Twilio's $37 Billion CEO Rejects Candidates Who Say 'I' Too Much

Twilio CEO Khozema Shipchandler turns down senior job candidates who fail to ask questions in the final 15 to 20 minutes of an interview. The boss of the $37 billion cloud communications company told Fortune that silence at that stage is, in his words, "a pretty big red flag."

Shipchandler's final-round interviews for senior hires typically run 45 minutes over dinner. In the closing stretch, he hands the floor to the candidate. What he gets back shapes the hiring decision.

"The number one red flag for me is when someone doesn't ask questions towards the end of an interview," Shipchandler told Fortune.

He elaborated: "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."

What is the second red flag Twilio's CEO listens for?

Even before that closing window, Shipchandler is tracking one word throughout the conversation: "I."

The guidance cuts against common interview advice. Job seekers are usually told to avoid overusing "we," which can sound passive. But leading every story with "I" or "when I was in charge of" can backfire, Shipchandler said. It signals the candidate is 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."

Why does the interview happen over dinner?

Shipchandler reserves the dinner format for senior hires whose resumes have already cleared the technical bar. By that stage, credentials are not the question.

"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.

He is also testing what candidates are 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?"

Which questions should candidates ask instead?

Drawing a blank when asked "Do you have any questions for us?" can sink candidates at any level, not just those facing a CEO. Jenn Bouchard, Meta's former global head of talent and now chief people officer at creative agency Figure 8, previously told Fortune the silence is a deal-breaker because it signals disinterest.

"An interview is a two-way experience," she said. "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."

Bouchard advised preparing questions in advance rather than improvising under pressure. Three that have impressed 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?

What else are bosses testing at the table?

Recruiters told Fortune the dinner setting exposes more than conversation skills. They said they assess how quickly candidates order, whether they wait for others to sit before eating, and the price of the items they choose.

The hospitality test extends further. One boss refuses to hire anyone who salts their food before tasting it, judging it a sign of impatience. Consultant Patrick Lencioni revealed on X that he knows a CEO who takes candidates to breakfast and secretly asks servers to mess up their order "to see how they'd react."

"Most people can fake it through a normal interview," Lencioni added. "Interview in a way that brings out true colors."

For candidates chasing senior roles at Twilio, the calculus is now explicit: come armed with questions, credit the team, and remember that the CEO is grading the conversation, not just the resume.