How to Ask Better Interview Questions


Interviewing candidates for jobs is one of the hardest business skills to master. It has been said that when we interview people we don’t actually interview the person, we interview their representative. Which is true, both the interviewee and the interviewer are putting on a show through the process. When everyone is puffing up their chests and fluffing up their resumes it is hard to make any real assessment on how they will perform on the job. This is why it sometimes feels like a different person shows up to work than the one who was interviewed.

What can we do to improve the broken interview process?

What we know through numerous studies is that structured interviews have a higher success rate than unstructured interviews. A structured interview process means that you are asking the same questions to each person interviewing for the position. When you structure the interview you have an easier time comparing answers, and studies show that this approach has a higher rate of success. So then the question becomes, what questions should I ask?

According to Adam Grant, an organizational psychologist from Wharton School of Business at University of Pennsylvania, the best questions to ask are behavioral, situational or questions that ask the candidate to demonstrate mastery. So questions that start with, “tell me about a time when…”, and “what would you do if…” or  having them role play talking to an irate customer are superior to the more common open ended questions. 

Research shows that these types of questions perform the best at giving you a preview of how the person will perform in the role. The answers to these questions should help you determine if the person has the right temperament for the role, the right values for your organization, and whether they have the right skills to perform the job.

Of course coming up with the right question is easier said than done so let's take an example position and review possible questions that would help us determine whether the candidate is a fit for the role. The position is an executive assistant reporting to the CEO. Let’s work through some good questions for this role.


Questions that will help you to determine the Interviewees temperament 

Let’s say that the qualities we need for the role include kind but firm, good instincts about people, a clear and candid communicator, takes responsibility for outcomes, and handles stress well. 

So what questions will help me assess if the interviewees possess these qualities? 

  • What would you do if you had to follow up with someone on a commitment that they made to the CEO that doesn’t seem to be completed and the deliverable is a week late? Can you role play a phone call that you would make to this person? (See if they approach it kindly but firmly.)
  • What would you do if your manager was hosting a company party and hired a magician and the magician backed out at the last minute? (See if they own the outcome.)
  • What would you do if your manager asked you how they did during a speech and you thought it didn’t go well and the crowd seemed to lack interest. It wasn’t totally embarrassing, but you could tell that the content was not connecting with the audience. (Are they strong enough to give negative feedback to their boss? Do they have the strength to criticise a superior? Can they give an example of doing it tactfully which will show if they have good people instincts?)
  • Let’s say this CEO has a sick parent and they are going through a hard time getting them the care that they need. This CEO is distracted and not getting back to emails promptly causing other people at the company to complain. Do you say anything? If so, what do you say? (Again, do they tell the truth about how their behavior is impacting the company? Are they a clear and candid communicator?)
  • Tell me about a time when you were stressed out in a previous role. What caused you the stress and how did you handle it? (The answer to this will determine their stress tolerance and how they manage it.)
  • Tell me about a time when you worked with someone who rubbed you the wrong way. What was it that rubbed you the wrong way and what did you do about it? (Trying to see if the person is drama or not.)
  • Tell me about a conflict that you were involved in at work and how you handled it. (Are they tactful and mature?)
  • Tell me about a time when you were totally overwhelmed at work and how you got things under control. (Another question about stress tolerance and ability to prioritize.)
  • Tell me about a time you got negative feedback at work and how you responded? (Are they drama or do they use negative feedback to improve?)
  • Tell me about a time that you solved a problem at work. Tell me what the problem was and how you solved it. (Do they have experience in a business environment solving business issues and are they creative enough to fix problems on their own?)
  • Tell me about a time when you had to work with someone who had a very different style than yours, how did you handle it? (Can they handle working collaboratively with diverse teams?)


Questions that will help you identify the interviewee’s ethical code

Now we need to know if they have the right ethical approach to the business. We need people who always put the long term health of the company and its reputation above short term gains. Someone who won’t cut ethical corners to get ahead. We want truly decent people. So what questions will get to the heart of the candidate’s ethical code?

  • Let's say that the company needs to get to a revenue goal for a high stakes investment deal that the CEO has their heart set on making happen. Certain departments are not making their revenue goals which are hurting the chances of this deal going through. You are a month out from when you need to hit the number. It almost seems impossible. As you are brainstorming with a department head on how to get to their target revenue goal, the department head says that he can falsify the reports and the investors will never know. How do you respond? (The correct answer is to see what creative approaches he can come up with to get sales and revenue to where it needs to be in a month, and tell him to NOT falsify the numbers on the report under any circumstances.)
  • Tell me about a time when you had an ethical dilemma at work and explain how you handled it? 
  • Let’s say that you know that the sales department is not acting ethically. They are over promising the clients something that you know the company cannot deliver. You really like the head of the sales department but you really think what they are doing is wrong and bad for the long term success of the company. Also the head of the sales department is a close personal friend with the CEO who you work directly for. You know if you speak up to the CEO about what the director is doing in the sales department the director will find out and they will be angry with you. How do you handle it? (We want to see if the person is willing to whistle blow at the expense of someone being mad.)
  • What would you do if you saw a senior executive berating, and yelling at a colleague? (Hopely the candidate shows empathy for the colleague and addresses the issue head on.)

Understanding someone’s work habits and abilities

Let's say you take over someone’s email inbox who left the company and it is completely out of control. Explain how you would handle the inbox. Explain how you would organize it. What would your process be to tackle it and what would you prioritize?

Let's say a client is yelling at you because no one got back to them how would you handle it? Would you mind role playing with me, I will pretend I am the angry client.

Tell me about a time when you rolled out a new procedure or software. What was the procedure or software and what steps did you take to roll it out?


Creating Good Questions on the Front End Prevents Problems on the Back End

It takes time to come up with thoughtful interview questions for each role. However, asking good questions that help you figure out who an individual is, and if they would be a good fit for the role. Doing the hard work on the front end can save you a lot of time and headache later.