Episode 4: Redefining Leadership w/ Deborah Harrington
“Things don’t have to last forever in order to be successful… Sometimes we get too caught up in ‘sustainability,’ which prevents us from experimenting.” - Deborah Harrington
In this episode, philanthropic trailblazer and seasoned strategist Deborah Harrington joins Mia to discuss how we can redefine leadership in ways that diversify group thought, create a culture of trust, and build mutual loyalty.
Deborah (she/her) brings to the conversation decades of experience leading in the public sector and social change philanthropy. She talks eloquently about how to reorient an organization’s leadership toward shared power.
Deborah and Mia discuss what often prevents organizations from building relationships (particularly in times of challenge), how vulnerability invites connection (which actively builds trust), and why organizational change can happen more quickly than we think.
Plus, they share the story of how they organized together in their Chicago neighborhood!
Listen to the Full Episode
What You’ll Learn in This Episode:
[6:00] How even the most rigid definitions of leadership can migrate toward shared power
[11:29] What prevents organizations from relationship-building (and what to do about it)
[20:30] Why improving leadership skills happens gradually… but often gets quick results
[22:52] How a community-building project in Deborah and Mia’s Chicago neighborhood had lasting effects for its residents (even after Mia moved away)
Featured On The Show:
Deborah Harrington is a philanthropic trailblazer and seasoned strategist & executive with significant experience in the public and nonprofit sectors. She has served as president and CEO of the Woods Fund Chicago and co-founder of the Illinois Black Advocacy Group and Chicago African Americans in Philanthropy. Deborah is now the CEO of her own firm, the Harrington Group.
Mia Henry (she/her) is the host of the Shared Power Podcast. Mia is the founder and CEO of Freedom Lifted, a training and coaching firm that supports leaders and organizations committed to justice and equity.
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Full Episode Transcript:
Mia Henry: Welcome to the shared power podcast, a limited series for organizations and leaders committed to collectively advancing justice and equity. I'm your host, Mia Henry. I'm the CEO of Freedom Lifted and the daughter of activists, educators, entrepreneurs, and survivors. I've had the honor of teaching, facilitating, and co-leading in nonprofits and schools for over two decades.
I've learned a lot, but it hasn't always been easy. There are conversations that I had, or I wish I had, that create the conditions for more effective collective leadership. In this podcast, We will explore some of these conversations, diving deeply into topics that will help us learn to build trust, navigate conflict, and lead in partnership with one another.
If you believe that relationship building is the foundation for effective work for justice, you are in the right place. Join me as we explore the ingredients of leading with shared power. Today's conversation will feature philanthropic trailblazer Deborah Harrington, CEO of the Harrington Group. Deborah has held prominent roles in the public and private sectors, including serving as president and CEO of the Woods Fund of Chicago, and co-founding Chicago African Americans in Philanthropy.
Deborah is also a mentor of mine. We met while she was leading the Woods Fund, and I was working for a grantee organization. Since then, she has taken me under her wing, offering invaluable support and advice, and linking arms with me as a community organizer in the neighborhood where we both lived in Chicago.
Now, this conversation will feature a look at leadership through the servant leadership model. We'll discuss the importance of leading with humility, vulnerability, and relationship building to create spaces for shared leadership in organizations and neighborhoods.
So Deborah, thank you so much for joining me today.
Deborah Harrington: And thank you for having me on your Shared Power Podcast.
MH: Yeah, yeah. I'm just so honored to be in conversation with you. I've often heard you say that you believe in servant leadership and you think of yourself as a servant leader. And I know this is an approach that you have taken when you've been in positions of power in state government and as well as in philanthropy. So I'd love for us to start by you talking a little bit about why servant leadership is important to you, and why do you believe this approach is so effective?
