Working Across Difference

Caroline Smith
Mar 8, 2019 · 13 min read

I was honored to give a keynote at the Student and Alumni of Yale Leadership Forum. This is a copy of my speech.

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Read a short article about the Leadership Forum here.

Thank you so much Steve for the opportunity to talk today. I remember attending these leadership forums as a sophomore in school — it feels like I’m coming full circle. It’s a honor to be here talking to y’all now.

For today, I’d love to cover three main things:

1. Background on me and the work I do in New Haven.
2. My core theory on leadership.
3. Four stories that center that theory on leadership.


I was born and raised in Lexington, Kentucky. I was a huge University of Kentucky basketball fan —and now a UCONN Women’s basketball fan. Most of my twitter is made up of tweets about New Haven and tiny rants about how women’s basketball deserves more attention and investment because it’s so good.

After I graduated high school, I took a long plane ride to New Haven to attend Yale. I graduated Class of 2014.

I fell in love with New Haven really, really fast. I fell in love with New Haven in large part because I fell in love with someone who had grown up in New Haven. I got to see the city through her eyes: go up on rooftops, go for runs, go to bars. New Haven became where my friends were; it became my community.

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One of my heroes, Elizabeth Warren says: You don’t win what you don’t fight for. I would take that one step further and say: You fight for things you love. New Haven became the place where I fell in love — and therefore has become the place I want to fight for.

After I graduated, I got lucky enough to stay. And, right now, I do two main things:

  1. I am the Co-Founder and Co-Director of an organization called Collab.
  2. Outside of Collab, I do a lot of community organizing in the city.

Collab is an accelerator for Connecticut entrepreneurs. Our main heart and mission is to make entrepreneurship accessible — and to address barriers to entrepreneurship to ensure everyone has the opportunity to have entrepreneurship be a means to their own economic and political power.

Our broader goal centers a vision for the state of Connecticut. Connecticut is the 48th largest state and it is one of the least equitable states in the country. We believe that those closest to problem of Connecticut’s inequities are closest to the solution. But what stands in the way of those closest to the problem making an impact, is that talent although is equitably distributed, opportunity is not. Collab aims to level the playing field for opportunity — building towards a vision of inclusive growth in Connecticut.

Outside of Collab, I was elected the Chair of the Downtown-Wooster Square Community Management Team. Every police district in New Haven has a Management Team, a group of residents that meet once per month to discuss quality-of-life and safety issues in the neighborhood. Born out of community policing, Management Team have expanded in scope to encompass development projects, community organizations — with the goal of being a space for community dialogue and equitable conversation. As Chair, I facilitate an Executive Board that runs these monthly meetings and activities.


My work is deeply place-based. It centers a stake in New Haven and, more broadly, this small state we call home, Connecticut.

A core theme in my work and my leadership is working across difference — with a focus on New Haven.

New Haven is the most representative city in America. New Haven’s major challenges, including divisions between neighborhoods, institutions, and residents, are representative of national challenges.

I believe learning how to lead communities and be lead in working across difference is some of the most valuable work I can learn to do.

I have two favorite kinds of book genres:

  • I like reading History because I deeply believe I need to understand what happened to understand how we move forward.
  • And I like reading Sci-Fi because I deeply believe I need to be expansive on what I believe to be possible in the future in order to understand how we move forward.
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I have been reading a sci-fi book by Ursula Le Guin called “The Dispossessed” It’s about an anarchist planet and a capitalist planet — and one physicist that is trying to break down walls and bring the two worlds together. In one part of the boo, he says: “Human solidarity is our only resource.”

In other words, to me, this means that our ability to come together and my ability to learn how to lead with others might be some of the greatest assets we have.

In fact, I’d go so far to say that I believe that the greatest, most valuable innovation of our generation will be less about any one decision or policy we make, but will be in how we bring folks together to make those decisions.

I’m a big believer that process equals outcome. The means equal the ends. The outcomes of our decisions will only be as strong, resilient, inclusive as the process we used to come to those decisions are strong, resilient, and inclusive.


I want to tell you four stories of leadership centering the theme of working across difference while doing work in New Haven. They start wider in scope (leadership across difference as you are building an organization, leadership across divides between different groups within a city) and then narrower (leadership across divides between two best friends and two strangers).

Story #1: Working across difference while building an organization.

What I love about building Collab is that it means I get to do work I love, in the city and state I love, with the people I love.

