Don Charlton

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Interview questions can be, by and large, either boring or annoying. Put yourself in a candidate’s shoes—how creative can you actually be with cut-and-dried questions that don’t actually get to the meat of a prospect’s experience or abilities? And as a hiring manager, does asking a dozen candidates the same rote question ever give you extra insight into one person versus the others?

The answer to both questions should be, unequivocally, no. When you’re prepping for your next hiring initiative, think about sliding in these 10 tricky interview questions you didn’t know you could ask.

Exploring the Past and Future

Finding out the reasons behind job hopping—in stealth fashion—can help you distinguish between a candidate who would be only a blip on your company’s radar and one who could contribute to longer-term success. Use these three questions to determine whether a candidate considers the role you’re filling to be a pit stop or somewhere to put down roots:

  1. If we spoke to your last three managers, what would they tell us about your contributions as an employee and why they feel you left each organization?
  2. If you’re offered this role, considering what you already know about it, what accomplishments would you strive to achieve in the first six, 12, 18, and 36 months?
  3. Let’s discuss your career progression plans: What next-level jobs would you like to obtain, and how would you set yourself up for future progression?

With these questions, you can better gauge how committed candidates would be to the role and where they see themselves in the future.

Checking for Fit

During an interview, you should determine how well a candidate will fit in with company culture, the open position’s team, and the open position’s boss. Candidates tend to be chameleons in this area—changing to fit with what they think you want to hear. Slide in these four questions to determine their true colors:

  1. Tell me, candidly, about the relationship you had with your last boss, and if I spoke with her, how would she describe her relationship with you?
  2. Who was your best boss ever? Why do you consider him the best?
  3. What most frustrates you about working on a team?
  4. Describe a time when you had the opportunity to contribute to a company’s culture: How and what did you do, and what was the result?

With these interview questions, you can measure how well an individual would actually interact in various work relationships and affect your company.

All about Attitude

A candidate is on his best behavior during an interview, but how he reacts under pressure is a better measure of how successful he may be in a new role. Digging into everyday behaviors may also be a good indicator of the employee you’ll get after hiring versus the angel sitting in the interview. Use these three questions to get to know the candidate as a real person:

  1. When you’ve been challenged in the past, either by work or personally, how have you responded? What are some things you can do to respond better in the future?
  2. How do your passions relate to the work you do? If you were tasked with something outside of where your passions lie, how would you react?
  3. How does your attitude differ when you’re working with a superior versus when you’re working with a subordinate?

With these questions, you’ll be able to build a fairly detailed profile of a candidate’s attitude.

When you mix these 10 interview questions with others directly related to the job’s functions and expectations, you’ll not only learn about a person’s technical fit with position requirements but also about what she’ll truly be like on the job. With that information, you’ll be able to make the best hiring decision possible.


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