LMSM 50 | Job Interview Questions


In this episode, we look at five of the most common job interview questions. We start by discussing the purpose of each question from a company’s perspective. Why are these questions valid and how do they help companies make better hiring decisions? Next, we approach each question from an applicant’s perspective. What are the best kind of answers and what should be avoided at all costs?

The five interview questions covered in this episode:

    1. “Can you tell me a little bit about yourself?”
    2. “What is your greatest strength?”
    3. “What is your greatest weakness?”
    4. “Can you tell me about a failure that you learned from?”
    5. “Why do you want to work here?”

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How To Answer Five Of The Most Common Job Interview Questions

In this episode, we look at the top five most common interview questions. We look at them both from a hiring manager’s perspective and also for a job seeker. We look at why a hiring manager would want to ask this question and what they should look for. We look at it from an applicant’s standpoint of what points they want to touch base if they want to impress someone that they’re interviewing with. I hope you guys enjoy this. This is a fun episode and it’s based on a couple of thousand interviews that Frank and I have done on both sides of the table. If you are new to our show, please hit subscribe and turn on notifications. If you are a longtime follower and you have not given us that five-star review on Apple Podcasts with some nice comments, please stop right now and take the time to do that. We’d appreciate it.

Frankie, how’s it going?

We got to get serious. We’re doing a serious topic. No cursing.

We are down to brass tacks. We are helping people find jobs that pay extraordinary amounts of money and get out of terrible jobs by interviewing better with the seven most common interview questions out there. Frank, do you know how I chose these seven interview questions?

Some half-assed internet research.

It’s right. I used the data on this. These were the most-watched answers on LinkedIn Learning center. They have a whole learning center in interviewing different interview questions. These seven questions that we chose to talk about are the most viewed. These are questions that people are interested in. In looking at the comments section, it’s interesting to me how much anxiety is around some of these questions, the ways some people react viscerally to some of these questions that we’ll get into, and the nerves that it gives them. A lot of that is largely misplaced. More of it is misunderstandings of what an interviewer is trying to do and probably a little bit of inexperience.

When I read this list, I remember worrying about these questions as an interviewee. If you count screening people at job fairs, it’s got to be into the multiple thousands, physically sitting across the table and interviewing people on well over 1,000 interviews. These questions are commonplace to me. They’re things that I don’t react to or get a visceral reaction from. I remember being a scared kid interviewing for an internship, for my first job, or a couple of promotions and thinking about these questions.

The theme for me is this, preparedness in an interview is incredibly important. You need to know who you are and what you’re interviewing for. That’s big. You’re big on research in the company. I’m big about coming into an interview prepared. When I would interview, I had a list of accomplishments and I had a list of faults. As I got older and I got more experienced, I could build on that list. Having good things to think about in front of an interviewer is critical.

I’m well north of 1,000 interviews myself. As a senior executive for many years, we had to hire 100 people. I had to make 100 offers to folks, which meant I was screening, reviewing, and interviewing 400 or 500. I’m screening resumes and looking at applications and things sent over my way. I didn’t interview all of them, but I’ve given a lot of thought to why I asked certain questions.

Figure out how to be yourself in a job interview. Click To Tweet

When you talk about anxieties around things, a lot of these questions that we’re going to cover, to me are softballs which I find interesting that someone would be so nervous about it. Sometimes I just want to get to know you a little better and I give you something open-ended. I always find it interesting what people choose to talk about. One of our first goals as an interviewer is to help you relax because I understand the anxiety that comes.

Some of these jobs are changing people’s lives, especially if you got a job that’s paying you $20,000, $30,000, $40,000 or more. It’s an executive role with equity. I understand the life-changing moment this can be for somebody. It is hard to get to know someone if they are stressed out. I feel like an interviewer’s first job in the first 5 to 10 minutes is to get that person comfortable so I can see who they are and get them comfortable with me personally. They’re not thinking about, “Don’t screw up,” which is human nature. I come into an interview as a kid out of college thinking, “Please don’t screw this up. Four years of college, I can’t blow this.” The sooner I can get that person to not thinking about screwing up and just thinking about being themselves, the better of an evaluation I can make.

The biggest mistake people make in an interview as the hiring manager is the hire for likeability. If you’re going to give yourself the best chance to be hired, be likable. The easiest way to be likable is to be relatable and can be communicated well in a way that you fit. You have to think about this. The person interviewing you is going to be working with you. Do they like you? Do you give off the vibe of, “This person will make my life better if I’m working with this person more and more?”

Those are the things that you want to strive for in an interview. If you are nervous, what I always default to, especially as I get older, is go to truth. If you’re nervous, say you’re nervous. “I screwed that one up. Can I get that one back? I thought of something different.” These are things we can talk about as we go through this. When I have had someone in front of me who has been honest, they’ve had a way better chance. If you screw up the first question, it’s not over.

These are the things that we want to reinforce. Come in with a plan. Mike Tyson said, “Everyone has a plan until they get punched in the face.” If the first question punches you in the face, try and regroup, figure those things out, figure out how to be likable, and figure out how to be yourself. Those are the things that if you convey it, you have a better chance of winning.

