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How to Talk to Your Boss About Race, with Y-Vonne Hutchinson
The CEO of ReadySet explains why evidence-based strategy and collective action are essential to building more equitable workplaces.
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Y-Vonne Hutchinson is an international labor and human rights lawyer turned CEO. A founding member of Project Include, her firm ReadySet has provided diversity, equity, and inclusion consulting to Fortune 500 firms and tech giants such as Salesforce, Airbnb and GitHub.
Hutchinson’s first book, How to Talk to Your Boss About Race, is out today. It’s a candid look at how marginalized employees and their allies can advocate for a “more participatory and egalitarian” approach to questions of power.
The book avoids an intellectual sleight of hand common to business books: the tendency to focus on what readers can do individually, rather than collectively. Hutchinson is an unabashed supporter of unionization, and sees it as a necessary check to corporate power in an age of weakened labor protections.
Our conversation ranged from the invisible hierarchies of “flat organizations” to helping CEOs process difficult feedback. Hutchinson draws on a wide array of references, and her perspective is an important counterpoint to the sanguine narratives that permeate the culture at so many hypergrowth companies.
The following conversation has been condensed and edited for clarity.
Ben Jackson: I’d like to start by putting this conversation into the context of the current moment: what many are calling the Great Resignation, or as NPR put it last week, The Great Renegotiation. How have the kinds of companies you work with been affected?
Y-Vonne Hutchinson: You’re seeing a confluence of factors that have fundamentally shifted people’s relationship to work. And we’re in the middle of multiple dramatic and destabilizing events: the political turmoil in the last election, or COVID, which, for many, demonstrated the hollowness of promises around valuing essential workers.
“As Americans, work is seen as a reflection of our contribution to society, and when it feels like employers are no longer holding up their end, people are gonna want to renegotiate.”
On the remote side, you saw the erosion between personal and professional, and the expectation people would just show up and perform as if everything’s ok when it’s clearly not. That’s worn many people out.
Finally, there’s a reaction to the expectation that we’ll also show up in toxic workplace cultures. When it comes to racism in companies, people, particularly Black and brown people, are just sick of it. And there’s a collective disillusionment that’s driving churn across the board.
The framing as a renegotiation is right. As Americans, work is seen as a reflection of our contribution to society, and when it feels like employers are no longer holding up their end, people are gonna want to renegotiate.
It seems like many people are slowly coming to the conclusion that their employers are approaching questions of culture from a place of bad faith, of pretending to care.
One of my former colleagues, Aaron Huertas, wrote that “the hallmark of a bad faith argument is that it disguises the core point of the debates rather than addressing issues, beliefs, and values head-on. Bad faith arguments aren’t real positions, they’re proxy positions people take for rhetorical purposes.” To use a term from professional wrestling, it’s a kind of kayfabe, or scripted dance.
Have you found any ways to help teams break that kayfabe and address the real issues?
Personally, I’ve found that if I have to convince a CEO to care, I’m not going to be successful, and we can be tempted into thinking that’s our job.
For everyone else, I recommend finding a way to safely collect the data. I don’t think it always makes sense for an organization to run their own surveys or focus groups, because employees value anonymity and there’s a lot of fear.
I recommend collecting quantitative data across demographics. I also recommend having one-on-one conversations and focus groups. Once it’s on the table, it’s amazing what people will tell you. And then the question is, Do you want to hear what they have to say?
I’ve heard a lot of HR leaders bemoan how leaders dismiss critical employee feedback, either as “anecdata” or “squeaky wheels,” rather than confront facts that threaten the corporate narrative or their self-image. What are some of the ways you’ve found to help leaders overcome this attachment to moral purity?
Going in, I try to model a growth mindset. No one should dismiss anything out of the gate, and critical feedback is not a reflection of character.
I also do a lot of social identity work to help separate intention from impact. When leaders get defensive, often it’s about, “Well, that’s not my intention,” and less about the impact on employees.
There are also different ways to get feedback. If you’re getting feedback all at once, or you haven’t heard it before, it can be jarring, and those defense mechanisms go up. And finally, if the upward feedback is the only indicator of performance [as opposed to formal metrics], that also might be a separate issue to consider.
“So often, the question of rights becomes subjective, and when the answers are not evidence-based, you’ll always default to the comfortable way.”