Because Collab is so deeply place-based, it makes it all more true that we are built of a foundation of relationships. Our funders, our entrepreneurs we work with, our partners — are also our neighbors, our fellow voters, are across the room from us at Firehouse (my favorite bar), and our friends. That makes a difference. It builds mutual stake.

We built Collab because we have things we believe in. Here are two fundamentals:

  1. We believe that brilliant, scalable ideas can come from every single neighborhood in this city.
  2. We believe that, in order to move forward as a state, we must prioritize the talent that is already here — right here, right now.

I believe the biggest parts of my leadership development and growth with Collab has been building those values and fundamentals and building those relationships — even when those values don’t always align.

Relationships and partnerships are hard — they are very, very human. Margaret (my Co-Founder, Co-Director with me with Collab) and I say that 2% of our relationships are hard — and those are the ones we think about the most.

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George Black, who is a Dream Director at The Future Project (an education initiative that started in New Haven) and one of our mentors, works with high-school students. High-school students he works with are sometimes quick to write others off (“They are haters, they are posers”) — but what George tells them and what he told us was: Keep people on the table.

Keep people on the table. In other words, keep the door open. If someone is willing to shake hands, sit across from us at the table, do the difficult thing — together — then Margaret and me are too. We have made that commitment. We will show up and always believe that there can be hope for love and progress.

Story #2: Working across difference between different groups in a city.

My second story is about leadership, working across difference — and the role of trust.

Being a Yale student, staying in New Haven, doing work in New Haven means that I am no stranger to early distrust. For so much of Yale and New Haven’s history together, there have been countless small and large experiences of broken trust, broken promises. The consequences remain and, at the very least, are deeply felt.

I acknowledge and honor that distrust — and feel equipped, ready, humbled, and confident to build trust slowly.

I experienced this past month. I have a lot of thoughts and experiences specifically with regards to Yale-New Haven distrust, but this story is about an experience while in my role in the Downtown-Wooster Square Community Management Team (DWSCMT).

Again, every police district in New Haven has a Management Team, a group of residents that meet once per month to discuss quality-of-life issues in the neighborhood and be a space for community dialogue. I am the Chair of the Downtown-Wooster Square Community Management Team which covers the Downtown and Wooster Square neighborhoods in District #1.

For the past 20 years, New Haven advocates have been advocating for a Civilian Review Board — a board to review cases about police misconduct. As we all know, there’s been a national dialogue and conversation around police accountability. A Civilian Review Board would evaluate and address civilian complaints about police misconduct, and an effective Civilian Review Board would promote greater transparency, integrity, and trust among the city, the police, and the community.

Finally, in early January, the City of New Haven Board of Alders passed an ordinance creating a Civilian Review Board. And, as part of the ordinance, Community Management Teams seemed to play a major role in deciding on the membership of the Civilian Review Board.

When I heard about the Community Management Team’s role in determining membership of the Civilian Review Board, I played close attention. As I noted earlier, Community Management Teams were originally born out of community policing efforts — which, understandably, for many advocates was seen as a conflict of interest. In part, because of the connection between Community Management Teams and the police, there had been mistrust built between Community Management Teams and some advocacy communities.

Knowing this, it was clear to me as a Community Management Team Chair that this recommendation and membership process needed to be deeply informed by and lead by the advocates and experts that had been doing this work for decades.

Our first step was for Community Management Teams and People Against Police Brutality, one of the main advocacy groups around this work, to host a community meeting in effort to come together to make the recommendation and membership process transparent, fair, and inclusive.

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Organizing this meeting was hard and complex. But, as Brené Brown says: “I can safely say that I’ve never done anything meaningful in my life that wasn’t hard and that did not take time.”

The ask was seemingly simple: a community meeting. But what made it more complex was that 1) the issue at hand deeply affected people’s lives and safety which means there was a lot at stake; 2) the partners were operating under conditions of mistrust. Neither of these are resolved in one meeting —but next steps and small stones are possible. The goal for this community meeting was to improve the recommendation process, but to get there the goal was building trust.

Some things, together as Management Teams and advocates, we did to build trust included: moving slowly, feeling the confidence to disagree, communicating clearly, and acknowledging past and present pain. We looked at each other; we didn’t hide from each other.

There’s a lot to say about the community meeting — it was this past Monday — it went really, really well. But the leadership lesson and takeaway for me was that: With trust, all things are possible. Consensus-building across divides, difference, and power dynamics is hard and building trust slowly, openly, and deliberately brings us forward.