You said something that’s important, where you talked about the biggest interviewer’s mistake is hiring someone they like. If you’re reading this and you’re preparing for an interview or you’re looking for a job transition, if I were researching something and giving you advice on what to research, I would look up for unconscious bias and I would study it because every interviewer has to fight it. It doesn’t mean that they’re prejudiced. It just means that they have unconscious bias. The whole concept of the unconscious is you don’t know you’re doing it. Primacy bias or first impressions matter. How do you make a good one?

I would say 50% of people win the interview in the first two minutes if they’re with an untrained interviewer. Recency bias, which is I remember first what I saw last. Did you close well? How did you do in the last 3 minutes or 5 minutes of the interview? Did you close strong? Just like me bias is the bias where you see somebody and say, “It reminded me of me when I was younger.” That doesn’t necessarily mean it’s going to make a great employee. It just means that you’re biased toward someone like you.

There are 25 biases that you can look up. Frankie, we should probably do an entire episode on this where we talk about bias in interviewing. I would look that up because your job as someone who’s interviewing is to take advantage of every opportunity you can. If that means playing to a bias that an interviewer has and doesn’t know about, so be it.

LMSM 50 | Job Interview Questions

Job Interview Questions: If you screw up the first question, it’s not over. Don’t lose hope. Keep going and make yourself likable.


Our goal is to get right into the meat. This is a perfect time to transition to question one. This is a question that came up number one on the list. This is always my opener. This is Ian’s opener. It’s some derivative of, “Tell me a little bit about yourself.” What I usually say to someone sitting across from me is number one, “Thanks for coming in.” I offer them something to drink. I don’t usually wear a jacket anymore. When I wear a jacket, I used to take it off and put it back on my chair and invite them to do the same.

Those things in some formal cultures get you to relax a little bit, and then let’s start with something easy. Tell me about yourself. It comes down to research, knowing the company you’re working with and the people. Tell me something about yourself is a wide-open question. I’ve seen people flub it and I’ve also seen people crush it. What Ian is talking about is strategically answering it as well. Ian, why don’t you dive into the ways that you’ve seen this work insanely well?

Frank is right. This is the number one most viewed question on the LinkedIn Learning page. From looking at the anxiety around, it freaks people out because it’s so open-ended. A typical interviewee likes specific interview questions. A lot of people would be worried about, “I have a lot of ways I can go here and I’m probably being evaluated on which route I go.” It makes them nervous.

It’s like a menu at a restaurant that has too many pages and it stresses you out because it’s a paradox of choice. The paradox of choice is playing here of, “Where do I go here? Do I go personal? Do I go business? Do I start to talk about my resume right away?” For both Frank and I, when we interview and ask you something like this, we’re trying to gauge what you’re going to say but also get a little feel for who you are as a person.

Sometimes when someone freezes up on this, I’ll get even more specific like, “Where did you grow up? What’s it like growing up in Kansas City? What things were you into growing up? Who are your influences?” I’ll get a little more specific if you don’t know where to go with this. Let’s stick to a bias that I already talked about. This is where you can play the just-like-me bias in your area. Frank, if you went and googled Ian Mathews and you clicked on the first 4 or 5 links that you could find, what are some things you’re probably going to find if you want to learn about me? You know me and my internet profile. If you had to go interview me and you looked me up, what are some things you can learn about me?

I would imagine the things that are going to come up first are probably Forbes, Twitter, Quora, and places where you write. I just look, Twitter is 1st, Forbes is 2nd, LinkedIn 5on4 Group is 3rd, and then different articles.

This show doesn’t turn out because no one’s watching it. The SEO is not good. You have to go to the third page of the results to find it.

Those are the things that pop up for you first. Clearly, what you understand quickly is this person has a footprint and you can look at it. If you click on Forbes, for example, it talks about careers and contributions. LinkedIn brings you right to his 5on4 Group. Ian’s big on this and he’s big on prep, knowing who you’re interviewing with, and being prepared to talk about those things and create likeability.

When I was prepping for an interview, the internet wasn’t as pervasive. There was usually a social event. The night before, there was somebody within the company. I would create some type of story or likability to that and talk about it. One of the things that are important is explaining the interview process that typically, interviewers are not doing. Ian and I aren’t talking about job fairs. We’re not talking about the phone screen. We’re talking about the physical in-person interview.

That’s different nowadays because we use Zoom a lot or some online camera app type of thing because of COVID and ease. Typically, if we’re hiring anybody of significance, not an entry-level position, there’s going to be an in-person. Not only is there an in-person, but you’re usually going to interview with a panel of people. If you were interviewing at my company, you might interview with me and three others.

Let’s explain why that happens. You do that because you get 3 or 4 different people looking at somebody. You need 3 or 4 different inputs because this is who’s going to manage them. This is relevant because you’re going to be telling many stories. You could do that on repeat or you can do it in a way that is unique. If you were to walk in with me and you interview with me last, and you stumble through this question, I’m going to think you’re probably not a good interviewee. If you were to say, “I’ve already talked to Angelo and Eddie about these things. Are you cool if I talk about this?”

