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Sarah Cooper
Honesty at work.
DILBERT NO MORE

The screwed-up experiences of women at work have been turned into A+ humor

By Corinne Purtill

There’s something instantly recognizable about Sarah Cooper’s comics about workplace behavior: the characters enduring office inanity with the expressionless fortitude of figures in an airplane safety manual; the perfect snapshots of power trips and microaggressions that would be painful—if they weren’t so funny.

Her first book, 100 Tricks to Appear Smart in Meetings, skewered the stupid things people to do to boost their own profile at work without contributing anything of substance (draw Venn diagrams with abandon; ask “Will this scale?”; when in doubt, pace). In her new book, How to Be Successful Without Hurting Men’s Feelings, Cooper probes deeper, finding the humor in the often-painful intersection between gender, identity, and the workplace. (As a bonus, the book includes several blank pages to doodle on while being mansplained to.)

Cooper knows these environments well. Before becoming a full-time comedian and writer, the author of the blog The Cooper Review managed the design team for Google Docs, Sheets, and Slides in New York. Quartz at Work spoke with Cooper about work, identity, and passive-aggressiveness in the G-Suite. This interview has been edited and condensed.

Scott R. Kline
Sarah Cooper.

QaW: At what point did you realize how much comedy there is in the workplace?

SC: I was always observing, when I was supposed to be actually paying attention. I was noticing how people were typing really loudly on their laptops or pacing around the room, or saying things like “Can I ask a question?” before asking a question. I’ve always just had this sort of outsider sort of view of it all, where I’m like, “I want to fit in, so I’m observing what other people do to fit in. I’m going to do all the things that I see successful people doing and imitate them.” But that made me realize how ridiculous a lot of these things were.

There’s a great section in the book about the silly things people do to look busy—leaving Google docs open forever, scheduling tons of private meetings so their calendars look full. It feels like we’ve just created digital equivalents of status markers like staying until after your boss leaves or keeping piles of paper on the desk. Why do people do this stuff?  

I was still working at Google when I wrote the blog post “10 Tricks to Appear Smart in Meetings.” I was scared to share it at first because I didn’t want my coworkers to think that I was making fun of them—which I totally was. But then afterward I had people coming up to me like, “I have a meeting trick! Put my meeting trick in your next post!” This one guy was like, “I do this thing where I schedule a meeting and then I’ll show up late to my own meeting so people know how important I am.”

A few weeks after the post came out, I was in a meeting with a VP and he was pacing around the room and he asked the presenter to go back a slide at the same time, two of the tricks that I had posted. He looked over at me and winked after he did that.

The title of your new book is How to Be Successful Without Hurting Men’s Feelings, but the book is really about how women, people of color, LGBTQ-identifying people, and others survive in workplaces mainly designed for white straight men of a certain age and pedigree. What was the experience of pulling comedy out of the frustration of being marginalized?

Sarah Cooper
Bringing your “whole self” to work.

That was tougher, because it was more personal to me. When something really affects you, it’s hard to find the humor in it sometimes. There’s are a lot of reasons why there are so many white male comedians, but I think part of it is that they are able to joke about a lot of things because a lot of things don’t affect them personally.

Whereas, for me, I’m a black woman, I’m an immigrant [Cooper was born in Jamaica], I have two sisters with disabilities. A lot of this stuff is so personal. There shouldn’t be so many things that are so sacred that you can’t laugh about them. Laughter is so important. But at the same time, sometimes I’m like—I can’t laugh about this. It isn’t funny to me.

I didn’t want to write the book at first because I didn’t think there was a way to make it funny. It just felt depressing. But after a while, the sadness turned into anger and I just got pissed off, thinking about all of these rules and expectations placed on women and how a lot of them contradict each other and don’t feel natural. We end up living this double life at work. We’re putting on this show, and it’s exhausting. So I thought, maybe the way into the humor is to create a book that’s just rule after rule after expectation after rule, until you see that it’s just overwhelming, and that’s when you can see the humor in it.

Sarah Cooper.
Juuuust right.

I wrote “Non-Threatening Leadership Strategies for Women” on the blog in July 2016. I had been working on a different book but when people kept talking about and sharing that post for months afterward, I realized: I’m writing the wrong book. Near the end of 2016 I changed concepts—much to the pain of my publisher—and decided to write this book instead.

The book was published in October, one year after #MeToo took off. What was it like to be working on this book while all these conversations about gender, harassment, and work have been happening?

I joked with my husband, “I hope we don’t tear down the patriarchy before my book comes out because my book won’t be relevant.” But it looks like it’s going to take a little longer than that.

Sarah Cooper
“Diversity” in tech.

The path to achieving your goals, as an entrepreneur or as part of a company, is just as important as reaching them. That’s something I hope men can see as well. If you’re going to be stepping on people to get there, that’s not good. It doesn’t matter if you get there if you leave a path of destroyed people behind you.