Illustration: Shira Inbar; Photography: Kelsey McClellan.

Into the Valley

Tech Can’t Handle Criticism: A Conversation with Anna Wiener and Jessica Powell

The authors discuss sexism, power, and diversity in Silicon Valley

This article is part of Into the Valley, a feature series from OneZero about Silicon Valley, the people who live there, and the technology they create.

IIt’s fitting that the most-discussed book about technology of the young decade is not a behind-the-scenes startup story or a hagiography of a tech titan, but a memoir about navigating mid-2010s Silicon Valley as an outsider. Those were the years, after all, when many of tech’s promises began to curdle.

Anna Wiener’s Uncanny Valley follows her immersion into the industry at the apex of its disruptomania — her entry point into tech is through a job at Oyster, a short-lived startup that wanted to be “a Netflix for books” — on through to the disinformation-assisted election of Trump and a growing discomfort with ubiquitous digital platforms.

Few know those environments better than Jessica Powell, the former vice president of Google’s Communications department. At one point, Powell was one of the highest-ranking women at the company; after she left, she wrote The Big Disruption, an acerbic work of satire that lampoons a power-mad tech company that’s going to absurd lengths to keep its male employees happy and productive. (Full disclosure: The book was published online by Medium.)

Given the successes of these books, the sense that a tech backlash is in full swing, and the rise of worker-led movements to protest gender inequality and climate policy in the industry, OneZero decided to bring these two authors together to discuss tech’s state of unrest. In February, Wiener and Powell came to Medium’s San Francisco office to discuss the nature of this percolating backlash, sexism in the industry, and the relationship between tech culture and its products.

The following is an edited transcript of that conversation.

OneZero: Let’s talk about how both of you first came to Silicon Valley. What drew your interest to the field?

Jessica Powell: I was not remotely interested in tech. But I ended up in London and had no visa or anything. So I applied for every job under the sun. No one, no one would call me back. I applied for every job in the Guardian ads. I applied for waitressing jobs, I applied for a CEO job, and across the board no one called me back. Google was the only place that I got an interview at, and they hired me as a contractor.

Anna Wiener: My peer group wasn’t thinking about tech at all, and I was an assistant at a literary agency. I was applying for other assistant jobs — this was just considered forward momentum — and I sort of fell backwards into the [tech] industry. I read on the Paris Review blog — the source for business information — that this startup was doing like a Netflix for ebooks product and they had raised $3 million. [In the article, there] was just this picture of these three men. They looked so happy, and I was like, ‘Yeah, I guess I would also be happy if I had $3 million to make something.’

This just seemed like they had a license, like this was the future. How can it not be? They’ve been given this funding, and they can just go forth and disrupt publishing, and I wanted to try that. It seemed like the version of tech that was related to my interests, which at the time were pretty much books and Tumblr. So that was how I got my start in tech. That job was also a contract position.

“[In the article, there] was just this picture of these three men. They looked so happy, and I was like, ‘Yeah, I guess I would also be happy if I had $3 million to make something.’”

Once you arrived in Silicon Valley, it seems as if some of the broader structural cultural issues become apparent pretty quickly. Anna, there’s a great line in your book about how it became clear that so much of the tech culture is built by young white men from “the soft suburbs.” And then that is being exported.

Anna Wiener: Well, one might say that a lot of American society is run by young white men from American suburbs, so it wasn’t like a total fish-out-of-water situation. When I started at my first company in Silicon Valley, it was almost entirely young men.

Anna Wiener.

I think this manifests in different ways: You have people who are quite young and who are quite inexperienced — professionally and also in life. They’re learning how to manage other people — some of whom are older than they are and have more experience — at the same time that they are figuring out how to scale, how to grow, how to be a professional, how to be independent in their twenties.

You end up with these cultures that, with that youthfulness combined with certain industry values, tend to lean toward the irreverent — this idea that this is like an anti-authority, anti-government, anti-bureaucratic form of business. When those two things collide, you get a workplace culture that can be quite alienating to someone who is on the outside in any way. I think you also just get a workplace culture that’s governed by the sort of business advice one might read on Medium from a semi-experienced venture capitalist.

OneZero: And that often results in what Jessica details in her book — institutional sexism. In Jessica’s book, it’s very explicit: The engineers are building internal hookup apps to keep the engineers happy. The message is pretty clear that the company culture in a lot of these places is serving a very narrow interest, which is the interest of the men working there. Jessica, can you talk about what in your experience inside Silicon Valley led you to register that critique?