If you’re strategic and you’re thinking about who you’re interviewing with, you pick things that make sense. If you had done the right research, you’re going to know that Eddie’s from Tennessee, Angelo is from Buffalo, and I grew up in Florida. You know a little bit about each of us and you pick something that allows the interviewer to grasp onto it.

The other thing is let’s say you’re out of a unique story and you’re out of facts about the people. Do this, “I told Angelo and Eddie a real personal story. Is it cool if I share with you something from the business?” Sure. You’re setting your frame. I’ve already done these interview questions with a couple of people. I know you all are going to talk. Not only that, I’m going to pick a different avenue for you here. The people whose eyes are like deer in the headlights are not great interviewees. People who understand what they’re doing can take control right there by telling me they’re prepared and they have their bearings.

You have to look at failures as opportunities to grow. Click To Tweet

Stay focused on the research. This is a rapport-building question and your goal is to try to connect with the interviewer. You know my footprint. You researched it. You know what I write about and what I podcast about because you’re with me every time. What are some interests that would pop out that are public or things that I’m interested in?

The things that pop out quickly are a lot about business like hiring, culture and people. If I get into it and click on a few of these links, it’s going to take me to the 5on4 Group, which I know the focus of the 5on4 Group is to create unfair advantages for people in the work environment, cases that will give you a leg up. There are tons to talk about there. If I go a little bit further, it would take me to your Facebook page, which most likely has a picture with you and some people in your family in it. There’s no doubt within the first seven pictures I clicked on, somebody’s going to be wearing something from Detroit. Very quickly, I’ve got twelve things that I know about Ian.

I am not the biggest sharer online. I’m in the bottom twentieth percentile of people that shares a lot personally, but if you click around a little, you’re going to see I’m a sports fan, I coach sports, I’m into baseball with my son, I love going to my daughter’s stuff, I’m married, and I’m from Detroit. You’re going to see all that, what I write, what I post, and what I talk about. It’s not hard to find those things.

My advice is to do a little homework on someone. I would say this for any sales call you ever make too. Do some homework and know the person as well as you possibly can. There are a million things I could tell you about myself that I’m interested in. I like to read books, travel and do all this stuff. If I’m meeting someone, I’m going to try to find some things that we have in common, so when you ask me to tell you a little bit about myself, I’m going to share things that I know are also your interest.

If I see that you happen to be a dad and you coach baseball, and I’m interviewing with you, why would I not lead with that? “A little bit about myself. I spend most of my time on baseball field coaching these days.” You’re immediately going to get the interviewer to cut you off and say, “Really? What’s the age? What group are your kids?” If they’re not into sports, “I’m a big reader.” Those are two very different things. “I coach youth sports and I love to read.” Neither of them is lying. There are different aspects of who I am as a person.

If I’m reading someone’s online persona and they happen to be talking about books all the time and favorite book clubs they’re in, I’m going to lead about, “I love to read. I’m a voracious reader. I read all the time.” That gives me the best chance of connecting with that interviewer early in the process. The reason why homework is so critical in telling me a little bit about yourself is that’s your opportunity not to show that you studied that person. It’s your opportunity to connect quickly and show, “You and I are similar people because we share common interests.”

I understand everything you’re saying but fundamentally, I have a different way of doing it. I don’t understand those things. I’m not an incredible researcher. It’s not my strength. What my strength is and what I retreat to is I try to tell interesting stories. If you have the ability to connect, do it. If you’re more like me and unlike Ian, and this is harder for you to figure out how to connect the dots before you get there, have a cool compelling story. Tell me something neat.

I was single into my 40s. There was a section in the dating section and it was Tell Me About Yourself. At the bottom, it was favorite books, favorite hobbies or favorite TV shows. If you were telling me on the second line your favorite TV shows, I don’t want to go out with you ever because there’s a section for TV shows. Tell me a cool story about yourself. Get me interested so you can figure out the angle and impress your interviewer with your prep, awesome.

If that’s not your style, tell a compelling story, just riffing. “I was raised by an electrician who was raised by an electrician, who is also a police officer and a cop. My family’s hard work is some of the cool things that we bonded over. I loved as a kid going out and working with my granddad and my dad on construction sites. My fondest memories were in construction and doing this. I always knew construction was a life for me since I was a little kid.” That was a story I told as a 22-year-old coming out of college because I was interviewing with construction companies. My guess is if you were in a construction company, you probably have a similar story. I didn’t know who it was. We didn’t have the internet but I told relevant stories. I didn’t go right in the clubbing in Ibiza. I told things that were relevant to an interview.

A lot of people try to steer away from the personal here. I never do that. I always say I’m the son of a steelworker and a teacher because it gets people to think a little bit and makes me a little more human than a suit with a resume. I did this all the time when I was at GE and I would talk to customers. I’d go meet a plant manager of an auto plant or something and they say, “Tell me a little bit about yourself. How did you get into this line of work?” I’d say, “My dad was a steelworker. His dad was a steelworker. I’ve been around industrial folks my whole life growing up in Detroit. Every uncle worked in an auto plant.” Immediately, I went from this punk college grad in his pleated Banana Republic pants to one of us like, “You’re blue-collar growing up.” I would share those little tidbits on purpose because they told a story without saying many words. A son of a steelworker means something to people like that.

