Crush the Interview. Strategies for Success.

A recorded interview with Chad Silverstein about how candidates can "crush" job interviews by being authentic, prepared, and intentional. Silverstein highlights common red flags (dishonesty, lack of preparation, not asking questions), recommends asking milestone-focused questions (e.g., "If we meet in a year, what must I have done?"), and emphasizes assessing cultural and role fit while listening to one’s gut. Practical tips include bringing a notebook, rehearsing 3 genuine questions, pausing to think on unexpected questions, and knowing what tasks you dislike to avoid poor matches.
Chapters
People have an agenda, period. At the end of the day, if you know what they're looking for and you feel like this is a good fit, it's not that hard to crush the interview. You have to come in with a notebook. You have to be prepared. You have to think about those questions beforehand and you really want to play them out and you want to know why you're asking those questions. I'd want to know, is there anyone else in the company right now who is currently doing the role that I'm being interviewed for and what is their performance like and how do those people, what's their career path look like? If you and I are sitting here a year from now, what do I have to do as the employee in order for you to be happy with my progress? And when I hear people say they don't have any questions, my mind used to explode because I'm thinking like, you're about to spend like all of your time here. You don't have any. You don't know anything about our company. You're not going to ask us any questions. Like, it just didn't make sense. I was trying to find someone real I wanted who's believable. If I could believe in you, and I can believe you and what you're saying, I liked you. I don't want to waste people's time. I've been in interviews in five minutes sometimes and I politely do it respectfully. But if I know right away, why would I want to waste your time?
All right, Chad, you've been interviewing people for more than 25 years. What are the most common things that you see people mess up in interviews?
That's a loaded question. There's a lot of things that I think people mess up. I think the most important thing for people is not to be so scared because they're so worried about trying to be someone that they're not. And that's really hard to do. I always used to say, when I used to coach people is that the hardest thing in the world to do is to be yourself. And so you have to know who you are. And unfortunately, people are going into interviews and they're trying to be someone that they're not. So it's like a double edged sword. They get caught trying to not be themselves because they want to be who they think the person who's interviewing them wants them to be, which is really hard do because you don't know what they want. And every interview is going to be different. Every hiring manager is going to be different. So you really have to know first who you are. And I think the biggest mistake people make is they try to be someone that they're not and they end up getting exposed in an interview. And it's just, it's a tough situation for somebody who's trying to get a job and trying to get somewhere where they're going to be for the rest of their life in a career that they love.
Right. And you think the reason most people do that is just because of nerves, really?
No, I think the first part is, you know, most people don't know who they are. They don't know, you know, what they want. And so they're so desperate to get a job because unfortunately, sometimes they're in a tough situation where they were suddenly either unemployed or, you know, laid off by their past employer or they've been out of work for a long time and they need to be able to pay their bills. You know, so people are, a lot of people are just in a tough spot. There's different calibers of interviews though, and it comes from both ends. It's the candidate, but it's also the hiring manager. You have to know who you're interviewing with. Because if you're going to want to work at a big company and you're going to be talking to a hiring manager that's 10 levels down from maybe the CEO, it's very different than going into a small company where you might interview with the CEO.
Right, right. So we'll get into preparation in a bit in terms of how much you should research what kind of questions you should ask and all of that stuff. But if you had to boil it down to, let's say, like three red flags that you pick up on on your end for whatever reason, maybe the person is coming in and they're super nervous because they need a job and so they start behaving in ways that are not authentic, let's say. But just from your end, if you had to boil it down to the three most common biggest red flags that you see as someone who's interviewing people, what would those red flags be?
The first is not being honest and transparent. They answer a question too fast and then they have to cover themselves up. Because if there's a follow up question and they weren't being genuine about whatever they were answering, you get caught. And there is nothing more uncomfortable in an interview than shooting out a question and having someone answer it very fast and then digging deep, thinking that you know something didn't sound right. And they hope that you're just Going to keep going and then they have to cover up what they said. And so then people end up rambling on and on and on and you kind of can see right through it. So that's the first thing for me, that was always a big red flag. The second thing is not being prepared and knowing anything about the company. Meaning that like they just interviewed it, set up as many interviews as they could, they spammed out their, their resume, they didn't do the proper research coming into the interview and they didn't know anything about the job. So that leads to the third most common problem was they didn't ask good questions. People would come in and my biggest pet peeve was asking people at the end of interviews, you know, do you have any questions? And giving them an opportunity to kind of flip the interview and have them interview us. Because I think it's just important for people to interview the employers as much as it is the employers to interview the candidates. And, and when I hear people say they don't have any questions, my mind used to explode because I'm thinking like you're about to spend like all of your time here. You don't have any, you don't know anything about our company, you're not going to ask us any questions. Like it just didn't make sense.
