A Conversation With Ellen Pao

I turned to Pao, looking for moral clarity in a dark hour.

For any of us who hoped that a Biden victory would make living through a pandemic, if not normal, at least calmer, and less political – those dreams have been dashed. It’s been hard to turn away from the steady stream of revelations about insurrectionists storming the Capitol. The more we learn about the riots, the more organized and nefarious they look.

Meanwhile, there’s a subsection of the tech industry that would prefer to debate whether Twitter should have stripped the outgoing President of the United States of his direct access to his millions of followers rather than reckon with its role normalizing Donald Trump.

Amid this moral crisis, I turned to someone who has always been willing to say uncomfortable truths out loud. We talked about the industry’s reaction to the riots, where the push to diversify Silicon Valley goes from here, the toll of remote work, and where she finds hope.

Ellen Pao’s early career reads like the ultimate insider. She went to Princeton and then received a JD/MBA from Harvard. She drafted deal terms at Cravath. She climbed the ranks in the business development world with stints at Microsoft and Tellme Networks. But she became Silicon Valley famous when she sued her employer Kleiner Perkins for gender discrimination. I remember trekking into the San Francisco courtroom to watch the case unfold. Listening to the testimony, I believed that she could very well win. But the jury didn’t agree. She lost the case.

With the benefit of hindsight, her lawsuit looks like the canary in the coal mine. Senior female executives at Carta and Pinterest sued their employers over unfair treatment. Pinterest settled with former COO Françoise Brougher for $22.5 million. Companies and venture capital firms have been slow to diversify.

After Kleiner Perkins, Pao led business development at Reddit and got thrown into the CEO job. Parts of the Reddit community turned against her as she tried to rein in some of its more pernicious elements. She banned the community /r/fatpeoplehate. Many posters at the time thought it was a mistake. “This seems like a crazy knee-jerk reaction,” one popular comment read. Half a decade later Reddit moderators generally argue in favor of banning toxic communities.

Now, Pao runs Project Include, a non-profit that works to show tech companies how to create more inclusive workplaces. She’s spending her time studying how working from home is affecting tech workers. I caught up with Pao on the phone on Tuesday.

Pao’s position on removing Trump from social media is unambiguous. “It seems so obvious that you can't allow your platform to cause harm to other people and you can't allow your platform to be used to overthrow democracy. What greater harm is there than an armed insurgency trying to conduct a coup? I don't understand why there's any controversy over why Trump and other participants should have been suspended.”

For what it’s worth, I agree with her. I think it’s convenient that hardcore free marketers want to dictate private companies’ content moderation policies. A company disagreeing with the sitting President of the United States about his right to spew false and incendiary information on the platform is literally the opposite of Orwellian. Conservative speech remains some of the most popular content on Facebook, day after day.

More time should be spent worrying about how we’re going to defuse the big lie that many Americans now believe – that the election was stolen. That’s a belief that’s not going to evaporate the day Biden is inaugurated. Tech CEOs cozied up to Trump and many venture capitalists chose to stay silent on the big political problem of modern times, tweeting about socialists in San Francisco instead. After the riots, Sequoia’s Michael Moritz published a piece comparing what’s going on in America to his family’s experience in Germany. It was a moving piece, but I missed the part where he took his buddy Doug Leone to task.

Wednesday, Leone issued a statement saying that he no longer supports Trump: “After last week’s horrific events, President Trump lost many of his supporters, including me.”

Pao makes the point that if social media companies had listened to people who were getting harassed on social networks much earlier, they could have taken steps to mitigate the problems they face today. “Certain groups of people have been harassed and pushed off platforms and swatted at their homes for years. Even before Gamergate in 2014, it's been a problem that they've chosen not to address,” she said.

Pao did not give Reddit a positive review for its content moderation policies. “They've taken a page out of the Facebook playbook,” she said. “I'm going to talk to the press. I'm going to leave these things alone. When something else happens, I’ll address that tiny piece. But I'm not doing the actual work to remove the bad actors. I want the traffic. I want the engagement. I’m addicted to the users.”