DH: Well, in government, leadership in the public sector by its very nature is a rigid and unforgiving culture. So if you get too creative and if you paint outside the lines, there are usually consequences. So for me, I felt it necessary to unleash the energy and brilliance of those with whom I worked. And the servant leader model empowers others to encourage diversity of thought. So in fostering leadership in others, it enabled me to create a culture of trust. And as the owner of positional power, I actively chose to lead with humility. And for me, this approach inspired mutual loyalty, insight, and a shared platform for creative thinking and the exchange of ideas. It also gave rise to opportunities for all of us to learn from one another about our different perspectives and possibilities. And most importantly, we were able to reach a point of consensus building, which is fundamentally a unifying exercise in the creation of shared ownership, and really having an opportunity to build something together. But even in my many years that I've spent as a so-called leader, I continue the process of reassessing and re-evaluating this notion of leadership, because it evolves and it's an iterative process. So I'm going to flip to the field of philanthropy and how that leadership sort of looks different from the leadership in the public sector. So in the field of social change philanthropy, while working alongside activists and community organizing, my definition of shared power expanded because I witnessed the challenges of high stakes, social and racial justice campaigns. You know, it's a space where leaders are constantly challenged and they're challenging the status quo, and they take a lot more risk than I saw in the public sector. And so at the end of the day, it is the fundamental relationship of building, and I can't stress that more – how important relationship building is that leads to trust, and that leads to greater transparency, more open communication, and serves as a prerequisite to share power influenced and collaborative decision making.
MH: So would you say it's easier to build trusting relationships in philanthropy? You found it easier to build it in philanthropy than you did in working in state government or in other fields?
DH: Yeah, I would say most definitely. There's something very rigid about government, and that's the culture. There's so many rules and regulations, like I said. It's hard to paint outside the lines. And so in philanthropy, you can be more entrepreneurial. And I think I had a unique role, in as much as I work with activists and community organizers, and they are creative people by nature. And so it had its unique challenges because when you're trying to remove structural barriers and change systems, at the same time that you're really trying to hone in on what leadership looks like, I think it creates a different kind of challenge. But by the same token, there's a sense of camaraderie among my peers in philanthropy, as well as the activists, and so even though it's challenging, I think it's a lot easier because of the relationships. And I go back to the relationship building and the trust, and that's a major prerequisite, I think, for moving toward shared power.
MH: And I totally agree with you on the relationship-building. It's my view on the world as well. What do you think keeps people from being able to focus on the relationship-building and really come back to each other, especially when things go wrong? Or when things are difficult, maybe not even when things go wrong, but when they have an immense challenge.
DH: I think there are a lot of different reasons. One that comes to mind is that some people like the hoard power. And that gets in the way if you are egocentric and you're mostly concerned about your own career or the own direction in which things go. It's hard to take time to nurture the kind of environment that's going to really lend itself to sheer power. And I think another thing might be that sometimes consensus building is messy. People are in a hurry to get to the end, you know, the end process. And so it's sort of like, “I would do it. I think it's probably a better approach, but it might slow me down.” So people are so busy focusing on the end game that they're really not willing to take the kind of time and intentionality that it's going to take to really build that trust and sheer power.
MH: I absolutely agree. I mean, there's the career-minded of folks and many people thinking or believing in individualism, right? And it's like, my way or the highway, because I have to prove myself or what have you. And I know that that comes from deeper insecurities for a lot of us too. I know I was certainly raised to treat people well, but also to take care of myself and look out for number one, you know, because no one else is going to do it. And so I understand how that can morph into not really feeling like we can trust others, especially if we believe our career goals might be on the line. And we don't want to place that control over our careers. We don't want to give that away, so I understand that. And then that “take action.” I hear that all the time. We got to act, let's go, what are we going to do? Let's do this. I remember working some years ago with Black Space out of the Center for Community Organizing in DC. Do you remember that?
DH: Oh yeah, very well.
MH: Yeah, and that whole point of Black Space was to bring – this was before, you know, Trayvon Martin. Even this was very much like it was to intentionally bring together organizers from across different cities. It would be within the city. So we did it in Chicago and L.A. Albuquerque and other cities – Dayton. But to intentionally bring together black organizers who knew each other, but didn't have relationships. And the whole point was for us to just get to know each other. That was the point of Black Space was to build relationships so that we would be ready to be able to work together towards something larger. So yeah, but Black Space, I remember it was so hard in the beginning. Because everyone was like, “Well, what are we going to do? When are we going to start doing stuff?” You know, and some people couldn't do it. They couldn't stay. They couldn't remain a part of the process. It was only a six month commitment, and some folks could not do that. Well, my impression. And I think that they communicated this, that it felt so antsy, right? They felt antsy. They felt like we weren't moving. And organizers are often taught that. It’s very difficult to detach urgency from the work.
DH: That's what I call the tyranny of the urgent.
