I recently went one-on-one with Tiffany Benjamin, CEO of the Humana Foundation.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here?
Tiffany: The person I am today was shaped more than anything else by the work of my mother. She was a single parent raising me while working as a social worker in the 1980s, at the height of the HIV/AIDS crisis. At that time, fear and discrimination defined how society treated patients. Many people were unwilling to sit with them, touch them, or even acknowledge their humanity. My mother did the opposite. She gave her time and heart to people who were often abandoned by their families, sitting with them as they told their stories, sometimes in their last days.
It was pre-HIPAA, so I would sometimes accompany her. I remember being a child and seeing people with visible lesions, struggling to breathe, surrounded by chosen family instead of biological relatives. And yet my mom treated each one with dignity, respect, and unconditional compassion. Those moments taught me not only empathy but also courage. It takes courage to love people when the world tells you not to, to stand in spaces that others avoid. That shaped my worldview: that everyone deserves care and dignity, no matter their circumstances.
Those lessons guided me into law. I wanted to build a career where I could ensure systems were being upheld for the benefit of people, especially those whose voices weren’t being heard. I worked in government because I wanted to strengthen the policies and institutions that affect communities. And ultimately, I moved into philanthropy for the same reason. Philanthropy is an extraordinary tool for impact when done well. It allows us to resource communities directly, experiment with solutions, and create partnerships that drive real, lasting change.
Adam: What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Tiffany: I believe that failure can be one of our greatest teachers. Early in my career as a lawyer, I experienced this firsthand. I was working on a major project, one that consumed all of my time and energy. I felt so proud when I finished it. My colleagues congratulated me, and I believed it was a defining win. Then an error was discovered. It was devastating. The client recovered, but they weren’t happy with us, and I felt like I had let everyone down.
What I learned in that moment is something I carry with me every day as a leader: resilience is essential. You have to own your mistakes, acknowledge them without excuses, and then get back up and prove yourself again. A mentor once told me, “What defines you is how you respond when things go wrong.” That advice has stayed with me.
It also shaped how I think about leadership. Real leaders understand that a single moment doesn’t define a person. None of us is the sum of our worst day. We are the sum of our persistence, our growth, and our willingness to keep moving forward. That perspective makes me more empathetic when I see team members stumble.
Adam: What are the best leadership lessons you have learned from leading a large foundation?
Tiffany: One of the greatest lessons is the importance of listening deeply. When you’re in philanthropy, there can be a temptation to assume you know what a community needs. But I’ve learned that the only way to serve effectively is to start with humility. You must sit with people, hear their lived experiences, and then design solutions that reflect their realities.
For example, we recently had a grantmaking system that we thought was accessible to all organizations. But when we listened to applicants, we heard that the process was too long and burdensome, especially for smaller nonprofits. That feedback prompted us to redesign the system, making it more flexible and equitable. We now have a two-tier application system that includes a short form application and then a longer form application for those who are eligible.
I’ve also learned that leadership is about surrounding yourself with differing perspectives. If you only bring in voices like your own, your perspective becomes the only worldview in the room. Some of the best decisions we’ve made have come because people with very different lived experiences challenged us to see a problem in a new light.
Lastly, and equally important, is the value of honesty about failure. Philanthropy often likes to celebrate successes, but some of the most valuable lessons come from what doesn’t work. I’ve found that when we openly talk about those challenges, we learn faster and build more trust with communities.
Adam: What are your best tips for fellow leaders of non-profit organizations?
Tiffany: Running a nonprofit is rewarding, but it is also incredibly challenging. One of my strongest pieces of advice is to seek out people who know more than you. No leader has all the answers, and the best way to serve communities is to lean on the wisdom of those who are experiencing the issues firsthand. In the same vein, collaboration is essential. Working alongside other mission-driven organizations allows you to multiply your impact in ways that go far beyond what any one group can achieve.
