What Dating Mistakes Can Teach You About Job Interviews, with Matthew Sorensen

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If you don’t have interviewing experience, you might wonder how to succeed at them. But if you’ve ever been on a date, there are lessons you can transfer to the world of job seeking. Find Your Dream Job guest, Matthew Sorensen, says don’t go too deep, too fast with your questions, and under no circumstances should you focus on your ex (employer.) If you get an offer, respond with enthusiasm, even if you aren’t sure you will accept. Expect to be nervous, but speak positively about how you see your future with this company and what you have to offer.

About Our Guest:

Matthew Sorensen is a former executive recruiter and search firm owner, and the founder of the  Candidate Club. Matthew’s company helps you improve your interview skills, avoid costly mistakes, and get the job offer.

Resources in This Episode:


Find Your Dream Job, Episode 354:

What Dating Mistakes Can Teach You About Job Interviews, with Matthew Sorensen

Airdate: June 29, 2022

Mac Prichard:

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When you interview with an employer about a job, it could be the start of a new and important relationship. 

And just like when you’re dating, you want to make sure it’s a good fit for both parties. 

Matthew Sorensen is here to talk about what dating mistakes can teach you about job interviews.

He’s a former executive recruiter and search firm owner and the founder of the Candidate Club. Matthew’s company helps you improve your interview skills, avoid costly mistakes, and get the job offer. 

He also hosts The Job Interview Experience Podcast. 

Matthew joins us from Des Moines, Iowa. 

Well, let’s jump right into it, Matthew. Why are job interviews like dating? Tell us about that. 

Matthew Sorensen:

Well, the reason I like to talk about this, Mac, is there are job seekers all over the world that want to learn how to improve their interview skills. That’s why they come to you. The challenge is that they are skilled in their area of expertise. Right? What they do every day at their job or want to do at their job, but that skill, it’s not interviewing. They don’t do that forty hours a week. But interviewing, like everything else, it is a skill. But how do we gain experience? It’s just to do it. 

So, one comparison I like to make for job seekers that are preparing for their interviews is just to say, interviewing is like dating. People might not have many interview skills, but they’ve likely been on a date. So, maybe there’s something that we can put together here and learn when we combine the two, and there are so many examples that, you know, we might not have thought of but just make sense. Most people wouldn’t expect just to go on one date with one person and then find the love of their life. It’s gonna take multiple dates with multiple people. The same applies to job interviews. It’s rarely one and done. We can dig more into this, but that’s kind of the starting point. 

Mac Prichard:

Do you think applicants see this connection? Or let me ask it in a different way, Matthew. When you work with job seekers, I know that’s what you do for a living, and you share this parallel with them, how do they react? What’s their reaction? 

Matthew Sorensen:

Well, I think it took a weirdo like me to make this comparison. I don’t think I’ve seen it anywhere else. But I do, and I should say I’m not a dating guru. I don’t talk about dating much on my podcast or at all, but I do see lightbulb moments when we use these types of comparisons between the two. I think it helps people. 

Like I’ve said, people have been on dates, and some of the things that they’ve done, that maybe they regret later on in the date, also applies to job interviews, a lot of the same logic. I think it helps just the average job-seeker, the average person who’s been on some dates, been on some interviews, connect the dots, and perform better. My job is to help them perform better in the interview. Maybe they’ll do a little better at their dates at the same time. 

Mac Prichard:

Well, I want to talk about the dating mistakes that you’ve identified people should keep in mind when they go into job interviews. But before we do that, give us other examples of how dating is like a job search. You mentioned that you don’t want to just go on one date, and you don’t want to just interview, likely, for one job and be one and done. What are other parallels that you see between the two experiences?

Matthew Sorensen:

Well, Mac, let’s start with the, let’s say, the first date, and one of the things you don’t want to do on a first date and you don’t want to do during a first job interview or early on in the process, is go too deep to fast with the questions that you’re asking or even the topics you’re bringing up. 