What I want to impart here is this. If you’re reading this and you’re interviewing, we aren’t. We’ve got jobs and we’re trying not to work. We’re dealing with the opposite. What you need to do is find that talk track that makes you uniquely you, that allows you to distinguish yourself at this moment. A business interview is mostly about business. If I asked you a personal question like, “Tell me about yourself,” if you do it properly, you go personal, and you build compelling things that I can pull on in my entire hour with you, but you have to recover from this.

If properly done the way Ian has talked about and the way I have talked about, coming from construction, coming from Detroit, it comes back. It’s almost like your thesis statement for the entire interview that can be drawn back to you. The trick here is there isn’t a trick. Be genuine, be yourself, say something compelling, and connect the best you can, but give the interviewer something that allows you to be likable, connectable, and wants me to ask more questions. If you do that, you’ve successfully started off the interview the right way.

LMSM 50 | Job Interview Questions

Job Interview Questions: You take that elevator pitch and adjust it slightly for your audience, so the story is similar, but the connectivity to the interviewer is quite different because of what you did in those little finite details.


You should be personal here because you have to be. How do you tell someone about yourself without being personal? You have to connect the personal to what’s in it for the interviewer or the hiring manager. Son of an electrician, I’m not afraid of hard work and getting my hands dirty. Son of a teacher which Frank also is. It’s been instilled in me from a young age to always put education first. I’m still a big reader. I’m always learning. I’m always trying to educate myself and get better. My mom taught me that. I like sports. That means I’m competitive. I’m a big team player. I grew up playing multiple sports my whole life all the way through high school. It instilled a deep sense of teamwork and competitiveness in me. That still lingers with me.

Those are all personal things that I shared but they also tell the interviewing manager, “This is why I’d be a great person to hire. If you like competition, if you like someone who’s not afraid of the work, the grind, who’s not a silver spoon, if you like a lifelong learner, a quick learner, an educated person, I’m a good person to hire because of those little personal tidbits that I shared with you.”

Here’s something else. As a human being functioning in society on Earth, spinning around the sun, you’re going to have opportunities to open your mouth in front of people your entire life. Sometimes it’s an interview and sometimes it isn’t. Having a personal elevator pitch is incredibly important. Ian has talked about it in front of steelworkers talking about his dad and his mom. Being able to quickly articulate what you do in 30 to 90 seconds is something you should always have. It should be evolving. The 22-year-old version of this and the 46-year-old version of this for me were different.

The point is if you have that in your head and you are ready to talk about it always, this question is a lot easier because you know who you are and you know that elevator pitch. If you’ve done it properly, the pitch is easy because you then move it to, “Ian, you might find this interesting coming from Detroit. As a baseball coach, I love this.” That’s how you take the elevator pitch and take it from good to incredible with a little bit of bragging.

Everything we said, I’ll show you how you link it to your homework. When I interviewed with NVR, I asked around a little bit about who I’d be interviewing with. I was interviewing with the CEO, Paul Saville, from Pittsburgh, who has a detailed accounting background. I was interviewing with Joe Madigan from Pittsburgh, more of a personal backslapping guy and his dad worked in the steel industry. I was interviewing with Bill Inman, who is a mix of both of them but came up in sales and his dad worked in an auto plant. I learned all that before I interviewed with any of them.

When I did my “Tell me a little bit about you” with Bill Inman, I was talking about all my time in Detroit being around auto workers my whole life because his dad worked at Ford for 40 years. When I met with Joe Madigan, I talked about steel mills. I brought that piece up. When I met with Paul Saville, I focused on my engineering and process background because that’s how he thinks. He’s methodical and process-focused. I share bits of who I was based on the homework I did on those three. It was all the same but it was nuanced based on who I was meeting with because I found out a little bit about them.

That’s how you do great. You take that elevator pitch and you adjust it slightly for your audience. The story is similar but the connectivity to the interviewer is quite different because of what you did in those little finite details. We’re making it so the person hearing you really heard you.

The number two question that people want to know about is, what is your greatest strength? There’s a companion question that goes along with this. I know this is a popular question. I’m curious, Frank. Do you ask this question?


I do not either.

I don’t ask this one or, “What is your greatest weakness?”

We don’t ask this question but it is one of the most common questions. You should probably expect that someone is going to ask this question when you go here. When someone asked me this, I like to be a little self-deprecating on this question. I’d like to tell a little bit of a joke. I feel like I have a lot of strengths. I don’t lack in the ego department. If someone asked me this, I’ll say something like, “I’m glad you didn’t start with weakness because that would take us all day.” I’ve said that multiple times in interviews and it always gets a laugh. I also say, “When you’re ready to ask me about weaknesses, I’m not going to be afraid to talk about them because I’m human and I have them.”

