How to Ask Three Uncomfortable Interview Questions

For HR professionals, a hiring decision is often the most uncertain and costly one they make. The whole point of interviewing a candidate is to gain information that will give the company more insight into the person’s personality, character, work ethic, and potential. There are so many interview questions, assessments, or job preview strategies available, that you must be really “picky” about what you choose.

Traci Wilk, former HR chief at Starbucks, says that asking interview questions about challenging work experiences can help discern whether a candidate is willing to learn from their mistakes and reveal if they have a growth mindset.

In this article, we will share three interview questions + a BONUS one that can predict success better than a candidates’ entire résumé. Also, we’ll offer you a solution on HOW to ask these questions in a timely fashion and save time assessing the answers.

Three Uncomfortable Interview Questions That You Must Absolutely Ask

1. Can you tell me about a time when you made a mistake? The answer to this question will tell you a lot about the person’s integrity. We have all made mistakes, and people who are responsible and mature learn from them. When you ask this question, you’re looking for candidates to be up front and honest and tell you how they resolved a real problem.
2. Can you tell me about a time when you had to show leadership or initiative? This question gives candidates the opportunity to boast a little bit about a time when they stepped up to the plate. When we see things that need to be done, we either do them or we shy away. The response will let you know if candidates are go-getters and results oriented.
3. Can you tell me about a time when you faced adversity? Life is all about overcoming obstacles, and we have all been presented with challenges to overcome.  We learn a lot about ourselves through how we handle these challenges. Candidates who are thoughtful and introspective will openly share their stories of overcoming specific difficulties.

BONUS Question – What Motivates You to Work?

How many interviewers ask this question? Not enough. This question isn’t to assess applicants’ mental health or emotional state but to see whether they can precisely express the things that drive them. People who cite a recent vacation or hanging out with friends, for example, are probably motivated extrinsically and may not put their heart into their work, whereas candidates who talk about relationships and health are worth putting on the shortlist.

How Do You Assess the Answers to These Open-Ended Questions?

The responses to these questions can offer important insights into candidates’ vision of the world and can predict success and growth. Can the answers to open questions, such as these, be measured and evaluated? What assessment tools are available to help HR recognize candidates who will be the best fit? How might we evaluate and compare ways of addressing the same open question?

eSkill’s Free Response questions let the employer ask such open-ended questions as part of an automatically scored skills test.  Candidates’ free responses can either be reviewed without numerical scoring, or eSkill’s Team Score tool allows a panel of reviewers within your organization to “blindly” grade responses according to a customized set of criteria. Using this feature, you can implement Free Response questions like the ones above with a standardized approach.

With Team Score:

• First, an HR administrator sets up the flow of the evaluation process, defining the criteria for scoring and assigning different in-house experts to individually assess pertinent responses.
• Each expert then reads and grades the responses as they come in.
• Finally, the administrator takes those individual assessments and compiles the test taker’s final overall score.

This feature significantly shortens the interview process, reducing as some companies report, the time-to-hire by more than 60 percent.  This is on top of the increased accuracy and compliance of standardizing the interview process prior to a bias-prone live interview.

You can see how the eSkill Team Scoring feature works in this infographic.

What other interview questions do you ask your candidates to make their personality come out?