When it comes to conducting interviews, most small business owners are still relying on outdated, time-consuming practices that focus more on the candidates’ personalities and enthusiasm rather than their actual qualifications. So, what can you do to make your interviews more effective? In
this episode, Gene Marks and Madeline Mann, CEO and Career Coach at Self Made Millennial, discuss several strategies and resources that will not only streamline your business’s hiring process, but will also help you evaluate each potential candidate more objectively.

Podcast Key Highlights

  • What Are The Most Effective Interview Strategies for Small Business Owners?
    • To avoid getting swept away by sparkling personalities or people who are really passionate, small business owners need to build a scorecard that will enable them to remain objective during the interview process.
    • Your scorecard should include a list of all the skills, traits, and competencies that you’re looking for.
    • You should also consider the questions you’re asking and then, decide what a bad, okay, and good answer to those questions might look like as a comparison.
    • If you plan on having multiple people conduct the interview, give each person on your interview panel a specific topic or competency to focus on, to avoid repeating questions.
    • Take notes immediately after each interview because as the day goes on, you’ll begin to forget the finer details of each meeting; when this happens, you may revert to your biases rather than focus on the actual facts.
    • Conducting structured interviews, in which you ask all candidates the same questions, helps reduce personal biases and makes it easier for you to keep notes.
    • Be as upfront with your candidates about the location and conditions of their interview beforehand so that they’re not caught off guard or distracted by anything during your conversation.
  • What Are the Pros and Cons of Giving Applicants Your Interview Questions in Advance?
    • Not every candidate has strong interview skills; providing applicants with the questions in advance gives people who are truly a good fit for the position, but who may not necessarily be good at interviews, a better chance of proving themselves.
    • Unfortunately, giving candidates more time to think about their answers, rather than asking them on the spot, may not always get you an honest reply.
  • How Can AI Help Small Business Owners Hire the Most Qualified Candidates?
    • Utilizing AI during the online application process helps cut
      through the influx of resumes so that the most qualified applicants rise to the
    • There are also one-way interview tools that use AI to parse
      what each interviewee is saying and will look for certain themes or certain
      types of answers that fit your ideal applicant. Once all the interviews are
      recorded, these tools will rank the candidates based on relevancy and genuine
  • What Is Currently Considered Appropriate Interview Behavior?
    • While formal business attire is no longer required for interviews, you should still strive to dress professionally, both in person and virtually.
    • Avoid asking applicants any questions that would force them to disclose their identity as a member of a protected class.
  • What Are Some Appropriate Topics for Rapport Building?
    • Sports Teams
    • Hobbies
    • Cities They’ve Lived in That Are on Their Resume
  • Do I Need to Refer to the Candidate’s Resume During the Interview?
    • You can set aside their resume for interviews where you’re evaluating certain skill sets or
      looking for certain attributes in their thought processes and work habits.
    • You’ll need to keep their resume in front of you if you’re
      conducting a “Who” interview, which requires you to go through each of their
      past experiences and ask them a series of questions for further elaboration.
  • Do I Need to Conduct Multiple Interviews?
    • Because of time constraints, it’s a good idea to hold initial interviews to confirm that candidates are genuinely interested and have the required skill set before asking them to go into more detail about their experiences.
    • Do not use multiple interviews as an excuse to stall or because you’re afraid to make a final decision.
  • Should I Record My Interviews?
    • It’s slightly coercive to ask a candidate to film them because they might be worried that declining your request could hinder their ability to land the job.
    • If you have a legitimate reason for filming the interview, you should be transparent with your applicants to help ease their concerns.
  • How Can Employers Make The Hiring Process Less Stressful for Their Candidates?
    • You should inform your applicants about what to expect during their next interview before they go into it.
    • Sending a kind rejection email can help soften the blow of not getting the job.



The views and opinions expressed on this podcast are for informational purposes only, and solely those of the podcast participants, contributors, and guests, and do not constitute an endorsement by or necessarily represent the views of The Hartford or its affiliates.

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Gene: All right everyone, thanks for joining us again on the Hartford Small Biz Ahead podcast. My name is Gene Marks. Glad to have you back here. Today I’m speaking with Madeline Mann. Madeline is the CEO and career coach at Self Made Millennial and also all over LinkedIn. And I want to tell you guys in advance, we’re not really having a conversation about LinkedIn today but I hope, hope, hope that Madeline will agree to come back in the future to talk about some advice on succeeding on LinkedIn. But today we’re talking about employees. And Madeline, so first of all, thank you very much for joining us today, it’s a pleasure to have you here. Thanks for taking the time.