You’ve mentioned in past interviews that ReadySet strives to take an evidence-based approach to diversity, equity and inclusion. One of the insights I’ve found helpful is that politics isn’t a dispute over which facts are true, but a dispute over which facts are most relevant to what debates, and what logic we should follow when setting and enforcing rules. When centering the evidence, how does ReadySet focus the conversation on the facts that are most relevant?
While I’d push back on framing my right to exist without harm as a debate, I will agree that data is, in some ways, subjective.
When we look at the evidence at ReadySet, we really center harm and the experience of the marginalized, as opposed to anyone’s intent. So often, the question of rights becomes subjective, and when the answers are not evidence-based, you’ll always default to the comfortable way.
So we center harm, and we do it with a frame that this isn’t a debate, or a discussion, it’s a question of values, and ethical choices. “Do you want to harm people or do you not want to harm people?” That’s where we start. So if you want to avoid harming people, let's look at the data for the harms people experience in your organization.
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In reading your book, I was struck by your focus on collective action and unapologetic support of unions. At the same time, I wonder about the tension between working to change the system from within and organizing a union. How do you see those two approaches interact? Do the same people ever engage in both?
Often, they start by trying to change from within, and if that doesn’t work, they move to unionization. We’re in this age of incredible corporate power that hasn’t existed since the early 20th century. And I, as a lawyer and an idealist, really believe in checks and balances, and unchecked corporate power is very dangerous.
“If I want to file a complaint with the Department of Labor, there’s a 2% chance they go forward. So there are just different tools we need to build worker power.”
At the same time, we’re seeing a rollback of labor protections and an inability for the state to protect employees in line with the labor laws already on the books! If I want to file a complaint with the Department of Labor, there’s a 2% chance they go forward. So there are just different tools we need to build worker power as a counterbalance to corporate power, and collective organizing is the way that we do that.
Since the rise of unionization in the U.S.—and I will acknowledge that unions, in some contexts, are very problematic—we’ve also seen the rise of this convenient myth that social change happens as a result of individual efforts. And that’s just not true. What usually happens is, there’s a group of people who work together to push forward the changes they want to see and are knowledgeable about the social and political context in which they operate.
To your point about checks and balances: You’ve worked with Bay Area tech companies like GitHub, Airbnb, and Medium. How do you see Silicon Valley’s attitude towards government influencing founders’ approach to corporate governance? And what kind of impact does that have on employees from marginalized groups in tech?
I won’t comment on any particular company, and there’s a diversity of views.
You do have these founders who are really idealistic, and there’s still a strong stream of libertarianism in Silicon Valley. While I never know the politics of the founders before we work with them, there is this idea that “the people” can make up for the failures of government.
With any company, though—and this isn’t isolated to Silicon Valley—you can have founders with really progressive values starting out, and then, a few things happen:
One, it scales to a point where they realize there’s no such thing as a pure libertarian or egalitarian structure when all these biases are built into the system. Flat orgs are the most unequal kind, because they default to informal power structures with opaque ways of gaining or losing power, and the hierarchies reflect larger social hierarchies and privileges.
Also, given the expectations of VC, you have people on your board looking to create as much value as quickly as possible with the same playbook they used. And that playbook is not one that’s egalitarian, or anti-racist, or inclusive. So founders get pressured into building those kinds of organizations to attract the capital they need.
Finally, capitalist structures make it hard to create truly democratic organizations. If you’re thinking, “How fast can we grow, and what’s the easiest way to recruit?” That way of doing business isn’t conducive to participatory, egalitarian values.
Have you found any alternate ways to run an organization that are more conducive to participatory, egalitarian values?
At a smaller scale, the co-op model works really well—though I’ve also seen those models fall apart without a clear process and values, just like everybody else.
In your comments about flat orgs and the pitfalls of worker-owned co-ops, I hear something that rhymes, which Jo Freeman outlines in her essay, The Tyranny of Structurelessness: that “the idea [of unstructured groups] becomes a smokescreen for the strong or the lucky to establish unquestioned hegemony over others.” What are some of the widespread misconceptions in tech about flat or structureless organizations?
The myth is that without hierarchy, we all have access to similar amounts of power, when there are different kinds of power—and also privilege, which impacts who gets hurt, believed, and centered. When we’re hearing ideas or assigning something, if we don’t have formal structures and processes, we go to the informal, and often, the informal is biased.
“The myth is that without hierarchy, we all have access to similar amounts of power—and also privilege.”