So, on a first date, or at least a good first date, Mac, it’s gonna be inappropriate to ask very personal questions. Right? Like, what’s the worst thing you’ve ever experienced? Or, you know, what’s your darkest secret? Most people wouldn’t do that, but maybe it would go there on some dates. That’s a big mistake. It’s gonna make at least one of the two parties uncomfortable, and it’s probably not gonna set up well for the second date if there is one. 

The same thing goes for your interview. Job seekers make this mistake. You don’t need to investigate what happened to the last person in the position. You don’t need to ask that. Job seekers shouldn’t ask about budgets or decision-making, or maybe if it’s a bigger company, what’s come up in the headlines, good or bad, if say you’re applying to a fame company a bigger company. A job applicant shouldn’t ask oh, you know, what happened here? What caused that? You know, what were people thinking at the company? 

So, don’t go too deep, too fast during your first interview. Be careful what types of questions you ask in general. Of course, you want to be polite and professional, but especially in those early stages, don’t jump in asking, say, what the salary is on your very first question on your very first interview. That would be an example of a parallel between the two. 

Mac Prichard:

So, don’t ask about salary, don’t ask about perhaps public challenges the company’s facing or what happened to the predecessor. Are there any other questions you should avoid asking in that first interview? And I’m guessing it’s probably a phone screen which is not as formal as, say, an in-person or a zoom interview. 

Matthew Sorensen:

So, here’s a question I’ve heard a lot during interviews, sometimes first interviews, second interviews, and it seems innocent, it almost seems like a smart question to ask, and it actually, it is a smart question for the candidate to think of, but I don’t think it goes over well with the employer. And that question is, you know, what happened? Why is this position open? If you get further along in the interview process, you’re probably gonna learn why – the company might bring up why. Maybe it’s just a brand new position at the company; maybe they’re expanding, maybe it’s a duplicate role, so now, instead of one accountant, there’s gonna be two. But there can also be some baggage there that really it’s not the candidate’s business, at least during the first interview. 

Again, I think it’s a fair question to think of. It’s probably a fair question to ask, but in the situation of a job interview, especially early on, it starts things off on the wrong foot. Kind of trying to dig; it almost seems like there’s a little suspicion there, asking what happened, and it might be an awkward situation for the employer to have to explain, even if they’re allowed to. 

Mac Prichard:

These are all legitimate questions to ask. What’s your best advice, Matthew, about when to ask them? Is it before an offer’s on the table or after an offer’s been made? 

Matthew Sorensen:

If you have big concerns, maybe some red flags, something that you know is not a simple question, something that you know goes a little bit deeper. Not a question like, you know, where will I be working? What’s the culture like? Those are great questions. You can ask those at any point in the process. But there’s something you feel like you need to get to the bottom of that is fine to have that professional conversation. That would be later on in the process. Maybe that would be a third interview. If you think it’s gonna be just two interviews, it could be your second interview. 

That’s something you have to feel out, and the company might tell you during the process, you know, our next interview will be here, or if you make it to the next stage, it will be a panel interview, or with an owner, or the manager. But later on is the right time to do that, and the question to ask yourself is how important is knowing the answer to this question? 

If you have, you know, concerns about how much longer the company will be in business or might be in your region, or if they’re gonna move or relocate or be acquired, is another thing. If you feel like you really need to ask that, go ahead. But wait till you feel like there’s an established relationship, they like you, and maybe you’re one of the few top candidates that you feel like are gonna be chosen for the role. 

Mac Prichard:

Well, another dating mistake on your list, Matthew, to avoid in job interviews is to be mindful about what you say about your last partner. What do you have in mind here? 

Matthew Sorensen:

I’m so glad you brought this up, Mac, because this is one of my favorite comparisons. Just like on dates, your employer is going to be turned off if you rant about your last employer. Right? Or your current employer. It also demonstrates a negative outlook. There are obviously good and bad factors about, say, an ex-boyfriend or girlfriend and a past job. There’s good and bad. So, what type of person just focuses on the bad? 