Madeline: It’s my pleasure.

Gene: First of all, what is self-made millennial? Let’s start with that.

Madeline: I was a human resources leader in the tech industry and I started putting out content of what I was seeing was leading to people successfully landing jobs and what was helping them to stay stuck. I put it out on YouTube and on TikTok under the term self-made millennial. Over time it blew up of just people getting so many success stories. And ultimately it became so successful that I left my HR career that I loved to do this full time. And so now I work with companies and individuals to really help them to elevate their careers and their hiring processes.

Gene: That is awesome. So you’re a career counselor, and I guess you do work… You said you work with individuals and you work with companies. If an individual wanted to use your services I guess they would pay you by the hour or by project as well to help them get a job I guess, correct?

Madeline: Exactly. We have a coaching program that really takes them A to Z of how to transform yourself from a job seeker to a job shopper where opportunities are coming to you, things are a lot easier. You’re not begging these companies for roles but that they are seeing your value and it brings… It makes the job search a bit more fun and less effortful.

Gene: Got it. That is very, very cool. And let’s talk about the other side, which is our audience, which are small business owners. All business owners of all sizes, businesses of all sizes. Tell us what services do you perform for your sort of corporate clients.

Madeline: I have helped a lot of teams learn how to interview. Which is so funny because I think a lot of people no matter if you have 10 months or 10 years of experience interviewing people, there’s so much that goes into it, and a lot of us don’t realize that we’re missing a lot of those pieces. So I really help to identify those and help people to be really effective interviewers who are picking the best possible people, not necessarily the people who go with your gut feeling.

Gene: Okay. So first of all, the good news for you is that this conversation is going to be between 20 and 30 minutes so we’re not going to give away the farm on all of your advice. Okay, that’s good. But let’s get some advice from you here because you talk about helping employers interview. I am awful at interviewing people, just terrible. And I am awful at judging people as well. To me, anybody that comes in and I see them… Everybody to me seems like … This seems like a good person, I’m sure they’ll do a good job, let’s hire them. Because if you’re dealing with different clients, I’m busy, I’ve got a lot of things to do, it’s critically important that I’m hiring the right people and yet I’ve got 15 other things I got to do so I tend to cut corners and I make mistakes. Give me some advice, Madeline. As a business owner, if you were talking to me as a client, just some general advice on interviewing a candidate. What do you tell your clients?

Madeline: Well, first of all, I think it’s phenomenal that you’re acknowledging hey, I could use some areas-

Gene Marks: Terrible at it.

Madeline: There’s going to be some growth there. Because a lot of people who are not good at interviewing think that they’re fantastic and they’re like “I’m just going to”… “I just feel it out and it feels good.” What I would say is… One thing that’s super helpful is to build your scorecard, right, of what exactly are the competencies we’re looking for. And I think where people stop is they stop there. They say, “Okay, I got the competencies” but let’s take it a step further. Let’s then look at the questions you’re asking. Okay, you’re asking them about their skillset doing X. Okay. Now I want you to decide what does a bad okay and good answer look like to that question.

Madeline: And this is the step that almost no one does because they just listen to the answer and they think okay, that sounded good, that person seemed to have a good answer, but they’re like “Wait, no, on my scorecard, if they didn’t touch on these things in their answer that’s a three out of five, not a four out of five.” And I think when we do it that way, suddenly our evaluation of people becomes a bit more objective. And I think especially for small business owners, often a lot of us as founders are also… We’re very emotionally involved and tied to the business, tied to even the money in the business as well so hiring is actually far more emotional than it would be if you were just someone on the team. To take the emotion out by using these types of things like scorecards, it helps you to not get swept away by sparkling personalities or people who are really passionate.

Gene: I love that answer. Do you recommend or do you… What do you think about giving interview questions to the prospective candidate in advance?

