4 Interview Questions to See the Truth in Every Candidate

I want to become a better interviewer. In fact, I’m quite obsessed with it at the moment. The irony of this is that for the longest time, I placed little or no value whatsoever in the practice of interviewing … I honestly didn’t think it was that important. I was wrong. As I talked about in my last blog on this subject, for the better part of a decade I figured I could get by on feel. I’m a good judge of character. I can tell a good candidate from a bad one. I recognize greatness when I see it … Don’t I? What else is there? By Brendan Reid, January 2017

For a while this perspective seemed to work for me. I managed some small teams, hired some people, fired some people – I did ok. But then I started managing larger teams, running more sophisticated projects, recruiting for functions I had no personal expertise in, hiring at scale. This is where my mindset started to show its flaws. My passive approach may have looked like it was working on a small scale, but when pressure tested, it didn’t measure up. I started hiring people and then having to let them go ninety days later. I found myself bringing people onto the team who seemed great on the surface only to discover they didn’t really have the qualities I imagined they did. Candidates who appeared to check all the boxes, candidates who felt good to me, weren’t making it. These failures forced me to take a hard look at myself and ask the tough questions:

  • Do I really know the people I’m hiring?
  • Do I really understand how these people think?
  • Do I really trust my judgement of how they’ll fit with the team?
  • Do I really believe they can make good decisions in practice once the interview is over?

The truth is, I couldn’t confidently answer ‘yes’ to any of these questions. My rather tepid approach to interviewing wasn’t giving me what I really needed. It didn’t go deep enough. Not so much in terms of technical diligence, but more so in terms of my real understanding of who these people were.

Having arrived at this realization I set out on a mission to test new interview techniques. I started experimenting with new questions and approaches to see if I could get past the surface level and start seeing the truth in candidates. You can read about my evolving interview philosophy in my previous blog on the topic. But for today I want to focus in on interview questions. Specifically, the four types of questions I’ve added to my arsenal which are designed to draw out a deeper understanding of candidates.

The Story Question

This is a question designed to take a candidate off script. There is just so much information out there on how to prepare for interviews that just about any half decent candidate is going to have a set of prepared answers to most basic questions. So asking people to tell you their top 3 strengths and weaknesses, or to walk you through their last four jobs just doesn’t make sense anymore. There’s very little value to be derived from the answers you’re likely to get. I’ve stopped asking these questions entirely.

You may be wondering, “but don’t I need to know the basic information?” “How am I going to find out these details if I don’t ask the questions?” The story question is a great way of still getting to the fundamental information you need but in a manner that reveals much more about the person you’re interviewing. And it takes the candidate off the prepared script and forces them to show you who they really are. For example, instead of asking the candidate to describe each job they’ve held for the last 10 years – a question they are no doubt prepared to answer straight off a script – I’ll go another way. I’ll ask something like:

Tell me the story of your career. Tell me what inspired you to become a Software Engineer. Tell me what made you fall in love with it. Tell me a story of where it tested you and where it rewarded you. Tell me the story of your finest moment in this chapter of your career.

When you change the structure and tone of the question in this way, you give the candidate an opportunity to tell you their authentic story. You get to hear the real truth. A person’s answer to this type of question will reveal so much about their passion, their ability to persevere, their self-awareness. It will tell you so much more than the basic career timeline run-through so many of ask for without giving it much thought.

The Decision Making Question

This is a question designed to understand how a candidate actually makes decisions in practice. Decision making, in my opinion, is way up there on the list of critical skills every candidate needs regardless of functional position or level. The normal set of interview questions aren’t well designed to uncover this quality which means we’re often left to rely on feel and intuition and references to ascertain how a person makes decisions. Sadly, more often than not, we don’t actually get to see how a person makes decisions until they’re already on the job.

