How to Conduct an Interview

Conducting an interview requires asking targeted questions that give you as much insight into the candidate as possible. Your goal is to learn as much as you possibly can about the individual in a short amount of time. Below is how I do that…

I structure the interview process into two parts. In the first part, I aim to learn as much about the individual as possible. In the second, I try to see if they are a good fit for the open position.

During these two parts to the interview, I am looking for intelligence and drive. You can’t teach smart, and you can’t teach hustle. You can teach everything else. That is primarily what I look for in the candidates I am interviewing.

Note that everyone is different here. Maybe you are looking for something different with your interview. If that is the case, make sure you plan to ask questions that potentially exposes the characteristics you are trying to find.

Part One – Learning About the Individual

The interview starts the second I meet the person. I will make notice of how they interact with my admin. I will take notice of their dress and appearance. I will note what time they arrived. I will pay attention to their handshake. I will even try to take notice of the car they drive.

I will also notice how comfortable this initial interaction is with me. If our walk to the office is awkward or strained, that is a giant red flag for me. It is very important that the individuals on my team are comfortable and easy to get along with.

Below are the questions I will ask and why I ask them:

Question 1: Tell me about yourself.

I have done my homework, and I have read the candidate’s resume. However, every interview in the history of the world has opened with this question, and for good reason.

One, it gives the interviewer all the basic information they need to know. It gives the interviewer instant feedback on the candidate’s communication skills. It is also the first opportunity to see how well the candidate has prepared.

If the candidate essentially explains their resume to me, I will not be terribly impressed. However, if they start explaining WHO they are and not WHAT they have done, I will be very impressed.

Here is a good video that is a great way to answer that question:

Two, it gives the candidate the opportunity to settle into the interview with an easy question. The candidate knows this one is coming, and it is on a subject where they have some expertise – themselves. This should put the candidate at ease, which makes for a much better interview.

Question 2: What accomplishment are you most proud of?

I purposely leave this question open-ended. Often, the candidate will ask me if I am interested in their personal life or professional life. I tell them whatever they want to share.

The true purpose of this question is to see if the candidate has the ability to accomplish big goals. I want achievers in my organization. I want winners.

Candidates who answer this question well explain to me a professional situation where they accomplished a monumental task and exceeded expectations. They quantify their results, and let me know the impact it had on their organization.

Question 3: What do you do in your personal life?

I was in the military. The foundation for the strength of a unit is the camaraderie amongst its members. I strive to create a team where everyone has to pass the beer test. By that, I mean that every individual on my team would be happy having a beer with anyone else on the team. If they dread that thought, then I have a problem.

To answer this question correctly, you have to be interesting. It doesn’t matter if you are a sports nut or an avid reader or someone who loves travel or loves the outdoors. What matters is that you have a passion for life.

Question 4: What are your three biggest strengths?

You will learn a lot from this question. The candidate will tell you the type of person they are and what they think is important. They will tell you if they pay attention to detail. They will tell you if they are outgoing or introverted. They will tell you if they work fast or if they are more methodical.

I love this question because it also puts them on their toes, but with a safe question. No one prepares for 3 strengths. Maybe one or two, but never three. It forces the candidate to think on their feet. That shows you a valuable skill as well.

Question 5: What are your three biggest weaknesses?

Like above, the candidate has probably prepared one or two weaknesses, but never three. This is probably the most important question I ask. It is important because if framed right, the candidate will give you an honest answer which is a true assessment of themselves. Let me explain:

More times than not, a candidate struggles to come up with three answers. There is awkward silence while the candidate thinks about how to answer. I let there be awkward silence to see how they react.

Eventually though, I tell them that this is a very important question to me. We all have things that we are working on. No one is perfect. I explain that I’m not looking for the BS HR answer, but an honest assessment of what they are working on.

I explain that it is important because I am looking for people who have a good self-awareness. In my business, you have to be able to judge the situation you are in. If you don’t have good self-awareness and can’t analyze yourself, how can I expect you to analyze a difficult business situation that you will eventually encounter?

Phrased that way, the candidate always lets their guard down and tells me their exact weaknesses. I’ve had candidates tell me that they lack motivation. I’ve had candidates tell me they struggle with people. I have had candidates tell me that they have drinking problems.

This question has told me more about a candidate in my experiences than any other I ask. It has saved me from making bad hires. The key though is to let them know you understand that we are all working on something, and proceed to watch them let their guard down and reveal their true self..

Part 2: Discussing the Job

Now that I have a good feeling for the candidate; I talk about the position.

I explain the goals of the role. I explain what success looks like, how they will be managed and who they will interact with on their assignment. I tell them the challenges of the position as I see it, and how they will interact with me as their manager. I give them as much information as possible so they know exactly what they are getting into.

However, I’m also recruiting here. I explain what success in this role will do for their career, and how I will ensure they are successful. I explain why they want to work for me, and what I’ll do to guide and mentor them. I will tell them about my team, and how we are winning and how it is always smart to be on a team that is winning.

Then I’ll flip it back on them, and ask the following questions:

Question 6: Why are you a good fit for this job?

