re-imagine who she is in a leadership role, and it was due to her own development as a human being.

Really, that weaving of values and analysis is what leadership is all about. It comes with the maturity that life produces. But this notion of trusting your internal narrative of the world through interacting with the world is something I’m very conscious of now.