But maybe imagine a first date where it’s a nice setting, maybe it’s a little romantic, and the person that you’re on a date with, the person across from you, just won’t stop talking about their ex, the last person they dated. First of all, you know, there’s a lot of thoughts that will probably go through a person’s head. They’re not over this person. This person consumes a lot of their thoughts, and also, they kind of hate this person. Then they start thinking, what would they hate about me? Maybe they’d think, I do that same thing. I always want to do that, or that sounds fun to me. 

For both parties, whether it be on a first date or a job interview, the future is way brighter than the past. The company you’re interviewing with didn’t bring you in because they wanted to hear about your bad manager, just like the person you might be on a date with didn’t go on the date with you because they didn’t want to hear about your ex; they want to hear about you. They want to hear about what you can do together and if you might be the right fit for each other. 

So, focus on that. Focus on the positive. If you do talk about your last employer, talk about what you appreciate about them, and you’ve probably heard this advice before, don’t say bad things about your employer during your job interview. I couldn’t agree more. But that doesn’t always get through to people, Mac. They still do it. Right? And they’ve even said to me, “I couldn’t help myself, I had such a bad experience at my last job, I went off about my manager or my boss from the company.” Drawing this parallel between maybe we’ve seen that on dates. Maybe someone has sat across from that person, who all they talked about was the last person they dated. Hopefully, that helps this concept click for some people and shows the benefits of focusing on the positive and focusing on the future together. 

Mac Prichard:

Well, this is terrific, Matthew. We’re gonna take a break, and when we come back, Matthew Sorensen will continue to share his advice on what dating mistakes can teach you about job interviews. 

Stay with us. 

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Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Matthew Sorensen.

He’s a former executive recruiter and search firm owner and the founder of the Candidate Club. 

Matthew’s company helps you improve your interview skills, avoid costly mistakes, and get the job offer. 

He also hosts The Job Interview Experience Podcast. It’s a terrific show. 

Matthew joins us from Des Moines, Iowa. 

And now, Matthew, before the break, we were talking about what dating mistakes can teach you about job interviews. I have to ask just one quick follow-up question about, what’s your best advice for people who struggle with not saying something negative about past employers? Do you have a tip for how to manage that and prevent that from happening for people who might still be dealing with some negative emotions around a past bad experience? 

Matthew Sorensen:

I like that term you use, negative emotions – because bad employers, that does stay with you, especially when you have to go into work every day, and the stress of being in a situation, being around people that are uncomfortable or unprofessional – when I say don’t talk about the past, you know, I don’t say that that’s easy. I understand. 

So, my first piece of advice would be to try and sort through it. Take time to think about it. Talk about it with somebody, depending on, you know, if it was just maybe an annoying coworker who bugged you, you know, some of that is you having to realize that, you know, you were paid to be somewhere, and every job everywhere is gonna have some coworkers that you don’t quite get along with or rub you the wrong way. You know, if it was unprofessional managers or bosses or things like that, people who really abused their role or made the workplace uncomfortable, find the right way to sort through that because, you know, those things do stick with you. 

From there, just like how you should communicate with the person interviewing you, you should think to yourself, that is the past, this new job is the future, what you can do together will greatly benefit this company. Hopefully, you can find some reward in the work using those great skills that you have—so combining those two things. Do take the time to think through it, sort through it, talk to someone about it, and then also think about what’s next, and leave behind as much of that negative workplace as possible, and then also, like I said, every workplace is gonna have some things that are less than perfect. 

It’s work for a reason. Right? That’s why they pay you because it’s not fun. It doesn’t feel like a vacation or a day out with friends. So, also realize the balance of what you have to put up with, whether it be a long commute, rough hours, or rough coworkers. Those are all things that, although we wish they weren’t around, and it’s great for employers that can eliminate that, it’s part of the reality of having to go to work and put in that time and get along with your coworkers.  

Mac Prichard:

Number three on your list of dating mistakes to avoid in a job interview is to accept an offer with enthusiasm. What do you have in mind here, Matthew? What’s this all about? 

Matthew Sorensen:

So, this doesn’t happen with everyone. Some people get a job offer, and they are thrilled beyond reason. It can relieve the pain of maybe not having a paycheck. Unfortunately, not having health insurance that comes along with jobs in a lot of countries. A lot of people are thrilled beyond reason. 

