• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military

2

'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032

3

Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there

1

Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military

2

'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032

3

Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
Successjob hunting

The top curveball interview questions executives ask—and what they reveal about job candidates

Ashley Lutz
By
Ashley Lutz
Ashley Lutz
Executive Director, Editorial Growth
Down Arrow Button Icon
Ashley Lutz
By
Ashley Lutz
Ashley Lutz
Executive Director, Editorial Growth
Down Arrow Button Icon
April 15, 2025, 12:44 PM ET
Gen Z worker at a table opposite an older worker
Executives dig deeper in job interviews. Getty Images

In today’s job market, landing an interview can feel like an achievement in itself.

Recommended Video

Impersonal LinkedIn job postings and surging online applications have left 72% of job seekers feeling like they’re “sending a resume into a black box,” according to a 2024 survey of over 2,000 people conducted by the American Staffing Association and The Harris Poll. Even more discouraging, 40% said they hadn’t received a single interview from applying. 

For job seekers who manage to land an interview, preparation can be the key to success and taking the next step.

At Great Place to Work’s For All Summit, top executives told Fortune Editorial Director Kristin Stoller the questions they focus on when vetting candidates. The leadership event hosted thousands of executives from more than 800 companies—and many are featured on the Fortune 100 Best Companies to Work For list. 

Read on for insights into what top bosses look for when they’re hiring. 

Beyond the resume

“What do you do on the weekend?” is one question that Michael Bush, CEO of Great Place to Work, asks potential candidates. “Usually, that’s unexpected, and I want to learn something about it.” 

The answer to this question can show whether the job seeker is honest and self-confident. 

“I want to see if they’re willing to be transparent and truthful, or if they’re going to be filtering their comments, feeling that they have a fear of being judged,” Bush said. 

Fadzlun Sapandi, EVP of Global Human Resources at DHL Express, wants to quickly find out whether the candidate has done their research, and how excited they are about a potential role at the international logistics and shipping company. 

“Why do you want to join us?” Sapandi asks candidates. This can help the company find those truly invested in a role with the company, versus those just looking for any job. 

Marriott also looks for candidates who deeply care about its mission. 

“Why are you passionate about travel?” Anthony Capuano, President and CEO of Marriott International, questions. Those with a demonstrated interest in hospitality will likely be able to predict the needs of customers and better serve them, which pays dividends for the hotel giant in the long-run. 

Jennifer Morgan, CEO of software and payroll company UKG, is interested in adjectives.

“I love to ask candidates, how would people describe them, who’ve worked with them or for them,” Morgan told Fortune. “How do they show up on their best day, and how do they show up on their worst day?” 

How candidates answer these questions can show the relationships they’ve built with colleagues, and how grounded they are. Will they remain vigilant on a good day, and how do they problem-solve through a bad one?

DHL Express CEO John Pearson takes a similar approach. 

“If I met a boss of yours, or if I met a colleague of yours, but not someone you work with, what five words would they use to describe you?” Pearson asks. “So the boss saying that, or a colleague outside of your company, that reveals a lot.” 

Finding good long-term fits

Kimberly Jones, Talent Strategy & People Experience Leader at financial services and tax firm PwC, says she digs into the applicant’s intentions when applying to assess whether they’re a good long-term fit. 

“I really like to understand what made them apply for the role, and not just because the role sounds good on paper,” Jones said. “I really want to know their motivations and where they’re trying to go in their life and career.” 

It can also be helpful to assess how the candidate feels they have been judged—or misjudged—by colleagues in the past, says Courtney della Cava, Senior Managing Director at asset investment firm Blackstone. 

“What is the most common misconception people have of them?” she asks. “It does a number of things: one, it helps me understand, do they have self-awareness? Do they understand what’s written on their back? Two, it helps me understand what is that misconception? Is it real, is it a first impression thing? How do they overcome it, do they have a learning mindset?” 

Done right, these questions lead to “insightful areas to probe,” Blackstone’s della Cava explains. 

As you apply for jobs, thinking through the answers to these questions could help you stand out from the pack. 

The Fortune 500 Innovation Forum will convene Fortune 500 executives, U.S. policy officials, top founders, and thought leaders to help define what’s next for the American economy, Nov. 16-17 in Detroit. Apply here.
About the Author
Ashley Lutz
By Ashley LutzExecutive Director, Editorial Growth

Ashley Lutz is an executive editor at Fortune, overseeing the Success, Well, syndication, and social teams. She was previously an editorial leader at Bankrate, The Points Guy, and Business Insider, and a reporter at Bloomberg News. Ashley is a graduate of Ohio University's Scripps School of Journalism.

See full bioRight Arrow Button Icon

Latest in Success

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Success

penn
North Americatransit
‘I’m not focused on names at all’: Rumors of Trump Station replacing Penn Station in New York batted aside
By Philip Marcelo and The Associated PressJune 9, 2026
16 hours ago
Alex Karp
SuccessView from the C-Suite
Palantir CEO Alex Karp says executives who brag about their AI cuts might as well ‘sign up for the Bernie Sanders manifesto’
By Preston ForeJune 9, 2026
16 hours ago
Stephen Schwarzman’s grandfather inspired the Blackstone billionaire’s philanthropy: It was ‘his privilege to help others in need’
Successphilanthropy
Stephen Schwarzman’s grandfather inspired the Blackstone billionaire’s philanthropy: It was ‘his privilege to help others in need’
By Sydney LakeJune 9, 2026
16 hours ago
wood
North AmericaObituary
One of America’s greatest historians just died at 92 after being hit by a car in a supermarket parking lot
By Hillel Italie and The Associated PressJune 9, 2026
16 hours ago
Teenage boy on laptop
SuccessJobs
Around 22 million teenagers are making their pocket money on video games, online reselling, and in-game platforms like Roblox
By Emma BurleighJune 9, 2026
17 hours ago
noah
SuccessMedia
This CEO says he’s helping journalists double their salaries by going to work for brands. But is it journalism—and does it matter?
By Nick LichtenbergJune 9, 2026
21 hours ago

Most Popular

Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military
Asia
Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military
By Kate O'Keeffe and BloombergJune 8, 2026
1 day ago
'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032
Economy
'We are rapidly running out of time': Watchdog sounds Social Security alarm after 22% cut confirmed for 2032
By Nick LichtenbergJune 9, 2026
15 hours ago
Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
Success
Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
By Preston ForeJune 8, 2026
2 days ago
Trump, who has repeatedly called climate change fake, is now threatening Brazil with tariffs over the deforestation of the Amazon
Environment
Trump, who has repeatedly called climate change fake, is now threatening Brazil with tariffs over the deforestation of the Amazon
By Sasha RogelbergJune 8, 2026
1 day ago
Current price of oil as of June 8, 2026
Personal Finance
Current price of oil as of June 8, 2026
By Joseph HostetlerJune 8, 2026
2 days ago
Current price of oil as of June 9, 2026
Personal Finance
Current price of oil as of June 9, 2026
By Joseph HostetlerJune 9, 2026
19 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.