Another way to joke about this is if someone says, “What’s your greatest strength?” You could say, “Clearly, it isn’t interviewing,” or something like that. Telling a little joke if it started off slow in your interview. This is where job matching matters. If I’m interviewing for a sales job, I’m probably not going to talk about my process mindset so much. If I’m interviewing for an engineering job, maybe I’m not going to focus on my ability to acclimate with the new crowd all the time as much and my ability to sell and persuade. Those are both strengths of mine, but what matters is you’ve studied the job description before you get this interview question.

You should know if it’s a project manager position. Let’s say it’s a construction project manager position. Being focused, task-oriented, getting things done, and meeting deadlines, those things are incredibly important. Frank talks about this a lot. You’re going to interview with three people and you probably are going to interview with the most junior person first. That’s your time to learn about as much as humanly possible what did the best people in this position do well. When you do your 2nd, 3rd and 4th interview, you better be listing strengths based on what the best people in the company already do well.

In a corporate environment like we would line up for interviews, we’d have lunch, and there was no way in hell there was ending early. In my business, if someone bombs interviews 1 and 2, you never make it to me. That’s real, “We’re a small business. It’s just not a fit.” To Ian’s point, you should be improving with every interview because the interview is part of the due diligence process. You’re in the crucible for the first time.

I’m going to blend strengths and weaknesses together and talk about this. Ian and I are both children of school teachers. We talked about this ad nauseam. I was raised to never show off, never run my mouth, never do those things. I struggled in an interview to talk about strengths for all of my twenties. I finally had an executive come up to me and say, “When someone asks you for your strengths, do not be a shrinking violet. Answer the damn question. You have strengths and you’re confident. Answer it.”

Someone else told me, “When you’re inside that room and the door closes, you’re Barry Bonds.” Barry Bonds in my 20s and 30s was hitting 70 dingers a year. He was a mouthy big guy. This is your opportunity to sell you. Do it how it’s comfortable and authentic to you, but be prepared and talk about it. If someone said, “Tell me about your greatest strengths,” I’m going to have a hard time with that but I’m going to say, “Can I tell you about a couple of accomplishments I’m proud of?” For me, I would do that because I like telling stories that have good endings. It’s compelling. That’s how I answered a lot of those questions. What it would do is it would give the interviewer 5 or 6 other things to ask me about.

One of the things that I was taught early is a good interview is about four questions. You say enough where the interviewer doesn’t have to look at the interview sheet to ask you more stuff. You’re going to get these seven questions thrown at you if your prep is wrong or if you’re not compelling. If you steer the narrative, take advantage of each opportunity, and tell your story, that person is interested.

I’ve got emails, phone, texts, and things to go do. I have to interview you. I want to hire you. It’s your job to take all that inertia and bundle it up in a way that gives me enough Easter eggs that I can continue to ask you questions. Whenever you talk about strength, be self-deprecating. Whenever you talk about a weakness, talk about the success that came behind a weakness. Tell a compelling story. If you do those things in an interview, it works insanely well.

Tell exciting and compelling stories about yourself in a job interview. Click To Tweet

Interviewers will ask you this question because it’s on their list. They might be inexperienced or this might be their favorite question they’d like to ask because someone asked them this question many times when they were interviewing. You’re going to get asked this. With an experienced interviewer, they don’t need to ask you this question if you handle the tell me a little bit about yourself right. Tell me a little bit about yourself that should have covered what your strengths are. Through the interview, by telling stories about your career and things you’ve done, you’re telling me your strength. That’s why I don’t ask what’s your greatest strength because I’m asking more about specific things like situations you’ve been in and how you handled it. By listening enough in there, I’m figuring out what you lean on and what’s your go-to pitch.

My first question is, “Tell me about yourself.” If you do that right, I don’t ask my second question. My second question is, “Tell me something you’re proud of.” I’ve gotten out of you whatever you think of yourself and you’re willing to share and something you’re proud of. If you tell me something you’re proud of, I’m going to draw strengths out of it. I’m going to then say, “What roadblocks did you come across inside of accomplishing this?” I ask those questions and work through them because I don’t follow the script. I want to dig that. If I’m following a script, you’re doing a terrible job of sitting in front of me because I’m not getting what I need out of you to ask compelling questions back.

I’m going to use another personal example to wrap this one up. I’m interviewing with the CEO. The operation that I was going to come in as a vice president had terrible customer service. It was an entitled sales organization that had long since given up on putting the customer first. I wasn’t asked, “What’s your greatest strength?” I was asked why I felt like I was uniquely situated for the position or what makes me unique as a manager of salespeople.

What I used in that situation is I said, “In my first sales job, I started with zero customers and everyone else had a big base of customers that they call farmers. I was hired as a hunter. I made 100 cold calls a day and people hung up on me, and it sucked. When someone finally spent money with me, trusted me, and gave me an order, I remembered what it felt like to have no customers and it never left me. I remembered how hard it was to go get my first customers and to keep earning their trust. As a leader, I’ve always been absolutely fanatical about listening to customers and doing everything I could to give them what they want. When someone reports to me who doesn’t have that in their gut, I have to find someone else.”

