Pregame Announcement: I’m excited to announce that I have joined the Board of New Yorkers Against Gun Violence. As someone who was in high school during Columbine, there has never been a time in my life when gun violence wasn’t a problem, but each new round of tragedies has become harder to stomach, and it was time to do something about it. I’m joining NYAGV because of the great work they do at the state level here in New York, approaching the issue holistically and with attention to the needs of communities most impacted by the issue.
My last Substack was a tribute to my recently passed friend, Andy Walton, and the leadership lessons I learned from him, so the concept of leadership has been on my mind.
One of my favorite parts of my job (VP for Political Strategy & Justice National Director for Dream.Org) is running our annual Dream Justice cohort, an intensive advocacy training program we run for directly impacted activists. While there are a lot of fancy “fellowships” in the nonprofit space for the all-stars in different fields, there is a serious shortage of programs that can take someone who is passionate but inexperienced and shape them into advocates who can win change in their communities. We recently finished selecting this year’s group, 28 awesome activists from across the country, most of whom I had the pleasure of Zooming with. The fire burns brightly in all of them.
Part of why I love our program so much is watching people grow into confident organizers; that taps into the educator in me. But now that I’m on the sunset side of 40 years old, part of it is also the relief that reinforcements are coming. We’re not on the verge of solving our problems any time soon, and we need more leaders - WAY more leaders - who are capable of launching and winning campaigns.
Scouting Report: Unfortunately, I don’t see nearly enough urgency across the movement to invest in new leaders. Most times I get invited to watch high-profile panels, the lineups look like they haven’t changed since 2017. Ditto for who shows up as newspaper quotes and media interviews. There’s been plenty of griping across industries that Boomers refuse to retire and make space. After all, we’re living through a political gerontocracy. But the problem isn’t just Boomers. Too many leaders - across age, race, gender, and class - behave in a way that boxes out new leaders from emerging. I can speak with the most authority in the criminal justice space, but from observations and conversations it’s a widespread problem.
We need a gameplan for elevating more leaders.
The Challenge: I get why letting go is hard.
When I started running the #CLOSErikers campaign at the beginning of 2016, we were explicitly focused on centering the experiences of people who had been incarcerated or impacted by Rikers, which meant my role was clearly going to be behind the scenes. Even though I was grinding away 6.5 days/week, I didn’t speak to the press or at rallies, and in political meetings my job was to tee others up. By mid-2017, as the success of the campaign grew, so did the number of invitations, and I got the green light to rep the campaign publicly. I’m not going to lie, there was a sugar rush of being invited to speak in front of friendly audiences, seeing my face on graphics, appearing on NY1.
For most people who toil in social justice advocacy, putting in long hours for low salaries, working on emotionally heavy subjects that they bring home with them, a little recognition goes a long way. A spotlight can feel validating. This is especially true if your lived experience (arrest, prison, homelessness) moves from something that made society discard you to something that gives you expert credibility, a seat at the table. Some people can get hooked on that attention, especially when we have a social media ecosystem that encourages it and a political system that rewards it.
One of my favorite Wire quotes comes from Bubbles, “Ain’t no shame in holding onto grief, as long as you make room for other things, too.” There’s no shame in basking in the spotlight, hard earned through life and work experiences, especially if you’re effective at it! But we need to make space for other leaders too, because that’s how we’ll actually build power in the long run.
Drawing Up Plays: If you don’t already know, I love basketball. I played it for years until my second ACL blew out. Reading NBA news during lunch has been my longest-running form of self-care. In recent years, I’ve taken to watching NBA roster construction and on-court strategy through the prism of successful team-building. (Like the new champs, the Denver Nuggets!) Even before my partner, Cristina got me the excellent How Basketball Can Save the World, I’ve been thinking about hardwood lessons that can translate into the advocacy space.
1. A team with more offensive weapons or a more coordinated offense, is less likely to get stagnant than an offense centered around one person. During the last few NBA seasons, “heliocentric” offenses that revolve around one amazing player doing most of the shooting and playmaking has led to great regular seasons that fizzle in the playoffs. When the going gets tough, it’s much better to have an offense that keeps everyone involved - like both the Nuggets and Heat, and it’s more difficult to gameplan against a multifaceted attack.
Likewise, organizations and campaigns that revolve around a single, charismatic individual can accrue some real short-term benefits. It’s easier to get media attention, fundraise, and inspire followers when you’ve got that one person who just owns the room every time they step up to the microphone. But that approach has its downsides, too. A heliocentric organization model can burn out people around the charismatic star, and strain relationships with potential partners who simply don’t like that leader. Political stakeholders also raise eyebrows when they see the same leaders over and over again, quietly asking, “Is there a movement behind you, or is it just you?”
