- 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 $16 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 tells 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 says it signals you’re not a team player—or a real leader.
“I don’t really think that demonstrates leadership particularly well. What I do is easy because people are supposed to listen to me. I can bark orders and ideally they follow them,” he explains. “But the hard leadership is when you’re not in charge. How do you get people, through data, passion, charisma, persuasion, to get people to do things? I really try to test for that.”
3 questions to ask hiring managers instead of drawing blank
It can be awkward when the hiring manager asks, “Do you have any questions for us?” because more often than not, there’s nothing left to cover. The usual topics—like what the job actually entails and how many days you’re expected to show face in the office—tend to arise naturally early on during the interview.
But even if you’re applying to a junior role and interviewing with a hiring manager or recruiter, instead of the CEO, not mustering up the effort to think of anything to ask can still cost you the job.
Meta’s former global head of talent, and current chief people officer at the creative agency Figure 8, Jenn Bouchard, told Fortune that it’s a deal-breaker because it signals disinterest.
“An interview is a two-way experience,” she added. “And so as much as I’m getting to know the candidate, I also want them to be curious about getting to know the role, the company, the culture, even the team that they might be walking into.”
Sweaty palms and drawing blank can get the best of us. So instead of relying on thinking of something great on the spot, it’s a good idea to have some questions up your sleeve to impress the hiring manager, Bouchard insisted. These are a few questions that have wowed her in past interviews:
- What’s the hardest problem that you’re trying to solve? What has the team not been able to solve? And why do you think that is?
- What are the top three strengths of the team? And how will this person add to the strengths of that team?
- What has the leadership team recently implemented based on employee feedback?
Other tests to look out for over dinner: The salt shaker, the waitress and pricey menu items
Shipchandler’s far from the only boss to opt a dinner setting for the final interview stages. He says it’s generally reserved for senior hires whose resume ticks all the right boxes.
“They’ve already got all the qualifications at that point. The question is, is there chemistry? Are we going to work well together?,” he says, adding that he’s testing what you’re like off the clock.
“It’s got to be fun too, not just all business,” Shipchandler adds. “What are their outside interests? No judgment from me, obviously, but can we have a conversation about that too?”
But be warned: When the interviews moves to the dinner table, bosses start paying attention to more than just your words, recruiters told Fortune they’re assessing your personality—and it’s not just what you say, that job seekers should be cautious about.
Other things CEOs could be testing you for over the course of the meal include how quickly you order, whether you wait for others to sit before sitting down to eat, and the price of the items you order.
One boss won’t hire anyone who salts their food before tasting because it apparently highlights a lack of patience.
Meanwhile, a aconsultant revealed on X that he even knows a CEO who would take candidates for breakfast and secretly ask the servers to mess up their order “to see how they’d react.”
“Most people can fake it through a normal interview,” @patricklencioni added. “Interview in a way that brings out true colors.”
Are you a manager who has a unique way of testing prospective employees? Fortune wants to hear from you. Get in touch: Orianna.Royle@fortune.com
