Elizabeth A. Gaynes

President and CEO, Osborne Association

How old is your organization? 88 years
What sector do you work in? Criminal justice
How long have you been working in this sector? 47 years
How long have you been with your current organization? 35 years

If you have worked with CRE in some capacity, what impact did it have?
We’ve worked with CRE several times, but most game-changing was our work together nearly 20 years ago, at a time when we were involved in a merger/acquisition that required bringing together a disparate group of staff and board members. It was like the US and the UK — two nations divided by a common language. It taught me to pay attention to that thin line between being righteous and self-righteous.

What has been the most significant development in your sector over the last 40 years?
Forty years ago, the US began its unprecedented rise in the numbers and rates of people in jail and prison, becoming the world’s warden with mass incarceration. Despite a small dip over the last decade, the US is still home to the most people who are confined or under supervision. Both the “war on drugs” and the insertion of the crimes of one Willie Horton into a presidential campaign in 1988 led to the 1994 Crime Act, Three Strikes, and an entire marching band of dog whistles that not only exploded the prison population with more people sent to prison for longer sentences, but also disproportionately targeted people of color.

How has communication — with staff, clients, and/or donors — changed over the course of the last 40 years?
When I first came to Osborne, we had a “mailing list”, and letters — including many that I wrote by hand — were the way we gave them information about our work and asked for contributions. We called people on the phone and had conversations. Our meetings were in-person. We didn’t work “remotely.” We didn’t have easy access to information about our donors or our participants. I imagine it is really annoying now to young folks to hear about how it used to be, or to have to convince me to edit things on Google docs, or ask me to write in block letters because they weren’t taught cursive in school. Some things have been lost, and some things have been gained.

How have your sector’s needs changed (or those of your clients) in the last 40 years?
The population of the US is aging, and so is the prison population, due largely to extreme punishment. While there is still the need to focus on young people caught up in the justice system, the demographics of prisons are changing. Also more men and women from upstate are coming into our prisons than from New York City. Maybe the needs are the same, but now we know more about how to meet them. We have learned much about brain development and about the causes of violence. What we used to call the “root causes of crime” are now the “social determinants of health” — and they all work together. There was a time when an organization could focus on one disease, one problem, one point of intervention. Many, like ours, had to become multi-generational and multi-service, with no wrong door.

How have nonprofits’ priorities shifted in the last 40 years?
In earlier times, “nonprofits” were known more as “charities” and were designed to “help the less fortunate.” There were also nonprofits that operated as think tanks and policy institutes. Today, organizations like Osborne recognize that policy and practice must go hand in hand. While we do offer concrete services, we are not “helpers.” And when we see that the same challenges confront so many of our participants, we have to go beyond resolving these problems at the individual level and confront the underlying policies, laws, and belief systems that continue to hold people back. I think that today many more nonprofits find themselves needing to be both service providers and policy advocates.

What is the single greatest challenge you face today in your sector?
America’s love affair with punishment and unwillingness to reckon with structural racism and white privilege.

What leadership qualities are necessary to succeed as a nonprofit executive today?
Curiosity, sense of humor, courage, thick skin, and a high tolerance for ambiguity.

What will nonprofits need to do to remain relevant and necessary to their clients over the next 40 years?
I have no interest in being necessary. Poverty is an entirely unnecessary fact of life today. Prisons are the direct descendant of chattel slavery, and it is my plan and desire that in 40 years people will look back at the time when people put other people in cages and ask WTF?

What are some of the trends you’re seeing today that will impact your nonprofit and your sector in the future?
Due to the investment of tax dollars into structures (like prisons) and services (like behavioral health), we will be competing with private companies seeking to profit from the huge investment in the criminal legal system. We see private equity and corporations capitalizing on (and impoverishing) people’s misery, from the telecoms and private prisons and halfway houses, to algorithmic risk assessments and electronic bracelets.

On the other hand, many communities are demanding an end to mass incarceration and re-investment of those dollars into the communities most affected. The trend of more private donors to support organizing, campaigns, and advocacy, could be a key factor in moving in this direction if we compete by offering high-quality services by a well-paid, well-trained, committed workforce that reflects and respects the communities we serve.

