An Interview with Tulaine Montgomery, Managing Partner, New Profit

Join us for this absorbing interview with Tulaine Montgomery, who shares many of her career highlights and inspirations, philosophy on self-care, and lessons learned from working at the intersection of philanthropy, social entrepreneurship, systems, and social change. This is the fifth interview is our continuing series, Black & Bold: Perspectives on Leadership. For more information, click here.

Tulaine Montgomery, Managing Partner, New Profit

Community organizer. Educator. Strategist. Social Entrepreneur. Musician. Playwright. Hip-hop enthusiast.

What are some of your career highlights?

Thank you for asking that question…gives me a chance to reflect in a way that isn’t always possible in our “filled to the brim” lives. Noticing that throughout my career I have functioned something like a “social impact doula”…I have tended to the healthy birth of timely ideas that advance opportunities for groups and communities. I have had the privilege of doing this work across a range of issue areas and geographies. I’ve been what some people in this space call a “serial social entrepreneur.”(Tulaine Montgomery pictured at right.)

Currently, I serve on the leadership team of a venture philanthropy that supports social entrepreneurs and systems-change leaders. For me, the work is not only about growing timely ideas into sustainable institutions, it’s also about recognizing the abundant talents, skills, and assets that exist within communities that are often labeled “under-resourced” and/or “underserved.” My career features a range of varied experiences, yet everything is anchored by my passion to both make sure good ideas grow and remove barriers to communities having what they need for long-term health, sustainability, and joy. This list of career highlights is not all-inclusive. As I’m getting older I’m learning that sometimes less really is more:

1. I was part of the founding team of Benjamin Banneker Charter School in Cambridge, MA back when the charter legislation was new. The school was founded by a diverse coalition of parents. Charles Ogletree, Harvard Law Professor, served as a valued thought partner and advisor. The intent was to leverage the talent and skills in the community to co-create a school that helped children excel both academically and developmentally. That experience was a powerful orientation to what it looks like to launch a social impact organization with community and family at the core.

2. Working with the House of Blues Foundation. The Founder of the House of Blues recognized that his business venture was going to make a lot of money showcasing Black people’s creativity and culture. He also recognized that as a nation we suffer from a general lack of awareness of the essential contributions Black people have made to our culture and economy. To help address that gap, he launched an educational foundation (House of Blues Foundation- HOBF). I joined the HOBF leadership team in its early days and helped grow its programs to multiple regions across the country. The foundation’s mission went beyond exposure to historical facts or current events. The work was about enabling teachers and schools to leverage the power of Black history, culture, and leadership to create an interdisciplinary curriculum that improved student outcomes and strengthened classroom instruction. I got to take my love of music, history, Black genius, and teaching and merge all those loves into one job through a varied portfolio of educational programs, scholarships, teacher trainings, and community events. Working with musicians, educators, and activists helped me sharpen my skills when it came to building and supporting diverse coalitions.

Mainstream education does very little to educate students of any race about the contributions and brilliance of Black people. I am thankful that, throughout my childhood, my family saturated me in stories of Black genius. My work at the House of Blues Foundation gave me the opportunity to amplify Black genius in a broader context.

3. I was a founding leader of Citizen Schools, a nonprofit organization that partners with middle schools across the United States to improve student outcomes. That work was an exercise in what I call “village building.” The African proverb “it takes a village to raise a child” is true, yet that village, even when it is healthy and vibrant, requires tending. In the case of Citizen Schools, we tended the village in a variety of ways. First, we engaged caring and skilled adults in young people’s education by enrolling them as “apprenticeship teachers.” Apprenticeships made it easy for a diverse network of adults to educate and support young people by sharing a skill or talent from their professional and civic lives. Secondly, we worked on a local level to convene adults committed to successful student outcomes: families, classroom teachers, district leaders, faith leaders, and others. Several dynamic collaborations emerged from those convenings. I learned a lot about how powerful (and challenging) it can be to support effective and sustainable coalitions.

4. I began my career in business strategy consulting, which gave me a set of analytical skills that I consistently put to use. When it comes to social impact, groups often skip the steps of “listening and learning” before “designing and implementing.” I try to avoid that by becoming a student of a community or issue before I step into leadership or design mode. My experience in business strategy consulting helped me learn helpful skills and frameworks that make it easier for me to apply the lessons I learn from listening into the program and activities I design.

5. My mother is a true renaissance woman. She is an educator, matriarch, mediator, consultant, minister, coach…she is also an artist who has written and produced several plays. My father is similarly talented and prolific — in addition to being a father, grandfather, and uncle extraordinaire, some of his roles include being a master drummer, ethnomusicologist, and college professor. All to say I spent a lot of time in the creative community and wrote and produced a few plays of my own over the course of my career. Being a creative has really informed how I think about social impact. When the goal is to get a production on stage, you have to use the resources available, care deeply about the impact, evaluate whether not your meaning is understood, and you must always persist. In many ways, I use similar principles to guide and strengthen my social impact work.

If there was a headline for your leadership journey throughout your career, what would it be?

Listen. Learn. Act. Improve. Repeat.

I’m fascinated by what it takes to grow an idea or solution into a movement or enterprise. Making things better requires internal work and external action in equal parts.

What are your favorite types of challenges?

I love to connect people and groups that often see themselves at odds or disparate. It’s challenging and energizing to bring people together to achieve something they can’t achieve independently. I enjoy the “village building” process. Systems and communities are fragmented on so many levels. I love the art and science of rebuilding villages so groups can have breakthrough results.