What kind of questions should, what kind of questions are good questions? One of the things that's difficult about that, I think being on the other end is that you want to go in prepared and know what questions that you want to, but you also don't want to sound like you're just asking canned questions that sound rehearsed. I think like ideally perfect world, you pick up on something, maybe that was, that was said during the interview that you can go back and forth and just ask follow up questions about. So I guess like my question is, how do you, what are some good questions to ask about the company that you're interviewing for? And how do you avoid sounding like you're just regurgitating questions that you've prepared and, and just sound, avoid sounding boring.
It's a great question, you know, So I think again, you know, it's loaded because I think if I was going to coach someone on going into an interview, what questions should you have prepared? There are two types of people. There are people who are insatiably curious about everything and they want to know more and they genuinely want to know so they can just on the spot ask great questions. And there are some people who just get frozen and they can't. So for those people who are frozen and they can't, I say you go to Google, go to ChatGPT, ask and get a list of questions. And then from that list, so that you don't sound the way you just explained it, I would narrow it down to the top three, the three that you genuinely want to know, so that it can come off like you, you really want to know. So you're going to ask it in a way that doesn't sound like you're regurgitating something that you read on the Internet and you want to obviously not copy it word for word, but why do you want to know it? People who are really good, though, in that they, they are interviewing the employers just as much as the employers are interviewing the candidates. Um, you know, they want to know, like, really important things that there's no way that the employers are going to share with the candidate throughout the interview process. So I'll give you a couple examples that I think are just great questions to ask people. The first would be, you know, what is it that's expected of me? And my favorite question was Dan Sullivan's question. I did this on the. On our insights, and it's, if you and I are sitting here a year from now, what do I have to do as the employee in order for you to be happy with my progress? So, like, if we're sitting here a year from now, like, what milestone milestones do I have to hit in order for me to have a great year with this company? And it's a great question because you'll get those hiring managers sitting back. And one, they probably don't know. Right? And if they don't know, that's a red flag because you know they're hiring you and expecting you to know what to expect when you come in and how to deliver results. But if they don't even know what the results need to be, that's a, that's a problem right off the bat. But if you talk to an employer and they know what's expected of you at a certain milestone, whether it be six months, a year from now, that's someone who's got clarity, they have goals ready for you, and I'd want to know what those are going into the job so that I don't have unreasonable expectations for me coming in. I mean, the biggest problem I saw with new employees is they didn't know what's expected of them. And that's either the employer's fault or because they didn't ask. And then they're in the job Three, six months in and they're just losing their mind because they didn't think it was going to be like this or they were told something else when they interviewed. You got to get everything up front in the interview process, in writing before you accept a position.
Yeah, I was thinking as you were talking, it's again like in the moment in an interview, it can be such a tense situation and you can feel so nervous. And when you ask a question, like, let's say that you have some sort of question prepared and you ask something like that, let's use the example that you gave, like, what's expected me out of me after a year? I've been in interviews before where like I'll ask a question and then I'm again, I'm just like overthinking things in my head that it's like so hard to actually just listen to what the other person is telling you, what your expectations are, you know. But I think what you're saying too is. And really a lot of people, job seekers, I think in particular, I've certainly been here where you don't really feel like you're. It feels like they're interviewing you and they are. But I think what you're saying too is like you should be interviewing the employer just as much to see if they're a good fit.