Where would you like to see your sector in 40 years?
If the criminal justice system has not shifted from retribution to reconciliation over the next 40 years, we’re all in trouble. I would like “public safety” to be understood as a component of public health. I would like “personal responsibility” to be understood as tied to social responsibility. If we addressed inequality in wealth — and devoted the dollars and donors to health care, housing, and education — the criminal justice sector could all but disappear. After that, if I were somehow alive (I’d be about 110 in 40 years), I’d be raising honeybees and working for the environment.

Why did you join this sector?
The Attica Prison Rebellion in 1971 profoundly affected my decision about what field I would pursue: first as a defense attorney for the Attica Brothers, then as a prisoners’ rights attorney; and, then leading a nonprofit that was committed to transforming prisons and providing services to people confined in prisons and jails, and offering services that would keep people out of prison or support their successful return home. I think of myself as a sort of recovering lawyer, because that world was filled with winning or losing, right and wrong while my work at Osborne has given me the opportunity to be part of a group of committed people who love the work, love the people, and love making a difference.

In what ways would others say you are a trailblazer?
Many of the programs we offer were the first of their kind, so people could say we blazed the trail, but the ideas for these innovations came from the folks who were actually doing the hard work. It might have looked like I was clearing the path, but the decision to go that way was inspired by people I trusted. Mostly, when I have gone where I can’t see the path in front of me, it has mostly been an act of desperation, insanity, curiosity, or just being lost, but now I will call it “trailblazing.”

Why did you want to become a CEO?
I’m a control freak, have problems with authority, and thought this was the best way to deliver on my stand for a world that works for everyone, with no one excluded.

What was your breakthrough moment in becoming a leader? / What did it take for you to break through to become a leader?
I participated in a program called the Landmark Forum and found out that my strongly held opinions were opinions and not the truth. It wasn’t good news, but it let me see that there is a very thin line between being righteous and being self-righteous. Knowing this allows for the one thing that leaders can’t live without: people who will follow. Not blindly, but trusting that their leader will stand up for them. If people want to follow someone who has ‘The Truth,” they are looking for a savior, not a leader.

How do you hire?
Apparently very well, since most of the people who report to me have been with Osborne for many, many years. My goal is to find people who are smarter than I am, know things I don’t know, and experience the world from another point of view. Diversity of age, faith, culture, language, race, and music has always been good for organizational success, and I wish I’d been more accomplished in that goal. I also try to find people who have full lives and big commitments, so their job isn’t everything. To work inside a jail or prison takes a toll on the soul. I look for people who can see the humanity in the keepers and the kept.

Please describe one of your most significant challenges during your career and how you overcame it.
Soon after I came to Osborne, my children’s father—to whom I had been married for several years — was arrested. My life, and the lives of my children — then 2 and 6 — were suddenly in crisis. I was very hesitant to share what was going on because at that time people were not embracing the idea of leadership by people with “direct experience” of the system they are seeking to change. I was concerned that my board, donors, and the agencies with whom I had to negotiate would see me not as a “credible messenger” but as an incredible mess. Over the course of the 25 years that he was incarcerated, with the support of a wonderful board, family, colleagues, and friends, I learned when and how to disclose my experience, and learned to appreciate the many ways that my children and I could actually contribute to the work of shifting the system from revenge and retribution to reconciliation and redemption.

If you were just starting out in your sector today, what advice would the person you are today give to the “newbie”?
Find a mentor. Do what needs doing, regardless of position. Find people in other organizations, government agencies, or businesses, who are at a similar point in their careers. Then, figure out which ones are the smartest and the boldest, and keep them close for the next 30 years, because they’ll keep moving up too, and you’ll always have a wide circle of people who are in a position to support your success.

What do you want your work culture to be like?
I want everyone to feel safe, appreciated, and respected. I want people to complain—to someone who can do something about it. I want people to go on vacation and take a long enough break to come back rejuvenated. I want them to use their medical insurance and stay home when they’re sick or when their children are sick.

Based on your experience, please offer one piece of advice to a person hoping to break through as a leader in your sector.
Remember the names of people who are kind to you and forget about the haters.


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