Trust, as Brene Brown says, is the one thing that changes everything.

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One other quote that comes to mind and helped a lot through the difficulty of trust-building in community work was by a personal hero Alexandria Ocasio-Cortez, our representative from New York City.

She said: “The power is in the person who is trying.”

The work was really hard, we made mistakes — but we were trying. And it is that that made us powerful.

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Story #3: Working across difference between two friends.

I’ve told two stories about working across difference at an organizational level and a city level, but working across difference is applicable at an individual level too.

It’s definitely applicable to me and my Co-Founder of Collab, Margaret Lee.

Mar and I share a lot of similarities.

We are both originally from Kentucky. We are both Korean-American. We both graduated from Yale in 2014. And we both fell in love with and built a stake in New Haven and Connecticut.

We’re also really different.

Margaret is unafraid to ask difficult questions, sensitive to values-alignment, and discerning in her preferences — which can help ensure we are building something worth fighting for, but also can lead to paralysis in decision-making.

I say yes easily, trust broadly, and crave implementation — which helps to consistently move us forward, but can also lead to less thoughtful and accurate decisions.

At our worst, we misunderstand each other. But at our best, combined, we challenge Collab to be better, stronger, and push farther.

Mar and I are a story of working across difference because we have to and because we love each other. It’s what needs to happen when you work very intimately with someone else.

I’ve adapted and changed for the better because of her. My main core values are: growth, gratitude, and family. I used to also value clarity. But then I have recognized that the hardest things I will want and need to do will often be unclear. I will not have all of the answers.

Margaret was more comfortable than I was at, what Brené Brown calls “staying in uncertainty.” To me, this means feeling comfortable being uncomfortable; spending time understanding the problem before solving it.

After working hard in partnership with Margaret to learn to stay in uncertainty, our conservations are totally different. Solving problems is easier and fun. Lack of clarity is not a sign I should retreat but a signal I should lean in and move forward.

Working across difference can also happen between two individuals and my learning from Margaret was to be comfortable with lack of clarity.

Story #4: Working across difference between strangers.

My final story is about working across difference between individuals who are all mostly strangers.

Yesterday, I saw a fist fight break out between two guys.

When the fight started near me, I got up from my table. As a I watched the fight trying to understand what was happening, one of my first thoughts was: “I can’t break it up; I’m a girl”.

I had this idea in my head of what needed to happen, an idea built around images from personal experience and cultural narratives: To stop the fight a male-bodied person, one larger and stronger than the two gentleman fighting, needed to intervene; and when he intervened he would do so by pulling them apart forcefully.

As I had this thought three things happened:

  1. The fight escalated.
  2. A group of teenagers started egging the fight on.
  3. I saw the staff of the establishment we were in picking up the phone — presumably to call security.

It was very important to me that the two guys were safe — avoiding unnecessary hurt or arrest. I was concerned that the fight would continue to escalate with the group egging them on. Additionally, although police are trained in deescalation, I also believe that involving police can be unpredictable. Police are not always the best solution to public violence; it felt like a moment where the community needed to step up.

In that moment, I left the thought of “I’m a girl” behind and stepped between the two guys. Another guy stepped in with me and held back one guy, as I held back the other. With the guy I approached, although I had this idea that I was supposed to forcefully push him back, I ended up just hugging him.

I hugged him, breathed with him to slow his breathing, and said “It’s ok, it’s ok, it’s ok”.

We slowly walked the guys away from each other. Eventually, arms around each other’s shoulders, I walked my guy back to another part of the library.

Again, I had this idea of what needed to happen during this fight: Only a guy was capable of breaking it up. And the way he would break it up is through strength and force.

But, for this fight at least, it ended up being a girl — hugging him.

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This experience was a reminder of one of my favorite Otis Redding songs: “Try a little tenderness.”

There’s no greater strength than tenderness. For this fight, the strength required was gentle and loving.

This kind of tenderness applies in all four of these stories. In working across difference, one of the most powerful strengths we can bring to the table is tenderness, being gentle — having a soft touch built on strong values.


I have built a stake in New Haven and therefore in a community that has divisions like every place in the world.

I believe what I can do to make a difference is to learn to lead across difference, divisions, and distrust.

Four core learnings I have had in working across difference include:

  1. Keep people on the table as you do work together.
  2. Trust can change everything.
  3. Leadership and hard stuff is unclear — so be unafraid to stay in uncertainty.
  4. There’s no greater strength than tenderness.

Thank you for listening!

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