108: How To Interview Like A Pro – Part 2

Asking the right interview questions will dramatically improve the effectiveness and you’ll look like a pro!
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Asking the right interview questions will dramatically improve the effectiveness and you’ll look like a pro!

In the last episode we learned about the preparation phase of the interview and on this episode we’ll learn about coming up with the interview questions.

One thing I forgot to mention on the last episode is you should call the applicant’s references before the interview. That may have already been done during the screening process and provided to you as part of the interview prep documents. If not, it’s best if you talk to them anyway because that’s going to help you prepare your questions.

Even though the primary objective of the interview is to gather information that will be used to make a hiring decision, it should be more like a conversation, and the questions should be designed to get that conversation started; and to keep it on track.

But, you also need to be flexible because, based on some of the answers, you’ll want to ask follow up questions that aren’t on your list.  Ok?

What questions should you ask?

So, what questions should you ask?

Well, there are thousands of possibilities.  I’ll provide a list of suggested questions you could ask AND a list of questions you should NOT ask, in the show notes.

For this episode, I’ll go over the different categories of the questions you’ll want to ask, and I’ll provide a few examples from each.

Here we go…

Introductory questions: 

This where you’re going to break the ice, set the tone and make them feel comfortable. For example, ask:

  1. How did you find out about the position?
  2. How long have you been looking for a new opportunity?
  3. What do you know about our company?


A well rounded person is more likely to be satisfied with their job. Questions from this category are also great for continuing to break the ice and getting them comfortable. Just remember, don’t ask any questions in a way that opens the door to discrimination.

Questions that have to do with marital status, sexual orientation, religious preference, age, and pregnancy should be avoided like the plague. You should never ask about non-work related activities – a question like, What do you do in your spare time – is a huge no-no.

Instead, ask questions like:

  1. What hobbies do you have that help you recharge?
  2. What are you passionate about?
  3. If you could spend 3 hours every day doing something you love, what would that be?


Based on the job, this may not be so important. If it does’t apply, skip it.

There are various forms of education, aside from the traditional university, that an applicant may not always list. They might be an avid learner taking courses on Udemy and Linda.com, for example, and that’s good to know. There are industry certifications and government licensing as well… so ask questions that uncover the full scope of their education.

For example:

  1. Besides what I see on your resume/application, have you taken any courses that you feel have prepared you for this position?
  2. What’s the last book you read or listened to?
  3. What certifications do you have?

Work History:  

I’m always very curious about their past job experience. I’m talking about the real story, and trying to get to the bottom of why they are moving on. What is it, really, that made them decide to leave? Were they fired but too ashamed to admit it?  Most people have been fired at some point. What’s more important, I think, is what they learned from it?

So, ask questions like:

  1. Why are you leaving your current job? Or, if they aren’t currently employed: Why did you leave your last job?
  2. Why did you leave the job prior to your current one? I like to go one level deeper.
  3. What will you miss about your last job?

Job Performance:  

It’s hard to evaluate past job performance. You obviously weren’t there so you’re going to get the Applicant’s perspective only here.

Before you start asking these questions, I like to ask them to explain their prior job’s duties, and what a typical day looked like.

Try to get in the past 5 years worth. After that, you can go into the performance questions, like:

  1. What’s one thing you wish you would have done better at your prior job?
  2. What skill stands out above all your other skills and how did you apply that skill at your prior job?
  3. What task or responsibility did you struggle with the most at your prior job

Career Goals:  

Let’s find out where your Applicant wants to go from here. I like people who have a plan and expect to advance. Even if that means they’ll be leaving you some day.

I’ve had great employees leave because they’re either in school and studying a different field so when they’ve finished they’ve moved into that field. And, I’ve had great employees leave because we weren’t been able to provide the advancement opportunities to keep pace with their growth.

Here are some career goal questions.

  1. Looking back, is there another career you wish you would have pursued?
  2. Why did you choose to make this your career?
  3. If you get this job, what position or job would you like to have 5 years from now?


Here I want to see what they think of themselves. These are hard questions to answer and I’m looking for confidence, determination, and even a healthy degree of arrogance …. with a dash of humility. Arrogance isn’t an excuse to be rude or condescending.

You can ask:

  1. What do you feel most confident doing?
  2. What are your top 3 best qualities?
  3. What’s your worst quality?

Problem Solving:  

I want to know if they can think. You might also call this creative thinking.


  1. What is one example of a recent work problem you solved or process you improved.
  2. Describe a situation in which you found a creative way to overcome an obstacle.
  3. What was the best idea you came up with at your last job, even if it wasn’t implemented?

Decision Making:  

The goal here is to see if they are able to make decisions. Weather they make the right decisions is another subject. John Lee Dumas of the podcast EO Fire said his military commander told him that a good decision now is better than a great decision later. Context is important, but the example is a good one because it applies to business as well.

Even if you have the luxury of time, a good decision now can be better. It depends on the situation.

Here are some decision making questions:

  1. What’s the hardest decision you had to make in the last 12 months, and how did you go about reaching the decision?
  2. What is the process you typically follow to make a decision about a plan of action?
  3. If you have multiple job offers, how will you go about deciding which one to accept?


Here let’s find out what kind of initiative your Applicant has. Are they a self-starter and life-long learner or just going through the motions.

Ask them:

  1. What about your current (or prior) job created the desire to excel?
  2. What work related reading material do you consume?
  3. Tell me about a time when you volunteered for a task.

I also want to go over some examples of questions that you SHOULD NOT ask, but we are out of time.

And, we still need to talk about conducting the interview… so, we’ll have to extend this out to Part 3.

Interview Questions Guide

I’m so sorry… I don’t have this finished yet. I want to make sure the Guide is awesome and it’s taking me longer than anticipated to complete it. Please check back on Thursday.


About the author, Thomas

I have 20 of years insurance industry experience in C-level management, focusing on all aspects of workers compensation, risk management, loss control, employee benefits, HR, payroll and professional employer organization (“PEO”) operations. Currently, I am the owner and CEO of Humanly HR, and founder and host of SmallBiz Brainiac; a podcast providing employer intelligence to small business owners.

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