Black Faces, White Systems - Part Two
By Paul Taylor, Co-founder of Evenings & Weekends Consulting, and teacher at Simon Fraser University.
We spend a lot of time celebrating representation. We should. We also spend a lot of time critiquing Black leaders when they fall short. Sometimes that criticism is deserved. Sometimes it isn't. Either way, it has a way of dominating the conversation. What we spend far less time talking about is what Black leaders actually need if they're going to lead with courage, humility, and humanity over the long term.
Who creates spaces where they can admit they're exhausted? Or where they can say, without worrying what people will infer, "I'm not sure I got that one right." I’ve often felt that's one of the loneliest parts of leadership. Actually, loneliness isn't quite the right word, isolation feels closer.
Leadership has a strange way of narrowing the number of people with whom you can think out loud. There are conversations you can't have with your staff because you're trying to protect them. Others you can't have with your board because you're trying to build confidence. Then there are the conversations you don't even have with yourself because slowing down long enough to ask the question feels like an indulgence.
I've also been thinking about something I've heard over and over again from Black professionals throughout my career. Stories about being deeply hurt by another Black leader. Being overlooked, pushed out, disciplined more harshly than others and fired. Those stories are real. What strikes me isn't simply that they happened. Every leader, regardless of race, has the capacity to cause harm. What strikes me is the particular heartbreak those stories carry. Beneath them sits an expectation we rarely say out loud. We hope Black-led organizations will feel different, not perfect, but different. Maybe safer, more humane, or more willing to see the whole person.
When those hopes collide with someone's lived experience, the disappointment runs deeper than an ordinary workplace conflict. It can feel like something larger has been lost. I've thought about those stories a great deal. Partly because I've never experienced being fired by a Black leader, but I've fired Black staff. I don't write that lightly. Leadership books tend to describe termination as though it's mostly a matter of process: document performance, follow policy, and then have the conversation. I’ve never admitted this to another person, but that's never been what it's felt like to me. Every time I've had to end a Black employee's employment, something has stayed with me. Not because the decision wasn't necessary, sometimes it absolutely was. But because I couldn't separate the individual sitting across from me from the broader context we were both carrying.
I knew how hard many Black professionals had worked simply to get into the room, or the barriers they'd already navigated before they ever joined our organization. I knew what it meant to finally work somewhere led by someone who looked like them. And I knew, whether they ever said it aloud or not, that there was often hope attached to that. Hope that this place might somehow feel different.
Sometimes, after those conversations, I've cried on my way home. Not because I regretted or doubted the decision, but because I understood that even necessary decisions can still carry grief. Leadership has forced me to hold truths that don't sit comfortably together. Someone can deserve compassion and still not be the right fit for a role. An organization can genuinely care about its staff and still make decisions that wound people. A Black leader can be deeply committed to liberation while exercising authority in ways that don't feel liberatory at all. I don't think we talk about those tensions enough. Instead, we often reach for simpler explanations.
When I was younger, I thought leadership was mostly about making good decisions. I certainly don't think that anymore. What occupies me now isn't only whether I made the right decision. It's what making those decisions is slowly doing to me. Power has a way of rewarding certainty. It rewards efficiency. It rewards confidence. Little by little, if we're not paying attention, we can begin to confuse decisiveness with wisdom. I've caught myself drifting in that direction. Usually that's the moment I know I need to slow down, to ask another question, to invite someone else into my thinking, or to remember that leadership isn't simply about exercising power. It's about remaining accountable to what power is quietly asking you to become.
Maybe that's also the work we don't talk about enough. Not simply changing organizations. Changing our relationship with authority itself. I hope I never stop asking myself uncomfortable questions. Did I really listen? Was I protecting the organization, or was I protecting my own comfort? Was there another path I couldn't yet see? Those questions don't make leadership easier. I'm not sure they're supposed to. They simply remind me that no title, no amount of experience, and no shared identity exempts us from the responsibility of examining ourselves.
Perhaps that's part of liberation too. Not believing that becoming a Black leader somehow frees us from the systems that shaped us but refusing to let those systems become invisible simply because we're now the ones sitting at the head of the table.
Sometimes I think back to those conversations when I’ve had to fire a Black colleague. I remember sitting in my car or riding my bike afterwards or trying to explain why I seemed quieter that evening.
Not because every outcome could have been different, but because leadership doesn't absolve us from our humanity. If anything, it asks us to carry someone else's disappointment alongside our own. I hope I never lose that. Not because I enjoy the feeling, but the day those moments stop affecting me is the day I should stop leading. Maybe that's what I've been trying to say all along. Liberation isn't simply about changing who holds power. It's about refusing to let power take from us the very humanity we hoped leadership would help protect.
