When It’s Necessary To Be A Jerk At Work

Sometimes you just have to make everyone uncomfortable in order to achieve your goals.

When It’s Necessary To Be A Jerk At Work
[Photo: courtesy of Drafthouse Cinema]

Andrea Cutright thinks it’s important to be a jerk at work–at least sometimes. She believes that it’s a skill you can and should develop as you get further along in your career, in the same way you would hone negotiation and team building.


Cutright’s had plenty of time to learn over the course of her career. After spending eight years at Yahoo!, she launched Foodily in 2010. When the social recipe sharing startup was acquired by IAC-owned in May, she was appointed chief operating officer of the Q&A social network.

Forget Compromise and Focus

Not long after she arrived, Cutright confronted’s leadership with a tough proposition. She wanted the business to focus on one target audience: 13- to 19-year-olds. That meant letting a lot of [older audience members] go, admits Cutright, who asserts that the teen group is 65% of’s current user base. Protest ensued. “There was a lot of, You can’t do it, I won’t let you, It’s the wrong thing,” she recalls. “And I would not yield.” Cutright insists that her stance came from a place of passion, knowing it was the right thing to do for the future of the business, even if it didn’t leave everybody in the room incredibly happy.

Later on, she says, others appreciated her very focused way of looking at the business, but you have to be 100% behind your idea to enforce a good outcome. “You have to follow through,” she explains. “And that is good for everybody.”

Cutright wants to clarify that she subscribes to a very specific definition of jerk. And that doesn’t include the typical tyrannical behaviors such as micromanaging narcissists, fearmongers, or bullies. “There should be an infographic spectrum for when you get to asshole,” Cutright quips. “That is not a skill set, that is a personality.” Those people don’t get results.

She agrees that no one wants to work with someone whose personality overrides the organization’s purpose and creates a toxic environment. Rather, she says, her flavor of jerk is someone who is ready to be unyielding in order to have the opposite effect: pushing a goal or a business model that is stuck. “Being unyielding can be powerful,” she says.

The Right Time To Be A Jerk

Cutright admits she didn’t always know how and when to break out the uncompromising tool from her kit. “I think you want to have a great work persona,” she says, one that makes people want to follow you, and who trust and believe in the way you operate. But she does admit that it’s a fine balance between knowing when to take a stand and remain steadfast, and being that so often that it becomes part of who you are as a leader. Cutright uses words such as assertive, firm, and forceful to describe the right way to appear in those situations. Used judiciously, she says, “Everyone sees that and can have respect for what you want to achieve.”


Although she was well-versed in compromising and reaching consensus in order to help drive people towards a goal, it wasn’t until she had to raise money for her startup Foodily that Cutright discovered the power of being uncompromising.

The Difference Between Like And Respect

“You want people to like you,” she says. “You want them to give you money.” But she practiced in the mirror, repeating the target dollar figure over and over until she knew she could stand firm and not take a penny less. Once in the room with potential investors, Cutright refused to sit down to keep her mind-set firm. The physical cue allowed her to hold her position, even though she confesses that she was “sweating on the inside” during the uncomfortable exchange that ensued when it was clear she wouldn’t budge. “I would say, I don’t mind leaving right now, I can talk to someone else,” Cutright asserts, ignoring the internal voice that whispered she might be pushing too hard.

In the end, she got her investment. “It is easier to act like a jerk when it comes from a place of passion, and when you want it to lead to a very specific action,” she says. “Being unyielding can demonstrate power in a way that knowing facts or being smart or being charming cannot,” she adds.

Know When To Back Down

Cutright is quick to note that it’s important to pick your battles. It’s harder at the beginning of a career when you might not have all the information and experience of a more seasoned colleague. But it’s important to step up, she says, if you feel the wrong decision is being made, by articulating your beliefs and pushing a little harder to be heard than perhaps you are comfortable with. There’s always a possibility you might be wrong, she says. Then it’s time to acknowledge you made a mistake.


“That comes from a place of confidence, that you have skills and capabilities and nobody’s perfect,” she says. “One of the best things you can do as a leader is admit you are wrong.” Cutright recalls pushing for a particularly tough-to-create product at Foodily. “It really bombed,” she admits. “I didn’t mind saying I really believed in it and it didn’t work,” she says. Recognizing mistakes is as powerful a team building exercise as being a jerk, says Cutright. “You just have to be polite.”

In the end, she contends, people want to work for someone they respect who is honest and doesn’t hide things from them, and more importantly, who would go to the ends of the earth for an idea they’re passionate about. Cutright asks: “Who doesn’t want to work for someone who believes so much in what they are doing?” Even if that person is a jerk some of the time.

Related: Are You The Toxic Coworker?

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.