Over the past six years, I have interviewed over 2,000 candidates. I’ve developed a personal system to uncover key traits of a candidate’s personality which help me in making the proper decision. Here are five questions that I have found helpful in revealing a candidate’s character, ultimately assessing if he or she will be the right fit for our team in driving company growth.

Candidate Question #1 – What’s motivated you to make your career moves in the past?

Today’s workplace is fluid, and I want to hire someone who has a clear sense of what they want to achieve.

Why has this person changed course in the past? I want to see that their career decisions follow a logic / structured path. What were the main motivators? A higher salary? A new challenge in a different industry or position? A former leader who got to chase them into a new company?

Candidate Question #2 – Tell me about a time when you worked on a project that didn’t succeed.

This is a tried-and-true test for self-awareness. When I ask about failure, I’m looking to understand two things. The first is how a candidate frames why he or she took the initial risk. What motivated them to act? How high were the stakes? How did he or she decide on their specific course of action? I want to understand their thought process and if they chose to approach the problem collaboratively or independently.

Secondly, I want to gain insight about their reaction to failure and if they recognize past mistakes as an opportunity to grow. How a candidate frames their failure reveals a lot about their integrity and personal values. Do they demonstrate accountability for the role they played? If a candidate only blames others for the problem and can’t admit their own faults, that’s a red flag.

I’m looking for someone who can take ownership of their mistakes and explain what they learned from them. In my experience, good companies learn more from failure than they do from success and so do candidates that will help your organization grow.

Candidate Question #3 – What’s your ideal work environment?

To determine culture fit, I tease out what the candidate’s previous working relationships have been like. Since every team is different, I want to learn as much as I can about how they interact with others to see if they would be a good fit for my team. The successful job candidate will share a passion for our mission and share our company values.

Beyond people fit, I want to get a feel for the type of environment the candidate thrives in, and if it’s conducive to how we operate. Ambiguity and change are a fundamental element of the startup culture, and it isn’t right for everyone.

To that end, if I notice a pattern of a candidate describing how they follow a specific process and do their best not to deviate from it, they might not be the right fit. To get a better understanding of how they might adapt and perform in a less structured environment, I ask about a time where they needed to forge their own path. The best answers will demonstrate the ability to create new, nimble processes that can easily pivot should priorities change.

Candidate Question #4 – What’s the most complex project you have ever led?

Hearing an example of how someone approached a complicated workplace decision reveals whose interests they prioritize – the company’s or their own. It also gives a clear idea of the seniority and of how complex were the problems that person had to deal with in the past, no matter the area they worked at.

Candidate Question #5 – Who is the hardest employee you’ve ever had to manage?

Can you adapt your leadership style to fit different employee needs? What would their employees say about them? If you are in constant communication with your team, you will know their answer, even if it’s that you don’t respond to their emails fast enough. If you are communicating with your team, you should be able to articulate what your team will say about you – good and bad.


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