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Favorite Job Interview Questions from the C-Suite

The SHRM Executive Network canvassed a group of C-suite executives to find out their favorite questions when hiring for leadership positions—and why and how they use those questions.

A woman talking to a man in an office.

Hiring for management and leadership positions is different than hiring for front-line workers—and that includes the job interview.

When you're hiring for leadership roles, the skills you're looking for may not be as obvious on the candidate's resume. That places more importance on how the person handles the interview, as well as on the skills of the interviewer.

There's some evidence that the employee-favored hiring market of recent years has led candidates to take a more relaxed approach to the interview process. In fact, "lack of preparation by job candidates" is the No. 1 pet peeve among hiring managers who conduct job interviews, according to a recent Paychex survey.    

"Good job interview questions should be consistent for the role that you are trying to hire," said Michael Couck, director of people and places at financial advisory firm Telemus. "It's the No. 1 item to plan in advance when recruiting."

So when recruiting for management positions, what are the most effective questions to separate the "must" hires from the rest? The SHRM Executive Network canvassed a group of C-suite execs to find out their favorite questions—and why and how they use them.


"Rank the jobs on your resume, from favorite to least."

Michelle Sims, CEO of talent placement firm Year Up Professional Resources (YUPRO), said the best interview questions allow the interviewer and interviewee to establish a rapport and build a relationship.

Sims likes to ask candidates to rank about three-quarters of the jobs on their resume from their favorite job to their least favorite. Then she asks why.

"This question allows the interviewee to react on the spot and critically think through their experiences and desires," said Sims. "The 'whys' behind their rankings uncover career path opportunities and preferences. Insight is gained not only from the jobs candidates choose to rank, but also those they choose not to."

The interviewee is also able to dig deeper into what was undesirable about jobs that weren't mentioned.

"Allowing interviewees to open up and share career aspirations, based on their path thus far, gives interviewers insight into whether the candidate is a culture add to the organization," Sims said.


"Tell me who you are."

Shari Hofer, chief marketing officer at publishing company Wiley, believes the way candidates answer interview questions can be just as important as the words they use.

"I'm looking for someone who can have a conversation, who knows when to pause and when to listen," said Hofer. "Listening is core to who I am as a leader, and I hire for people who also value it."

Hofer's favorite question is simple.

"I ask candidates to tell me who they are," she said. "That's different than asking them to walk me through their resume. I have their resume. I want to know who they are as a person and where they come from. How they answer that question shows me the level of self-awareness and emotional intelligence that they have."


"What's your greatest failure?"

When interviewing for leadership roles, Lisa Sterling, chief people officer at Perceptyx, a management consulting firm, always asks about the candidate's greatest success.

"I'm purposefully looking at what brings them satisfaction and if they are a servant leader," Sterling said. "I've found that a great leader talks about the success of others, rather than their own accomplishments."

The flip side of that success question may make the applicant uncomfortable, but that's by design.

"If I'm interviewing someone for an important role, I like to ask them about their greatest failure in their career, the impact of it and how it shaped the future of their career," Sterling said. "This helps me understand how much of a risk taker someone is, if they view failures in a positive light and how they handle themselves when things don't go as planned."

She added, "It's really important to see how any candidate views the challenging and not-so-challenging moments in their career."


"How will I know when you are stressed out?"

Amy Spurling, CEO and founder of Compt, a benefits services company, is deeply involved in the hiring process for her fledgling firm. And because startups can put big deadline pressure on employees, it's important to know how people will react.

That's why one of Spurling's favorite interview questions is, "How will I know when you are stressed out?"

"This question helps me understand how the person manages their task load, what signs I'll need to keep an eye on to make sure they have the support they need, and how well they know themselves," said Spurling.

"I want to know that when you're overwhelmed and on a deadline, what's your next move? I want to learn whether this person is more collaborative and will talk to their manager or if they keep drinking from a firehose," she continued. "That wouldn't rule them out for a role, but it would help me better understand how to manage them."


"What's more important: strategy or structure?"

"I've heard cringe-worthy stories about companies asking off-the-wall questions, like, 'Let's say you're an astronaut and you had to figure out how many stars are in the galaxy. What would you do?,' " said Couck, from Telemus.

Instead, he likes to use creative questions that are relevant to the role. Couck frequently asks candidates, "In your opinion, which is more important: strategy or structure?"

"This question is simple and effective. It gives the candidate the opportunity to explain what they personally deem important," he said. "Also, the more they talk out loud their rationale, the more they tend to tie the creative question into their actual role. … Better yet, it provides great insight, and it's not a curveball for the candidate."


"Why shouldn't I hire you?"

"I rate interview questions extremely high on my list" of candidate criteria, said Rudy Mawer, a well-known marketing executive and founder of Mawer Capital. One of Mawer's favorite interview question is, "Why shouldn't I hire you?"

"One job candidate answered, 'Because I become obsessed with my work,' which led to me hiring this person who ultimately closed hundreds of thousands of dollars of sales calls," Mawer said.

As with the "What is your greatest weakness?" question, quick thinkers may be able to turn this into a way to promote a positive characteristic. But the phrasing of this version will stump many.


20 More Interview Questions to Identify Leadership Skills
(from SHRM's Job Interview Questions resource page)


1. Give me an example of a time when you needed to help other employees learn a new skill set. What did you do?

2. Have you ever been in a position in which you had to lead a group of peers? How did you handle it? Tell me about problems you had and how you handled them.

3. Have you ever managed a situation in which the people or units reporting to you were in different locations? Tell me how this worked.

4. Tell me about your experience working with a board of directors. What approach and philosophy did you follow in working with boards?

5. Tell me about a time when you organized, managed and motivated others on a complex task from beginning to end.

6. Give me an example of how you have motivated your employees.


7. A new policy is to be implemented organization-wide. You do not agree with this new policy. How do you discuss this policy with your staff?

8. A subordinate regularly questions your authority. What do you do?

9. The board of directors elects not to reward bonuses this year and tasks you with communicating the board's decision to staff. How do you do this?


10. Describe an ideal supervisor or manager.

11. Tell us about your management style—people, teamwork and direction.

12. What is the largest number of employees you have supervised, and what were their job functions?

13. Tell me about your experience in leading and managing an organization similar to ours.

14. Tell me about your experiences with staff development.

15. What is your own philosophy of management?

16. What do you do to develop employees you manage?

17. Do you find it more natural to point out what's wrong so employees can accomplish tasks competently or to praise employees for their work and then later point out what may need correcting?

18. What is the most significant contribution you have made to team cohesiveness?

19. What is the most significant contribution you have made to unifying a department, division, plant or so forth?

20. What do you think are the most valuable traits in a good leader?


Brian O'Connell is a freelance writer based in Bucks County, Pa. A former Wall Street trader, he is the author of the books CNBC Creating Wealth (John Wiley & Sons, 2001) and The Career Survival Guide (McGraw Hill, 2004).


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