I ask this question because I want to see if they understand the position and if they can see themselves in it. I look for candidates that are eager and creative, and those candidates will have their mind racing a million miles an hour thinking about the role and how they would be a good fit.

This is the part of the interview where any relevant skills come out, or past experiences or relationships. If a candidate has experience and can hit the ground running, that makes my life a lot easier and make the candidate very attractive to me.

One of the best candidates I ever interviewed absolutely nailed this question. I explained that her experience left her unqualified for the position. What makes her think she can do the job?

She agreed with me that she was inexperienced, but said that she has clear understanding of the position and what success looks like. She then spent the next hour explaining in great detail the problems I currently have and her solutions on how she could fix them.

I was stunned. I asked her how she could know so much about the position? She explained that she reached out to several people who were very knowledgeable about the position and she reached out to members of my team. She interviewed them as if she had the job and pieced the information she gathered together to develop a strategy.

I was so impressed by her hustle and eagerness for the position that I offered it to her on the spot.

Question 7: What do you know about the company?

Again, I’m looking for hustle and drive. This question will tell me how well the candidate has prepared for the interview.

It is very obvious to me how much time a candidate has spent researching my company.

The worst candidates will tell me what we do at a very high level. That shows me about 10 minutes of commitment.

A good candidate will go to our company website and learn about our current initiatives. They will go to Yahoo Finance and check our financials. They will look at our social media and watch our marketing videos on YouTube. I love people who are prepared, and this shows me a deep level of commitment.

I have hired people because of their performance on this question alone. If a candidate wants the job bad enough that they will go to the extreme to prepare for it then they are probably my kind of person.

Question 8: What concerns you about this job?

If I like the candidate, I’ll ask this question. I am very decisive, and at this stage I probably know if I want to hire the candidate. Likewise, I’ll also know if they aren’t a good fit. If they aren’t a good fit I’ll skip to the next question and save us both some time.

I ask this question because if I think the candidate is a good fit I am back to recruiting. If they have any hesitations, I want them on the table for us to discuss. I would hate for the candidate to leave the interview with concerns when I could have alleviated them.

Question 9: What questions do you have?

This is very important. I look for individuals who are naturally curious. Think about it this way:
The person I plan on hiring is going to be paid tens (if not hundreds) of thousands of dollars, and will end up committed years of their life to work for me. This will become a huge part of their identity.

If they don’t have a bunch of questions, then something is wrong.

Note that I don’t want HR type questions here. I am very dismissive if they ask benefits or compensation questions. I explain that we can discuss those things later if they get an offer.

I want to hear questions about the position. I want them to ask about the challenges. I expect them to want more about the team and their career path. I would expect them to want to know more about me, and how I lead the team. They should ask questions about our industry and the competition. They should ask what makes us different than other companies.

There are literally hundreds of questions that can be asked here. What is important to me is that some are asked, and that we have a free-flowing discussion about them.


At the end of the interview – thank the candidate for their time. Their time is valuable, and they probably put a lot of time and effort into your meeting. Be sure to acknowledge that and thank them for their interest.

Also, explaining the follow-up steps and timeline. They have the right to know what happens next.

When it comes time to make a decision, there are some things to remember. If you are part of a group, and not the ultimate-decision maker, be sure to give your opinion in a non-confrontational way. Give the facts you gathered, give your opinion, and then sit quietly.

If you are the decision-maker, then this is a little different. Take the opinion of others, but realize that ultimately it is your call.
I was part of a group interview where the group decided the wrong guy was the right candidate. The boss put everyone’s vote up on the whiteboard, and it was nearly unanimous for the wrong candidate. I was the only hold-out for the candidate who should have been chosen.

The boss put himself in a very challenging position. If he chose the right candidate, and he agreed with me who was the right candidate, then he would be telling everyone else on the team that their vote didn’t matter and that he didn’t respect their opinion.

As such, he ended up going with the recommendation of the group, and it was a colossal failure. I ended up hiring the other candidate for another position, and that took all doubt who was the right candidate.

The lesson is that if you are the boss, you need to realize that you cannot defer this decision to the group. If it doesn’t work out, the group won’t be held responsible, the boss will. Never, ever defer your responsibility as the hiring manager.

Final thoughts:

Interviewing is hard. The price paid for a bad hire can be crippling for an organization. That makes the interview process so important.

Realize that you don’t need to make a decision after one interview. If there is more you need to know, then schedule another interview. You have to make the best decision possible or you will have a problem on your hands for months.

Finally, be sure to have enough class to call the candidates that you won’t be selected in person. Don’t send an email, pick up the phone and make the call.

I have had to make this painful call way too many times. Trust me when I say that the candidate won’t want to be on the phone any more than you do when you share the news. I always try to give honest feedback that they can help them use in their future job searches. It may help, it may not, but it is my way of thanking them for their time and interest.

Interviewing is hard. Hopefully the plan above will help you conduct your interview a litte better.

Below are some other resources that I find helpful:

8 Tips on Conducting Great Interviews

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