Care & Cooperation: Leadership Rooted in Humanity

By Ivan Kilgore, UBFSF Founder

When I first began reflecting on this month’s theme—care and cooperation—the answer came to me almost immediately. What surfaced was not a theory, framework, or abstract leadership principle, but something far more fundamental: the imperative that we, as nonprofit founders and executive directors, must genuinely care for our people.

And by “our people,” I don’t mean only those we serve. I mean the people who make the work possible: the staff, volunteers, board members, community partners, collaborators, and, just as importantly, ourselves.

In the nonprofit sector, care is often framed externally. We focus on beneficiaries, communities, and impact metrics. Yet too often, the internal ecosystem that sustains this work is neglected. Burnout is normalized. Overextension is praised. Self-sacrifice is confused with sustainability. Over time, this erodes not only individuals, but the very mission we claim to protect.

Care is not a luxury in leadership. It is infrastructure. My wife often reminds me of this truth with a phrase that has stayed with me: “Health
is wealth.” It’s something she says plainly, without flourish, yet it carries the weight of lived experience. If there is one lesson incarceration has taught me—one that no leadership book could convey—it is that time, energy, and well-being are finite resources. If we do not intentionally care for ourselves and one another, the work will eventually collapse under its own weight.

Care does not require grand gestures. In fact, it is most powerful in its simplicity. I begin every meeting with a check-in. Not a procedural one, but a human one. How was your week? How are you really doing? How is your body, your mind, your spirit holding up? This small practice sets the tone. It signals that people are not merely valued for their output, but for their presence. It also creates space for honesty—something essential for trust.

Care looks like flexibility. It looks like patience. It looks like understanding when life intrudes on work, as it inevitably does. It means learning who people are beyond their roles, what they are working toward, what inspires them, what burdens they carry. When leaders take the time to know these things, cooperation ceases to be transactional and becomes relational.

Personally, the stress of the cage, my incarceration, has forced me to confront the consequences of neglecting self-care. There is no escaping one’s inner world when external freedom is stripped away. Over the years, I have been fortunate to develop a consistent exercise routine, healthy coping mechanisms, and, perhaps most transformative of all, emotional intelligence.

That last piece did not come naturally. I credit it largely to working with a leadership coach. This relationship challenged me to interrogate my reactions, refine my communication, and lead from awareness rather than impulse. I recommend coaching to anyone in a leadership role—not as a sign of weakness, but as an investment in clarity and longevity. Leadership magnifies our strengths, but it also exposes our blind spots. Without intentional development, those blind spots can cost us dearly.

Care, when practiced consistently, becomes the foundation upon which cooperation is built. Cooperation is often misunderstood as agreement or compliance. In reality, it is far more demanding. True cooperation requires structure, clarity, and accountability. It demands systems that clearly articulate expectations, deliverables, development pathways, and feedback mechanisms. Most importantly, it requires coaching—ongoing, thoughtful, and responsive.

I have learned that cooperation is rooted in care because people are far more willing to collaborate when they feel supported rather than surveilled, guided rather than micromanaged. When individuals understand what is expected of them, and know they will not be abandoned when they struggle, they show up differently. They take ownership. They innovate. They stretch.

Building synergy within a team is challenging under any circumstances. Doing so across time zones, life stages, and institutional barriers is even more complex. Having been incarcerated for over two decades, I have learned that inspiration is not optional—it is essential. People do not rally around perfection. They rally around authenticity.

I lead with my imperfections. I speak openly about my mistakes, my doubts, and my daily struggles. Not to center myself, but to normalize humanity. In doing so, I give my team permission to be human as well. I cultivate a culture where it is okay to make mistakes—where experimentation is encouraged, where trying a new software, proposing an unconventional idea, or learning an unfamiliar skill is met with curiosity rather than fear.

Innovation dies in environments of punishment. Cooperation flourishes where people feel safe to fail forward. Another critical component of cooperation is tending to motivation. People are driven by different forces: learning, purpose, recognition, belonging. Understanding these drivers allows leaders to align responsibilities with strengths and aspirations. In our organization, which is largely staffed by student volunteers, this insight is particularly important.

I often challenge the young men and women we work with to see themselves not as experience-seeking, but as experience-creating. Too many students are taught to accumulate credentials rather than cultivate competence. I encourage them to embrace trial and error, to see discovery, of systems, of skills, of themselves, as the true value of their contribution. Watching this transformation unfold is one of the most rewarding aspects of my work.

Cooperation also demands realism. It requires understanding both individual and organizational limitations. It means defining roles clearly, being transparent about capacity, and simplifying operational processes wherever possible. Complexity masquerades as sophistication, but it often undermines execution. Clarity, by contrast, empowers people to act decisively.

Over the years, I have learned to recognize when to push and when to pull back. Not everyone who wants to help is able to commit at the level required. I often remind myself with a saying that has become something of a personal mantra: “God bless the soul that wants to save the world yet doesn’t have the time to commit to the struggle.” This is not judgment, it is discernment. Cooperation is contingent upon alignment between intention and capacity.

Burnout is another reality leaders must confront honestly. Volunteers, in particular, can become disillusioned when long-term visions are not accompanied by short-term markers of progress. When people feel their efforts disappear into an endless horizon, motivation erodes. This, I have learned, is a leadership failure, not a personal one. Leaders must mark the journey.

Acknowledging and celebrating milestones is not cosmetic, it is sustaining. Recently, our project manager, Ian Wilson, completed the organization’s first comprehensive impact statement for our Nonprofit Coaching & Leadership Training for America’s Incarcerated. The process was anything but glamorous. Developing content, launching the program, and collecting data from over 10,000 participants was tedious, confusing, and often unrewarding.

Yet when everything finally came together, that moment of completion mattered. It mattered for Ian, who could see the tangible result of months of labor. It mattered for the team, who could recognize their collective effort. And it mattered for our student project managers, who witnessed how cooperation, when guided by care, can deliver meaningful, high-quality services to thousands of incarcerated individuals across the nation.

Care and cooperation are not separate virtues. They are mutually reinforcing practices. Care humanizes leadership. Cooperation operationalizes it. Together, they create environments where people can contribute fully, grow authentically, and sustain their commitment over time.

From inside the cage, I have learned that leadership is not about control—it is about cultivation. It is about tending to people with the same intentionality we apply to strategy. When we care well, cooperation follows. And when cooperation thrives, impact becomes not only possible, but inevitable.

This, to me, is the true work of leadership.