Madeline: That is something that I think is… Could potentially be great. In the way that it is helping them… You’re not interviewing someone to hire the best person who’s good at interviewing, you’re interviewing people to pick who’s the most talented for that role. I think in that way, giving some heads up about what you’re going to ask I think is fantastic. And I’m talking more hush, hush to the employers here, is it’s harder to lie if it’s something that’s on the spot. So if you are asking a question like where do you see yourself in five years? Someone can come up with this fluffy answer if they had several hours ahead of time to think about it. If they’re on the spot and they basically say they want to work in a completely different industry doing completely different things, when you ask that question okay, maybe you just got your answer that this person is not a long-term fit and a long-term investment.

Gene: That is a great answer as well. There’s no right or wrong answers to any of these questions, right, I mean, it really depends on the job seeker and the employer as well. I always thought giving people questions in advance, if they’re more technical in nature, gives them a time to think through the answer, right?

Madeline: Yes, yes.

Gene: Because I mean, listen, if we have a technical issue in our company, I wouldn’t expect somebody to give me an off-the-hip answer anyway, right, they would think it through.

Madeline: Exactly.

Gene: Your point is well taken as well. There are other questions that I would like to just sort of spring on them to see what the first thing that comes to their mind so maybe it’s a combination of the two. Okay. Where about interviewing? I have some clients that like to interview people in coffee shops or restaurants, other people in the office, other people by Zoom. Give me your thoughts on what you would advise clients where to interview a potential candidate.

Madeline: I would say that it’s not so much a matter of the best place to interview someone, but what I think makes it better is to make sure that all of the interaction is explicitly understood by both parties. Such as if we’re going to meet in a coffee shop maybe ahead of time say, “Hey, don’t buy a coffee I’ll be grabbing them.” If it’s in an office and its meetings booked all day, making sure that there is a time for them to go to the bathroom and to use… And to get some food and something like that. It’s these aspects of the dynamics you’re putting job seekers in where there’s a lot of unknowns and they’re unsure how to act, they’re unsure what to ask for. If you can think through using child’s eyes of what would it feel like to have someone in this situation?

Madeline: I mean, I just had clients the other day talking about how they had a panel interview, there’s four people virtually, and all four people had their cameras off. I don’t necessarily think that’s terrible to have your cameras off for a call, but what they should’ve done is they should’ve told the candidate right up front “Hey, we’re a cameras off organization, feel free to turn your camera off.” Versus this person did not have the confidence or the right moment to address, hey, I’m feeling really weird. Four people are staring at me and I have no idea who anyone is. Should I turn my camera off, turn my camera on? Having that conversation with that person, making them to feel at ease is going to actually give you a better answer for your interview questions because you want them to perform as best as they can in the interview, it’s good for everyone.

Gene: Sure. That’s great, that is great. Groups of interviews. Are you a fan of having multiple people interview a candidate? Because most companies do that mainly because we don’t … At least I don’t have the self-confidence to make a decision on my own I need to … Somebody else to vouch for me so if we mess up the decision … If we make a bad decision I could be like “That was your call not mine.” You would probably have more than one person interview a candidate. And if that is the case I’m curious, what type of strategy would you recommend for doing that? Who should be doing these interviews?

Madeline: I think a lot of people will just throw a bunch of people onto the interview panel and they don’t think through it so they’re just like “I trust Chelsea she’s going to do a good job. Chelsea, you ask whatever questions you want to.” And then you know what Chelsea asks? She asked the same questions you ask and it’s just… We’re not getting any new information about the candidate. I was once interviewing at a company, just me as a candidate, I had four interviews in a row, every single interview started off with “So tell me about yourself.” And I just thought, are we really wasting our time here? First of all, I wrote a resume that tells you about myself, and then all of your other colleagues asked me the same exact thing.

Madeline: I think that what’s important is that each colleague should be evaluating just a couple of things. Usually a role there’s a series of maybe five different things. Possibly it’s two different types of behavioral things like they must be able to take initiative, they must be really detail oriented, and then maybe three skills like they must be really great at Excel and so on, right?

Gene: Sure.

Madeline: You want to divide those up. Some of you will have overlap, but you want to divide it up so that you’re not squishing into a half-hour five competencies. So you’re dividing it up, and then you’re coming to the table and each person is responsible for providing insight on the competency that they were assigned to. So now we’re having a more holistic view of this very complex multifaceted person in a way that’s more efficient than us just repeating the same questions and just trusting that our colleagues will ask good questions.