Another critical lesson is to stay grounded in your mission. When difficult times come, and they will, it’s easy to panic and change course. But if your strategy is sound, hold steady. Reassess when external circumstances shift, but let your mission remain the anchor that steadies the organization. Equally important is to maintain an evidence-based approach. Data, both quantitative and qualitative, allows you to measure whether your programs are truly making a difference. Finally, I try to encourage leaders never to view a “no” from a funder as a permanent rejection. Priorities change, timing shifts, and sometimes alignment just isn’t there in the moment. That doesn’t mean your work isn’t valuable; it simply means the opportunity may come later.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Tiffany: The qualities I value most in leaders are curiosity, passion, empathy, and humility. Leaders who remain curious are constantly learning, asking questions, and evolving their understanding. Passion is critical because it not only drives your own commitment but also inspires others to join you in the work. Empathy ensures that you truly see people, not just as employees or stakeholders but as human beings with unique perspectives and needs. And humility reminds leaders to leave their titles and egos at the door, making themselves accessible and approachable.
For those looking to take their leadership to the next level, adaptability is key. The world is always changing. New technologies, innovations, and social shifts are constantly reshaping our landscape. Effective leaders are not those who fear change, but those who lean into it. Whether it’s embracing new tools like artificial intelligence or rethinking traditional approaches to organizational strategy, great leaders are willing to learn early, adapt quickly, and model that openness for their teams.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Tiffany: The first tip I share is to be patient. Real change rarely happens overnight, especially when you are addressing complex social challenges. Some of the Foundation’s programs take years to show meaningful results, and leaders must be in it for the long haul.
At the same time, patience must be balanced with nimbleness. Circumstances shift constantly, and the leaders who succeed are those who can pivot and adapt without losing sight of their larger vision. Agility is essential, particularly in times of uncertainty.
Finally, leaders should be bold. Boldness means being willing to take risks, even when outcomes are not guaranteed. At the Foundation, for instance, we decided to narrow our health equity focus to mental health and nutrition, even though it meant ending some long-term partnerships. That was a difficult choice, but ultimately it allowed us to have greater impact in areas of deep need.
Adam: What is your best advice on building, leading, and managing teams?
Tiffany: I believe the most important responsibility of a leader is to create a culture where people feel safe enough to succeed and to fail. Teams won’t take risks or pursue bold ideas if they fear being punished for missteps. A good leader shields their team when things go wrong, while still holding them accountable, and in doing so creates the conditions for innovation.
Curiosity is another cornerstone of effective teams. I encourage unyielding curiosity, where every member feels comfortable asking questions and offering ideas. This not only sparks creativity but also allows the organization to benefit from the diversity of thought. Recognizing contributions is equally important. When employees feel their voices matter and their work is valued, they bring more energy and ownership to their roles.
Lastly, I believe in leading with a whole-person perspective. Supporting both the physical and mental well-being of employees, creating opportunities for social connection, and making space for joy and fun are essential. At the Humana Foundation, we intentionally create time for conversations, team building, and activities that bring us together. An example of this in practice is Community Day, a nationwide day of volunteerism and service that engaged thousands of Humana and Humana Foundation employees across the country. In a large organization with people dispersed in different places, moments like these are vital for fostering camaraderie and a sense of community service.
Adam: What is the single best piece of advice you have ever received?
Tiffany: Two pieces of wisdom guide me. The first came from a close friend and senior finance executive at a Fortune 500 company, who told me to approach life with a mix of courage and curiosity. That balance, being brave enough to take risks while also staying open to new knowledge, has shaped how I approach leadership and change.
The second came from my mother. Through her actions, she showed me that the most impactful way to drive change is simply to sit with people and listen. Solutions are better when they are built on listening. Outcomes are stronger when people feel heard. The philosophy of listening first has become the throughline of my leadership.
Adam: What can anyone do to pay it forward?
Tiffany: To me, paying it forward is not optional; it’s a responsibility. The legacy of a leader isn’t the policies they wrote or the dollars they distributed; it’s the people they invested in along the way. That means mentoring others, giving them opportunities, and making sure they understand not just what to do but why it matters. It’s about pulling people forward so that when your time in a role ends, the work continues to be stronger than before.
I see it as an obligation to ensure that my legacy is not just my own accomplishments, but the growth and success of the people I’ve supported. If you really care about your work, you have to ensure it outlives you.
Adam: Is there anything else you would like to share?
Tiffany: At the core, everything I do comes back to one simple question: Are we improving lives? Titles, awards, and recognition fade, but the impact you leave on communities and people’s well-being lasts.
True leadership is about empathy, resilience, and boldness. It’s about listening first, staying grounded in mission, and lifting others as you go. If we can do that, whether in philanthropy, business, or civic life, we can create the ‘lasting change’ everyone is after.
