Black Faces, White Systems - Part One
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. I've been thinking a lot lately about what it actually means to build a Black organization. Not a Black-led organization, a Black organization. Those aren't necessarily the same thing.
Over the past several years, we've celebrated important gains in representation. More Black Executive Directors. More Black CEOs. More Black board members. Every one of those milestones matters. For generations, Black people were excluded from the rooms where decisions were made in our sector. But representation can’t be the finish line because representation and transformation are different projects. I've been wondering whether we've quietly started treating representation as though it were the finish line. One changes who occupies the chair, while the other asks whether the chair, the room, and even the meeting needs redesigning in the first place.
None of us learned leadership in a vacuum. We inherited ideas about professionalism, productivity, accountability, hierarchy, and success from institutions shaped by colonialism, capitalism, white supremacy, patriarchy, ableism, and countless other systems. They taught us what "good leadership" looked like long before most of us ever supervised another person.
Many of us learned to move quickly, to anticipate risk, to stretch impossible budgets, to make funders comfortable, to reassure anxious boards and always doing more with less. Many of us became successful because we learned those lessons exceptionally well. They weren't simply strategies for advancement. They were strategies for survival. I don’t think there's anything shameful about that. For many of us, survival is an achievement, but survival isn't liberation.That distinction has been sitting with me for months – if not longer.
The conversation about Black leadership often assumes that once more Black people occupy positions of authority, organizations will naturally begin to work differently. Sometimes they do. I've seen extraordinary examples of leaders rethinking governance, redistributing power, and centring care, which has excited me more than I’ve been excited in years. I've also seen something else. I've seen organizations that looked different from the outside but felt remarkably familiar once you stepped inside. The faces around the board table changed. The executive director changed. Yet the rhythms of urgency, scarcity, overwork, perfectionism, and constant performance remained almost untouched.
This didn’t happen because Black leaders failed, but because systems are stubborn things. You can inherit a different office without inheriting the freedom to redesign it. That, I think, is where our conversation needs to evolve.
The Unfunded report was an important turning point. It gave language and evidence to what Black organizations had been saying for years: they were receiving a disproportionately small share of philanthropic funding while being expected to carry enormous responsibility. The report challenged assumptions, shifted conversations, and helped unlock new investments. That progress matters, and it should be acknowledged and celebrated. Still, I've found myself returning to another question. Not who gets funded, but what gets funded.
Most funding supports programs, deliverables, and measurable outcomes. That's understandable. Funders want to know what their investments accomplish. But transformation rarely begins with a deliverable, it usually begins with time. Time to notice, question, play and imagine, which can be remarkably scarce resources in our sector.
Black organizations are expected to respond to community needs, deliver services, raise money, report to funders, manage staff, navigate racism, reassure boards, build partnerships, avoid pissing off the wrong white person, and somehow continue innovating while doing all of that. The expectation borders on impossible, and yet we rarely stop to ask what conditions actually make transformation possible. New ideas don't emerge because someone squeezed another meeting into an already impossible calendar. Organizational redesign doesn't happen between grant deadlines. Different ways of leading don't appear because people are exhausted enough to finally become innovative. They emerge much more slowly, sometimes around a retreat table, during difficult conversations that don't lead anywhere obvious, or after months of reflection when someone finally finds the courage to ask a question everyone else had quietly accepted as settled. That work is real work.
Imagine supporting leadership teams not because they already had the answers, but because they needed the freedom to search for them. What if organizations received resources specifically to rethink governance, supervision, compensation, conflict, workloads, or how to centre joy and care. Not because someone already knew the right model, but because they deserved the opportunity to build one. That kind of investment requires patience. It also requires trust, both also seem surprisingly rare.
This isn't only a conversation about Black organizations. Every organization has inherited assumptions worth examining. Every sector has operating systems that deserve scrutiny. But Black organizations occupy a particular place in this conversation. Many were created precisely because mainstream institutions failed Black communities. If that's true, then surely, we should expect more than simply placing Black leaders inside inherited structures. We should create the conditions for entirely different structures to emerge.
That takes courage, and it also takes funding. Not just funding to deliver, but funding to pause, to experiment, to make mistakes, and most of all, to imagine.
I don't pretend to know what those organizations should ultimately look like. If anything, the older I get, the less interested I become in prescribing answers. If you couldn’t tell, these days, I’m much more interested in asking questions – different questions. What really interests me now are the conditions that make different answers possible. The transformation that I think is possible doesn't grow particularly well under constant urgency, it needs breathing room.
If philanthropy genuinely wants organizations that work differently, lead differently, and care differently, then perhaps our next challenge isn't simply funding more Black organizations (although keep doing that!), but also funding their imagination.
That's where I think real transformation begins.
