Twilio CEO Khozema Shipchandler says candidates can undermine their chances in a senior-level interview by failing to ask questions or by repeatedly centering their answers on the word “I.”

Shipchandler, who has led the $37 billion technology company Twilio as chief executive since January 2024 after previously serving as its chief financial officer, told Fortune that most interviews for senior hires last 45 minutes and take place over dinner. Candidates who have already demonstrated the required qualifications are then assessed on whether they would work well with the company and its leadership.

“The number one red flag for me is when someone doesn’t ask questions towards the end of an interview,” Shipchandler said. During the final 15 to 20 minutes, he gives candidates an opportunity to ask about the role, the company, how they might work together, chemistry and culture.

“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,” he said. “That’s a pretty big red flag.”

Why Shipchandler listens for “I”

Even candidates who arrive with questions can create another concern during the rest of the interview by using “I” too often. Job seekers are frequently advised not to rely too heavily on “we,” because it can make their contributions sound passive. But Shipchandler said repeatedly beginning anecdotes with “I” or phrases such as “when I was in charge of” can suggest that a candidate is not a team player—or a strong 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 said.

“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.”

His comments add to a series of reports about unconventional hiring tests. One CEO has reportedly rejected candidates who said they could start immediately, while another would not hire people who failed a coffee-cup etiquette test.

Three questions candidates can ask

Failing to ask questions can be a problem even when the candidate is applying for a junior role and interviewing with a hiring manager or recruiter rather than a CEO. Jenn Bouchard, Meta’s former global head of talent and current chief people officer at creative agency Figure 8, told Fortune that having no questions can signal disinterest.

“An interview is a two-way experience,” Bouchard 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.”

She recommended preparing questions in advance rather than relying on inspiration at the end of a stressful interview. Questions that have impressed her in past interviews include:

• 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?

Topics such as the job’s responsibilities and how often employees are expected to work from the office often arise naturally earlier in the interview, Bouchard said. Candidates can therefore use their final questions to explore challenges, team dynamics and how the organization responds to employee input.

What employers may observe during dinner interviews

Shipchandler said dinner interviews are generally reserved for senior candidates whose resumes have already met the role’s requirements. At that stage, the focus shifts to chemistry, working relationships and how candidates behave outside a formal office setting.

“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.

“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?”

Recruiters told Fortune that employers may pay attention to more than what candidates say during a meal. Potential observations include how quickly someone orders, whether they wait for others to sit before sitting down to eat and the prices of the items they select.

One boss reportedly will not hire anyone who salts food before tasting it, viewing the behavior as a sign of impatience. Consultant and author Patrick Lencioni, who wrote The Five Dysfunctions of a Team, also said on X that he knows a CEO who invites candidates to breakfast and secretly asks servers to make a mistake with their order to observe their reactions.

“Most people can fake it through a normal interview,” @patricklencioni wrote. “Interview in a way that brings out true colors.”

A version of this story originally appeared on Fortune.com on September 10, 2025. The story was originally featured on Fortune.com.