MH: Yeah. But that's understandable because people are fighting for people's lives. And oftentimes their own experiences, our own experiences, are the reason why we're in the fight. So it's a tension there, I think. And that need to feel like we're doing something or taking action often does get in the way of our ability to really sit with each other, and connect with one another. So I appreciate that.
DH: Yeah. And I think people think about processes sometimes, as we said, slowing down. And it's not valued as an activity that can really grow and build. I think another thing is some leaders are just straight out insecure. I mean, I've heard people talk about imposter syndrome and all these other things. And so they may just be too insecure to really take the time that's needed because they don't really want to unpack a lot of the things that have to be involved in sharing power because they may be exposed, and so that might make some people who are more secure in their role as a leader, more reticent to step out. I think I would challenge them to say that it might be just the opposite in terms of an outcome, because once you reveal yourself, your authentic self, and allow yourself to be transparent, it could lead to probably greater things, because vulnerability is not a negative. I think it tends to draw people in, and you want to feel like, “How can I be a part of the solution?”
MH: Yeah, and absolutely. And I think trying to figure that out, like how vulnerable to be, and still feel secure or like we're not oversharing. We want to keep in and respect people's boundaries, but also be open about our own journeys and our concerns and fears because so many of them are shared, right? We share so many of these things. We realized that when we do talk about the issues that plague us, and when we talk about it with someone else, it always means that they have gone through it, or they know the feeling, or they know someone who's gone through it, right? So it's so important to be able to share stories. I believe that deeply is part of relationship building, taking time to share stories and taking time to talk about our fears honestly, because we do all have them. But being able to talk about them keeps the fears from taking over. And I think that's where it comes in with imposter syndrome, is this idea of we don't belong in this space. We all have that feeling, but when do we let it take over? You know, keep us from living into our power. So that's the piece.
DH: And it's unfortunate because a lot of people have the skills and the talent and they become retrenched, and not allow that to grow and thrive for, you know, fears that are internal. Some insecurities when they could really be strong and powerful leaders. And so there's just so many reasons why leaders sometimes don't tap into that full potential. And I think sharing power is really sometimes easier said than done because we've grown up in a hierarchical environment in society. And so that's sort of like what we're used to, this pyramid. And so how do we kind of rid ourselves from that, and say that that is not the natural course of things. It's supposed to be about building relationships and through that, building one another. And that's really what's powerful.
MH: Yes. Building up one and one another, like what, who are we here for if not each other?
MH: Just a quick break to note that the Shared Power Podcast is sponsored by Freedom Lifted and our flagship training program, Justice at Work. Justice at Work offers blended learning and professional development for organizations and individuals who are strengthening their commitment to justice and equity in their workplaces and in their communities. This training combines discussions with online modules that teach frameworks and critical history to help you examine the relationship between identity and power. You'll even have opportunities to join live group discussions facilitated by me, Mia Henry. Go beyond diversity and inclusion to find your role in building a more just and equitable world. Learn more and sign up at freedomlifted.com.
MH: It's just so wonderful always talking to you, but talking to you specifically about these issues that I find so many leaders are dealing with right now and organizations, many of whom are in deep introspection. COVID has made everybody rethink everything in deep introspection about their missions. The individuals are trying to figure out what positions and titles and roles are even needed in organizations that have either gone completely virtual or hybrid or have quickly gone from local to national level stage because of the ability for technology to spread people's messages. So I think so many organizations are taking a deep look at who they, are and so many leaders are as well. I want everyone listening to begin to understand the ways in which we all have power in our organizations, regardless of the titles of positions we have. We have to be able to get out of this place because the positional power in our organization has to dictate our personal power. And I know leadership has so much to do with this. As you said, just the way you created a culture of consensus-based decision-making. You have nurtured a culture where people learn from each other, and knew that they were all teachers and learners, right? Sharers and listeners. So I'm wondering what do you think leaders can do right now to create the kind of culture you created, Deborah? You know, regardless of the role in their organization. I'm interested in how you ran a meeting, right? Or how you made this happen.
