Finding the right interview questions

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Interviewing sounds easy: find someone who is interested in working with you and ask them some questions to make sure that they are a good fit for the job.

What people tend to forget is that if you don’t ask the right questions – the ones that help you figure out if this candidate is a good cultural fit, that they have the soft skills you need them to have for the job, and if they will fit cohesively into your team – you can hiring the wrong person.

The wrong person, especially on a small team, or in a small company, can be far far more costly in time, money, and heartache than waiting for the right person.

So, with that in mind, consider that you should be asking questions with a purpose. With every question, ask yourself:

  1. Why am I asking this question?

  2. What am I learning about the candidate?

  3. What kind of answer am I looking for?

  4. Does the answer indicate success in the role?

For example:

You’re hiring for your first marketer. You are super pumped. So you ask:

Tell me about a time you managed a difficult client relationship


Great question.

  1. You are asking because you have a difficult client.

  2. You are learning if this candidate has experience dealing with this kind of situation.

  3. You are looking to hear a real life example of success in a similar situation as your own. (You may also get some free advice on how to handle your current issue)

  4. Yes. Someone who has successfully handled this kind of thing before is more likely to be successful in this role (and won’t be afraid to come in and fix things).

Then you ask:

If you were in a Disney Movie, which character would you be?

Terrible question.

  1. You want to know if this person sees themselves as a villain, hero, or damsel in distress.

  2. You are learning how much they like Disney.

  3. No idea. Heroes and villains are stereotypical and not real.

  4. Nope.

Don’t ask that question. Not only are you not learning anything useful, but now you’ve put a candidate on the spot for no good reason except your own amusement.

Instead of talking princesses, here are some culture-fit interview questions that I ask in every interview. Feel free to use them in your next hiring endeavour!

Culture Interview Questions:

1.  On a scale from 1 to 10 how lucky or fortunate would you say that you are?

This question is very predictive of attitude in the workplace and correlates with people who are happy, can handle setbacks, and who take accountability for their actions.

I don’t hire anyone who answers with less than 7. As a baseline, anyone sitting in front of you in an interview is pretty fortunate to be smart enough, healthy enough, and good enough to be there.

2. What would you say is the biggest misconception that other people have about you?

This is my favourite question. It gets the candidate to tell you how they’re perceived by others. Because it’s framed in “but it isn’t true”, they’re more likely to tell you an honest weakness. Perception is reality, and if their team or friends think that they’re lazy, they’re probably not contributing equally, much less going above and beyond.

High performers will answer with: “That I have my shit together”  or “That I’m really outgoing but I feel shy”.

Low performers will answer with “That I procrastinate” or “That I’m really stupid” (true story, someone actually said that to me).

3. What would you say is your biggest or best accomplishment?

This question indicates that your candidate can set goals and meet those goals. I actually don’t care what their accomplishment is – just that they have one. It also means that they can handle road bumps, because, let’s face it, no accomplishment that makes you super proud was easy to complete.

4. Tell me about a time that you failed.

Again, don’t care about the failure. I want to know that you can handle failure gracefully, and feel comfortable telling me about said failure. People who are like “I have never failed”?  DO NOT HIRE. High performers often see something that wasn’t a real failure because they fixed it, as a failure because it wasn’t good enough. You want those people.

5. Describe your ideal boss.

I want to know if you can work with your manager.  If your candidate says “someone who praises me and makes me feel important” and they’re going to report to someone who never gives praise… no one’s going to win. It’s not their fault, but they will be unhappy in their job, and people will quit for a bad boss. Even if that boss is only bad for them.

Good luck building an awesome team!

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