Meet the woman who left Google to become a comedian... and now has serious advice on breaking the glass ceiling (ie, make a man think he did it for you)
Sarah Cooper tells Meadhbh McGrath how her experience of 15 years in the tech world shaped her new book, which takes a tongue-in-cheek, and occasionally reflective, look at succeeding in a male-dominated workplace
Lean in, but lean back. Speak up, but not so shrill. Have confidence in yourself, but don’t get arrogant. Be yourself, but also a good culture fit. As if the modern workplace wasn’t enough of a minefield, women are regularly bombarded with contradictory advice on how to get ahead.
The ways women navigate this obstacle course are at the heart of comedian Sarah Cooper’s new book, How to be Successful Without Hurting Men’s Feelings, which offers “non-threatening leadership strategies for women” on everything from job interviews (“Smile not too much and not too little. Try practising a smile that is somewhere in between, even if it makes you look like you’re having a stroke”) to sexual harassment (“Ask yourself, how can I put my personal safety aside to create a more fun work environment?”).
In the introduction, Cooper outlines the book’s central thesis in typically tongue-in-cheek style: “Scale the heights of your career and break that glass ceiling, but do it very quietly and gingerly, and be sure to make a man think he did it for you.”
Much of Cooper’s material is drawn from her 15 years’ experience in the tech world. She worked as a visual designer at Yahoo! before joining Google as a user experience designer and later a manager and design lead for Google Docs.
When we speak on the phone from New York, she recalls a particularly memorable office meeting where she noticed one of the managers was playing on his laptop and hadn’t contributed to the discussion.
“Then he got up and drew a Venn diagram. It was this ridiculous Venn diagram that didn’t make any sense, and I thought someone was going to say how ridiculous it was, but instead everybody tried to help him draw this diagram, and he just handed the marker off to someone else and went back to not paying attention on his laptop,” she says. “I wrote down in my notebook, ‘How to look smart in a meeting: draw a Venn diagram’.”
That was eight years ago, and it ended up as one of Cooper’s ‘10 Tricks to Appear Smart in Meetings’, a viral online post that became a hit satirical book in 2016, 100 Tricks to Appear Smart in Meetings. “That was the first time I took my love for comedy and combined it with what I really knew, which was the corporate world and the show we put on in meetings, and that’s what started this path of writing humour about the workplace,” she explains.
Cooper, who was born in Jamaica and moved to the US when she was three, studied economics before completing a master’s degree in digital design, which led her to a string of corporate jobs.
Four years ago, she decided to leave Google and pursue comedy writing and stand-up full time. As well as her books, she runs a popular blog, The Cooper Review.
“When I left, they told me if I wanted to come back that I could at any time. That made it easier to leave, because it was scary — Google is one of the best places to work and I still truly believe that,” she says.
Yet in her book Cooper is scathing about corporate culture, lampooning the self-aggrandising diversity reports, claims of ‘authenticity’ and dubious mental health policies (in one savage gag, she writes: “Your company absolutely supports you focusing on these issues and getting the help you need as long as it never comes up at work and you get all of your work done on time).
“It’s this fake authenticity,” she explains. “All of these things that don’t quite make sense, like ‘be yourself’ but also you have to get along with everyone and be part of the team. There’s a lot of passive-aggressive behaviour because everybody wants to be polite, but at the same time we can’t always be polite.
“People in healthy relationships are supposed to fight, but then at work you’re not supposed to fight, so you end up having these passive-aggressive situations. Then there’s the performance aspect of it, of saying how excited you are about a conference call when it doesn’t really make sense to get excited about a conference call. If you take a step back and see it from a human perspective, it’s not normal human behaviour.”
Cooper doesn’t pull punches — chapters include ‘Gaslighting for Beginners’, ‘How to Bring Your True Self to Work and Then Hide it Completely’, and ‘How to be Harassed Without Hurting His Career’ (“Consider that the higher the performer, the more egregious the harassment will need to be before we barely acknowledge it, then reprimand you for letting it happen,” she writes).
Her favourite joke is a graph indicating that 86% of staff in a company “see no problem with sexism in tech”, while the other 14% are, of course, women. “I think it’s funny that you can slice and dice the data any way you want and make it look like things are good, when if you look at it, it’s not really that great,” she says.
“A lot of companies are struggling with this, so they put out these diversity reports to make it seem like they’re really on it.”
As well as sharply insightful career guidance, the book features Cooper’s own illustrations, ‘Men’s Achievement Badges’ including, ‘Didn’t refer to watching my kids as ‘babysitting’, and exercises such as a checklist to help you keep track of all the things you may not yet have apologised for today.
Women reading the book will likely find themselves laughing, then wincing, at the acuity of Cooper’s observations, many of which she describes herself as guilty of.
“I remembered all of the things I would do to seem more likeable and approachable at work, even if it wasn’t how I would normally be — putting smiley faces and exclamation points in emails; making sure that if I have an idea to first say, ‘This is probably a stupid idea’; smiling at sexist comments. If someone was explaining something to me and they were kind of important, I would let them explain it to me even though I already knew about it,” she says, laughing.
“I’m definitely a people-pleaser, but I’m a self-aware people-pleaser. I see myself doing this and I hate myself for doing it, so I really wanted to call it out. I really enjoy getting emails from people like, ‘I do this! I hate that I do this!’ and I commiserate with them.”
As How to be Successful Without Hurting Men’s Feelings reaches its conclusion, Cooper turns reflective, finishing on a serious note: “I set up to write a book for women but ended up deathly afraid of what men would think, imagining every possible scenario.”
Now that the book is published, she has (mostly) put those fears behind her.
“It’s been really eye-opening. On the first page, I say, ‘What’s the worst part of a being a woman in business? We asked these three men what they think’. I didn’t realise how true that would become,” she says.
“I have all these men that say I don’t know what I’m talking about and this isn’t true. It’s so funny, because they’re just proving my point, ignoring all of the women who agree with me and trying to tell me what it’s really like for women.
“Maybe if you’re a man in a female-dominated industry, you have a similar experience, but the fact is that most of us are women in male-dominated industries and most of us are in that situation. There just isn’t an analogous situation for men.
“I was feeling a lot more trepidatious about it when I was writing the book a few months ago, but now I’m like, ‘Just look at the reality of what most offices look like’. So many women are agreeing and identifying with the book, and that reinforces it and makes me feel better about it.”