How to Answer the TOUGHEST Interview Questions

Hey guys, welcome to the podcast. This is a solo episode that I call how to answer the toughest interview questions. This is going to be a lot of fun. You guys are going to love it.

Before I get into that, couple of quick announcements. It is time to register for Fierce Pharma Engage, which used to be Mass West. Um, it takes place every year in San Diego. It's an awesome event. This year it's April 22nd to the 24th. And this event's different. It's larger than it used to be. It's not just medical affairs. Um it also has other crossunctional areas such as um marketing and communications, business development and licensing and um yeah pharma marketing, PR and communications, business development and licensing and medical affairs. So, register on, you can go to Fierce Pharma Engage. Um, just Google that, go on to the Fierce Pharma website, register for this event. I'll see you out there. It's going to be awesome and they do a great job every year.

Um, second thing is I want to thank each of you, so many of you that have reached out to me with condolences. I had mentioned on my last podcast or recent podcast that my mom passed away and so many people reached out and were like, "Oh, Tom, I'm so sorry for your loss." Um, and then my son Dean started working here in the office at the Carolyn Group with me. He's he's going to be one of my executive recruiters. And then so many of you guys wished him well on LinkedIn. Congratulations. And so I just I really feel the love and I just want to thank you all before I get started on this episode. Um you guys have been such a huge part of my life, such an amazing community and I can't thank you enough for the support that you've given me for this show. Um and I'm excited to keep it going.

So this is going to be fun, this conversation. Um because I think we've definitely covered a lot of interview episodes in the past. This is going to be different because we're going to be talking about maybe, you know, questions, interview questions that you may not have heard before or you've heard them, you just don't now know how to answer them. So, I'm going to jump right into it. We got a lot to discuss.

So, first and foremost, you get this question on an interview. How do you answer it? Here's the question. If I called your current or prior boss, what would they say you need to work on? Guys, a lot of these questions are like a trap. This is one of them because it's very similar. It's almost the same as what's your greatest weakness where you don't want to bury yourself, but you also don't want to give like a false answer. This is a question that they're almost disguising the weakness question by giving you like kind of this real life scenario of, hey, if I talked to your boss, what would they say that you need to work on? So, it's like you don't want to tell them exactly what a prior boss might say unless there's something in there that has a positive connotation to it. It's just like answering the weakness question. How would you answer the weakness question? You answer it honestly, but with something that is not a deal breakaker weakness. You don't want to incriminate yourself to the point where they say, "Oh my god, I can't hire this person because of what you just said." So, you want to choose, here's the framework. You want to choose a real but non-critical weakness. You want to show ownership. And then you want to demonstrate improvement. What you don't want to do is skirt it. Skirt the answer, not say anything. You don't want to say, "I'm a perfectionist." It's just it's so typical. It's like a buzzword. Um and you don't want to blame anything on your boss. You know, maybe maybe an example might be and I'm looking down. I took a lot of notes for you guys here. So maybe example would be, oh, you know, my prior boss would likely say that sometimes I take on too much um because I'm committed to delivering at a higher level. Over time, um I've worked at delegating and being more intentional um and prioritizing impact over volume. So, it's the old I often times go above and beyond or or do more than I need to. Um, so as a way to protect my time, I've had to learn how to delegate more and blah blah blah. So, is that kind of similar to the perfectionist thing? Yeah, but just don't say perfectionist. That's kind of my my advice there.

Number two, what's one thing? So, here's question. What's one thing you hated about your last job? Guys, this is a trap. You could see it coming from mile away. What's behind this? They want to see how negative you're going to go about your prior organization. That's what this is. This is a self-control answer. You want to be careful in how you go about this and you want to make sure that you're not burying anyone. You don't want to talk bad about your prior boss, about the prior company. You don't want to go overboard in making it sound like you're sour grapes in any way. Okay, so that's the that's the idea of what they're trying to do. So, you want to like reframe. So, here's the framework. You want to reframe hate into like misalignment. Um, and just keep it about fit and not about people in, you know, specifically. Um, and then maybe you just connect it to why this role that you're interviewing for is better. So, it might be something like, I realize that I thrive in environments with more crossf functional collaboration. My prior role was more siloed which helped me recognize how important team interaction is to me. Now again guys that's just an example of what you know you might consider saying in certain situations. It may not be exact for your specific position in your specific situation. The whole idea is you want to check the negativity situation. Check yourself. Um, you want to remain professional and culturally aligned. You don't want to make this an opportunity for it to be like a session where you're just, and this happens all the time. Way too many people fall into that trap.

Question number three, describe your best boss. Okay, good question. I think this gives you the ability to really impress the person who you're talking to because they may actually be your eventually be your boss. So what I would say framework-wise is maybe identify two to three leadership traits, explain how those traits improved your performance and then subtly align with the current organization if you can. So maybe you say something like, you know, this reminds me of, you know, my prior boss or my boss at XYZ company who was really good at setting high expectations but also giving autonomy. He provided consistent feedback and trusted me to execute and I really appreciated that about him or her, whatever. Um, so I I think that this is a really good opportunity to show professionalism. Um, and also be complimentary towards your prior boss. Obviously, um, you don't want to say something like, "Oh, you know, I I I I prefer a boss that just leaves me alone and lets me do my job." Like, now obviously you're not going to say that, but um or they never question me or something along those lines.