Look, you're going to spend all your time there, you know, so many. There's a reason why they say 70% or whatever the numbers are. People hate their jobs. I mean, that's sad. It's really sad. But it's because they took the wrong job. It's because they just needed a job and they got an offer. And when you're, when you're in a position where you need to be working, you know, you're gonna want to accept any type of an offer that you get. But you, you really have to be selective and picky and, and that's really. It starts with before the interview even starts, you know who you're targeting to try to get an interview with. But you know, if I'm in an interview and I'm not prepared, yeah, it's gonna be. You're gonna get tongue tied. You have to come in with a notebook. You have to be prepared. You have to think about those question and you really want to play them out and you want to know why you're asking those questions. I mean, I'd want to know, is there anyone else in the company right now who is currently in doing the role that I'm being interviewed for and what is their performance like? And how do those people, what's their career path look like? You know, what do they do in order to be recognized with an increase in pay? You know, when does that happen? I want to know those. Because the worst thing ever is bad surprises, right? And I'm saying from both sides, the employer and from the candidate. There's nothing worse than having a bad surprise easier from the employer though. They have that upper hand 100% of the time. And if you're an employee and you know, a year goes by and no one says anything about an increase and you're wondering, have to say, that's on you because you never even asked the question about when do we get increases and what do I need to do in order to get an increase?
Right, right. And that's appropriate to ask in an interview. You think like, I think lots of people are scared too. Is it like, is there a, is there a skill to knowing when to ask that? Is it ever inappropriate to ask?
Yes, yes, yes, there is. And it's timing. I mean, timing there it is definitely a skill. There's no, the first interview is usually not the best time to ask that question. You know, I mean, I really want to determine if, if the job is the right fit. That's the most important thing, if it's the right fit. And I would determine if something's the right fit using two criteria. One, that the job is the right fit, meaning that I can use my unique abilities and I can perform what is expected of me and I enjoy what I'm doing and I'm good at it and I can deliver results. I can exceed what they, you know, exceed their expectations. And then the second part is going to be that it's a culture fit. And to me that's just as important because, you know, depending on if you just want a job or if you want a career or if you want to be part of a company that has more of a purpose driven kind of common goals that are shared amongst the team. You know, you got, you got to ask those type of questions and know if this is the right culture because, you know, every culture is different. And it doesn't matter what they have posted up on the walls or what's on their website or in their market materials. Those types of questions are again questions you'll want to ask whoever you're interviewing so that, you know, if they can give you a shoot in their eye and tell you about their culture, that's a good sign. That's a good sign.
How much. How much of that too though, is. Is gut feel. I was thinking as you were talking about an interview that I was part of. I think I was. You know, I was telling you about this interview that I was doing. This was like a year and a half ago. And I remember getting on this interview and for whatever reason the person who was interviewing me, we just didn't have a great vibe together. It was one of those intangible things that you can't really. You don't really know why, but you just feel a little off with this person. Your jokes aren't landing like they normally would. Whatever it is just feels a little bit off. How much of the culture or I guess just how you feel about. I mean, it goes both ways too. How the employer feels about you and then how you feel about working for this team. How much of that does a gut feel? How much do you listen to your gut in that situation?
Oh, man. I will tell you that. You know, it's funny you make that comment. When I used to interview people, I probably interviewed over a thousand people easily. It's amazing when people walk into the office, when you get that weird feeling, it doesn't make sense, right? Because you don't even know the person, right? And you don't want to judge anyone. But like, there is a weird vibe sometimes that you have a certain individuals and you can't explain it. And just like that, on the flip side, sometimes you just click with people right away. So whatever reason and whatever's behind that, I do listen to my gut because I've learned that usually people are bringing their best foot to an interview. So the good things that you see, you know that's their best. You're going to see people at their best. The bad things that you maybe aren't feeling so good about, you can multiply that by about 10. Because that's what you're going to see a month from now and two months from now, because they're bringing their best. So if you're getting a weird feeling now, imagine what you're going to feel six months when they're feeling a little bit more comfortable at home in your office. So from an employer's perspective, I listened to my gut and I was a pretty hardcore interviewer and a little bit more blunt with people in a nice way. But I really had a goal for what I was looking for. I knew exactly what I was looking for. And again, that's part of the problem with the interview process is that people are walking in. It's like Russian Roulette. You don't know what you're walking into. You don't know. I, I will tell you this, though. People have an agenda, period. And at the end of the day, if you know what they're looking for and you feel like this is a good fit, it's not that hard to crush the interview because really you are just trying to tell them what they want to hear because they're desperate. You know, the one thing that I think, you know, job seekers can benefit from hearing from me was that, you know, you have to understand it from the hiring, Hiring employers perspective. They are, they have an empty seat in their office. You know, everyone's hurting to try to find great people so they have a job to fill. So if you're looking at a hiring manager who's like an HR person, they want to check the box, they want to move on and get to their next, you know, responsibility. So, you know, usually, you know, they're trying to fill seats, and so you just have to kind of tell them what you want. But again, you have to be careful doing that because if it's not the right job, you'll get what you want and it's not the right job. But I think being able to connect your skills to what they're looking for is the best thing that a job seeker can do. So if you know that their responsibilities on a job description, say xyz, then you want to be able to say that you can do xyz and then give them an example, one example from your previous job of how you've done that so that they can paint a picture in their head and see that. Yeah, I could see this gal doing that. They did it at their last job. And a lot of times people just, they're so, so trying so hard to impress the person and giving them information that's not helping them that they, they missed the point of the interview, which is these people are just thinking about themselves. They want to fill the role, they want to move on, they want to hire this person. And, you know, you're trying to overthink it and you do get nervous. And I think that does. It just, it messes people up. And I think there's just a kind of a level of comfort that you need to feel when you walk into an interview that if it's not going to work out and they don't want me, that's okay. That's. That's probably a blessing in disguise.
