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After working 26 years in the for-profit capital sector of our economy and nine years working with the poor, forgotten and demonized people in our society, I see life much differently. I feel like I’ve awakened to a new understanding of the rules of how we interact for the good of society. The Homeboy Way is the “how” of mutuality, compassion and relatedness for a better society.

Homeboy Industries is the largest and most successful gang reintegration program in the world. It was founded and is run by Father Greg Boyle, a Jesuit priest, who dedicates his life to helping men and women get out of the gang lifestyle. By transforming their lives, these men and women show us why people shouldn’t be defined by the worst thing they’ve done. Homeboy has helped thousands of people heal from complex traumas and become contributing members of our society, even when it seems everyone in society has let them down. In many ways, this effort can be seen as a fight against racial and economic inequality – because the population we serve is made up of poor people of color who have never had a fair chance in our society.

As a human services nonprofit, Homeboy has always struggled to secure the financial resources to stay afloat. I came to Homeboy exactly when they needed someone like me with the skills to lead successful organizations. I also came at a time when I needed to know more about myself and my spiritual journey. Working with Homeboy Industries has given me knowledge and insight into my own spirituality and the plight of the people Homeboy Industries serves.

I have made friendships and relationships that are remarkable. I have experienced more heartbreak and more joy in recent years than in my entire life before that. Along the way, almost by providence, I have been able to see how business can be run with a different set of priorities so that everyone benefits: owners, management and those who have never been able to maintain a job but are doing so now. I learned how to help the “unemployable” to become employable. I participated in the development of business models that provide not only economic impact but social impact. Doing business the Homeboy Way is the direction in which we must lead our collective efforts and a roadmap to revamp capital markets.

In today’s environment, we have massive tidal currents around the issues and causes of social injustice and racial inequality. What I didn’t know then, but what I know now, is that I was lucky enough to be on the front line with those involved. I became not only a non-profit CEO of a social service agency, but more importantly, a participant in the fight to bring resources and help to those on the margins of our society.

I learned a lot about leadership development for racial equity. Every organization, be it a non-profit or government agency and especially a for-profit business, must address this issue and strive to improve the lives of everyone around us.

The struggle for any organization is to develop the next generation of leaders from within, and at Homeboy, that’s not just vitally important to the mission, but an order of magnitude more difficult. Our ex-gang population needs to see people like them in leadership roles so that the actions we take are genuine and have the best interest of the client in mind.

Outside organizations have the luxury of hiring mid- to high-level executives into their organization and can groom them to be the best leaders. For Homeboy, to have leaders who share the lived experiences and stories of those we serve – gang life, incarceration and trauma – we must prepare our people from the bottom up. They start as customers to transform their lives and, when ready, become frontline workers, followed by a series of supervisory jobs before moving into middle management. Once in middle management, they acquired a combination of positive leadership and some functional skills. However, going beyond middle management at Homeboy or any organization is about knowing how many other functional skills one can pick up along the way. When one becomes a senior leader, they function like a general manager. This is where the task becomes the greatest challenge, as it is partly about the motivation of the individual and the ability of the organization to provide such learning experiences.

Motivating our clients can be complicated. One of the ideas of our founders is that young people, who are stuck in the gang lifestyle, don’t see themselves living past 30. (That’s one of the reasons tougher sentencing laws don’t deter crime, because they don’t feel like their lives are going to last long anyway.) When they come to Homeboy to change their life, this is the first time they start dreaming and planning a long life. Once they complete our 18-month program, they rightly feel like they’ve accomplished something magical: “What’s next and how can I move up the corporate ladder?” is no longer so far from their thoughts. However, many just want to revel in the life they now have, “the good life”. I’ve had many conversations with interns taking that first step into management and they’re ecstatic and don’t even want to think about the next step. They are now a success for their children, their families, their friends and themselves.

Another aspect of developing a career is that you need to be aware of your “work flaws”. When our homies reach “the good life”, it’s after so much deep introspection to transform their lives, they avoid considering another level of introspection concerning life at work. This period of calm can last a few years. Then, for some, they start wanting more and developing more. When that time comes, we can start discussions about further developing business and managerial skills.

We have to keep in mind that the only organizational structure our peeps have known is the gang hierarchy, which is a very different structure from the grassroots-based nonprofit world and the corporate world of matrix organizations. In the world of gangs, the leader must make a call and everyone must follow and listen. When our insiders first become managers at Homeboy, they expect absolute authority, which rarely happens, and so a clash occurs. This can cause them to question their own worth or even stir up a desire to fire everyone. For them, realizing this issue and changing their own mindset usually takes time to overcome.

The final area of ​​challenge is organizational mundane things like emails, phone calls, and report writing. This is where Homeboy’s insiders struggle the most: they don’t see it as a priority, and some see it as “women’s work” and think it’s a waste of their talent. If they refuse to do so, it often becomes their biggest obstacle to career advancement. However, after a lot of “straight talk” type coaching, they come back and eventually come to a point of reconciling these issues.

Even with these challenges, we have wonderful managers who have overcome their obstacles and reached high leadership positions. The effort to develop the leadership team that is partly made up of leaders with family backgrounds requires time, money and, most importantly, a mindset that the entire organization must adopt.

From a broader societal perspective, I believe one of the key drivers will be how to lift more people out of poverty and into quality jobs that ensure growth on the economic ladder. It’s not enough to provide entry-level positions (usually at minimum wage), but work that leads to something more substantial. This would mean an over-investment in terms of developing people’s job skills while they work. A proactive approach for people of color with the same type of lived experience is to provide counseling, mentoring and coaching. I suspect that the same factors that present challenges for Homeboy will be the same factors that other organizations face when trying to really push people up the economic ladder. Our hard-won lessons should be a model for other organizations wishing to follow a similar path and work towards racial equity.


Written by Thomas Vozzo.

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Rodney N.

The author Rodney N.