Number four, what's something you're really good at that's not listed on your resume? This is an interesting question because you may almost think that you have everything listed on your resume that you want them to know, but there's always other things that really aren't mentioned that could be really positive for you. So obviously you want to show them some of the hidden strengths um that you possess that maybe isn't totally apparent. So here's the framework. Choose a meaningful skill, maybe a soft skill. Provide a brief example and tie it to a performance impact. So an example of what a you know a soft skill might be would be you may be able to say one of the things that isn't apparent on my resume is I'm extremely organized. I've been known as the go-to person on my team for the guy that organi that is the team organizer and really is is great at setting things up and um and that sort of thing. You could say something like, um, um, I've been known to be very good at diffusing tension in meetings and bringing clarity when discussions become a bit unfocused. You know, that's that's kind of an example as well. Um, what you may not see on my resume is that, um, I'm a I'm a doer. I I have a lot of energy. I'm I'm full of energy and I like to I like to be the go-to person. I like to be the person I like I'm I'm the doer. I'm the go-to. Like so on my team when that, you know, it's almost like when you look at my team, if we were, you know, picking teams on the schoolyard, I would be the first to be picked because I'm going to get it done. That's the type of person I am. Guys, these things aren't on your resume, but it's it it's great material to talk about. So, I love that question. I think it's a great question. If you get it, I think it's a slam dunk.

Um, if you were to start your career over again, what would you do differently and why? This is another kind of sort of trap tricky trick question in the sense that you don't want to lead with regret. You don't want to be like ah, you know, if only I knew this, if only I did that. You you don't want to go into any type of negative self-reflection. You want to reflect, but you don't want to be negative. um you want to show a growth mindset and ownership. So what I would say as a framework is um identify something that would be kind of a strategic shift that you noticed um and maybe share a lesson that you learned and how you may have applied it today. So I'll give you an example like one of the things that I might say is um my my professional career and my life changed when I understood the value of getting up super early. I get up really really early every day. I didn't always, but I've worked my way into this really habit and system of trying to get to bed earlier, getting up earlier, becoming a morning person, but also carrying that through the rest of the day. That's made me a totally different um human and and professional. And it's it's paid off in so many ways that if I if if I had to do it over again, um that's the one thing that I would would make sure that I did consistently. That's, you know, that's that's something that is somewhat of an intangible that's a strategic shift in your life. Um, and it just it shows positive growth habits um that the most top performers possess. So when you explain that to somebody, it it's probably going to resonate. So I I love that as an example and hopefully that's that's one of the things that you know maybe might you know come to your mind first and foremost if you get asked that question.

Um, number six, what's something you used to struggle with professionally that you've improved? So um as a framework I this is this is again one of the things looking at this is it's almost another weakness question like we're getting back to they may ask this question versus describe your greatest weakness. It's the same. It falls into the same category. So, as you prepare for the weakness question, you also want to be able to have that ready for one of these oddball questions that's just asking you the same thing. I don't imagine that they're going to ask you the weakness question and this question in the same interview. It would be ridiculous. They're literally asking the same question over and over. So, as a framework for this, what I would say is you want to again, you want to share a real past weakness, something that's not totally incriminating, is going to be a deal breakaker. Um, explain the action that you took. What was the action taken? Um, and then maybe try to see if there's a way you can demonstrate measurable improvement. Again, the same way you would do the weakness question. So maybe you say something like earlier earlier in my career I struggled with executive presence in highlevel meetings. I didn't speak up enough and maybe I didn't have enough confidence but I worked on that through preparation through concise messaging and seeking feedback as well. Um, and now I am totally confident in meetings. I believe I've matured a lot and I'm really comfortable leading discussions. That's a I mean that's a really wellthoughtout answer. It does talk about a real weakness, but it also shows your evolution and your improvement.