How honest is, is too honest or how can, can you be too open sometimes? I think it's easy to prepare for questions that are common in every interview, like, tell me about yourself. Or, you know, you expect that you're going to talk about certain skills that you have and how those skills relate to the job opening that you're interviewing for. But I think in. Well, maybe not every interview, but at least every interview that I've done myself, there come up some questions that you can't prepare for. The last interview that I did, for example, someone asked me, the person who was interviewing you, me, asks me what the last piece of advice that I got was and how I dealt with it. And I was thinking the first thought that came to my mind. I was living at my mom's place at the time. I was in between moving to a new place, and she had that morning told me that I should not leave my clothes on the floor and that.
I've got to like.
And it was like a ridiculous thing like that. But it was like literally the last piece of advice that came to mind in the moment in the interview. That's the first thing that came to mind. And I went forward and said that was the advice that I got. And it was kind of like. Like it was kind of awkward and funny, and I think I did okay with it and actually turned it into something okay. But I remember thinking maybe I should not have. Maybe I've. I should have thought of a better example. But I guess, like, what about moments like that where you're kind of asked an unexpected question, you don't know what to do with it? How honest should you be? Is it. Is there a way that you can be too honest and that where it actually hurts you? What do you think about situations like that?
So I'm pretty transparent. So I tend to overshare when I'm talking. And it's gotten me in trouble for sure. But I'd rather just be myself, you know. But I would say that I have been in many interviews where someone would answer a question and I was thinking, wow, was that a bad answer?
Can you give an example?
No. And I'll tell you why I can't give you an an example. Because I was thinking about the answer I was going to give you, which is that if you don't have an answer, don't answer it. Just say, you know what? I can't think of anything right now. Do you mind if we come back to that question? I'll think of something. I'll tell you, I always appreciate when people are honest like that because, like, it's so much Better just to be real like that than to try to, like, come up with something and talk about my mom doing. And I think there is a time and a place if you have a vibe with the person. You can. You can laugh, you can laugh, you can. You can kind of be silly like that. And people hire who they. Who they like. So if you're connecting with someone, play into it. But usually most interviews are formal. They're uncomfortable, and you don't have that. You. You. I know you, so you have that type of personality. Most people don't have that, and they don't feel that comfortable. So I'd say the best thing is when you get tongue tied and you feel like you've got a tough question. And there are always going to be tough questions. Pause, you know, don't answer so quick, think about it, sit back in your chair and say, wow, that's a really great question. Do you mind if I think about that for a second? People appreciate that because it shows that you're a thinker. It shows that you're, you know, that you can take something and, you know, process it and then deliver a great answer. Typically, your first answer always is the worst. In our leadership program, we always used to ask people to stand up and speak and give us their answer about whatever we were working on. And whenever they gave us an answer and they kind of fumbled, we'd say, say it again, and they'd say it again, and then we'd say, say it again. And by the third or fourth time, they nailed it. And the reason is because usually you're just spitting things out. So how. How deadly is that in an interview? Like, you get one shot, you know? And so I used to ask people a tough question. I'd say was. I'd say, are you good in math? And a lot of people wanted to show off. They say, yes. I'm like, what's 10% of 300? And I would catch people, right? And I didn't care if they knew the answer or not, because you got a calculator. Like, what do I care? Like, I could care less. But it was always interesting to see how quickly would just try to throw out an answer and then, like, get it wrong and, like, kind of play it off. And I always appreciate it when people said, you know what? You caught me. Hold on a second, let me think. And they always took time. It showed me that they're. They're a thinker. And I like that.