DH: Yeah, I think you have to adapt to different situations as a leader. Maybe it's situational leadership. I don't know what you call it. But I know that being in philanthropy, I found myself with another grant making foundation, which operated under a traditional hierarchical framework. And as a result, I found myself with staff who were demoralized, unmotivated, and operations had suffered. I was pretty surprised because in most organizations, there's a certain culture of activity, but people were very sluggish. And so I just decided I'm going to come in here and try some things, and see if it works. So in the process of deprogramming this autocratic culture, I was intentionally making team building my first and top priority. To impress upon everybody there that are radically new shared leadership approach was in process, and so through team building, it really opened up an opportunity to leverage the power of listening and something that you just said, sharing our stories. And so with the team building, it seemed as though people were able to exhale and relax, and just begin to think about possibility, just early on. But gradually, we became like a really close knit group of people who trusted each other, built strong relationships. So upon liberating these extraordinary folk, we lived happily ever after in a space of collective leadership with high performing systems, and we achieved excellent outcomes.
MH: But it sounds like it took time.
DH: It took time, but it really didn't take a lot of time. Because they had not, at this particular organization, they had not had staff meetings. And so they were working in isolation and that must be terribly difficult. So they weren't able to connect the dots and they weren't able to see how their work impacted the whole. They didn't have close relationships among each other. I mean, they saw each other every day, they spoke to each other, but they pretty much worked in isolation. And so I think first with the team building to say, “We are one, and we're going to get this done.” And I'm here to, like I said, liberate you so that we can just work together. But getting past that, it was just like an engine just getting fired up. And because of that, there was a high level of engagement and productivity. And I passed over a lot of decision making authority to them, because they were all experts in the areas in which they worked. And so they never had that, you know. I wasn't looking over their shoulder. I said, you know what you're doing. And so we became just a wonderful, wonderful team. And I really didn't feel so much like I was the leader. I felt that we were all in this together. And so it's possible. And like I said, it didn't take as long as maybe one might expect. I also think it's important to note that collective leadership is a practice that, once incorporated into organizational culture, it has to be constantly reinforced. It's not just a team-building exercise, but a dynamic, intentional, and continuous shared leadership process that touches every aspect of the organization.
MH: This is wonderful. Well, I want to ask you a little bit about our organizing time together in South Shore. You and I had the joy of working really close together to build a reclaiming South Shore for all, again with some other phenomenal residents. And that came out of, if I remember correctly, my house was broken into a couple of times. And I think after the second time, I was like, I'm just going to invite everybody I know who lives in South Shore to come over to my house, so I can feel reconnected to the neighborhood. Because the psychological effects from the break ins, and I'm definitely from this space of, you know, people break in because they need to break in, right? For whatever reason, they have something driving them to do that. So I wasn't really angry, but I was scared. I felt like I wanted to reclaim South Shore for myself as a neighborhood that I belonged to and believed in and didn't feel targeted in. And so I invited everyone over. Remember, it was like, I don't know, maybe 15 people or something came over, accepted it, came over. We had soup. I made soup. Everybody could eat, right? Vegan, gluten free, all that. And that's how we decided we would build this organization in this space. And we knew we needed a political angle to it as well, right? There were just too many of us in the room who had done work organizing, or done policy work. Or, youth development work. Everyone in the room had been involved in some kind of way in making Chicago better in some kind of way. And so they were bringing all those talents and that thinking to my house. It wasn't just about getting together and having soup every week. We wanted to do more.
DH: No, we wanted change.
MH: Yeah. What are your memories of that?
DH: One thing that reclaiming South Shore for all impressed upon me is that it was an exciting experience and almost like an experiment in community building that I would call meeting the moment. You know, it was sort of like all these events were coming together in South Shore that were impacting us in a negative way. And I think that we were also in a moment where we had ineffective political representation that we felt was detrimental to our community. But I definitely give you credit for meeting this critical moment and galvanizing residents to respond and to address some of the issues that we were concerned about. But part of what I think may have manifested was that far too often, people who live in urban communities become isolated and this prevents the building of collective power. And sometimes our elected officials depend on this dynamic because it gives them free reign over decisions that directly impact us. And because of that, you know, you feel overwhelmed, you feel helpless, and it's sort of like, where do you start? And so I think that you provided sort of a wake up call to say to us as residents, that yes, we are upset and fed up with this dysfunctional community and political leadership, lack of strong representation. I think what followed was a primer on this powerful confluence of preparation and opportunity, and it really ignited community engagement. And I think this work was also inspired by rich examples of power by way of community and civic engagement. And for me, the most important part of it was experiencing the creation of this rich gumbo of dedicated neighbors. People I really didn't know, or I just knew enough to say hello. We ended up with identifying all these different skill sets that people had, all these different relationships and connections that we could use to bear upon really making a difference. People were volunteering time. We were planning together. We were leveraging unique skills. We were canvassing, petitioning, cooking meals, like you said, eating together and sharing power. And in the building of this grassroots organization, we claim, and a campaign on behalf of our beloved community. And so, it really, to me, showed, I think, the tenacity and the possibility of stepping out. And I think it's a model for community building. And if more communities, I think, did that and were able to sustain that, I think that we'd be a lot further along than we are now.