But I’ve actually seen something before when making offers to candidates, and I can’t say that we see this a lot in the dating world. But, Mac, since I’ve decided to draw comparisons on your show today, why not end with one last comparison? And by the way – this, I don’t compare everything about interviews to dates. These are really kind of the three points I have to help make some connections here. 

Imagine when a partner says they want to get serious or married after years of dating, receiving that. Seeing a marriage proposal of, a partner gets down on a knee and says I want to spend the rest of my life together. Will you marry me? And the person being proposed to says something like, “sure,” or “yeah,” or “I guess that will work,” or maybe something along these lines. “I have a vacation to go on. Can I let you know in six weeks?” 

Once a job applicant has gotten through all of these interviews, met with multiple people at the company, and learned what you need to learn about the company, they’ve invested time in you. You’ve invested time in them. So, now’s the time to decide before your offer if this is the type of company that you want to work for. Yes, you can negotiate, of course. But when you accept, accept with enthusiasm. Be happy and make sure that you act happy. Candidates that get offers and give the “yeah, sure” answer, it just starts things off with the wrong foot in such an uncommitted and uninterested way. Showing a little enthusiasm, showing that you care, it goes a long way and gets things started right.  

And by the way, Mac, I think I know why people sometimes have that unenthusiastic response, and I don’t think, it’s not their fault. It’s not that they don’t care. A lot of times, they have other interviews in their mind. Maybe they’re expecting offers from other companies, and they’re just not sure if this is the best deal. I completely understand that. That’s a frequent place to be in. I actually get a lot more letters than I used to about people who are getting multiple offers at once. So, I can understand that tone of that lack of enthusiasm coming through because you have other things on your mind. You have other things. You have big decisions to make. 

So, my advice, if you’re in that situation is, at least, for the sake of the, say, the manager or the boss that’s calling you, or the recruiter calling you with this offer, do your best to at least sound enthusiastic, so that they know that you do care about this offer and the company, and then maybe, you know, within a couple of hours or minutes, you can sort through if this is the right direction for you. 

Mac Prichard:

If you’re uncertain or you’re convinced that it isn’t the right offer, should you say no on the spot, or in the absence of any other offer, should you just continue to play along until you get a better offer? I think I know what you’re going to say, but I want to draw you out on this.

Matthew Sorensen:

I’m really glad that you clarified that because I did miss something here. Say that you do want to think about it. Right? Some candidates, it’s the job that, you know, they want the first job that comes through that’s perfect, the first offer that comes through that’s great. 

For those that maybe have some other options, some other, maybe, interviews or offers in the air, here’s what I would say to do. Still have enthusiasm. The enthusiasm doesn’t have to be saying, I accept. The enthusiasm could be, thank you so much for thinking of me. I’m so thrilled to receive this offer from you. Just be enthusiastic. Be grateful, and then you can say something as simple as, I’ve given this a lot of thought, but it’s important to me on all big life decisions to sleep on it, to give it twenty-four hours, and then move forward with a concrete solid response. Is it okay with you if I do that? If I sleep on this and then get back to you early tomorrow? 

A response something like that, and you have to make it your own, of course, but letting them know that this is so important to you, that you want to make sure that you go through with this a hundred and ten percent committed. That’s an industry standard. You can ask for two days. It does, to me, it does get a little weird when people start to say a week or two. You know what that’s about. At that point, a recruiter or manager will know what’s going on, which is fine. They might wait if you’re the perfect candidate, but if they need someone to get moving in the position soon, that then does put you in a less than ideal situation. 

Does that answer the question, Mac? 

Mac Prichard:

It does. And I wonder, as you’re talking, if you can be equally interested and enthusiastic about two very different offers and might, in that situation, ask for a few more days or a week or more? Do you see that happen in your work with candidates, Matthew? 

Matthew Sorensen:

I see it all the time, and people ask me this question, and this is a question that I tell listeners. I tell them what I told you. I sometimes try and sort through some of the options, but what it comes down to if, say, there’s multiple offers in the air, or you have to wait, you have another offer maybe that you anticipate receiving, but you haven’t yet, this is a question that I can’t answer for you because it’s very specific to your situation. 