And when that happens, it also happens invisibly. So it’s even harder to identify what’s happening, to have a recourse, to know who to even talk to when stuff like that goes down! I talk a lot about how bias and exclusion are perpetuated through lack of transparency and access to information. And the flat organizational model is a place where that happens quite often.
I’m struck by your emphasis on transparency, especially given how Silicon Valley tends to lionize transparency and openness. I also find it really interesting how some parts of tech have appropriated the language of democratic movements.
So I’m curious: there are a lot of ways language at work—what some call thought terminating clichés—reinforces the status quo by shaping our unconscious frames. The word “meritocracy” is a prime example. What are some of the more subtle or pernicious ways you see language used uncritically at work?
There’s a book by [Charles] Tilly called Durable Inequality that outlines how bias spreads in organizations through adaptation, where we tell ourselves particular narratives to adapt to the bias we see, and those narratives help solidify that bias.
If you have a myth of meritocracy and think the problem is outside your system, there’s no incentive to change. If you’re the beneficiary, it means you have more merit than anyone, which is a self-serving narrative that feels really good and can be difficult to disrupt.
My book warns about sea-lioning, the kind of gaslighting that happens through constant requests for more data. If you say, “I am logical, I am neutral,” but you’re emotional and the default is always “me,” then it’s hard to convince you otherwise, because you’re so personally invested in that story.
I’d like to touch on politics at work, and while I understand they may not come up explicitly with your clients, there are certainly political undercurrents to DEI work. In a number of high-profile cases over the past year, CEOs have taken very public stances against discussion of politics in their workplaces. I’m thinking right now about a certain crypto company whose CEO wrote, “we’re going to focus on being the best company we can be and making progress towards our mission, as compared to broader social issues.”
What would you say to a leader who worries that discussions of justice, equity, and representation could distract the company from its core mission?
That’s a false dichotomy.
With the company you mentioned, one of their missions was economic empowerment. If you don’t talk about what keeps you from achieving economic empowerment, you’re not going to achieve that mission. And to talk about that, you have to talk politics, whether that’s tax policy, or inflation, or economic discrimination.
“It’s disingenuous to say you don’t want politics at work. What you’re saying is, you don’t want the politics of race, gender, and identity at work.”
I read a great quote recently: “Any organization of human beings working together for a particular purpose is inherently political.” So to me, the idea you don’t want politics in the workplace is cowardly. It’s saying you, as a CEO, don’t want to address the needs of your workers. And it’s unrealistic, because the politics will always be there.
And there’s a particular kind of politics that we’re discussing, right?
It’s disingenuous to say you don’t want politics at work. What you’re saying is, you don’t want the politics of race, gender, and identity at work. So if you’re saying that, what you’re asking is impossible for many of your employees, which is, you can’t show up as yourself.
We’re seeing that, in terms of the future of work, people are the central thing that’s going to drive business. We were already seeing it with the Great Renegotiation. We’re seeing it with the increase in organizing. We’ll continue to see it as Gen Z starts work and their expectations misalign with those in older organizations. We’ll continue to see with the rise of Asian, anti-Semitic, anti-Black violence that affects the people who have to show up and pretend everything’s okay as white nationalist movements push for political instability.
While these things continue, organizations can’t just choose to opt out. If you’re choosing to opt out of this, in my mind, eventually you have chosen to opt out of the marketplace. It’s like me saying, “I don’t want to talk about taxes anymore.”
What’s something important you feel most tech CEOs haven’t considered enough?
I don’t think they’ve given enough consideration to resiliency, for a few reasons:
When a CEO comes to me, they’re often venture-backed, and that has created a cushion. The traditional VC model is rooted in the idea that so long as you’re performing well—not profitably, but well—capital is available. And that has, in some ways, insulated us from dynamics outside our spaces—in the marketplace, and socially and politically—that naturally impact business.
Second, I cannot understate what an incredible time of instability we live in. I don’t like to use the word “unprecedented,” but there’s this moment of global pandemic, societal unrest, increased misinformation and politicization. And climate instability—we always forget about climate. I have workers who call me and say, “I don’t know if I can hop on this meeting—there’s a hurricane headed my way.” And like I said before, we’re in the midst of a generational shift.
So CEOs who are used to thinking about growth, who are not used to thinking about any of these external factors and have the venture padding to do it, are going to have a really gnarly wake up call, because this is a fundamentally unstable environment.
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