Because is that the purpose of a question like that? Is it more to obviously you don't care if they can get 10% of 300, but are you asking them to see just how they respond to something out of the flood field?
Yeah, my interviews were very. Were very. I mean, I was. I tried to do things very differently, and I was trying to find someone real I wanted who's believable. If I could believe in you, and I can believe you and what you're saying, I liked you. I felt like we can train people. I want to make sure they didn't hate what they're going to be doing. I had a tough company. We had a collection agency. People were on the phones calling people. And I was trying to hire really nice people, right. So I would ask people, like, why do you want to be here? Why do you want to call people on the phone? Why do you want to try to, like, you know, negotiate with them? And I was looking for people who are genuine and real and authentic, and I wanted to catch them. I wanted to catch them and make them a little uncomfortable because I knew that when they came in on the job, they were going to be made to feel uncomfortable out on the floor next to the person they're working for. And if they weren't going to be able to handle it well with me, I wanted to see and kind of like feel like, is this going to be a future indication of how they're going to be when they're out working in the job and they're caught and they're in a sticky situation with either a teammate or someone on the phone? And so I like to put them in those situations a little bit and just see how they react to it. And again, I didn't care as much about the answer as much as I saw, you know, who they were. Right. I used to tell people, I'm like, let me ask you a question. I'd stop them in the middle of an interview. I'd say, if you and I were having a beer on Saturday night, is this who I'd be talking to? Because it doesn't seem like this is who you are. And so a lot of times that would loosen them up. And they'd say, no, actually, I'm really nervous. And I'd loosen them up and I'd say, well, be that person, because that's who I want to hire. I want to hire you. I don't want to hire who came in here with a suit in a casual atmosphere, like, that's not who you are. And I understand you did that out of being respectful, but it probably wasn't the best move because that's not who this culture is. Right. But people, again, they're trying to be someone that they're not.
Yeah, yeah, I think you're good at that. I think employers on the other side, other side of things could do a lot better job of recognizing that every single person they're talking to is super nervous to be there and it's an uncomfortable situation and just do things to make them feel more at ease. On the topic of difficult questions, my brother, when he was going through like med school interviews, I remember he got asked to compare himself to a fictional character. And why did he think he was like that character? That's a nightmare of a question to be put on the song for it really.
I don't know. I don't know what purpose it serves. I'm not sure.
Well, I think it serves the same purpose that, that your math question did, which is like, how does this person think on their feet? The problem with that question is that like, you're really opening up the door. I think for someone to shoot themselves in the foot with like a bad character, you don't want to compare yourself to like Tony Soprano or something in a, in a job interview.
So I think people, people usually don't come prepared. And you should, you know, when people, why should we hire you? Like, you should, you know, tell me about yourself. Like, those are typical, you know, what's your, what's your strength? What's your weakness? I mean, these are typical interview questions. That much most HR folks are asking. And you need to have that 30 second pitch. You need to be able to give them a little nugget that sounds professional, sounds, you know, like it rolls off your tongue. And I always connect things, I always like to connect things. If I'm coaching people on interviewing and that you're connecting them to something that you've done in the past that will show that person that is interviewing you that you have the capabilities of whatever it is that they need, because that's what they're hiring for. And if you can't demonstrate that you can do what they need, why would they hire you? And so I think people forget that. And that's the most important thing about the interview process.
Let's dive into those fundamentals a little bit more. Like you said, there are these questions that will come up in every single interview. Do you have any general high level tips for the tell me about yourself questions, the skills questions, even things like what you would wear to an interview, like the fundamental stuff that, that people maybe are just not thinking about.
Yeah, look, you got to have your go tos, you know, like, so you got to know, you got to know yourself. So you got to know what you're good at and what you like. And if you don't, that's a whole other issue that I think people.
That's the second time that's come up. So how do you know yourself? What if. Tell me more about what you mean by that.
