A realistic sense of one’s own strengths and weeknesses would seem to be a desirable quality in a job candidate, right? Jessica Greenwalt thinks otherwise. The CrowdMed cofounder thinks women in the technology industry need to be take a cue from the men around them and be more arrogant and grandiose in their self-assessments. 

Greenwalt was one of five “Women of Influence” I interviewed onstage last March at an event hosted by Tech in Motion: Silicon Valley. (I’m resurfacing her comments now as part of our editorial spotlight on the Most Innovative Women in business.) 

The discussion touched on all the usual culprits for the underrepresentation of women in tech industry leadership roles: discrimination in the workplace, the “pipeline problem” of too few girls studying math and science, the difficulty of balancing motherhood with the demands of a startup. 

But one factor that doesn’t get enough attention, Greenwalt said, is the difference between the way men and women present themselves in professional situations. “The only environment I’ve worked in is with a bunch of guys,” said Greenwalt, whose company uses crowdsourcing to diagnose mysterious medical conditions. “They always come to the table like, ‘My idea is the best. You want to go with my idea. I’ll be nice enough to let you use my idea. I’m nice enough to be here and give you the honor of working with me.’” 

That sort of bluster is surprisingly effective, she said. “It sounds crazy, but people see that and think, ‘Maybe there is something great about this guy. He certainly thinks so.””  

Greenwalt said she rarely sees anything approaching that level of confidence from women job-seekers. That’s hardly surprising, given the research showing that women who speak up in meetings or otherwise assert themselves face negative consequences. 

But even worse than being talked over in a meeting is not getting a seat at the table in the first place. Women who go out of their way to signal humility put themselves at a disadvantage when they're up against men who grade themselves on a generous curve.

“I do too many interviews where you ask women what’s great about them or the accomplishments they’ve had, what they’re most proud of, and they’re so sweet and so modest,” Greenwalt said. “You’re competing with a guy who’s going to champion the hell out of himself and then you’re going in there like, ‘Oh, I’m OK. I try my best.’ 

“Don’t do that. You are awesome. You are better than anyone else in that room and that’s the attitude I want to see more women go into tech with, and go into whatever it is they’re trying to achieve with.”

Watch the video of Greenwalt's answer, which earned her a spontaneous ovation.

Published on: Sep 28, 2015