Pao surprised me, however, when I asked her whether she thought members of the Trump administration should be categorically denied jobs in the tech industry. She said that she knew someone who went to work for the administration “because she wanted to help people, because she wanted to keep that institution going.” Someone like that is worth hiring, she said. On the other hand, Pao said, “There’s a whole set of people I would never hire – you're purely self-motivated around power and wealth and that's not something that's good for companies.”

I asked Pao whether she thought the push for racial diversity would have an equivalent to #MeToo. “It’s easy for a tech executive to say, sexually harassing a woman with inappropriate touching or lewd language or otherwise inappropriate behavior is something that I can see. I see people don't like it and I can get rid of that,” Pao said. But when it comes to race, a lot of the problems start with the industry’s reluctance to appoint black candidates to senior positions, she said. Tech executives, she said, “a lot of them are fundamentally biased, racially biased, and they cannot see hiring someone who doesn't look like them for a C-level role and that's what's stopping a lot of progress. They are fundamentally racist, and you could never call them that because they don't believe they are. They don't believe people are qualified for these top-level roles.”

There’s definitely a sense among some in the tech industry that they’re exhausted by the constant diversity push. Few would say it publicly. On the other hand, Pao marvels at just how little progress has actually been made. “How is it that at Google there are still security guards who are challenging black employees for their badges? We've heard about this problem so many times. It still comes up. How is it after all these years, they have not figured out how to train security guards not to do that? It doesn't seem like rocket science.”

I asked Pao if she saw herself as part of “Silicon Valley” – a place with less of a physical presence as tech investors flee to Austin and Miami and as all our work is done online.

“I've never been in the in-group in Silicon Valley, so I’ve never considered myself part of the traditional Silicon Valley,” she said. “I don't know if I love San Francisco, but I feel very strongly about San Francisco. It's been bad to see a lot of the changes over the past years as that massive wealth has really changed the culture and the nature of the city. I’m hopeful that having some of this massive wealth leave helps San Francisco return to some of its roots.”

Pao’s Project Include is researching the effect of working from home on Silicon Valley’s workforce. The group surveyed over 3,000 people and is in the process of tabulating its findings. The official results will come out in a few months, she said. I asked her whether she’d come to a conclusion as to whether remote work is better for workers. “I don't think there's one answer,” she said. “I think it's good for some employees. Definitely having some flexibility is good for people who have time commitments or picking kids up from school or dropping them off. But I do think there is something about people being together too. It's different working with somebody that you don't see face-to-face. We've heard anecdotally that being able to report problems at work is harder because before you could stop by your manager’s desk. Now you have to schedule a meeting, and you have to tell them why you want this meeting, and it becomes a little potentially less private.”

Her team’s research is also finding that people are more anxious and working longer hours. “I'm sure you've heard anecdotally that's what everybody is experiencing,” she said.

Despite her frustration, there are things that give her hope. She’s excited about the labor organizing at Google. She thinks that tech companies that have pitched themselves to employees and the public as supporting diversity will now be held accountable for those statements. “Companies have branded around diversity and employees are holding them accountable, so this gap between what companies say they are and are selling themselves as to employees and candidates, and what they actually are and what they actually want to do – now people are calling them out for it,” she said.

Pao thinks groups like the TechEquity Collaborative, Black Girls Code, and The Human Utility are doing important work.

Perhaps most of all, she’s optimistic that a new generation of workers is bringing its values to Silicon Valley. “I'm excited about this new generation of employee that's starting to flood the workplace. They are more progressive. They are more values driven and the numbers on how Gen Z voted in this election – they're what I hope to see in the world. They're more inclusive. They're pro-government helping people. They believe that Black Lives Matter. They see police bias. They see general bias against black people. I think because they can see, they can hopefully fix it, and they're organizing to make their companies change in a way that we've never seen before in tech – and it's working.”