Leadership Requires Action: Interview with Stanley Richards, CEO of The Fortune Society

I recently went one-on-one with Stanley Richards, CEO of The Fortune Society.

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? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Stanley: For background, let’s start at the beginning.

I was born and raised in the Bronx in a New York City Housing Authority complex called Soundview Houses. Early on in my life, my mother passed away, and my father raised me and my three siblings. He worked extremely hard to hold us together and provide for us. My sense of loss soon turned to anger and hopelessness, which eventually led me to cutting classes and eventually dropping out of school, and then to the streets and gangs. When I was turning 17 and my father demanded a resolution, I enrolled in the Army like many young people at that time. That decision and unsuccessful experience was not fruitful, and I soon ended up back on the streets. My return to the streets resulted in multiple arrests, drug addiction, and a return to hopelessness. Upon my last arrest in 1986, I was sentenced to state prison for a maximum of nine years. During my incarceration, I went to school and obtained my GED, and went on to college and graduated magna cum laude. In that moment, I chose to dedicate my life to supporting those impacted by incarceration, showing them that they could break free from the cycle of prison and build a new path forward. Upon my release, I was given an opportunity to work at The Fortune Society as a counselor. That experience was the springboard for my now 34+ years in the human service sector.

Fast forward a bit, and in 2021, I was appointed to be the First Deputy Commissioner of Programs and Operations at the New York City Department of Correction by Commissioner Vincent Schiraldi, First Deputy Mayor Dean Fuleihan, and Mayor Bill de Blasio. It was a full-circle moment, as the NYC Department of Corrections was a place I cycled in and out of multiple times as a young adult. In 2022, I returned to The Fortune Society as Deputy CEO, and on September 13, 2023, I was appointed President and CEO by the Board of Directors, and assumed that position on January 1, 2024.

My journey to this point has been shaped by trauma, hopelessness, and profound loss. Yet my turning point came through the discovery of hope and possibility in education, the love and support of my wife and family, and the steady anchor of my faith in Jesus Christ. Each day I wake up grateful for the privilege of doing this work, and I hope to reflect back to others a deep sense of hope, the promise of a better future for themselves and their families, and the belief in endless possibilities.

Life’s road is filled with challenges, setbacks, and opportunities. In New York City alone, more than 700,000 people live with criminal convictions. Yet, as The Fortune Society’s Founder, David Rothenberg, often reminds us, none of us are the worst thing we have done. I am grateful to play a role in helping so many people build a path forward.

Adam: What are the best leadership lessons you have learned from leading a non-profit organization?

Stanley: Over the course of my career, I’ve learned and observed many leadership lessons. For example, leadership is not just a position; leadership requires action, and those actions must include listening, engaging, and developing authentic connections with people. I’ve learned that effective leadership means creating space for others to step forward, lead, and grow into leaders themselves. A strong leader recognizes that the collective wisdom and impact of the team will always exceed that of any one individual, including the leader. I’ve also come to understand, as organizational psychologist Kenneth Sole observed, that “the health or pathology of those in authority will be manifested in those with lesser authority.” In other words, the well-being, integrity, and behavior of a leader inevitably shape the culture and performance of the entire team.

Adam: What are your best tips for fellow leaders of non-profit organizations?

Stanley: I would tell everyone in a position like mine to lead with integrity and transparency. Build authentic relationships and be accessible by making time for people, and allow others to lead by delegating tasks and projects to them, without overly micromanaging them. Leaders must also value and demand diversity of thought and perspective, as well as own their mistakes and acknowledge any missteps.

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?

Stanley: In my experience, the qualities of a good leader include remaining humble, being a lifelong learner, motivator, and good listener, and being a person who uses the information gathering process as the foundation for good decision-making and problem-solving. Furthermore, a leader who values the diversity of skills and experiences within the organization and the power of the collective over the power of an individual will oftentimes succeed.

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

Stanley: The best leadership lessons are universal, no matter the sector. First, a leader is only as strong as the ethos they cultivate—the vision they set and how it aligns with the business or mission. Second, leadership is defined by the organization’s operating values, demonstrated in how people are treated, engaged, supported, and appreciated. Finally, it’s critical to understand that the process by which outcomes are achieved, through inclusion, transparency, clarity of roles, and diversity of perspectives, is just as important as the outcomes themselves.

Adam: What is your best advice on building, leading, and managing teams?

Stanley: Get the right people on the bus first! Know your strengths and challenges, and hire or recruit people who bring skills and strengths that complement your skills. Recruit and build your team based on diversity of skills and perspective. Remember, the sum of the team is greater than any individual. Allow people to lead by providing your team with clarity of the decision-making process and then delegate the decision-making authority necessary to achieve success.  Finally, being a leader demands that you are willing to allow others to shine. Building, leading, and managing teams demands that you build trust throughout the organization and operate from a place of valuing the contributions of everyone on the team, regardless of role, and appreciating that if the plan doesn’t work, you may need to change the plan while keeping your goal in sight.

Adam: What is the single best piece of advice you have ever received?

Stanley: One of my favorite quotes is from Maya Angelou: “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” As a leader, we must remember that the most valuable asset in any organization or business is our colleagues. As such, we must ensure that our colleagues feel valued, appreciated, included, and supported.

Adam: What can anyone do to pay it forward?

Stanley: At The Fortune Society, we tell every new employee that our one rule is deep yet simple – treat your colleagues, the people we serve, and our community stakeholders the way you or your loved one would want to be treated. Treat people with dignity by seeing the best in them, even when they can’t see it in themselves, and lead with hope. Love is seed planting, which allows us to create the world we wish we live in, one interaction at a time.