{"id":6502,"date":"2026-10-11T19:25:31","date_gmt":"2026-10-11T19:25:31","guid":{"rendered":"https:\/\/www.vaultinsider.top\/?p=6502"},"modified":"2026-10-11T19:25:31","modified_gmt":"2026-10-11T19:25:31","slug":"twilio-ceo-interviews-candidates-for-45-minutes-over-dinner-and-if-you-say-i-too-much-or-dont-ask-any-questions-you-dont-get-the-job","status":"publish","type":"post","link":"https:\/\/www.vaultinsider.top\/?p=6502","title":{"rendered":"Twilio CEO interviews candidates for 45 minutes over dinner\u2014and if you say \u2018I\u2019 too much or don\u2019t ask any questions, you don\u2019t get the job"},"content":{"rendered":"<p><img decoding=\"async\" src=\"https:\/\/fortune.com\/img-assets\/wp-content\/uploads\/2025\/09\/GettyImages-1485222107-e1757415514967.jpg?w=2048\" \/><\/p>\n<ul class=\"wp-block-list\">\n<li><strong>EXCLUSIVE: Twilio CEO, <\/strong><strong>Khozema Shipchandler,<\/strong><strong> always gives hopeful new hires<\/strong> time to ask questions at the end of the interview\u2014and will turn candidates down if they don\u2019t. The $37 billion tech boss warns job seekers that even if they pass that test, there\u2019s another red flag he\u2019s listening out for while you speak: Using \u201cI\u201d too much.&nbsp;<\/li>\n<\/ul>\n<p class=\"wp-block-paragraph\">Previously, we\u2019ve heard from a CEO who rejects job candidates who say they can start right away and another who won\u2019t hire anyone who fails his coffee-cup etiquette test. Now, Twilio\u2019s CEO says there are two more ways to tank a sit-down interview.<\/p>\n<p class=\"wp-block-paragraph\">Picture this: You\u2019ve spent weeks polishing your resume, navigating multiple rounds of interviews, and finally, you land a 45-minute dinner with the boss. You think you\u2019ve won him over. Then he asks, \u201cDo you have any questions for me?\u201d<\/p>\n<p class=\"wp-block-paragraph\">If your answer is a blank stare or \u201cNope, I\u2019m fine,\u201d consider yourself on thin ice.<\/p>\n<p class=\"wp-block-paragraph\">\u201cThe number one red flag for me is when someone doesn&#8217;t ask questions towards the end of an interview,\u201d Twilio CEO Khozema Shipchandler exclusively told <em>Fortune, <\/em>while adding that most interviews for senior hires will go on for 45 minutes over dinner.&nbsp;<\/p>\n<p class=\"wp-block-paragraph\">\u201cFor all of them, in the last 15-to-20 minutes, I give them an opportunity to ask questions\u2014and if they don&#8217;t have any, I think that&#8217;s a pretty significant mark against them being curious about what they&#8217;re interviewing, the company, the way we might work together, chemistry, culture, all of those things. That&#8217;s a pretty big red flag.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And before that, even if you have lots of questions up your sleeve, there\u2019s one word he\u2019s listening out for throughout the interview that could cost you the job: Using \u201cI\u201d a lot in conversation.&nbsp;&nbsp;<\/p>\n<p class=\"wp-block-paragraph\">It\u2019s perhaps surprising, as job seekers are often encouraged to avoid using \u201cwe\u201d too much, as it can sound passive. But leading every anecdote with \u201cI\u201d or \u201cwhen I was in charge of\u201d can actually backfire. Shipchandler said it signals you\u2019re not a team player\u2014or a real leader.<\/p>\n<p class=\"wp-block-paragraph\">\u201cI don&#8217;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,\u201d he explained. \u201cBut the hard leadership is when you&#8217;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.\u201d<\/p>\n<h2 class=\"wp-block-heading\">3 questions to ask hiring managers instead of drawing blank<\/h2>\n<p class=\"wp-block-paragraph\">It can be awkward when the hiring manager asks, \u201cDo you have any questions for us?\u201d because more often than not, there\u2019s nothing left to cover. The usual topics\u2014like what the job actually entails and how many days you\u2019re expected to show face in the office\u2014tend to arise naturally early on during the interview.&nbsp;<\/p>\n<p class=\"wp-block-paragraph\">But even if you\u2019re 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 <em>anything<\/em> to ask can still cost you the job.&nbsp;<\/p>\n<p class=\"wp-block-paragraph\">Meta\u2019s former global head of talent and current chief people officer at the creative agency Figure 8, Jenn Bouchard, told <em>Fortune<\/em> it\u2019s a deal-breaker because it signals disinterest.