6 Questions Great Leaders Should Ask at Every Interview

Hiring and firing decisions are critical to a company's reputation and success. (Just ask anyone at reddit HQ right now.) Whether you're on-boarding a rockstar or giving someone the boot, it all traces back to the initial interview.
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Hiring and firing decisions are critical to a company's reputation and success. (Just ask anyone at reddit HQ right now.) Whether you're onboarding a rockstar or giving someone the boot, it all traces back to the initial interview. Incisive interview questions can result in hires that transform the future of a company; bad ones can lead to disgruntled, underperforming employees down the road.

I've learned this the hard way. As the founder and former CEO of MedPreps, my first experiences as a hiring manager were fraught with trial and error: I hired 20 people in the space of two months, which amounted to at least five bad hires and several mediocre ones. I discovered really quickly that what happens in an interview has big ramifications down the road.

Research suggests a combination of behavioral interviewing, cognitive or skills-based tests, and other assessment techniques offers the best insight into a candidate's suitability. One of the most popular strategies, behavioral interviewing, explores a person's past behavior in order to make predictions about how they'll perform in a new role in the future (e.g. "Tell me about a time when you had trouble working with a coworker--how did you resolve the problem?").

What this means in layperson's terms: Asking questions that incite candidates to articulate their values, goals, and drive can help distinguish a mediocre hire from a great one. Below are six questions guaranteed to get these conversations started.

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1. Describe an instance when you were so focused on an activity that you lost track of time.

This question gets at something critical: passion. It helps clarify what gives a candidate a sense of purpose and motivates them to keep working despite the odds. In any company, but especially in the world of start-ups (where long hours and small salaries are common), it's ideal for people to show up to work for more than a paycheck. Understanding the purpose that underlies a person's actions can help determine whether they'll be inspired to rally around a company's cause.

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2. What's the biggest misperception other people have about you?

CEO of Zappos Tony Hsieh recommends this question as a means of determining a candidate's self-awareness. A person who lacks understanding of their personal strengths, weaknesses, and character will be less prepared to properly delegate tasks, manage stress, or knock projects out of the park. An inability to consider other people's perspectives may also contribute to personnel conflicts down the road.

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3. Name a project you recently completed and describe how you could have done it 10 times better.

This one comes from Aaron Levie, CEO of enterprise cloud company Box. A thoughtful answer indicates an ability to think big and constantly innovate on new or existing projects. In contrast, a reply that's akin to "nothing" may signal an inability to think flexibly or creatively or push the company forward.

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4. Tell me about a time when you felt you were right, but were required to follow directions that went against your conviction.

A candidate's response to this can say a lot about their profile as both a leader and a follower. It's a given that employees will, at times, disagree with policy--and that can be a good thing if it pushes the company to improve on the status quo. What's important is how a person responds to those conflicts of opinion. Proactive employees continue to prioritize a job well done but also find a way to address the issue in order to improve things moving forward.

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5. What will you miss from your current work if I hire you?

Reportedly a question asked of applicants at Apple, this zeroes in on a candidate's values and aspirations--i.e., what makes them tick. It can also provide insight into the attitude they have toward employers. If an applicant can't come up with anything good to say about a position, that may signal a rigid or toxic personality. A good follow-up question: What would your current employer need to offer in order to keep you?

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If an interviewee wants to be an astronaut and you're hiring for an iOS developer, they might not be the best fit for the job.

6. What do you want to gain from this experience?

It may seem obvious, but this is an important question to ask both during the hiring process and down the road if you extend an offer. A person's response speaks to their drive as well as how they view the role: Is it a means to make money, the fulfillment of a personal dream, a step on the path to a larger goal? (How you judge those answers is up to you).

This question can also determine whether the role is a right fit for the candidate (Let's not forget that employment is a two-way street). If someone wants to gain sales experience but the majority of the work will involve behind-the-scenes project management, for example, then the candidate's goals may not be aligned with the position at hand. Finally, knowing a potential employee's aspirations will help you plan workflow accordingly if they're hired.

The right people can steer your ship to even better seas; the wrong ones can function like anchors dragging the company down. Asking strategic questions during interviews with potential employees is hugely helpful in separating the wheat from the chaff. Happy hunting.

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