Some interviewers try to tease out decision making ability with questions like: “Tell me about a really tough decision you had to make at your last job and how you managed through it.” That’s not the worst question in the world, but again I feel it’s one most people have prepared for in advance and you’re going to get a canned answer much of the time. I like to change it up a little bit by getting more specific and forcing the candidate to talk about a decision of my choice instead of the one they were prepared to answer walking in the door. I’ll often ask something like:

Tell me about the moment you decided leaving IBM was the right path for you. How did that feel? What were the pros and cons? Were there other options? What pushed you over the edge? Who did you talk to when you were contemplating it? In retrospect, how do you feel about that decision? Would you do anything different if you could go back in time?

It might not seem on the surface like my question is significantly different than the one above it, but the specificity is what makes it more effective. First off, I’m choosing what decision they need to talk about so it’s unlikely they’re fully prepared to answer it which means I’m going to garner some truth about them. I’m also forcing the candidate to reveal the model or framework by which she makes decisions. I’ll quickly understand by the answer whether or not this person follows a logical decision making process which will hold up in practice and under pressure.

The Mindset Question

This is a question I use to understand how a candidate views the world. Are they a positive person? Do they have self-belief? Are they resilient? Can they handle uncertainty? Right up there with making good decisions, in my experience, is the ability to thrive in a changing environment. Many candidates can perform well when everything is going to plan, but how often is that the case? I don’t’ think I’ve ever worked for a company where things always went according to plan. A most places you’re likely to work, things are a complete mess, change is the status quo. I want to hire people who see a changing and chaotic environment for the opportunities it provides, not for the perils and problems it presents.

Some interviewers will try to ascertain a candidate’s mindset by asking questions like, “Tell me about a challenge you faced at your last job and how you overcame it.” For me, that question is just too easy to prepare for. Nine times out of ten you’re going to get some well choreographed answer they’ve recited 20 times at home in front of the mirror. I don’t think you’re going to gain much real insight from whatever answer here. I prefer to ask something that places me inside the candidate’s head and heart. Something more like:

Put me inside your head at the moment you heard your company was getting bought by IBM. How did that feel? How did the people around you feel? What did you tell your husband that first night when you got home? What did you do differently that next morning when your whole world had changed? What were the next 60 days like? 

While my question isn’t fundamentally different than the first one, it has a level of depth that is designed to get past the surface-level answer. It’s designed to get you inside the candidate’s head to understand their mindset and it forces them to go off script and reveal some truth about themselves and how they really feel about change.

The Empathy Question

This is a question to gauge empathy and self-awareness in a candidate. These are extremely important attributes for me in a team member, and they’re not always the easiest ones to ascertain in a standard interview. Most of us rely on intuition and feel to discern whether or not a person possesses these qualities, but I can tell you from experience it is not a foolproof method. Sometimes interviewers will ask a question like, “Tell me about a time you had conflict with a co-worker and how you went about resolving it.” That’s not the worst question in the world but it doesn’t quite get deep enough into the psyche of the candidate for me. I prefer to structure the empathy question more like:

What must it have felt like for people on your team, when they found out you had been promoted to Senior Manager last year? Were they all happy for you? Were any of them jealous? What about the people you beat out for the promotion, how do you think they felt? How do you think that promotion changed the way people thought of you? How did it change the way you interacted with them?

I really like this type of question because nobody is prepared for it and it can be somewhat disconcerting to talk about other people’s feelings about you in this way. If you’ve read my previous blog on interviews, you’ll know I always want candidates to feel comfortable in the interview, but I also want to push them a little bit. I have found the empathy question, when structured in this manner, is a great way to measure how self-aware a person is and how he thinks about the people around him.

I find it’s getting harder and harder to tell good candidates from great ones. Everyone is just so prepared these days. There’s an unlimited amount of information available to hone interview skills and prepare for questions. If you want to be a good interviewer you need to take your game to the next level. I’ve spent many months now trying to evolve my approach and the questions I use and I hope these four questions will help you too.

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