Twilio CEO interviews candidates for 45 minutes over dinner—and if you say ‘I’ too much or don’t ask any questions, you don’t get the job
EXCLUSIVE: Twilio CEO, Khozema Shipchandler, always gives hopeful new hires time to ask questions at the end of the interview—and will turn candidates down if they don’t.
The $37 billion tech boss warns job seekers that even if they pass that test, there’s another red flag he’s listening out for while you speak: Using “I” too much.
Previously, we’ve heard from a CEO who rejects job candidates who say they can start right away and another who won’t hire anyone who fails his coffee-cup etiquette test.
Now, Twilio’s CEO says there are two more ways to tank a sit-down interview.
Picture this: You’ve spent weeks polishing your resume, navigating multiple rounds of interviews, and finally, you land a 45-minute dinner with the boss.
You think you’ve won him over.
Then he asks, “Do you have any questions for me?” If your answer is a blank stare or “Nope, I’m fine,” consider yourself on thin ice.
“The number one red flag for me is when someone doesn’t ask questions towards the end of an interview,” Twilio CEO Khozema Shipchandler exclusively told Fortune, while adding that most interviews for senior hires will go on for 45 minutes over dinner.
“For all of them, in the last 15-to-20 minutes, I give them an opportunity to ask questions—and if they don’t have any, I think that’s a pretty significant mark against them being curious about what they’re interviewing, the company, the way we might work together, chemistry, culture, all of those things.
That’s a pretty big red flag.” And before that, even if you have lots of questions up your sleeve, there’s one word he’s listening out for throughout the interview that could cost you the job: Using “I” a lot in conversation.
It’s perhaps surprising, as job seekers are often encouraged to avoid using “we” too much, as it can sound passive.
But leading every anecdote with “I” or “when I was in charge of” can actually backfire.
Shipchandler said it signals you’re not a team player—or a real leader.
“I don’t really think that demonstrates leadership particularly well.
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