Favorite Questions of Executive Recruiters

Helpful hints for hitting a curveball out of the park.

“If you were a tree, what kind would you be?” TV journalist Barbara Walters was widely ridiculed after she asked Katherine Hepburn this airy question during a prime time television interview.

If you sit down to an interview with an executive recruiter, it’s likely you won’t enjoy such a softball question. But you may be asked something equally unexpected that you can’t easily prepare for in advance.

All recruiters like to ask unusual queries in hope that you’ll respond spontaneously and they’ll learn something about your character and how you’ll fit into an employer’s corporate culture. Behind each question is a motive — something the recruiter is trying to learn about you. Yet if you take their questions at face value and don’t think about what the recruiter really wants to gauge, your answer could trip up your candidacy.

Curveballs are tricky, because, like Ms. Walters’ tree question, there’s no right response. (By the way, Ms. Hepburn said “oak.”) Can you prepare for them? Not really, says Chicago recruiter Ted Martin, founder and chief executive officer of Martin Partners LLC. “That’s why they’re good questions. It shows how you think on your feet.” Besides, he adds, candidates shouldn’t be prepared for every question. “If you’re ready for all of them, you’re running a process, versus showing how you think,” he says.

Anatomy of a Question

Mr. Martin says his favorite question to ask candidates is, “If you had to do it all over again, what would your career choice be and why?” If a candidate answers that he or she is in the right career, Mr. Martin follows up with, “Has your career progress met your expectations? Why or why not?”

Regardless of the answer — whether the candidate has met all of his or her expectations or would have chosen another career — Mr. Martin says he gains a surprising amount of insight into how the person thinks. “It’s just an insight gainer,” he says. “It wouldn’t knock them out of the running.”

Is it fair to call such a question a curveball? That implies that the batter — you — can’t hit it. But recruiters want you to be able to answer their favorite queries, says Jim McSherry, managing partner of McSherry & Associates in Westchester, Ill. Those who know themselves and are confident about their abilities will respond with composure to whatever they’re asked and aren’t bothered by questions they can’t anticipate, he says. That in itself says something about a candidate.

Mr. McSherry’s favorite question? “If I were to talk with the people who know you best, how would they describe you?” By answering it, candidates usually give him a thorough self-assessment based on what others have told them, Mr. McSherry says. “It summarizes and confirms what I’ve learned about them during the time we’ve been talking.”

Self-Knowledge Is Key

Larry Stevenson, CEO of The Pep Boys, a 600-plus automotive and aftermarket retail store and service chain based in Philadelphia, met with between eight and 10 search firms while determining his next career step. Mr. Stevenson, 47, began looking for a new assignment after selling Chapters, Canada’s largest bookseller, in 2001, and taking a year’s hiatus. He started his Pep Boys job in May.

Search executives asked Mr. Stevenson many open-ended questions, such as “How would people describe you?” and “What is your biggest weakness?” However, he doesn’t view such questions as unfair or deceptive and says the recruiters he was introduced to were “particularly straightforward.”

Executives at his level should be able to answer just about any question that’s pitched to them, he says. It’s crucial to know yourself well and present yourself honestly when interviewing, says Mr. Stevenson. Otherwise, while you may convince an employer to hire you, you won’t be suited for the job or enjoy it.

His biggest weakness? “Not getting the balance right between family, leisure and the rest of it,” he says. “At senior-executive levels, we tend to have an on-off switch. I don’t know if we’re very good at balance.”

A Manager’s View

But Phil Timm, division manager, AT&T Solutions, in Florham Park, N.J., says an unexpected question is by definition a curveball. He’s been on the receiving end of more than a few from recruiters and, as a hiring manager, likes to ask them himself.

“It’s a curveball because you’re throwing them off the rehearsed interview process,” says Mr. Timm, 53. “Candidates come in here thinking they’ll just get standard questions, so the idea is to throw them a curve because that’s what happens in business.”

Mr. Stevenson says he doesn’t do much advance preparation for interviews with recruiters, especially when the meeting is an introduction. If he’s being interviewed for a specific job, he’ll do research on the company, he says. When he’s met with recruiters in the past, Mr. Timm says he prepared thoroughly by reviewing books and material on the Internet about interviewing. A half-hour before his meetings, he made a point of relaxing and not thinking about the interview. “The best impression you can make is that you’re composed, you have answers and you trust your accomplishments and communication skills will effectively convey your abilities,” he says.

One question he views as particularly tricky is “Are you the right person for this job?” Answering is difficult because even if you aren’t suited for a position, “you want to say yes, and people would tell you to say yes,” Mr. Timm says. “I’ve said, ‘I would like to know more, I certainly have the talent but would have to explore it,’ ” he says.

Helpful Hints

The following are some tips from executives and recruiters themselves on fielding their unexpected questions:

Know what the meeting is for. An interview with an executive recruiter is typically different from a meeting with an actual hiring manager. Some recruiters schedule meetings just to introduce themselves to a top executive. But if a specific opportunity is being discussed, recruiters want to learn about your intangibles — if you would fit the company’s culture, get along with your future boss and colleagues and so on. “My goal is to get the candidate in a free-form discussion — to understand how he thinks,” says Mr. Martin.

Understand yourself. To honestly demonstrate who you are and how you think, you must have good insight into your values, interests, temperament and motivators. When you know what you enjoy and motivates you professionally, you’ll provide unforced answers that indicate whether you’d be a good fit. “It’s in your best interest to let the recruiter know what you like and what kind of organization you’d thrive in,” says Mr. Stevenson.

Think before you answer. Don’t say the first thing that comes into your head. Pause for five or 10 seconds or longer before offering your response. “If I don’t get an immediate response, it tells me I’ve asked a worthwhile question,” says Mr. McSherry. “I’ve forced a candidate to think a little bit.”

Consider the underlying intent to the question. Every query is designed in some way to relate to the opening and whether you would be a good hire, says Mr. Martin. “They always relate to the search,” he says. “What I ask depends on what the company is looking for and is tailored to the assignment and cultural fit of the company.”

Realize you don’t have to respond. Sometimes the right answer is “I don’t know” or “I don’t have an opinion,” says Mr. Timm. “People who have an answer for everything often have the wrong answer for everything,” he says, “so sometimes it’s OK to take a step back and say you’d like to think about something.”

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