It resonated with the CEO when I told that story because he was sick and tired of hearing about his entitled salesforce. To have someone that had that in their gut, which is true about me, but I could have used 100 different strengths. When he asked me that, I chose that for a calculated and specific reason to share it because I knew that’s what they needed in the organization to fix the problems they were trying to solve.

The next one we’re going to get into is, “What is your greatest weakness?”

Weakness and failure are similar. We cover weakness because we can do that now that we’ve been on the other side.

If you’re going to talk about a weakness, I will lead into the next question, and that’s, “Tell me about a failure you’ve learned from.” I would never bring up a weakness that I didn’t have already solved. What Ian talked about is how he used that feeling with the CEO. The CEO, if you’ve never looked him up, has a house in Palm Beach and has a private plane. He’s probably a billionaire, even though he’s private and quiet but he remembers starting. Everybody remembers starting. Anybody who’s ever gotten to that level can still resonate with starting.

What I have always found as a success recipe is it’s not starting a new position or succeeding in a new position. It’s, “Can you identify the path you took? Can you show me how I learned a skill? Can you show me the first time I learned a skill that was hard?” The second time I learned a different skill, I used those first lessons and adapted them into a second lesson. How did I do that in a third lesson? In my career specifically, I went from being a home builder. I didn’t know how to summarize it when I was interviewing, but when I was physically building houses, I could tell you the process.

When I moved into sales, it was a slightly different process, but the recipe was similar. There’s frustration and things you got to overcome until you can master it. Managing people was third for me. When I stacked all these things up against themselves, they all had the same pattern. When you get into an interview, you talk about, “I stunk at this. This is the process. This is how I did it. This is how we went through it. This is how it was when I became a master. This is how I can do it from sustainability.”

Ian took all the way to the bottom in that process and he got granular with it. That’s how he won the CEO over because, at its core, that’s what that business needed. Ian had multiple successes but he told a good story to someone who’s an engineer, smart and detail-oriented. He knew that that was the friction point in the business and he focused there.

I needed to prove to them that I was the solution to a problem they had. I was smart enough to understand what their problem was and that I could fix that problem. Telling them about strengths that wouldn’t fix that problem would be nice to have, but I showed them the strengths I had that they need to have. This is number three. “What is your greatest weakness,” is typically a companion question to, “What is your greatest strength?”

An interviewer will typically say, “What is your greatest strength?” List them for that, and then next on their list of questions is, “Converse me. Would you like to share with me your greatest weakness?” I’m going to start by saying a couple of things you shouldn’t do here. Bad advice is to list something that’s a strength. Someone might say something like, “I’ve been told that I cared too damn much about my teammates,” or something nauseating like that, where they’re listing an actual strength and they’re trying to be cheeky. They’re trying to mask it as a weakness. “I’m too organized,” or, “I’m a perfectionist. I have to do things right or I work too hard. I work too late into the night.”

LMSM 50 | Job Interview Questions

Job Interview Questions: Being focused, task-oriented, and meeting deadlines are all important.


A decent interviewer is going to see right through this. I would not do that. There’s a couple of reasons why anyone would ask about a weakness. One, they want to see if you have enough intelligence to not list something that’s going to blow you up. A place here is not to say, “I’m a sucker for some good marijuana.” You’re not going to say something dumb here. This is an intelligence clue. You’re not going to come out and do that. Also, they want to see, “Are you confident enough to list something?”

If you get asked this question, list a weakness that you know isn’t going to hurt you in the position. Let’s say it’s a position where you’re going to work in a team and you already know that. This can be a highly team-oriented position. If someone says this, “List the weakness here,” you could say, “I’m an extroverted person. I’ve learned about myself that I work best within teams. I struggle in work situations where I’m isolated for a long period of time where I don’t get interaction with the team.” Now you’ve listed a weakness, “I don’t do well when I’m isolated for long periods of time,” for a position that never gets isolated for long periods of time.

You’ve listed a weakness that isn’t going to hurt you and isn’t going to make the hiring manager think, “That is a red flag. We can’t hire that person.” I wouldn’t list that weakness if this were an engineering role for computer programming where there is no interaction with the team and you’re just banging out code all day with headphones on. If I’m the manager, I’d be thinking, “I isolate my engineers for long periods of time. He’s going to hate this job.” I would only list that weakness for a job that I know wouldn’t hold you back.

Situational awareness is critical in everything in life, but it’s critical in an interview. Pick the right stories. The company brought you in because they want to hire you. That’s the goal. We don’t want an endless interview. If you give us enough good nuggets to pull it forward, that’s the point. What Ian is talking about is a strategy that goes around that, but still being honest with the weakness.

A similar but different question is, “Tell me about a failure that you learn from.” Frank, I always ask this question. This is a staple. If I only can ask you three questions, this is on there. Have you asked this question ever?

I will ask something similar to this almost always. If it doesn’t get volunteered, I ask something similar.

