When I’m in a professional setting and I see a conversation about race materializing, my heart beats faster and I become acutely tuned into the room’s social dynamics. My whiteness is top of mind. I interrogate my observations and comments before sharing them. I load my statements and questions with qualifiers the way you might pack a fragile vase to be shipped cross-country by freight.
And I shipped truckloads of freight on Tuesday night.
Education Pioneers (EP) hosted an alumni event called Black Lives Matter to the Education Community, where I joined about 20 education leaders representing EP’s diverse network to reflect independently and engage in small- and large-group “courageous conversations about race” prompted by the tragic deaths of Michael Brown and Eric Garner.
It’s my understanding that the event was first-come-first-served, so the demographics were largely a function of chance. Even so, the room was fairly racially diverse, although there were fewer black attendees than I would have expected considering the topic.
The Education Pioneers’ program team is full of expert facilitators so it wasn’t surprising to see a thoughtful agenda that began with introductions and brief check-ins on everyone’s feelings and expectations for the evening. “Eager,” “vulnerable,” “nervous,” and “open” were common sentiments.
But even with the best facilitation and when everyone’s part of a trusted and familiar professional network, there’s always a fair bit of hesitation to dive into a discussion about race with semi-strangers. Raising issues about race in a professional setting can be fraught with risks including personal discomfort, poorly received messages, and marginalization. As a result, public dialogue tends to be academic in nature and disassociated from lived experiences and feelings. In general, this was the tenor of the conversation on Tuesday too, but there were moments when people left their comfort zone to share their perspectives. In those moments, the room seemed quieter and participants were more reverent, sensing that something uncommon was happening.
“How incredible would it be,” I thought, “if these moments were the rule instead of the exception.”
I’ve recently vowed to be more proactive and vocal around issues of race and class in my work and am always looking for patterns, barriers, and opportunities to improve myself, my colleagues, Bellwether, and our clients. So here are my three big takeaways from the night:

First: Even the most socially-sensitive, well-educated, and well-informed education leaders feel ill-equipped to initiate and sustain productive professional conversations about race.
How is it that a room full of people from all walks of life trained at a variety of the country’s best universities eager to attend an event to discuss race feel like they lack the interpersonal tools to talk about race in the workplace? My colleague Becky Crowe suggested that this runs deep because “we live and operate in highly racially and economically segregated worlds and we aren’t taught, anywhere, how to have productive conversations across differences.” Two other potential culprits here:  First, colleges and leadership development programs that don’t prioritize this to a great enough extent, and second, education organizations that are inhospitable to questions and dialogue about race.
Second: More. More. More.
There was so much demand to attend EP’s event that they had to create a waitlist, signaling a huge appetite to engage in productive conversations about race especially as it relates to education. The few of us who were fortunate to attend happily let the conversation run late into the evening. There are few quality professional outlets to talk candidly about race and class, and I’m glad to see EP using its convening power to fill this vacuum. Education Pioneers and potential funders can expect me to advocate for more events like this in the Bay Area and across the country.
Third: Events like this are important and we need more of them, but they must be seen as a means to a much more complex end.
Institutionalized racism is a product of the decisions made daily by people in power, yet conversations about race are commonly compartmentalized into workshops, retreats, professional development sessions, or diversity working groups. A heavy burden is placed on participants to bring the lessons they learn from trainings, where norms for safe conversations are established and followed, to a much more complex environment, where their daily work occurs and effects are profound and lasting.
We need to begin to think about how to prepare leaders to feel confident addressing inequity in situ where crucial organizational and programmatic decisions are made.
If we’re going to disrupt cycles of inequity and dismantle racist institutions, we need education leaders who habitually initiate conversations about race and class, identify barriers to diversity and inclusion, and doggedly pursue positive outcomes. We’ll need leaders who employ anti-racist habits of mind, or as one fellow alumnus put it, “a lifestyle where you’re constantly examining your biases.”