Some of The Most Effective Interview Questions I Use

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In a recent conversation with some very smart people, I’ve been asked how do you assess self-awareness in candidates that you are interviewing?

I enjoyed the conversation that followed that question, and it motivated me to write this whole article.

In my career I have interviewed hundreds of candidates for dozens of roles, going from IT Support Technicians, to Software Engineers and Product Managers, all the way up to C-level executives in Product and Engineering.

No matter what the role is, I always have a set of questions that I ask each end every candidate. Or at least I try: sometimes the conversation gets so deep in certain areas that I don’t really have the time to ask all of them.

This means that for every candidate I’ll have a set of “standard” questions that I ask everyone, and then specific questions that are focused around the specifics of the role, the personal journey of the candidate and the main purpose of the interview I’m holding.

These questions are not silver bullets, and there is no question that guarantees you that you’re making the right hire. I’ve used them time and time again to filter out candidates that clearly raised some red flags with their answers. It has been quite effective in eliminating candidates that otherwise might have passed the whole process.

I alway open with the same question that helps me provide the context and set the overall tone for the conversation, regardless on whether the candidate has been sourced or has applied spontaneously.

What is your main motivation for investing your time in this conversation?

I find this question extremely useful to give me a clear first impression of some key aspects of the person I'm about to interview:

• How clear are they in their minds about why they’re in this interview? Sometimes, but luckily not too often, I have been surprised at the lack of clarity and reasonable arguments provided as an answer.
• How good is the candidate at conveying something that can be very intangible, vague and personal in such a way that it’s easy for someone else to understand? No matter what role people have in an organisation, their ability to communicate clearly and be understood is a key skill that is required at every level.
• What are their values? Are they interested in new challenges? More responsibilities? Money? Understanding what drives people is key to be able to gauge whether or not they would be a good fit in the team and in the organisation.
• Are the moving towards something, or are they running away from something else? In itself this data point is not providing a positive or negative connotation to the following conversation. If this first answer is the first clue in a pattern that emerges throughout the conversation that tells you the candidate has a tendency of “running away” from something they’re not happy with on a regular basis, you might want to pay extra attention.

Last but not least, this question allows the candidates to talk about something that is important to them. It also offers further opportunities to the candidate to demonstrate their ability to think and reflect about themselves, a good indicator of their level of self awareness.

What has been a recent piece of feedback that you have received and decided to take action upon? What was the feedback? Who gave it to you? Why did you decide it was important? What did you do about it? What has been the result?

Let's use an analogy to explain this one. Except for Donald Trump and a bunch of other lunatics, who in their mind would not answer “Yes” to the question “Do you think that it’s important to actively take action against climate change?”.

Try asking instead “What have you done in the past 6 months to decrease your carbon footprint?” You can still make up an answer to this question, but it would be very difficult to sound credible unless you have prepared it in advance.

The same goes with feedback. You don't want people to tell you they like feedback, you want them to give you clear examples.

I’ve had a lot of good and not so good answers to this question. They tend to be a great indicator of two key abilities:

• Obviously, the ability to listen and handle feedback constructively and take action upon it. Don’t take it for granted, not everyone is great at this
• The candidate’s honesty and ability to show vulnerability: the could decide to mention something very marginal — some does — or to reveal something that had a huge impact for them and required a lot of energy and personal improvement to accept, overcome and even talk about in the interview

Ask for further details, they’ll often reveal the depth of the work the person has done on themselves through the process.

If I would ask your colleagues and close collaborators, what would they say about you?

This is probably the one that is most centered around pure self awareness. Of course there is no way to verify whether the answer provided corresponds to reality or not, unless you’re able to do some reference checks with such colleagues.

Still, if a candidate provides examples that tend to be only positives, you should raise your attention level to 11 and ask further inquisitive question. Beware of those candidates that would come across too good to be true, because in most of they case they’re just that.

What has been your biggest fuckup / the biggest mistake you’ve made in your career? What happened? How did you handle it? What did you learn from it?

Finally, the question I use to close every interview. I take it at the end because by now — usually 40 to 50 minutes into the conversation — the candidate should be very much at ease and a feeling in a psychologically safe environment.

What I’m looking for with this last question is really a combination of honesty, self-awareness and growth mindset. I’m not really looking for anything spectacular — not everyone has dropped the live production database during Black Friday — but something that the has marked the person’s career in one way or another. I want to see how they handle mistakes: are they punishing them or are they taking a constructive approach? Did they try to hide anything, or did they take responsibility for the issue?

Most of the candidates I have ever interviewed came up with good answers. Some of them might require a minute of two to think about a good example, some others might jump immediately and say “Oh yeah! Let me tell you the story”.

So far I’ve only been in a single situation where the answer to this question turned what was a quite clear thumbs up into a definitive thumbs down. I’ll never forget this interview.

It was for a senior role — Head of Infrastructure, reporting to the CTO — for one of our most important marketplaces. The person had a very solid experience and track record, coming across very self-confident with their answers to all my questions… until this last one.

After hearing my question the candidate hesitated for a few long seconds, and then said the following: “No… I don’t think I ever made any mistake, none that I can remember. I mean, I had to deal and fix many mistakes done by my team, but nothing directly caused by myself”.

That was enough for me to reject the candidate without hesitation. Such a low level of self awareness, compounded with the tendency of throwing their team under the bus, constituted an undeniable red flag. It would have been too risky to ignore this datapoint despite the very solid technical background.

These questions are not infallible and I don’t pretend they’ll work for you the way they did for me. My recommendation is that you come up with some key questions that you ask consistently to all the candidates. Of course you need to know what you’re looking for when asking them.

Feel free to share your observations and tips in the comment section below!