Gene: Got it. There are a lot of new software tools and AI tools that are available to help in the interviewing process. Some of them are controversial and some state… New York state I believe just passed … Or is it New York City, just passed a law that said that using these AI tools, you have to actually justify the algorithms behind the tools because they could be potentially biased. I’m curious if you’ve bumped into any of these software platforms. And if you have any thoughts or opinions on them? And if you’re recommending them to your clients?

Madeline: It is really interesting. The thing is that the online application process is one of the worst things to happen to job seekers. Really what’s happening is every time someone applies to a job, that job is flooded with other resumes that are actually not even related to the role and there’s just so much noise. What I do admire about these AI tools is that they’re trying to help it so that the candidates that are legitimately qualified and interested are rising to the top. While I think a lot of job seekers find it to be like a robot is determining my fate, instead it might be like okay, we’re trying to use these tools to hopefully get it so that these people who are just hitting easy apply to every single title they see online, to get those people out of the mix and focus on the right things.

Madeline: Now, when we’re looking at these tools, I think there’s a lot of tricky things. I’ve studied the one-way interview tools if you’ve heard of these, where you basically are recorded. A lot of these tools what they’ll do is they’ll use AI to parse what the person is saying, look for certain themes, look for certain types of answers. It takes dozens or maybe even hundreds of interviews until the AI is able to really build out a robust sample size to be effective, and then they’ll rank people from most relevant to what you’re looking for to least relevant. So it’s not actually rejecting anyone it’s more about shaking up the pile and making it so that hopefully the pile, when you start at the top, you’re not wading through people who really had no interest in this job and ideally someone who’s actually more legitimately qualified.

Gene: I agree. I don’t think we’re going to ever get away from these tools as well. I mean, in addition to what you said, I know some of the platforms I’m familiar with their super creepy sometimes. I mean, they’re looking at your eye movements, your facial expressions, they’re recording your voice and judging based on the inflection of your voice, and then they’re scoring and ranking these candidates. It is a little off-putting and a little bit creepy. At the same time, if you’re trying to streamline the process and qualify, like you said, to certain candidates to use them as maybe a potential tool in the process could help. They definitely come with some reservations.

Madeline: Absolutely.

Gene: We’re talking about interviewing. Some questions on behavior, okay? More than half of the business owners in this country are over the age of 50. So you’ve got a lot of older people that are… Like I said earlier, we’ve never had so many generations in the workforce as we have now all the way from baby boomers down to Gen Z. Can you just give us some of your thoughts for business owners of all ages, but really think of all of us people that are over the age of 50 just… In 2023, what is the appropriate behavior? Your dress, your attitude, things you should be saying, not be saying when you’re interviewing a potential candidate?

Madeline: That’s interesting. So what are the norms now versus potentially what they’ve been in the past?

Gene: What warning signs do you say… If you were giving advice to me and you’d be like “Hey, Gene, when you interview this candidate just make sure you don’t say this or you don’t show up to your interview in shorts and a t-shirt.” You know What I mean? The workplace has changed. And I’m just wondering if you’ve seen… If you have any advice for these business owners to just make sure they’re not going to say anything inappropriate or behave the wrong way. How should they be addressing an interview in 2023?

Madeline: I do think that the idea of the way we dress is an interesting thing because this has come up a lot, especially now that my clients are doing more virtual interviews than ever, and how are you supposed to dress if you are at home? If you’re doing the exact same interview but not at home would you dress differently? In my thought is no, you would dress the same. I think it is a little bit absurd to maybe do a full-on suit in your own kitchen or something like that. I think we’ve moved away from the highly formal apparel unless that is really your industry. Looking polished and expecting that from the person on the either side is I think completely valid. And I think it really stands out on both sides just to show that you value this interaction, you are showing up for it.

Madeline: Additionally, I think one thing that’s just always super important to remember, and this is my HR background coming out, is we just always have to be really buttoned up and tightened up when it comes to asking about some personal aspects of someone’s life that can sometimes feel like it’s a conversation like oh, do you have any kids? You can’t ask something like that. If someone is maybe younger and you see what college they went to, you cannot ask them, because you have a nephew who went to the same college, oh, what year did you graduate? I think my nephew is there at the same time. That’s a proxy for their age and that’s a protected class. Or even asking, hey, I love your accent where is it from? That also is verging over into a protected class. I’ve found with a lot of my clients, these barriers are continually crossed over and over again. It does put employers into legal hot water but also it leaves a weird taste in the employees or the potential employee’s mouth of okay, they seem to be crossing some lines here.