<\/p>\n<p class=\"wp-block-paragraph\">\u201cAn interview is a two-way experience,\u201d she added. \u201cAnd so as much as I\u2019m 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.\u201d<\/p>\n<p class=\"wp-block-paragraph\">Sweaty palms and drawing blank can get the best of us. So instead of relying on thinking of something great on the spot, it\u2019s 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:&nbsp;<\/p>\n<ul class=\"wp-block-list\">\n<li>What\u2019s the hardest problem that you\u2019re trying to solve? What has the team not been able to solve? And why do you think that is?<\/li>\n<li>What are the top three strengths of the team? And how will this person add to the strengths of that team?&nbsp;<\/li>\n<li>&nbsp;What has the leadership team recently implemented based on employee feedback?<\/li>\n<\/ul>\n<h2 class=\"wp-block-heading\">Other tests to look out for over dinner: The salt shaker, the waitress, and pricey menu items\u00a0\u00a0<\/h2>\n<p class=\"wp-block-paragraph\">Shipchandler\u2019s far from the only boss to opt a dinner setting for the final interview stages. He said it\u2019s generally reserved for senior hires whose resume ticks all the right boxes.<\/p>\n<p class=\"wp-block-paragraph\">\u201cThey&#8217;ve already got all the qualifications at that point. The question is, is there chemistry? Are we going to work well together?\u201d he said, adding that he\u2019s testing what you\u2019re like off the clock.<\/p>\n<p class=\"wp-block-paragraph\">\u201cIt&#8217;s got to be fun too, not just all business,\u201d Shipchandler added. \u201cWhat are their outside interests? No judgment from me, obviously, but can we have a conversation about that too?\u201d<\/p>\n<p class=\"wp-block-paragraph\">But be warned: When the interview moves to the dinner table, bosses start paying attention to more than just your words. Recruiters told <em>Fortune <\/em>they\u2019re assessing your personality\u2014and it\u2019s not just what you say that job seekers should be cautious about.&nbsp;<\/p>\n<p class=\"wp-block-paragraph\">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.&nbsp;<\/p>\n<p class=\"wp-block-paragraph\">One boss won\u2019t hire anyone who salts their food before tasting because it apparently highlights a lack of patience.<\/p>\n<p class=\"wp-block-paragraph\">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 \u201cto see how they\u2019d react.\u201d<\/p>\n<p class=\"wp-block-paragraph\">\u201cMost people can fake it through a normal interview,\u201d @patricklencioni added. \u201cInterview in a way that brings out true colors.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong><em>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<\/em><\/strong><\/p>\n<p class=\"wp-block-paragraph\"><em>A version of this story originally published on&nbsp;<\/em><em>Fortune.com<\/em><em>&nbsp;on&nbsp;September 10, 2025<\/em><\/p>\n<p class=\"wp-block-paragraph\"><strong>Read more career advice from Fortune&#8217;s Orianna Rosa Royle:<\/strong><\/p>\n<ul class=\"wp-block-list\">\n<li>Millennials are winning the AI talent wars\u2014they\u2019re getting 60% of all the top AI jobs and earning $236K salaries. But most of them are men<\/li>\n<li>He failed the military pilot eye test\u2014so he built a $1 million-a-day traffic company and bought flying lessons. Now he\u2019s Top Gun\u2019s stunt pilot&nbsp;<\/li>\n<li>31-year-old millionaire has zero sympathy for unemployed Gen Z\u2019s \u2018excuses\u2019\u2014he says \u2018it is scarily easy\u2019 to build a business and get rich right now<\/li>\n<li>$25 billion CEO says one-hour interviews are a waste of time\u2014he puts candidates through six hours of tests and wants them to order wine at lunch<\/li>\n<li>Google DeepMind\u2019s chief AI exec started out detasseling corn in Indiana for around $1 an hour at 14: \u2018I grew up in really humble beginnings\u2019<\/li>\n<\/ul>\n<p>This story was originally featured on Fortune.com<\/p>\n<p>#Twilio #CEO #interviews #candidates #minutes #dinnerand #dont #questions #dont #job<\/p>\n","protected":false},"excerpt":{"rendered":"<p>EXCLUSIVE: Twilio CEO, Khozema&hellip; <\/p>\n","protected":false},"author":1,"featured_media":6503,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[2],"tags":[8135,283,9599,2268,2592,544,3792,4081,9598],"class_list":["post-6502","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-finance-news","tag-candidates","tag-ceo","tag-dinnerand","tag-dont","tag-interviews","tag-job","tag-minutes","tag-questions","tag-twilio"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v28.1 - 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