What is one book that was meaningful or influential in your development as a leader?

To Be Young, Gifted and Black by Lorraine Hansberry is one of my absolute favorites. She puts forth so many important questions in that book – questions like “what cause are you willing to sacrifice your comforts for?” I’m also a big fan of Upile Chisala’s soft magic.

Work in the social sector can be very personal and linked to one’s values. Can you think of a time when your values were in tension during your career and how you reconciled that tension or not?

We are all working within imperfect systems. If you look closely at the “industries” of philanthropy, public education — just about any system — it’s easy to identify where funding or revenue models are broken, where access to resources is inequitable. The more you learn, the more you can see.

I am currently a Managing Partner at a venture philanthropy firm. Working in philanthropy, I’ve had to pay close attention to those types of systemic gaps. Philanthropy is a market that is at best broken. The people and communities receiving services are rarely entrusted with decision-making authority. They don’t get to determine which programs and services will be well-funded. In the social sector, the “consumer” doesn’t influence product design or market share. Decisions (and funding) are often driven by people without proximity to the experiences they are working to address or improve. Philanthropy doesn’t feature the rapid feedback loops often seen in product innovation, so it’s often hard to get a full, current, or accurate picture of impact.

The social sector tends to prioritize the “supply side” of the work. The “demand side”…i.e., the beneficiaries, the communities, the networks being offered services and interventions…that’s where we have historically put much less attention. That trend needs to shift in order to achieve transformative, systems-level impact.

This summer, Democratic Representative Maxine Waters coined the phrase, “reclaiming my time,” as she thwarted Treasury Secretary Steven Mnuchin’s attempts to waste her time with nonsense. Can you share an experience in the workplace where you have had to reclaim your time? What was the context? How did you navigate it? What was the outcome?

I love Ms. Maxine Waters! That moment reminded me of when Ms. Fannie Lou Hamer was before the Democratic National Committee’s credentials panel (on behalf of the Mississippi Freedom Democratic Party) in 1964. She was still tending her wounds from being beaten while registering voters but she was standing tall and walking proud…even brought her purse up with her to the podium! President Johnson was so terrified of the impact of her words that he interrupted the news stream with a spontaneous presidential announcement at the same time she was making her televised address. Black women have consistently been at the forefront, doing the work required to honor the promise of democracy — both throughout history and today. We continue to be on the leading edge and we have always had to fight for our time. We do not stop even though we’ve been at it since this nation’s inception.

When have I had to fight for time?

Diverse leaders and organizations often face a disproportionate burden of proof when seeking the funding they need to survive and grow. A significant portion of the work I do at New Profit is about advancing support for diverse leaders and organizations in the social sector. As a nation we can’t afford to restrict our access to the innovation, quality, and smart design that leaders of color bring to the table. Diverse leaders are addressing our most pressing and entrenched challenges. This work is still in process but to date it has resulted in raising growth capital for diverse leaders, expanding pipelines of diverse talent, and highlighting the stories of leaders of color as they lead their organizations and advance opportunity for all Americans.

I was recently with a group of Black teachers, healers, and practitioners in Bali. One of them said, “This is a time when we cannot be careful with our medicine.” I take that to mean now is a time to be both generous with our gifts and honest about our experience and perspective. That is a way we can all reclaim our time.

What’s your approach to self-care? Are there any rituals you use to survive and thrive?

I have learned that tending to self is very important. I meditate. I give thanks. I sing. I dance. I have a prayer practice. I’m a comedy connoisseur and pursue experiences that make me laugh until my cheeks hurt as a regular thing. I need all these things to be courageous, creative, effective, discerning, and generous.

I used to feel like that was too much, like: Isn’t it more efficient and “boss-like” to just hop out of bed and face the world? Why all the extra padding? Now I understand that as individual humans we are a lot like the planet earth – precious and finite. The earth requires protection and restoration…and nothing is more of a boss than the planet. I am also precious and finite, like the earth, so whatever I have to do to protect and restore myself is a testament to my value as opposed to evidence of my weakness.

One of the challenges can be when we as women try to combat the patriarchy by replicating what we think a man would do. For Black women we are dealing with both patriarchy and racism. We have to navigate both external and internalized bias. I consistently strive to create leadership that is powerful and results-driven while also featuring grace and love.

Black women get a lot of messages about how hard we are supposed to work to have value in this society. We are often prompted to work well beyond what any human can sustain. Shaking off that oppressive mythology, leading with equal parts power and love, requires daily vigilance… because it’s counter culture.

What advice would you offer other Black women trying to develop or amplify their voice and become self-advocates?

The “strong Black woman” archetype can be tricky. It’s so deeply entrained into our national consciousness, yet too often it is a stagnant model that doesn’t welcome the differences that exist among Black women. Black women can do the difficult work change requires without sacrificing love, joy, and tenderness with ourselves and others. Our work and power come from being aligned.

My advice would be to trust your brilliance — whatever it looks like. Regardless of how you talk, think, or look, recognize that the time you spend nurturing yourself is not a luxury. Don’t exhaust yourself into illness before you prioritize self-care. Or if you have already done that, do your best to forgive yourself and build a new set of habits. Value yourself enough to know that you, your ideas, and your inspirations are like the earth…precious and finite, so restore and protect your wellness and wellbeing. Self-care is not only for women with disposable income or leisure time…it’s for all of us.

Consider the words of poet Nayyirah Waheed:

‘i love myself.’

That’s Tulaine’s two cents…thanks for asking.

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