Here’s some examples. If someone’s in a position where maybe they’re really low on funds, they need that income right away, maybe they need health insurance, maybe it’s not the time in your life to take a risk and stretch this out for a couple of weeks and see if you can get a better offer. That’s not up to me. That’s up to you. But that might be a situation where it’s better to, if there’s a company that, say it’s your dream job. A dream company to work with, and you can’t believe you got your foot in the door, and you’ve had a couple of interviews, but they haven’t made the offer yet. That might be a situation to hold out a little longer. 

And then here’s the last thing, Mac, that I think is really important, and it’s why I’m glad you brought this up. There’s something you can do that I’ve seen work many times. I’ve given this advice many times to listeners that write to me. 

Say that you’re in this situation where company A has made an offer, but company B is the dream company to work for, and maybe you’ve had an interview or two interviews with them. It’s perfectly okay to do this. Write to company B. 

Again, that’s the company that hasn’t made an offer yet. Send them an email and say, “Hey, I have this situation where I received an offer from a company. But you’re actually my number one choice by miles.” And then say in your email, “I don’t want to put any pressure on you. If this doesn’t seem like the right fit, that’s totally fine. But if you’re as interested in me as I am in you, I wanted to let you know my situation and see if it would be possible to fast-track this process. This is my timeline that I need to get back to this company. But, really, my goal and my dream is to work with you because of the great things I think we can do together.” That helps. It doesn’t buy you more time with the company that made you the offer, but if you are in this situation where you think that there’s an offer incoming from your first choice, that happens frequently, but they’ll never know to fast-track things unless you tell them. 

Mac Prichard:

It’s been a terrific conversation, Matthew. Now, tell us, what’s next for you? 

Matthew Sorensen:

The Job Interview Experience podcast is growing quickly. My goal for listeners is to give them real-world interview advice. I put out episodes every week, listener Q and A, with situations like this that I just described, and then my answer to listener’s question. You can listen to me ramble about the interview process. There will be good content there, and then special guests as well. New episodes every week, so I’d invite listeners that might want to check that out to check out the Job Interview Experience. 

Along with the Job Interview Experience, I’ve also created the online interview platform Candidate Club, where I take that real-world advice and condense it to several courses to help job seekers really work through and get hands-on with things like interview questions, cover letters, and about everything I think you need to see to feel confident in your upcoming interviews. 

Mac Prichard:

Well, terrific. Well, I know listeners can learn more about the podcast and your other services by visiting jobinterviewexperience.com, and we’ll be sure to include that URL in the show notes and on the website, as well. 

Now, Matthew, given all the great advice you’ve shared today, what’s the one thing you want a listener to remember about what dating mistakes can teach you about job interviews. 

Matthew Sorensen:

Mac, both situations, they take experience. For people who are new to maybe going on dates or new for job interviews, you’re gonna be nervous beforehand. You’re gonna look back and maybe regret the way you said something or what you said. But remember to stay positive. Be professional. Be kind. But also be yourself. 

The right company or the right person, that person is gonna like you for who you are and what skills you have. It’s good to do great at your interview, but those little mistakes you make like saying, um, things like that. A good company, that’s not gonna keep them from making an offer or from liking you. A great company and a great person are gonna like you for you, and what you can do together. 

Mac Prichard:

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Next week, our guest will be Jackie Dunckley. 

She’s an HR leader with almost 20 years of experience. Jackie is also the chief talent officer at OnPoint, Oregon’s largest credit union. 

Unemployment is at a record low. But the best jobs can still attract dozens or even hundreds of applicants. 

How can you get an employer’s attention when this happens? 

Join us next Wednesday when Jackie Dunckley and I talk about how to stand out in a crowded field of candidates.

Until next time, thanks for letting us help you find your dream job.

This show is produced by Mac’s List. 

Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media.

Our sound engineer is Matt Fiorillo.  Ryan Morrison at Podfly Productions edits the show. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week.