Okay, this is a good one. So number seven, if you were an animal, what animal would you be? This this is one of those goofy questions that you might get like every once in a while you're going to get this goofy question. This is one of them. I've seen this, not consistently, but this is something that has come up um in the past. So, what they're looking for is they're trying to see if they can learn about you um through kind of a different lens and a and a way that you can maybe describe yourself a little bit differently than what they're seeing on the resume. And it's almost like a tell me about yourself question what but with a you know with a twist right so um I would say that the framework for answering this question would be um be be very intentional about the animal that you pick and be able to I would say divine define three traits for this that you could talk about. So this is almost like I would call it um you know a way to incorporate your strengths like what's your greatest strength question. This is almost a different way to incorporate your answer for that question. Um and then you take those traits and tie them to performance. So, like the one thing you don't want to do is if someone says what if you were an animal, what animal would you be? Like you don't want to say a lion, you know, a tiger. Like you answer the question like have a it's a conversation and I've seen people do that. I've seen people like I didn't know what to say so I just said you know I would be a whale because I like whales you know. I'd be a penguin because I love penguins. They're so cute. That's why I like penguins. like no, like this is an interview and there's a reason they're asking. They want to learn about you. They don't want to know what your favorite color is. Um, so maybe you could say something like, again, you're speaking about yourself through this animal in positive traits. So maybe you say, you know, that's a great question. I would say a dolphin. Dolphins are collaborative. They're intelligent. They're adaptable. And I do my best work in a team environment um where communication is key. And I know that that's a common trait. You know, dolphins, they, you know, they they really travel in packs and they're very communicative and um they're very docel animals. And I think that that's a great way to describe the type of person I am. What you don't want to do is you don't want to don't get cute with this. It's if they're asking it, it may sound like it's a joke, but anything someone asks in an interview is serious. It's not a joke. They want to see what you're what are you going to do with this crazy question. Guys, you you have to make sure that and the reason I'm giving you frameworks is you have to make sure that your answers are structured, that you don't get thrown off your game, that you don't freeze, that you don't like clam up. Like, it's okay to pause. It's okay to get a little creative. It's okay maybe to not have the perfect answer. What's not okay is if you have no answer, if you scoff at, you know, the the question or laugh at the question or if you just make it seem like you're annoyed. And I've seen people that do that. I've seen people that have been like, "My favorite animal. I don't I don't know. I mean, I have a dog. I guess I I guess a dog." Like, no, just roll with it. have fun with it, you know, and and and recognize that the structure of the answer is as important as the substance of the answer. So, the only other thing I'll say about that question to be careful is don't say like don't say a snake or a rat or even like a shark. like you you don't want to come across as overly aggressive unless you have a really good answer which even so snakes and rats probably not good to throw in here because such a negative connotation. Um so I would just be careful in what you pick and choose.

Okay, last question and then we'll wrap it up. This is this is a real question that I've heard people mention more than once. It's the brick question. So, there's a brick on the person's desk and the and the person interviewing says, "I'm going to give you this brick. How would you use it in this office?" People get stomped by this question, guys. And the one thing again you don't want to do is you don't want to freeze. You don't want to deflect. You don't want to ramble without structure. You want to answer this in a concise structured fashion. So here's the framework. So first of all, organize your thinking in your head out loud. I'll give you an example what I mean by that. Speak methodol methodolically and maintain your calm composure. This is all about really the question is kind of more to see how you react and what kind of structured answer you give them. and the creativity behind the answer. So maybe you say something like, well, you know, it's a that's really interesting. So hm, how would I use that brick this brick in the office? Well, I'd probably think of this in three categories. Practical uses, creative uses, and symbolic uses. um and then give them an explanation as to what that means. For example, um I think a practical use for this would be a doors stop. I think it's heavy enough and I think that, you know, we could put it, you know, in such a way where it'll keep that door open. So, I think that there's a really good practical use for it. As far as creative uses, I mean, I think that the the brick could be used if if you want to do like calf raises in the office, you can use this brick one leg at a time. Get your exercises in, get those calf calf raises in. Um, that could be a really good functional and kind of creative use for it. And then as far as a symbolic, you know, um, use for this, you know, I think if if if there's somebody in the office that's an artist, like maybe they can take this one side panel of the brick and, you know, maybe paint or draw a little something um, you know, like the company logo or something and um, because you need to keep this brick in the office for all the uses we talked about, maybe make it look a little bit, you know, uh, less of a brick and more of a piece of art. Um, that that's kind of how I would go about it. Now, what did you just do? You you answered the question with a really good answer. Was it the best answer? Was it the right answer? Could it have been better? Yeah, guys, that's the whole point. Like, you want to leave the interview having left the impression that, wow, this person is calm under pressure. They are very conversational. They had good answers. They were wellprepared and and they want to see you as somebody that's going to be successful in their organization where I can take this person and feel confident that they have awareness, that they have professionalism, that they can think on their feet. So all of the curveballs that got get thrown at you in those questions are really a good way to set you up to shine. If you can get through these tough questions, I mean, this could be the deal breaker here, guys. Getting good at answering these tough questions could be the difference between you getting the job and not. Now, were these questions specific to like an MSL role or a medical affairs role? No, not at all. There's probably going to be other questions that are specific to the role. You need to do equally as good on those. But these are the questions that could be for any position at any company at any time that could trip you up and it could cost you the interview. So, I want you to take this stuff seriously. Hopefully, this was helpful. One thing I would say is that if you want to use if you want to, you know, practice this a little bit further, go to chat GPT or your favorite AI tool and ask, "Hey, I need to prepare for an interview. If you can come up with um a list of 10 of the toughest interview questions, most bizarre interview questions and see what what AI is giving back to you as some common difficult interview questions and then ask for the answers. Ask for the framework what I just gave you. ask for that so that you will have more ammunition and be more prepared for some of these wacky questions that come along. I wouldn't go too crazy cuz you have plenty of other questions to prepare for. Don't go too crazy, but be ready and be comfortable to answer the tough questions through this system and this framework. I think it'll make a big difference. Guys, as I said, thank you again for all your support. Thank you for sharing and and um telling others about this show. really appreciate each and every one of you. Love you all and uh we'll see you next time.