Confidence, Instinct, and Knowing When to Fight Back: An Interview with Canonical CEO Jane Silber

By Features PCmag

On her first day conducting artificial intelligence (AI) research for Japanese chemical and pharmaceutical company Teijin, Jane Silber was asked to wear a uniform. Silber was the only westerner at the company, the only woman, and she didn't speak Japanese—the whole experience was foreign and new. Despite the deluge of information, responsibilities, faces, and egos, one important thing was abundantly and obnoxiously clear: None of the men at Teijin wore uniforms.

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Silber politely declined. She was told wearing a uniform would be good for her, that she would save money on work clothes, and that she would be able to spend money on her weekend clothes instead. She continued to politely decline.

"I don't think they would have let a Japanese woman get away with it," Silber said. "I kept smiling and saying 'No thanks, I don't want to.' They finally let me get away with it."

Unfortunately, two aspects of Teijin and Japanese business culture were unavoidable: forced daily calisthenics and low-level sexism. The former was announced over a loudspeaker every afternoon, at which point everyone in the company would stand at his or her desk and perform stretches and exercises. The latter was a bit harder to decipher.

As a new manager, Silber was put in charge of a "hot-shot graduate from the top Tokyo University," a man who made it very clear he did not like working for Silber. Struggling to reach her subordinate, Silber finally approached him directly to determine what could be done to rectify their working relationship.

"He felt it was an insult to work for me," Silber said. "I'm not sure if it was because I was a foreigner or a woman. But, in fact, the company was trying to develop him. [Putting him to work for me was] recognition of his potential, it gave him international exposure, and a language-learning experience. Once I figured that out, we were able to talk about it, and everything was fine afterward."

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All in all, Silber felt that working at Teijin was a great experience, "it wasn't awful and backwards," and it helped prepare her for a future of awkward low-level sexism and run-of-the-mill interpersonal workplace dramas. Teijin also gave her the management experience necessary to propel her to CEO of Canonical, a 750-person company with employees in more than 42 countries around the world.

Canonical is best known as the company responsible for driving the development of Ubuntu open source software, a product designed to democratize technology by making computer use free and fair for everyone. Ubuntu is also well-known for its cloud and application performance management (APM) solutions.

I spoke with Silber about what it's like to be the leader of a major tech company, what it's like to be a woman in a male-dominated industry, and which devices she carries with her every day.

PCMag: In the US, only about 30 percent of information technology (IT) workers are women. Yet you're the head of a major tech company. What's that like? What have you had to overcome that perhaps your male counterparts might not have?

JS: It's very difficult to answer that. I don't know what it's like to be a man in IT. The gender disparity is certainly a very obvious thing to me. I feel it in meetings, at conferences, it is present in the room.

That doesn't mean it's present in a negative way. That doesn't mean there's an abundance of sexism in the room at all times. It's present in meetings when men and women tend to have different ways of expressing themselves. In a meeting with good conflict, the men have louder voices than I do. I've learned strategies to make sure I can be heard. I tend to listen more than I speak and, therefore, when I speak, people listen to me. I try to make sure what I'm saying is meaningful. That sounds trite, but I think a lot of people start talking and try to figure out what they're going to say. I try to be very crisp in my communications. I don't know if that's a gender thing or if I've just developed it because I've found it to be effective.

[As for what I've overcome personally], nothing major. There certainly have been minor things. I've been fortunate in my career to be in an environment and at companies where there hasn't been egregious behavior. There is rampant low-level sexism across society but I haven't been face-to-face with egregious examples. Nothing has held me back personally or career-wise.

Early in my career, there was more than one occasion where male colleagues and customers were headed to a strip bar to continue the night of fun. They invited me along and, unsurprisingly, I declined. You're face-to-face with a social/work environment and clearly you're the outlier. I don't feel as though that impacted me in my career progression, but it was a very clear, exclusionary thing, even though they invited me and I wasn't excluded. It still stuck with me.

So what can be done about the gender disparity? You're in charge of a company; what have you done or what can you do to help fix this problem?

It's amazing and frustrating to me. There's no single simple answer as to why it's happening or a single solution to fix it. I talk to teenage girls. I have two nieces and I talk to them and their friends. They say they like computer and math classes, but they say they won't take those courses in college because they're full of men. It's a self-fulfilling prophecy and this frustrates me. At that level, it's important to have role models and examples to show them that it's possible and that they'd enjoyed it.

