The key to any successful interview is asking the right questions. It can be extremely difficult to gather meaningful information from a candidate in the time you have during an interview. Couple this with the candidate telling you what they think you want to hear, and you may not be getting to know the real person.

Asking questions that show you how candidates think that guide them to answer in more specific details can give you real insight into the candidate and help you make a more educated hiring decision. Consider these off-beat questions:

“Why are manhole covers round?” “How many times heavier than a mouse is an elephant?” “How many golf balls can you fit in a school bus?”

Most hiring managers have heard about using these “creative” questions to identify the best candidates. Fortunately for smart, well-qualified candidates everywhere, such brainteaser questions—made  famous by Silicon Valley and Wall Street—are just as silly as they sound. Even Google phased out these questions from their interviews nearly a decade ago.

But when you’re interviewing people to join your team, you have to get creative somehow. There’s only so much that questions like “What was the last book you read?” and “Where do you see yourself in five years?” can reveal about who your candidates truly are.

To give you some ideas for the next time you’re screening candidates, here are some of the best job interview questions to ask with the answers you should expect.

1) “Tell me about a time you set difficult goals. What did you do to achieve them? Walk me through the process and purpose.”

If you’re looking for a candidate who is goal-oriented and results-driven — as most hiring managers are — then this question will help you gauge whether they’ll be able to handle the audacious goals you have in store for them. A comprehensive answer shows they understand what difficult goals are, and they put a lot of effort into attaining their goals while maintaining a high standard of work quality.

2) “Sell [name of your company] to me as if I were buying your product/service.”

This is a unique and more challenging approach to the generic “What does our company do?” question. It forces candidates to drum up the research they’ve done to prepare for the interview, and also to craft a compelling message on the fly. This will come more naturally to some candidates than others — for example, someone interviewing for a sales or marketing position might find it easier than someone interviewing for a more internal-facing role — and that’s okay. You aren’t necessarily assessing their delivery. But it’ll be interesting to see how each candidate thinks through and gives their answer.

3) “Tell me about the relationships you’ve had with the people you’ve worked with. How would you describe the best ones? The worst?”

Each team is different, so this question helps you tease out whether the candidate would be happy, productive, and well liked on your team. Their answer will tell you how they interact with others — and which kinds of interactions they want to have happen. Many candidates are hesitant to bad-mouth their coworkers and bosses, so it will also be interesting for you to hear how they navigate a question about their worst working relationships.

4) “What single project or task would you consider your most significant career accomplishment to date? Walk me through the plan, how you managed it, how you measured its success, and what the biggest mistakes you made were.”

Lou Adler, author of The Essential Guide for Hiring & Getting Hired and Hire With Your Head, spent ten years searching for the single, best interview question that will reveal whether to hire or not hire a candidate — and this was the one. Candidates’ answers will tell you about their prior success and sense of ownership. A great answer will show they are confident in their work and professional choices while being humble and giving credit to others. 

5) “What have you done professionally that you succeeded at, but isn’t an experience you’d want to repeat?”

A candidate’s answer to this question will give you an idea of how they viewed work they weren’t very happy with, which is bound to happen to everyone in every job at one point or another. HubSpot’s VP of Global Customer Support Michael Redbord says candidates’ answers generally fall into a few categories:

1. Something menial (e.g. envelope-stuffing). Pay attention to whether they understand the value of getting this done for the business, or whether they just think they’re too good for a job like that.
2. Something really hard. Why was it hard? Was it because it was poorly planned, poorly executed, or something else? Where do they put the blame on it being such an unpleasant experience?
3. Something team-related. Follow up with questions about the team, what their role on the team was, and so on.

Even the category of what they consider an experience they wouldn’t want to repeat is interesting, says Redbord. When you talk about extreme experiences that get people emotional, it can be very revealing.

6) “Is it better to be perfect and late, or good and on time?”

For most companies, the correct answer is “good and on time.” We’ve written before about the importance of letting something be finished when it’s good enough — because let’s face it, every blog post, email, book, video, etc. can always be tweaked and improved — but at some point, you’ve just got to ship it. Most managers don’t want someone who can’t hit deadlines because they’re paralyzed by perfection. 