The reason why I always ask this question is I’m judging your reaction to it. Does it freak you out that I asked you about failure? The answer to this question tells me so much about a person’s confidence. It tells me about their mindset. Do they have a growth mindset? Do they have a fixed mindset? Someone with a growth mindset sees failures as part of the process like a scientist. It’s part of the process of their maturity and growth. They’re almost grateful for failures. They’re almost glad that they’ve happened so that they can take their next step in the evolution of their career. For me, I will always ask this because I like to work with people. One, they’re not afraid to fail, but two, they look at failures as ways to get better and grow because that’s life.

If it’s not about a failure, I try to get it and pull it out of what I’ve already gotten from you so far with, “Tell me about yourself and give me some strengths.” What I might ask for are hurdles that you’ve overcome. It’s always something along those lines. This comes back to what I said earlier. Telling the story about learning. Learning is not a straight line. It’s a jagged up and down process. In the process of learning or becoming a pro at something, if you can identify the failures, you’re going to connect with the interviewer because they have felt that. I’m going to ask you a different question, Ian. Do you specifically care about the answer to your question if the person tells you a compelling story?

I’m going to say it depends. A compelling story is good. The one area where I am paying attention to is, was failure an issue of judgment? There’s a difference here. When you get this question, when you put together your list of failures, I will typically ask for a second. I dive into failure. I love to see how people talk about it. I have a couple ready. There’s a difference between an effort failure, an ambitious failure, and a judgment failure. They’re very different.

If you are showing me failures that are consistently bad decision-making on your part, you’re probably going to be a bad decision maker here. If you’re showing me failures where you went for it like, “I finished fourth in qualifying for the 100-meter breaststroke for the 2008 Olympics.” That’s a pretty good failure to share with me. To me, that is not a failure. To you, it is. You are ambitious and came up a little short. Versus, “I qualified for the Olympics and then didn’t get brought on the trip because I got caught for doping.” That is a different failure. One would make me pause and one, I would say, “That’s a good failure. I’m impressed.”

The reason I asked that question of you is this, tell me about a failure you’ve learned from. I am way less fixated on that question than I am on what you say about it and what you tell me about it. If we use the example of you finishing behind Michael Phelps and two other people to get in the pool in the Olympics, that’s a pretty incredible story. I can ask some questions about it and dive into it. To me, it comes down to the process and what’s happening.

I like how you’ve determined it as an effort fail or a judgment problem and you’re trying to pull at that. Those are the things that you can do on the fail side that impress people in the interview process. We’ve all failed. We’re lying to you if we say we haven’t failed. Understanding it and knowing the process and how you get over it is huge. If you can say, “Now I’ve identified what I’m getting into failure and prevent it from happening and I’ll go past it,” to me, that’s a big part of the learning process that happens inside of businesses.

Start with some humor because the interviewer is looking for your confidence here. They’re looking to see how you see it. Are you confident enough to talk about failures? Start with a little humor, like, “You might want to clear your schedule for the rest of the day because we’re going to be here a while if you want to talk about my failures or how much time do we have?” Get them to laugh a little because you’re showing, like, “There’s a lot of them. I’m not afraid to tell you I’ve failed a lot. That’s why I’m sitting here getting interviewed because I’ve learned from them all.”

“I did everything I could to keep my resume to two pages mostly with successes. However, if it was failures, it could have been a small book.”

Have a little fun with it. Joke around a little bit. A big thing here is you want to pick examples where you have a subsequent example where you showed that you learned, evolved, and took a different approach, “I hired a manager and it was a poor decision. What happened was I promoted the best person in my office instead of promoting the best leader. Here’s how it went bad. Here’s what I learned from it. The next time I had to make a promotion, here’s how I did it completely differently. Here’s the result. Here’s what I learned from it.” You always have like, “I failed. Here’s what I learned. Here’s the next time I was faced with the same decision, and here’s how I went a different direction because of a direct result of that failure.”

Being prepared in an interview is incredibly important. You don’t simply show up without a plan. Click To Tweet

The learning process is so big. When you can show that you’re getting smarter every single time you go through a failure, that is what an interviewer looks like. Your goal at a company is to get promoted a bunch, which is going to give you opportunities to fail a bunch. If you are the type of person who has short-circuited the learning process and can speed through it, you are the person I want to pay a ton to because I know I can give you a lot of things to handle.

Wrapping this one up, pick some failures where you shot for the moon and came up short. Pick some goals that are going to impress the person in front of you like, “Damn, you went for it.” When you talk about failure on a goal that’s weak in the first place, where you set the bar low and then came up short, you’re showing me that you don’t have a lot of ambition. Even with that ambition, you still aren’t getting it done.

Number five, for whatever reason, this question irritates people. It comes across as arrogant which is, “Why do you want to work here?” From looking online, a lot of people are like, “What makes you think?” It’s like, “Easy. This is meant to be a softball as well.” This question, I won’t always ask it exactly like this but I’ll ask, “What have you learned about our company? What has you interested in us?” I won’t ask, “Why do you want to work here?” I will ask, “What has you interested in us or this position?” It’s because I’m curious.

What I’m looking at is, “How prepared are you? How much homework did you do? Do you have a reason for wanting this job? Is it a paycheck? Is there something about our company and the way we do things that you want to work here and you could see yourself making an impact?” Motivation matters. Inspiration matters. Feeling like they have a purpose when they come to work for you, they’ll be better workers. That’s the reason why I’m going to ask some variation of, “Why do you want to work here?”