There's also a statistical drop-off where women enter the workforce in technical roles and then change careers or drop off that path. I don't have a great solution or answer there either. I think it's a broad range of factors [that causes this drop-off]. The stories I've read deal with the impact and the culture of the environment they're working in as the driver of those dropouts.

Our statistics [at Canonical] are roughly in line with the Silicon Valley [gender disparity] numbers. In some areas, we do better and in some areas we do a bit worse. I'd love to say we've cracked this problem but we definitely haven't. We recruit globally. We work largely on a distributed basis. We have 750 people in 42 different countries. Most people at Canonical work from home. This provides a certain degree of flexibility that is particularly welcome to women and working mothers. That's one of the things women in the company have cited [as a reason for staying in their roles]. At a cultural level, there's something about this topic and open source in general. The open-source community tends to have worse statistics than the general environment. The open-source community should be able to overcome some of these biases. A group and community focused on getting things done should be able to have diversity bloom there. Unfortunately, the statistics show something else.

If working from home and work flexibility are important factors driving female retention, why aren't more companies doing it?

I think working on a distributed basis works well in some disciplines and less well at others. Engineering work lends itself very well to that. You can share a screen and do pair programming with someone in Brazil. Our design team is co-located here in London because their workflow isn't conducive to distant collaboration. That flexibility is something that women cite and appreciate but there is a downside to it as well. We have people—men and women—that leave Canonical to join a company where they are in an office environment because they miss the social context, the casual conversation, and the social bonds they build. Our experience doesn't prove this out, but I wonder if there's something there that creates a counter-incentive to working at home and having that flexibility.

What advice do you give to young women who would like to pursue a career in IT?

People will often ask me for advice to encourage their daughters or sisters or family members. I think one of the learnings I've taken away from the studies and articles that I've read is women have to be confident and think of themselves as engineers. Don't think of yourself as a woman engineer; just be the best engineer you can be.

When was the moment you realized you could be successful as a professional in technology?

In college, I wrote a program for course evaluations with a friend. We put the scheme together, we figured out how to work with Haverford College to put it together. People loved it. It was a valuable contribution to campus life. That was the first time I'd written software that was used outside of a class project. It made me feel great. I thought, "How cool is this? How I can use my skills to change the lives of those immediately around me?"

Who was your first tech influence?

My father. In all of my life, including the years when I didn't have the confidence to believe in myself, he told me to trust my judgement, that I could do it. He was full of support and confidence building. When you're feeling alone in an environment, someone saying you can do something is really valuable.

He was excited by everything I did. Me being in tech made him go out and buy a PC. He tried to understand what I was doing. His goal was to encourage me to do whatever I wanted to do. I grew up wanting his advice but he would just tell me, "You've made good decisions before, follow your instinct." It was kind of frustrating, to be honest. But he helped me to learn to trust myself and my own judgment. Women in the workplace need to have that trust in themselves.

Where will the tech industry be in 10 years?

Tech will be so pervasive and throughout our lives that we will take it for granted and not even notice it. I don't know how we made any plans without our mobile phones 10 years ago. In terms of personal computing, the categories of devices will be very different. We'll have a lot of augmented reality woven into the fabric of our everyday lives, workplaces, and homes that would be unrecognizable now.

What would you be doing today if you hadn't gone into tech?

I've always harbored a not-so-secret desire to be a novelist. I'd like to live someplace warm and sunny and write. Or I'd be constructing crossword puzzles somewhere. Or be a continual student [Editor's Note: Silber has a B.A. from Haverford College, an M.S. from Vanderbilt University, and an M.B.A from The University of Oxford]. I like modern American fiction. Authors like Ann Tyler or Richard Russo.

Our readers love to know what devices people carry with them. Which gadgets are you using these days?

I carry two phones: An Ubuntu phone, the Meizu Pro 5, and a Samsung Galaxy S6. As much as I would like to not carry the Samsung phone, a lot of my social life takes place on WhatsApp. My laptop is the Dell XPS 13 with Ubuntu. I smiled when the box came and I saw the Ubuntu sticker on the laptop.

Editor's Note: This interview was edited for length and clarity.

This article originally appeared on PCMag.com.