Jessica Powell: Everyone thinks I wrote the book when I was at Google. I was at Google for a long time. Then I went to a startup in London and then went back to Google. This startup was pretty horrific. Like one time I came in and there were, like, dildos on my desk. Not like dildos. There were dildos on my desk.

When I started writing, I had no idea it was gonna be a book. I was just writing because I was mad, but I didn’t even know if I had the right to be mad. On the one hand, it seemed so obvious that what was happening around me was bad. But no one seemed to care. That’s probably not true. I think probably people did care. But when something becomes normalized, you really doubt yourself. Whenever I would raise some of these issues, people would be like, “Oh, don’t freak out about it,” — I’d be the only woman on the management team — and, “Oh, but you just care about that because you’re a woman.” Maybe.

Generally in the Valley, we really have bought into this idea of it being a meritocracy. And certainly if I think of my own career, going into Google at 26 and, you know, running my department by the time I was, I think, 37 or 36, I don’t think that would have actually happened in any other industry. If you were there to catch the ball, and you could catch it, then you kind of continued to advance. So, I do think there is something really special about the Silicon Valley culture in that sense. But it’s a total myth that it’s a meritocracy.

The problem is that we think of our platforms as neutral. We think of our company structures as neutral, and we don’t always look at the inequalities that exist within them. At Google, we had a TGIF [meeting]… where you have the Q&A and the founders get up and they’ll answer any question, which is great. That does not happen in every industry. But we would assume that because we put the mic in the room, that meant everyone had equal access to the mic. But that’s not how it works.

Guess what happens? Who are the majority of people who go to the mic? It’s a bunch of men, primarily white men. They should absolutely have the right to ask those questions. There’s nothing wrong with them, but we’re wrong to assume that tech is neutral. And I think that is how a lot of the sexism and racism and ageism — we never talk about ageism, but my God ageism! — I think that’s how that all happens. We keep thinking we’re all wonderful, fair people, and so we don’t interrogate enough how our tools and how our structures in the company are used.

OneZero: You both explicitly said that you hope your work has a political element, that you hope it engenders change. What would that look like?

Anna Wiener: I think [tech] is an industry that’s quite hostile to criticism — not just [an industry that] doesn’t want to think about any critique, but is actively dismissive of criticism. I think criticism is inherently political, especially when you’re criticizing power. And I do hope my book is politically useful in the sense that I want people to see how people speak and how they think and what the intellectual figureheads are in a culture that has amassed such a high concentration of wealth and power so quickly.

My reason for writing the book as memoir was I felt that—especially as a nontechnical woman with the story I had—if I had disguised it as fiction, it would not be taken seriously. I wanted people to understand that these things all happen, the good and the bad, that my experience here was as fortuitous as it was disenchanting.

[By not naming companies or executives in the book,] my point was that this is more about people or institutions in a structural position, and the behavior is what’s important — not any particular company. People have come to me since the book’s come out and asked, “Did you work at X analytics company?” and I did not.

OneZero: Because their experiences so mirrored what they saw at their workplace?

Anna Wiener: A concrete example: There’s a part in the book where I talk about my team being brought into a conference room and our manager asking us to write down the names of the five smartest people we knew. We all wrote down our friends’ names, and then he was like, “Why don’t they work here?”

A woman I know emailed me after reading this, and she was like, “The same exact thing happened at a company that I worked for in a totally different part of the industry — they must have just read it on the same blog post.” I just feel like there are these cultural ticks — I want to point out that this is not hyperspecific.

OneZero: Jessica, what’s been the response to your book as a piece of satire? If you’re reading between the lines, some people may or may not be super favorably rendered in there.

Jessica Powell: Yeah, there’s no one-for-one matching. Everyone has an opinion about the [character of the] nymphomaniac CEO. They all have guesses, which are actually super-good guesses. But the biggest inspiration [for this book] was definitely working at that startup. I don’t think the head of that startup liked the book. In fact, there was a huge exposé of him last summer, about all the misogyny and racism at their headquarters. I gave a quote for the article, and his response was, “Jessica’s just trying to promote her book, along with all the other people who had spoken out.” And I was just like, no one even cares about your company. If I was going to promote my book, I think I’d talk about Google’s sexism.

Jessica Powell.