Gene: I mean, you bring up a great point. And it’s really why I asked the question because I’m gearing this towards the older audience that are business owners and managers. We come from a generation where that stuff was okay to talk about, it was okay to be more conversational. You ask anybody my age or older saying like oh, ask what year they graduated doesn’t… We’re just making conversation here. But times have changed, right? I guess what you’re saying is a younger employee or a younger candidate might be uncomfortable by some of those questions. So what’s the advice here? Is the advice to just stick to job-related questions? Is the advice also if you’re… Not to have a conversation but just to have just a Q&A format to keep it as sort of as vanilla as possible? Is that what you’re saying?

Madeline: I think that personal conversations, rapport building, I think that’s still one of the cornerstones of interviews and all of that. Really truly building that relationship. You’re going to be coworkers, you’re going to be colleagues. To talk about those things I think is totally fine it’s just we… You have to let the candidate volunteer anything that would fall under a protected class. So they can volunteer where their home country’s from, they can volunteer that they have children, they can volunteer that they are married, but you can’t really ask questions like that. What I would recommend talking about, sports teams, hobbies, cities they’ve lived in that are on the resume.

Gene: Puppies.

Madeline: Even their outfit. Oh, my favorite color’s blue, that’s my favorite shade of blue, blah, blah, blah, right, whatever it is. I think we just want to just maybe review what are the more sensitive topics and steer away from those.

Gene: Fair enough. Okay. Resumes. How much weight do you put behind somebody’s resume in an interview? Are you running your interview off of the resume or is it more like background material?

Madeline: Well, there’s multiple different types of interviews. For some of the interviews the person… Their resume was accepted, you almost set it aside, right? If we’re evaluating certain skill sets or we’re asking for specific examples of, tell me about a time in your career when, and we’re looking for certain attributes in the way that they think and work. I’d say probably even set aside the resume then.

Madeline: I do think your resume should be front and center is… Sometimes on the screening calls but also… If you’ve ever heard of the book Who, or it’s called a Who interview where you go through each of their past experiences and you ask them a series of questions. What did you do with this job? What was your least favorite thing about the job? What was your favorite thing? If I was to talk to your manager, what would they say about how you did in that job? And you do that for every single job in their past. And then you also learn why did you leave that job? By the end of the interview it has painted a very thorough picture of this person’s career path. And I think in that way the resume is pivotal.

Gene: All right, that’s great. That is great advice. What are your thoughts on multiple interviews as well? If you were interviewing a candidate for a job, would you interview that person more than one time or do you feel that a one-time interview is sufficient?

Madeline: It really depends on what information we need to make a decision. We’ve gone through essentially an interview to understand do they have the skillset we need, then the next interview is a bit more of a case study or more getting… Diving into their skills. Then maybe the final interview might be something like a who interview where we really dig into… Because that who interview minimum takes an hour minimum, right? To start off the bat with every single candidate doing a who interview is extremely time intensive. So in those cases you might delay that part and make the initial interview a little bit more concise, then confirm that they have the skillset, and then deep dive into their … The way that they’ve worked in the past. So I do think that multiple interviews can be valuable as long as we’re not doing multiple interviews because we’re indecisive. That’s what a lot of people do they do it to stall because they’re really … It’s fear-based versus you already have a plan of the purpose of each interview.

Gene: I worked for nine years at KPMG in Philadelphia so it’s a big worldwide accounting consulting firm, and every year I would go back to my college and interview kids, they were seniors in college, to be… Your class. It was always fun but it was from 8:00-6:00, a full day, of just back to back to back 45-minute interviews. It was brutal. And I had a hard time segregating out, you know what I mean, the different candidates. It’s not that different from an employer who lines up a day of interviews of different candidates for a specific job and keeping them all straight in their mind. If I was going in, Madeline, to… For a day of interviews where I was going to be interviewing six or seven different candidates for a specific job, what advice would you give me to sort of keep things separate? How would you approach a day like that? It’s not easy.