Well, it starts with knowing what you don't like. And most people, that's not hard. You know, we used to do an exercise that we learned where we, we drew a circle and we put all the things that we're really good at that we really like inside the circle and all the things we hate that we don't like outside the circle. And we were doing this with our team and people put public speaking and they put it outside the circle. Some people put, you know, doing math outside the circle. But, you know, it's a hard exercise to do. But you got to do something. Whether it's free online assessments, whether it's doing some, you know, personal excellence work on your own. You have to know what you like. So if it starts with knowing what I don't like, that's a great start. Because you don't want to take a job where you're going to have to do things that you can't stand. When I hired people who didn't like to be on the phones and their job was to be on the phones, I remember sitting with them thinking, like, why did you take the job? Right? And looking back, of course I know why they took it because they liked our culture and they needed a job and they wanted to get paid. And so it's just a way. The, it's the worst thing that you can do for yourself because you're going to end up being just miserable. I always say it's like dying a slow death professionally. It's inevitable that you're going to get fired, your performance is going to lack and you're just going to hate it and you're going to loathe it and then you're just going to be miserable, make everyone else around you miserable. So staying away from the things that you don't like is the first piece of advice that I would give someone. So if you know what those are, you want to make sure that you ask in a job interview, am I going to be having to do any of these things? Especially if they're in the realm of whatever it is you're being interviewed for, because if I'm in marketing, for example, and I don't like to write in copyright and I don't want to have to do emails and I don't want. Then you should ask, you know, I like to do graphic design. I like to be in the art, you know, design, you know, part of their business. So I'd want to know what I don't like and make sure that I'm not, you know, set myself up for failure and for what I do. Like you just have to have a few things that you enjoy if you're great with people. I love talking to people. I like helping people, customer service. I like working in a team environment and being able to collaborate with other people in the company and, and working towards a company. Go. If it's a specific, you know, job, specific responsibility, you should be able to speak about that. Especially if you've done it in the past and all you have to do is think about what you've done in the past and what you enjoyed about what you did and what you didn't enjoy, about things that you, you want to stay away from and just have a few, you don't have to give a whole discourse about like every single thing that you're going to be doing for that, for them, but you want to be able to speak about it. Same thing with, tell me about yourself. You just have to have three or four bullets about yourself, where you're from, a little bit about you personally, where you grew up, where you went to school, what you enjoy and then professionally what you're looking for. So I always say you keep it within that, you know, 30 to 90 seconds when you're rambling on. It's enough. You know, I think people just, they get caught talking and saying too much and that's when they get themselves in trouble in an interview and the other person sitting there going, oh my gosh, can we just stop this? Can we just end this interview? And so you have to be able to read someone and pick up and have some self awareness that if you feel like you're dragging on and on and you see that look on the other person's face or you see them fidgeting in their body language, stop, end it.
What about the career goals and aspirations question? This comes up a lot where it's like, where something like where do you see yourself in five years? And I remember when I used to work at a restaurant years ago, this came up in an interview and I wanted to be doing my own business in five years. And I just said that honestly, and it felt okay because I think that in the restaurant industry, especially like me working as a server in my twenties, that no one expects you to. You're not going to tell people, it's like my dream to be a server for the next five years or whatever, so it's more acceptable. But what about a position that you're interviewing for where maybe, I guess, how do you just answer that question in a way where you don't shoot yourself in the foot so that, you know, it's like five years from now? I want to be doing something where it's just completely incompatible, compatible with the position that I'm interviewing for.
Yeah. So, like, you know, again, my interview style is a little different. I like when people were honest about that stuff. No employer wants to hear that, though, just so you know, like, nobody wants to hear that. So I think it's really important.
Nobody wants to hear that you want to be in your own. Do your own business, or no one.
Wants to hear anything other than what they want to hear, which is that if I'm the. If I'm interviewing you, I want to hear what you're going to do for me, because I'm.
More from Chad

Carl Banks Interview Trailer: Two Time Super Bowl Champ Talk Business and Leadership.

Ty Montgomery Interview Trailer: The Goals and Grit of an NFL Player With a Heart of Gold.

Brock McGillis Interview Trailer: Hockey Hero Breaking Barriers and Embracing Identity.