An alternative approach is to tie power back to an organizational brand. Take the ACLU. A ton of incredible lawyers there. Can you name any? Especially outside your professional field? (*Since I wrote this, Dale Ho has been confirmed as a federal judge, so I hope you learn his name, he’s going to be great!) Most people can’t even identify Anthony Romero by name or face, even though he’s been at the helm there for more than 20 years. The Sunrise Movement is another good example. Decentralized movements like Occupy and Black Lives Matter also have had a presence and impact scale well beyond the individuals most associated with them.
That said, centering a brand can be effective, but it’s not always feasible or the most effective approach. Reporters want to talk to people. Legislators want to negotiate with people. Small, local campaigns with no budget or history can’t lean on century-old reputations like an ACLU. In those instances, the optimal approach is to have several effective leaders, especially if they each thrive in front of different audiences.
2. Beware “the disease of me”, and focus on giving opportunities to leaders around you. The phrase “disease of me” comes from Bill Simmons’ excellent Book of Basketball, and refers to the challenge successful teams have over time when certain people feel like they aren’t getting enough credit for that success. This can happen in the advocacy space, especially when there are a small number of people who are always at the front of the room in a coalition or on a campaign. The criminal justice field can feel like a revolving turnstile, with people jumping ship to a similar sounding org to do similar work every 18 months (Heck, this is my third job running national criminal justice campaigns), and while sometimes this happens due to salary or poor management, it’s just as often because people don’t feel appreciated in the roles they are in.
This is not always an easy problem to solve - most organizations have limited size and budgets, so you can’t just promote everyone every year. But there are plenty of things you can do to share credit so people feel valued.
Pass along media opportunities. Sometimes a fresh face is a better fit. This is especially true with podcasts - while a short television hit requires sharp message discipline and practice, a longform interview often brings out the best in anyone with a good story.
Run meetings. People should get their shot at head of the table, especially on their own projects, even if someone more senior is present. I actually like rotating team meetings every now and then, so everyone gets a taste of what it’s like to manage the pacing and energy from that perspective.
Pass them the ball in important stakeholder meetings. Ever been involved in a development meeting or some other pitch situation, where five people are present from an organization, but only the leader does all the talking? That tells the funder / prospective client that this leader doesn’t trust their team.
And if you’re reading this as someone trying to move up and crack into a bigger leadership position, consider what opportunities you actually want, then ask directly for them. You only get a small percentage of the things you don’t ask for.
3. Draft for talent. In the NBA, scouting departments scour the world for untapped talent for each year’s draft, trying to get an edge by looking beyond the obvious college standouts. When I first got into this line of work, the most important criterion for achieving early career success was an impressive academic pedigree, preferably Harvard or Yale. In the last eight years I’ve hired dozens of formerly incarcerated people for advocacy positions across the country, because people closest to the problem are going to fight hardest to fix it and are the least likely to give up and move on. When I’m hiring, and the choice is between someone with better conventional credentials but who doesn’t otherwise stand out, and someone who is more unpolished, but has long-term leadership potential, I’ll usually go with the latter, especially if they have lived experience. Most of the people with lived experience who I’ve hired remain in the movement, making an impact one way or the other.
Lastly, shifting from the NBA to other current events…
4. Build a better succession plan than Waystar. No spoilers here, but obviously the last four seasons would have been a lot less interesting if Logan Roy had a transparent plan for who would replace him, and prepared that person for success. The overwhelming majority of organizations I’ve worked for/with and observed closely are more like Waystar than they’d like to admit. The critiques of heliocentric organizations I raised earlier were assuming that things were going well at an organization. When scandal hits, and those leaders get taken down, so much of their organization’s momentum collapses with them. Even when departures are more benign, like retirement, it’s very hard for an org built around one personality to keep going at the same level of success.
For the first time in my career, I’ve devoted a considerable amount of energy to “working my way out of a job,” that common non-profit refrain, and will turn over much of what I oversee now to other people in the organization whose leadership I’ve tried to cultivate. This should create bandwidth for me to explore new ideas and initiatives while giving new leaders a chance to improve on what I’ve built.
Post Game Analysis: The criminal justice movement is quietly undergoing an interesting moment, as several prominent leaders shift out of high visibility roles, with more prominent changes at the top coming in the months ahead. These transitions are taking place at a time when the movement seems to have weathered the storm: crime is declining again in most parts of the country, the “tough on crime” messaging of 2022 had limited political effect, and organizations (including Dream.Org) had success passing bipartisan criminal justice bills this session. That means we could be looking at an exciting opportunity for a new generation of criminal justice leaders to take the reins. Will the field make space for them? Will the field recognize that we are more powerful when there are more of us?
What’s On Deck: There is a lot to say about the terrible news about Rikers Island, before we even get to the question of what’s going on with the plan to close it. Will be writing up about that in my next piece.
Great piece. I’d like to chat about your next piece.