If your candidate responds with “It depends,” then hear them out — the interview question itself is phrased in such a way that candidates can sense there is a right and wrong answer, and they’ll be looking for signs from you they’re heading in the right direction. Try to remain neutral as they feel out their response. If their conclusion errs on the side of “good and on time,” then their priorities are probably in the right place.

7) “In five minutes, could you explain something to me that is complicated but you know well?”

This is a much better test of intelligence than a college GPA, and it’s also a great gauge of a candidate’s passion and charisma.

The “something” in this question doesn’t have to be work-related — it can be a hobby, a sports team, something technical…anything, really. Their response will tell you how well they comprehend complex subjects and how well they can articulate a complex subject to someone who doesn’t know much about it. Candidates who are passionate and knowledgeable about something — and can convey that well — are more likely to be charismatic, enthusiastic, and influential at work.

8) “What’s your definition of hard work?”

Some organizations move at very different paces, and this question is an effective way to tell whether your candidate will be able to keep pace with the rest of the team. It also helps you identify someone who is a “hard worker in disguise,” meaning someone who might currently be at a slow-moving organization or in a role that is not well-suited to them, but wants to work somewhere where they can really get their hands dirty.

9) “If I were to poll everyone you’ve worked with, what percent would not be a fan of yours? Then, if I were to interview these people, what words would they most frequently use to describe you?”

At work, you can’t please everyone all the time. The answer to this question will help you find out if your candidate has enough drive and conviction to have alienated a small percentage of their colleagues, but not so many that they are a polarizing figure. The word-cloud follow-up is more important than the percentage they give in the initial question. In their answers, you should be encouraged by words like “passionate” and concerned by words like “stubborn.”

10) “Tell me about a time you screwed up.”

An oldie but goodie. This is a tried-and-true test for self-awareness. (Honestly, well-prepared candidates should see it coming and have an answer ready.) Someone who takes ownership of their mess-up and learns something from it are usually humble and mindful. Candidates who blame others or give a “fake” screw-up (something like “I worked too hard and burned out”) are red flags.

11) “Who is the smartest person you know personally? Why?”

These questions test what the candidate values and aspires to by forcing them to think of a real person they know, and then articulate what makes that person smart. Ideal answers vary, and can include specific examples of the person they’ve chosen’s ability to think ahead several steps and execute. They could also touch on the person’s decision-making skills, ability to connect, desire for learning, or application of the things they learned.

12) “What is something you’d be happy doing every single day for the rest of your career?”

While it’s important to hire for skill, it’s also important to hire someone who’s likely to be happy in the job you’re hiring for. A question like this will help uncover what makes each candidate happy at work — which is a great way to gauge whether they’d enjoy their role and stay at the company for a long time. 

13) “If you had $40,000 to build your own business, what would you do?”

This question is a favorite of HubSpot Hiring Manager Emily MacIntyre‘s. First, the type of business they choose to talk about can reveal a lot about their interests, values, and how creative they are.

Second, it will give you insight into how business-savvy they are. By giving them a specific amount to work with (in this case, $40,000), they have the opportunity to parse out how they’d spend that money. The best answers will get specific: They’ll offer an overview of the business, and get into the logistics of where that money would go, whom they’d hire first, and so on.

14) “What’s the biggest decision you’ve had to make in the past year? Why was it so big?”

Here’s a great way to figure out how a candidate approaches decision-making. Were they quick to make that big decision, or did it take them a long time? Did they spend most of their time reflecting on it by themselves or fleshing it out with others? How did they make a plan? Their answer could be work-related or personal — and if they ask you to specify, tell them either. 

15) “What’s surprised you about the interview process so far?”

This is a question no candidate can really prepare for, and it’ll give you some indication of how candidates are feeling about the whole thing. Plus, you can see how they think on their feet. You’re looking for specifics here — something about the office space; the personality of the team; or an assignment they were given to complete.

We hope these questions inspire your hiring efforts. By providing a direct link to great people, we’re here to help you build great teams!

• The Artizen Staffing Team

written by Danielle Foster and Catrina Walker

As always, we welcome your feedback on this unprecedented journey and look forward to hearing what works for you, your friends, and your family! 

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