Black Faces, White Systems
By Paul Taylor, Co-founder of Evenings & Weekends Consulting, and teacher at Simon Fraser University.
I've been sitting with this piece for a while. I've written versions of it, deleted them, rewritten them, shared fragments of it with friends and colleagues, and then put it away again. Part of me wondered whether I should write it at all. Not because I don't believe what I'm about to say, but because I know I don't have all the answers. And because conversations about Black leadership can get personal very quickly. People assume you're talking about specific leaders, specific organizations, or specific experiences when often you're trying to make sense of broader patterns that many of us are navigating.
Still, I keep coming back to these questions. So, I'm sharing them. One of the things I've been thinking about is what it actually means to lead differently as a Black leader. In our sector, we often talk about representation as if it is the destination (i.e. a Black Executive Director, CEO or Board Chair). And don't get me wrong, representation matters. It matters because access matters. It matters because decision-making tables have historically excluded Black voices. It matters because many of us grew up without seeing ourselves reflected in positions of leadership.
The longer I've been in leadership, the more I've found myself wondering whether representation and transformation are sometimes getting confused with one another, because representation and liberation are not the same thing. The truth is that many of us became leaders because we learned how to navigate systems that were never built for us.
We learned when to challenge and when to accommodate, how to speak the language, to read the room, to make people comfortable, to code switch and ultimately to survive. Those aren't small things. They are the very skills that are often the reason doors opened for us in the first place. Recently I've been wondering whether some of the same skills that helped us succeed inside these systems can also make it harder to imagine something fundamentally different once we're leading organizations ourselves.
We are all shaped by the systems we move through. White supremacy isn't just something external. The same is true of patriarchy, capitalism, colonialism, ableism, transphobia, and all the other systems that shape our institutions. We absorb lessons from them. We internalize assumptions about what good leadership looks like, what professionalism looks like, what productivity looks like, and what success looks like. Having a Black leader at the helm of an organization doesn't automatically mean those assumptions disappear. Sometimes they do get challenged, and sometimes they don't, and when they are challenged, the resistance can be significant.
I've watched boards become uncomfortable with ideas that felt too unfamiliar. I’ve watched funders become cautious when organizations wanted to work differently. I've watched conversations about bold people centred change suddenly become conversations about risk. The older I get, the more I think that what often gets protected isn't effectiveness, it's familiarity and the status quo.
I've also been thinking about something else that I’ve been talking with quite a few people about recently. Many Black people carry stories about being hurt by another Black person in a workplace. Being overlooked, disciplined, pushed out and fired. Those stories are real, and they carry a particular kind of pain because they often collide with expectations we don't always say out loud. We want Black-led organizations to feel different, and we want Black leadership to feel different.
I haven't experienced being fired by a Black leader. I have, however, had to fire Black staff. And every single time it has stayed with me. Not because the decisions weren't necessary. Leadership sometimes requires difficult decisions, but because I understood the broader context. I understood how hard many Black professionals have had to work for opportunities. I understood the barriers people were carrying before they ever walked through our doors. I understood the hopes people sometimes place on Black-led organizations. And if I'm honest, I've cried privately afterwards more than once.
Those experiences forced me to confront something uncomfortable, and it’s that shared identity does not automatically produce liberation. Black leaders can reproduce harmful systems. Not because we're bad people or because we don’t care. Sometimes it’s because we’re exhausted, barely surviving or because the systems around us make alternatives difficult. I think it’s often because we haven't yet given ourselves permission to imagine something else.
That's part of why the Unfunded report hit so many people the way it did. For years, Black organizations had been saying they were overlooked, underfunded, and expected to do more with less. The report provided evidence for what many already knew through lived experience: Black-led and Black-serving organizations were receiving a tiny fraction of philanthropic funding and were often being funded in ways that made long-term sustainability nearly impossible. It also highlighted deeper issues around representation, relationships, trust, and power. Since then, important progress has been made. Resources have been made available, more conversations are happening, and more funders are paying attention.
That matters. Truly. But lately I've found myself asking whether funding inequity is only part of the story. We need to examine the ways anti-Black racism, white supremacy, patriarchy, capitalism, and colonialism continue to shape how the nonprofit sector functions? What if the question isn't only who gets funded? What if it's also what gets funded to challenge anti-Blackness in the ways that we work?
Who is funding four-day work weeks, enhanced benefits packages, ongoing coaching for Black leaders, access to elders, healers, therapists, and culturally grounded wellness supports? Who is funding campaigns encouraging nonprofit workers to simply work the hours they are paid to work? I ask these questions because I've started to wonder whether we are still operating within assumptions that were never designed for Black flourishing. We have become more comfortable funding Black organizations. But are we ready to fund Black organizations differently?
If we take anti-Black racism seriously, if we understand the health inequities, the cumulative impacts of discrimination, and the intergenerational effects of exclusion, then surely our response can't stop at funding programs. We need to centre about healing, rest, joy and would it would actually take for Black people to thrive. I hear Ubuntu referenced often in conversations about Black leadership - "I am because we are." It's a beautiful philosophy, but I sometimes wonder whether we've spent more time quoting Ubuntu than designing around it.
What would happen if we took it seriously enough to build organizations around it? Not as a value on a website, but as an organizational operating system. It could help dictate
How many hours people work, how much vacation they receive, how benefits are structured, how conflict is navigated, how decisions are made, how care is practiced and how success is measured. Maybe the next chapter isn't simply about increasing the number of Black leaders. Maybe it's about collectively defining what it means to be a Black organization. Not just in who leads it, but in how it works what it values, how it cares for people and what it refuses to reproduce.
I don't know exactly what that looks like yet, that's part of why I'm writing this. I don’t have answers, but I think we need better questions, more space to imagine, and to dream in colour about what is possible for Black staff, Black leaders, Black communities, and Black organizations. Not what is possible within the rules we inherited, but what becomes possible if we rewrite them.
