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 résumé, 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 last 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 [for]—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. What I do is easy because people are supposed to listen to me. I can bark orders, and ideally they follow them,” he explained. “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 a 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 for a junior role and interviewing with a hiring manager or recruiter (and not 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 creative agency Figure8, Jenn Bouchard, told Fortune 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 a 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 is far from the only boss to opt for a dinner setting for the final interview stages. He said it’s generally reserved for senior hires whose résumé 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 said, adding that he’s testing what you’re like off the clock.
“It’s got to be fun, too, not just all business,” Shipchandler added. “What are their outside interests? No judgment from me, obviously, but can we have a conversation about that, too?”
But be warned: When the interview 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 consultant 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: [email protected]
A version of this story originally published on Fortune.com on Sept. 10, 2025.
Read more career advice from Fortune’s Orianna Rosa Royle:
Millennials are winning the AI talent wars—they’re getting 60% of all the top AI jobs and earning $236K salaries. But most of them are men He failed the military pilot eye test—so he built a $1 million-a-day traffic company and bought flying lessons. Now he’s Top Gun’s stunt pilot 31-year-old millionaire has zero sympathy for unemployed Gen Z’s ‘excuses’—he says ‘it is scarily easy’ to build a business and get rich right now $25 billion CEO says one-hour interviews are a waste of time—he puts candidates through six hours of tests and wants them to order wine at lunch Google DeepMind’s chief AI exec started out detasseling corn in Indiana for around $1 an hour at 14: ‘I grew up in really humble beginnings’This story was originally featured on Fortune.com
Hence then, the article about twilio s 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 was published today ( ) and is available on Fortune ( Middle East ) The editorial team at PressBee has edited and verified it, and it may have been modified, fully republished, or quoted. You can read and follow the updates of this news or article from its original source.
Read More Details
Finally We wish PressBee provided you with enough information of ( Twilio’s 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 )
Also on site :
- Social Security COLA Announcement Is Oct. 14, and a New Forecast Predicts a 3.5% Increase
- Newcastle United vs Coventry City Live: Kickoff Time and TV Coverage
- Why the Boss of Leonine, Germany’s Top Indie Film and TV Company, Is Backing Skydance: ‘David Ellison and Ynon Kreiz Are a Very Strong Team’