A Career Expert Shares 5 Questions She Wishes More Candidates ‘Had the Guts to Ask' During Job Interviews

Korneeva Maha | Twenty20

Many people forget that job interviews are a two-way street — and that, when done right, turns into an engaging conversation between the candidate and the interviewer.

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As a director at the Kellogg School of Management's Career Management Center and a former recruiter of 10 years, I've found that even the most qualified candidates fail to distinguish themselves by asking hard-hitting — yet thoughtful — questions. (Usually, they only ask generic ones that they can easily find answers to via a quick Google search.)

Below are five questions I wish more candidates had the guts to ask during job interviews. While some of them may seem too intimidating or awkward to ask, doing so will not only impress your interviewer, but it will help you leave the interview feeling more confident and better informed about the position.

1. 'What are the biggest challenges I'll face in the first 90 days, and how will success be measured?'

If you're interviewing for a high-level position, this is a question that you might get asked. But if not, then you need to bring it up.

Ninety days is the typical probationary period when a company determines whether hiring you was the right decision. So it's good to be prepared and have a strong understanding of what the expectations are and whether your experience and skills indicate you're right for the role.

Don't be overwhelmed if the challenges sound daunting, because as a new hire (and particularly early into the position), you won't necessarily be judged on your knowledge. If you really want the job, you must be willing to learn and do what it takes to get on track and excel.

2. 'Is there anything about my background that makes you hesitant to move me forward in the interview process?'

Hiring managers love when candidates ask this question because it shows a sense of self-awareness.

The response you get may be hard to digest, but it's better to know now, during the early stages of the interview, so you have a chance to address the employer's perceptions and change the narrative.

Let's say you're told: "I'm worried you might not be happy in this job because it's not a client-facing position." You can course-correct by saying, "I understand your concern. But that's exactly why I'm pursuing this job. I've been in client-facing positions for most of my career, and I'm interested in doing something different."

3. 'How does my background compare to other candidates you're interviewing?'

You never want to be in the dark about how your skills stack up against your competition.

If the interviewer mentions an area where you appear weaker, you can explain how your experience demonstrates those desired skills. Or, you can use the opposite tactic and discuss the unique skills you have that the other candidates might not.

If you don't ask this question, two things could happen:

  • You move forward in the interview process, but emphasize all the wrong points about why you're the most qualified person for the position.
  • You don't move forward ... and you have no idea why.

4. 'I know the pandemic has caused unprecedented disruption for many companies. How are you, as a manager, doing?'

This question brings in a human element, which is rare in job interviews. You're asking the interviewer to move away from company talking points, and to instead reflect on their personal experience. 

A good manager's response will come across as honest and authentic. It will also show that they have quality traits such as empathy and emotional intelligence.

Here's a great example: "I've noticed that it's not easy to manage a team remotely. I've been more understanding of how difficult it is to balance work and family in the same environment. And I've been doing [X, Y, Z] to make the workflow more efficient and less stressful for my team."

They might even ask how you've been dealing with the pandemic, allowing the two of you to connect on a deeper, more personal level.

5. 'Reflecting on your own experience, what have you seen the company do to promote diversity, equity and inclusion?'

Some people are hesitant to ask this because they don't want to seem like they're putting the employer on the spot. But it's absolutely necessary!

The goal is to get a personal perspective that reflects the company's commitment to diversity, equity and inclusion. Has the company made any changes in the past year? Have they created resource groups? Is there a team dedicated to advancing equality of all sorts? Have the results been positive?

The response will help you determine how purpose-driven the company is, and whether their values align with your own.

Liza Kirkpatrick is the director of full-time MBA programs for the Career Management Center at the Kellogg School of Management. Before joining Kellogg, she spent almost a decade as a recruiter at a staffing firm. Follow her on LinkedIn.

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