As for Google, the people I consider my friends have all been great. There were a ton of Google employees who reached out and were just like, “Wow, I feel like you’re making us eat our vegetables, and we’re talking a lot about it.” That is super rewarding to hear. There were definitely some people who were not happy about it, who all of a sudden stopped talking to me. And that hurt, definitely, in the first beat of it. And then I had a moment where I was like, wait a second, so we are not friends because I criticized the industry you worked in? That’s way more dystopian than anything I wrote in that book.

Anna Wiener: Jess, I’m curious if you’re worried about credibility. As a fairly low-level employee at these companies, I worried about people dismissing my account because I’d only worked in the industry for five years. I wasn’t even a programmer. I wasn’t super ambitious in my career after a certain point. Did the question of credibility come up for you as someone who had worked in the industry for a much longer period and had become an executive? Was that on your mind at all?

Jessica Powell: People like to position critics as outsiders trying to undermine the credibility of [the industry]. And even more so if you’re not technical. Then they can kind of, you know, bucket you as, “Eh, they don’t really understand the tech.”

“The problem is that we think of our platforms as neutral. We think of our company structures as neutral, and we don’t always look at the inequalities that exist within them.”

OneZero: In 2014, the founder of GitHub stepped down after serious sexual harassment allegations led to a companywide probe of the startup’s culture. Anna, when you joined the company, it had adopted a number of measures to try to make structural changes, to deter harassment and promote inclusion. You detail some of the ways those were and weren’t successful. What do you think of such efforts put forward by the industry so far?

Anna Wiener: We have to look at these as structural issues. We have to look at the incentives of the industry, the incentives of the business model, the incentives of venture capital. I think there’s a lot of really important work being done at a lot of startups and larger corporations with diversity and inclusion. I think there are people working really, really hard to change cultures internally. But I think until those people are really given a seat at the table, really given power internally, we’re unlikely to see any sort of meaningful cultural shift. Unless you see a shift in the business model or in these incentives, we’re unlikely to see a shift in the way the products are used.

I’m not saying we should dismantle capitalism, exactly, but I do think these problems can’t be solved at the company level, because it’s not in anyone’s interest to do so. Until we can really acknowledge that and reckon with that, we’re unlikely to see meaningful shifts. I can’t speak to what happened at GitHub. I wasn’t in the room for important meetings, but my understanding of the work people were doing around diversity and inclusion is that [it] was going to take time, and it was going to require people to slow down. It’s going to require certain changes to the product itself. And that’s not in the interest of the company that is gunning for an IPO or for a multibillion-dollar acquisition by Microsoft.

I think there are things we haven’t tried yet, which makes me really excited. Some of the recent organizing we’re seeing in tech is really compelling. I think employees having a seat at the table or employees on the board, that’s a step in an interesting direction — collective ownership. For an industry that has so many smart people and so many optimistic, idealistic people, we haven’t been super imaginative.

Jessica Powell: I’d like to see more engagement from tech with the outside world. [Anna was] saying earlier that it’s an industry that does not take kindly to criticism. I think that’s very, very much true. And so what happens is, say Facebook does something dumb or controversial on the content moderation side, and everyone gets all worked up. What happens if you are at Reddit, YouTube, Twitter, any kind of UGC platform? You totally close ranks. You don’t say a thing. You don’t want to get pulled into that, on a policy side, on a press side. So you don’t say anything.

And so then you have this vacuum of largely reporters or politicians weighing in on these debates. You get this vacuum and anti-tech vitriol. [It’s] not always super informed. But it’s a problem of our own making, because we don’t do anything. We keep our heads below the parapet. And so I think we kind of deserve it.

On Twitter, I’ve got my media feed and I’ve got my tech feed. It’s very funny to watch them sometimes. All the tech people are like, “Oh, the media. It’s all fake news and they hate us and so they make things up.” And yeah, sometimes it’s a little extreme, but it’s also because we don’t do a whole lot.

There’s so much anti-tech sentiment. Everyone just kept on trying to put me into this hole of, like, “You’re this whistleblower, you hate tech, da, da, da, da.” The thing is, I don’t. I still work in tech. I think it’s something that’s really, really special — the questioning of assumptions and trying to do stuff even if you don’t know that you can do it. I love that there are people trying and failing. [But] can we all just behave better, please?

Update: This article has been updated to clarify Jessica Powell’s role at Google.

Senior editor, OneZero, books, futures, fiction. Author of The One Device: The Secret History of the iPhone, founder of Terraform @ Motherboard @ VICE.