MH: I found myself as you were talking, feeling bad because it's not active anymore in the same way. I mean, I think actually on social media, it's very active. There's hundreds of people in the community who are still in the Facebook group and they're these guidelines in that group of not disparaging people, like this is really about building, and it's not another Next Door or something where people are just like reporting incidents. It's more than that. And so I'm happy about that still. It's a part of what reclaiming started, but then I was feeling bad. Because we don't do those dinners anymore. I moved away and I know that. Things kind of changed after a new alderman was elected. We won't name any names. But I have to go back to what I believe – that things don't have to last forever in order to be successful.
DH: Oh, certainly
MH: I think that that's something that's so important that sometimes, we get caught up in building something. We talk about sustainability. We get caught up in building something that's going to be around forever. I think our ego and need for legacy can play a role in that instead of being experimental. It keeps us from being experimental, and from just moving forward, even just in the spirit of building period. And so I think Reclaiming South Shore For All was wonderful. I know that my relationships with the people are still strong.
DH: Well, I think it was hugely successful and, I have relationships now with neighbors that I would not have were it not for Reclaim. And it really gives one the understanding of people power. To put that in action, to know that people can come together and make a difference, and not with technology, like you said at the very beginning, just in terms of organizations ebbing and flowing and morphing and doing all of this because of the pandemic and because of technology. The same thing is going on with movement building. It's not always reach out and touch somebody, you know, but it can still make a difference. And I think the Facebook aspect of this really keeps people connected and keeps people woke in terms of thinking about what's going on in the community, and then they can decide whether or not to opt in and opt out. But I think it creates this portal of possibility and activity.
MH: Yeah, I love it. It's making me want to reach out to all these wonderful people. That's the other thing is, I haven't talked to some of the folks in a really long time and because of the relationships we've built though, I feel like I could right now pick up the phone, send a text, send an email and hear right back from them and everything would be fine. Like that's how strong those bonds were.
DH: Are you suggesting a Reclaimed reunion?
MH: Yeah, after the recording, let's discuss. We're coming close to the end of our time, and I have enjoyed talking to you about this idea of leadership and shared power, redefining leadership, servant leadership. This has been such a rich conversation, Deborah. So is there any other advice that you would give to leaders about what it means to redefine leadership to ensure shared power in the organizations?
DH: A couple of things. I would invite listeners to re imagine the cultures of their organization. And to intentionally build organizations that share power. We have to all actively figure out how to get out of our own way and share power and let others lead. And that's going to require continuous recalibration, and realignment. I would think that people could also reexamine and assess how do we perceive and use our own power, not just in the workplace, but in interactions with others, and in different settings, and reflect on the lessons we gain from those insights. And I think we have to combat fear and isolation by sometimes you get into a situation where you feel like you're all alone or you don't trust the people around you. And so I think that we have to surround ourselves with supportive and trusted allies. And this will provide us with a steadfast hedge of protection. And the last thing is that I think all of us are fighting a righteous fight, and we have to prioritize our own wholeness and balance and wellness and prevent burnout by practicing stress management or whatever that means. I know for me, it's trying to stay positive. It's actively practicing gratitude, and I have found that acknowledging my daily blessings to be tremendously meaningful. So those are my thoughts. And I just want to thank you again for inviting me, Mia. It's been a real pleasure to participate in our conversation on shared power.
MH: Yes. Oh, I couldn't think of a better person to have this conversation around leadership and shared power. Deborah, thank you so much. Thanks for tuning in to this episode of the Shared Power Podcast. This podcast is a production of Freedom Lifted, a company that provides training, facilitation, and coaching for leaders rooted in justice and equity.
It is produced and edited by Cassandra Sampson at It's 97. Production support also provided by Alicia Tate, Amber Kinney, Alicia Bunger, and the AK Collective. For more information about our work, visit freedomlifted. com. Or follow us at freedom lifted on Instagram, Facebook, or LinkedIn. Join us next time as we continue to unlock the ingredients for leading with shared power.