Have you ever finished interviewing a candidate only to realize that you didn’t actually get a good sense of whether they’re right for the job? Many of the most common interview questions to ask candidates are also the ones they have the most polished, prepared answers for and thus yield the least insight.

The best interview questions to ask candidates are the ones that get beyond their prepared answers and reveal what kind of employee they would truly be. For example, approaching a common question from a different angle can trigger a more honest response. Asking for illustrative examples forces candidates to back up their assertion. And putting forward critical thinking questions forces them to think on their feet.

What Are The Best Interview Questions to Ask Candidates?

As an executive recruiter, I know all of the tricks for identifying great candidates. The next time you’re picking interview questions to ask a candidate, try these 10 out:

  • Based on everything you know about me, this company, and the role, why do you think you’re a good fit?

Right off the bat, you want to know whether or not the candidate has done their homework and given substantial thought to whether they are a good fit, not just for the position, but the company culture and the team.

  • Tell me about a time when….

Behavioral questions are fast becoming the gold standard for interviewing – asking how someone acted. Any question that asks the candidate to tell a story will go beyond abstract responses and see if he or she can demonstrate various assertions. This works well as a follow up question. If a candidate says they have experience negotiating deals, ask them to tell you about a time when they negotiated successfully or unsuccessfully.

  • If you could start your career again, what would you do differently?

This is another way to ask candidates about mistakes or weaknesses that they generally will not have prepared for. It’s also less confrontational so you’re more likely to get a thoughtful, honest response.

  • In your most recent review, what areas in need of improvement were brought up? What would your supervisor tell me you need to improve on if I call them?

The loophole in asking a candidate about his or her greatest weakness is that they can bring up a weakness that has already been addressed or one that isn’t really a weakness like the classic “I’m a perfectionist.” This question prevents candidates from taking those easy outs. And bringing up that you might call for a reference makes it highly likely that you’ll get a genuine answer.

  • How would you handle it if…

Hypothetical questions force candidates to think critically on their feet about real life situations and reveal their problem solving approach. Ask something industry specific here that could be a challenge faced on the job. How would you handle it if you were tasked with reducing manufacturing costs by 10%? How would you handle it if an unhappy client said they want to move their business elsewhere?

  • What is your definition of success?

This question is purposefully vague since it can be revealing what direction the candidate takes it in. You’re hoping to learn what the candidate values and whether it matches the company’s culture and compensation structure.

  • Where do you see yourself in five years?

Although this is a relatively common question, it reveals how ambitious the candidate is. It can also tell you how committed the candidate is to building a career within the company depending on whether their response is generic or tailored to the growth opportunities within your company.

  • What do you not like doing?

No candidate enjoys every task associated with his or her job. Of course you’ll get some innocuous responses like “I hate filling out timesheets” or “I hate dealing with Asia because calls get scheduled for 3am.” But you’ll be surprised how many candidates will tell you they don’t like essential job functions and that’s something you definitely want to know, as employees are never as good at tasks they don’t like.

  • Tell me about a time that you failed.

This is a really difficult question for candidates and I’ve found that, when answered well, it really separates a candidate from the pack. You’re less interested in the failure than the candidate’s assessment of why they failed, how they learned from it and how they continue to apply what they learned.

  • Do you have questions for me?

Of course this is the traditional final question but it doesn’t mean that it isn’t still a great one to end on. You want to know that the candidate has prepared for the interview and is asking questions that show his or her passion for the position and desire to genuinely understand if this is the right fit for them.


There are dozens and dozens more great interview questions, so be creative. The best interview questions to ask candidates is truly dependent on what you’re trying to learn about them. Any time you can force a candidate away from their pre-planned answers, you’ll get more insight into whether they’re right for the job. Assuming the interview goes well, click here for more questions to ask in a second round interview.

What are your favorite interview questions to ask? Share your favorites below.