Madeline: And I think a lot of interviewers say, “It’s all up here, it’s all in my noodle. I’m just going to sit in this interview and I am going to soak it all in, and I’m going to give the person the appropriate attention,” which I admire but you need to be taking notes. After the first or second interview things are going to start to run together. Even if you only had one interview that day, if you do not write down your thoughts immediately after that interview or whatnot, a day or two is going to go by and this is where our biases seep in. It’s where we just start to think in impressions and feelings. If I thought that that went well, I think she did a good job. Instead of saying, “No, no, no, she scored a four here, a five here, and a two here versus this candidate that today did this.” You need to take these notes, you need to be… Set it up in a way, with your scorecard, where it is very regimented.

Madeline: I think also it’s important to do structured interviewing which is essentially where you ask the same questions every time. It doesn’t mean that you can’t build rapport, it doesn’t mean that you can’t ask follow-up questions and have slight detours here and there, but the structured interview again, reduces bias, helps you to keep your note-taking and all that stuff. And where you’re comparing apples to apples versus one conversation that you decide to take in one tangent, the next one in another direction, and it’s… Neither of them got to all the points that you were expecting to get to in that interview.

Gene: That is great, that is great advice. Only a couple more questions and I’ll let you go. I have a client that likes to record his interviews, video record them, okay? He does ask for permission from the person that he’s interviewing because that would be not good. I’m curious what your thoughts are on that. Would you ever consider recording… If you were interviewing a few job candidates for a job, would you consider having a video recording of those to try to get over those biases that you just talked about, to have some record of going back and looking at them again?

Madeline: That’s really interesting. One thing that we’d have to think about is it’s slightly coercive to ask a candidate, can I film this because they might be worried that if they say no that could hamper their ability to land the job. That’s just my first warning. Even if you ask, they might do it in a way that they’re still uncomfortable. I mean, I think maybe if there’s some sort of explanation potentially like hey, in an effort to reduce bias or blah, blah, blah, or this person was unable to attend this interview but we really want them to get to know you and see your background, all of that, would you be open to us recording this? I do think there is value there. I’d have to think it through, but we just want a way that didn’t feel coercive.

Gene: Madeline, these are great, it’s so helpful. I mean, we spent almost half an hour just talking about interviews because it’s that important and it’s what every business owner has to do when they’re considering a candidate for their job, and you’re an expert in helping business owners do this. Is there anything I’m not asking or any final advice that you might have that we didn’t… We covered a lot. For employers who are in the interview process that you might want them to consider when they’re looking at candidates.

Madeline: You know what’s really delightful is… Candidates are a little bit fearful in the interview process. Oh, they’re ghosting me, they’re not responding, this, that but they’re also incredibly tickled and appreciative of employers who just go a slight extra mile. So if they just fill the person in on what to expect in their next interview before they go into it, that feels amazing. Sending a really warm rejection email that says, “Look, you were amazing, we just had”… “It was a really competitive process. We genuinely would love to see you back in our process in the future. You have my email address, reach out.” They love stuff like that as long as it’s true, right? If you don’t actually want that then don’t say that. So just thinking about ways that you can maybe add … Sprinkle a little bit of extra love in the process. As a job seeker, even if you have a lot of options it’s still a scary emotional process so anything you can do to soften that does stand out as an employer.

Gene: Madeline Mann is the CEO and Career Coach at Self Made Millennial. Madeline, how can we get in touch with you? I’m sure on LinkedIn, right?

Madeline: Absolutely. You can find me on LinkedIn, Madeline Mann, and you can also find me at www.madelinemann.com.

Gene: An appropriate-sounding website. Thank you very much. Great advice and great tips for all of us who are looking to interview people which we are always in the midst of doing. Thanks, Madeline, we appreciate your time.

Madeline: My pleasure.

Gene: Guys, you’ve been watching The Hartford Small Biz Ahead podcast. My name is Gene Marks. If you need any tips or help or advice in running your business please visit us at smallbizahead.com or SBA.thehartford.com. Again, my name is Gene Marks, thank you for watching or listening. We will see you again next time, take care. Thanks so much for joining us on this week’s episode of The Hartford Small Biz Ahead podcast. If you like what you hear please give us a shout-out on your favorite podcast platform. Your ratings, reviews, and your comments really help us formulate our topics and help us grow this podcast so thank you so much. It’s been great spending time with you, we’ll see you again soon.

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