As the employer, you need to know who you are and what your company is. I wouldn’t have asked this question for the first maybe eight years we’re in business. I would ask, “What’s compelling about this position? Why are you interviewing?” The company was hard to discern what the hell was going on with the company. I do ask that now. I ask that question and I want to drive that, “What is it? Is it you can’t find something else? Is there something specific we’ve done? Have you heard about us?”

An interview is an opportunity for an interviewer to understand what the market thinks of it to get an unbiased opinion and its data points. If you’ve done the research and so and so speaks highly of you or I saw this or I know someone or I watched something and I thought it was interesting. I’ve always wanted to get into this line of work. “I flipped a couple of houses and you guys do hundreds of them. I found that appealing because I understand how hard this is.” Something interesting that draws us in.

What it comes down to is anybody can check the box. We want people who are passionate about checking the box, doing the job. I don’t want to hire you and hope that that’s the job that you have forever. My hope and goal is that you are someone who can move up in the organization and make us better. If you give a compelling answer here about, “I saw this as an entry-level position to hopefully be something else if I’ve earned it.” Those are things that you can turn into not the company but you, and you frame it inside what the company has put out there.

I’m going to come back to it again. If you’ve done your homework, this is where it should come out. If I were interviewing Frank, I could see that he posts videos online. There’s a lot on his website. There’s a lot of social media about his company and the things they do philanthropically. There are a lot of things I could bring up here where I would say, “This is why I’m excited about working here. Honestly, Frank, you’re the reason why I want to work here. I’ve watched a lot of your material. This is what I’m excited about.” This is where it should come out.

Let’s say you’d say, “This company likes to promote from within. I see you’ve been with this company for twelve years as a manager. This company obviously must treat people well. You’ve been promoted several times since you’ve been here. That motivates me. You weren’t hired from the outside. You obviously must like it.” You can turn that around, “What about the culture that keeps you here for so long in this position because that’s unusual?” You’re proving, “I’ve done my homework. I have a good reason for being here and wanting to work in your company.”

As good interviewers, we know where you got information. I might know you got it from Carla, Eddie, and then Angelo. Ultimately, you sit down with me and you state things that they told you. I’m okay with that. That means you’re adaptive. That means you’re thinking. That means you’re striving to win an interview and you’re using new fresh data and using that in front of me. That’s positive stuff. That’s how you can build a compelling case, “Carla had done these two jobs. Eddie has done these three jobs. Angelo has done this.” That’s incredible. “I came in here excited. I’m even more excited after meeting them about what could be the future.” That’s a great answer.

Frank, we said we’re going to keep this to one hour. I know that we build this as seven interview questions, but we are going to save two as a bonus for the next time we do this. We wrap this up with five questions. We have two juicy ones, but you’re going to have to turn in at a different time to get those two from us because we wanted to keep this under an hour.

It’s a cliffhanger.

You want to tune in next time for the next two. It’s like those old Batman episodes.

Job Interview Questions: It’s your job to take all of that inertia and bundle it up in a way that gives the interviewer the interest to ask you more questions.


I’ll close and I’ll turn it over to you and you can put a bow on this thing. Be prepared. Know yourself. Know the company you’re working with and who you’re talking to. Don’t just send the same formal letter to everybody. Be prepared. Be honest in your assessment, “I’m strong here. I’m weak here. These are things that I’m good at.”

If there are huge dark secrets in your life, stay away from those and strive towards things that show good decision-making. Always striving for a little bit more, being likable, being a team player, and showing some successes. If you can do that in an interview, you can win an interview. That’s it. I saw something on LinkedIn about this woman who interviewed with 85 companies and she finally got a job. Eighty-five is a ton. I immediately thought, “There has to be fundamentally something not happening in those interviews if you interviewed 85 times.”

I hope she reads this episode. You should do a little bit better than that. The last thing I’ll say is we live in a world where everything is public and everything is on social media. The entire goal of social media is to only show the tiny little snippets of your life that are perfect and put on a better show than what is going on.

If you’re interviewing a manager that is interviewing you and has any experience at all, they can see beyond that crap. I am always refreshed by a vulnerable person who is confident enough to show me the great stuff and some of the not-so-great stuff. I’m always impressed by someone who did their homework, prepared a little bit, and wants to show me the best aspects of how they can help it.

The last thing I would leave everyone with is to be vulnerable. That goes against everything you think you should do in an interview where you want to come across as Superman and bulletproof. It is refreshing when someone is sitting in front of me who is confident enough to say, “I’m not perfect. I’m far from perfect, but I’m getting better all the time.” I love a vulnerable and confident person with a growth mindset like that. I’ll hire them every time because I’m going to like working with that person.

Being honest, being you, and properly curating you for the interview environment you’re in and the person you’re in front of is a magic formula.

I hope this helps everyone. We’ll get working on the outline for the next one. We’ll do five more interview questions you’re going to get asked. See you, Frankie.

See you, Ian.


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