This Is Woman's Work with Nicole Kalil - How to Turn Job Seeking into Job Shopping with Madeline Mann | 318

Episode Date: June 16, 2025

We’re flipping the script on your career mindset - because you’re not just looking for a job, you’re shopping for the right fit. Today’s guest, Madeline Mann, is here to help you ditch desperation and embrace discernment. Madeline is a former HR and recruiting insider, career coach, and the brilliant brain behind Self Made Millennial. With her new book Reverse the Search, she’s helping people stop chasing jobs and start choosing them. She’s been featured in The Wall Street Journal, The New York Times, ABC News, and was named a LinkedIn Top Voice — and for good reason. This episode is your no-BS, highly caffeinated guide to getting strategic in your job search. Whether you’re recovering from a layoff, eyeing a career change, or just wondering WTF is next, Madeline shares tactical tips and refreshing perspective on how to stand out, stop settling, and land a role that actually fits your life (not just your résumé). You’re not here to get picked. You’re here to pick well. Connect with Madeline:  Website: https://www.madelinemann.com  Book: https://www.ReverseTheSearch.com IG: https://www.instagram.com/self.made.millennial/  Tiktok: https://www.tiktok.com/@selfmademillennial  LI: https://www.linkedin.com/in/madelinemann/  YouTube: www.youtube.com/selfmademillennial  Related Podcast Episodes: How To Pitch Yourself (And Get A Yes) | 300 Belonging (At Work) with Dr. Beth Kaplan | 286 How To Know When It’s Time to Quit with Goli Kalkhoran | 266 If you found this episode insightful, please share it with a friend, tag us on social media, and leave a review on your favorite podcast platform! 🔗 Subscribe & Review:Apple Podcasts | Spotify | Amazon Music Share the Love: Learn more about your ad choices. Visit megaphone.fm/adchoices

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That's TIWW for 40% off sheets and everything else. Sleep cooler, lounge lighter, and stay cozy. No Frills delivers. Get groceries delivered to your door from No Frills with PC Express. Shop online and get $15 in PC Optimum Points on your first five orders. Shop now at nofrills.ca. I'm Nicole Kalil and you're listening to the This Is Women's Work podcast. We're together. We're redefining what it means, what it looks and what it feels like to be doing woman's work in the world today with you as the decider.

And if doing woman's work means showing up in the world with purpose, owning your value, and making moves that align with who you are and what you want, then yeah, woman's work absolutely includes your career. And not just the part where you're crushing it in your role, but the part we don't talk about enough. What happens when that role ends? Or it doesn't fit anymore? Or is never right for you in the first place? Because let's be honest,

many of us have bought into the myth that if we're just really good at our jobs, the rest will take care of itself. That promotions will fall into our laps and recruiters will magically appear in our inboxes offering dream gigs right at the right times. Except that's not how it works. Not anymore, maybe not ever. I read a quote from today's guest

that hit me like a ton of resume-padded bricks. Being good at your job and being good at job searching are two different skill sets. Let me say it louder just in case you didn't catch that. Being great at your job and being great at getting a job are two completely different things. And how many of us have really developed that second skill? And I'm not just talking about Googling how to write a resume

or praying to the LinkedIn algorithm gods, but really understanding how to find, pursue, and land a job that's worthy of your talent. We spend years, decades, honing the first skill, and we avoid the second like I avoid conversations before I've had my coffee, because it feels awkward or soul-crushing, and maybe because we secretly hope

we'll never actually need to do it. But layoffs, mergers, bad bosses, burnout, or just wanting more means there are plenty of reasons even the most capable among us find ourselves feeling like we're back at square one. The average person will hold 12 jobs in their lifetime and change careers five to seven times so I'm going to just go out and say it. Job searching is a life skill. But what if we stopped thinking about it as job searching and started approaching it more

like job shopping? That's the perspective shift offered by today's guest, Madeleine Mann. She's an HR and recruiting insider turned career coach and author of Reverse the Search. Through her award-winning platform, Self-M Made Millennial, she has helped millions of professionals land jobs that they actually want at companies that are lucky to have them. She's been featured in the Wall Street Journal, the New York Times, ABC News, and is recognized as a LinkedIn top voice. So Madeline, thank you for joining us. And I want to start by asking you to explain the difference between job searching and job

shopping. I find this concept fascinating. Well, the idea that job seekers have is that they are just hoping that the company will deign to give them attention and that there's this power dynamic there. Whereas when I was working in human resources, I saw the other side of it.

I saw the way companies were reacting to candidates. And companies know that it's better to wait for the right hire and take longer and maybe even pay a little bit more for that hire than to hire too quickly and hire the wrong person. So I saw companies going above and beyond for candidates who they really liked moving around their schedules, giving them a little bit more money, you know, really

pursuing these candidates. And I said, these candidates are job shopping. They have these companies in their clutches. And this is even in a highly competitive job market. Even in competitive job market, companies will just not hire anyone at all versus hire someone who they're not 100% sure on. So this idea of job shopping is how do you be that candidate who is in a league of their own that makes these companies drop everything and say, you're the one, what can we do to get you to join us? Okay, so I have lots of questions how to position yourself that way so that you come across that way. But, and this might be a tired

or potentially even inappropriate analogy, but it feels a little bit like dating. It's this idea that I have to decide whether I like you and you decide whether I like me and we're determining if there is a mutual fit and we're both gonna kind of put our best foot forward as opposed to when you go in really like with that desperation or please like me feeling

it never feels good for both parties. So is my dating analogy awful? No, I mean, it comes up a lot because it truly is a mutual experience. And it's also something that can change the trajectory of your life. So if the company on the other end basically gets the feeling that you are not properly vetting this opportunity, they're saying, Hey, I'm about to make a big purchase. I'm about to basically buy your services for tens of thousands, maybe

even hundreds of thousands of dollars. Do you really want this back? Because if they get the smell that this person is just kind of getting a job versus the right job, they worry that this person is getting a job for now and not getting a job for the long term. So you're absolutely right. The company actually really wants you to approach the interview like a mutual process, like you're vetting it yourself because that's advantageous to them. Yeah. Okay. So then how do we do that? Because I would imagine for a lot of people that are job searching, it could feel like a period of time or confidence is a little lower, especially if you got laid off

or if you aren't having immediate luck. How do we position ourselves confidently even when the feeling might not be at its highest? Is my question making sense? It makes total sense. So this is going to be tough for your listeners if their confidence isn't really high. But the very first step they need to do is they need to get extremely clear about the

type of the role and industry they are targeting and then not get distracted by other opportunities. Now let me tell you why that's so hard is because first knowing what you want is actually a pretty big challenge. A lot of people, I mentioned in the book that 53% of my audience said that the reason that they chose the career they're in right now is because they stumbled into it. So they didn't even choose it, right? So now I'm putting you in a position you have to choose and you have to cut off other opportunities, which paradoxically leads you to have many more opportunities. So you have to get targeted and that will actually give companies more confidence in you and attract the right opportunities.

So when someone is kind of in desperation mode or not even desperation mode, but just trying to land a job, they think let me be open to as many opportunities as possible. And that is actually one of the major things that's keeping them stuck right now. OK, that makes sense. Can you give us some ideas of what to get targeted on?

So you mentioned industry, but the type of people you like to work with, the type of people you like to work for, the job functions, role clarity, I mean, what are some of the types of things that we should be clear and get targeted on? So ideally, if I was to ask you, what job are you going for? The sentence should be short, right? I'm going for VP of Human Resources roles

at growth stage startups. Clear, crisp, done, right? If that answer starts getting convoluted, that's a sign that you are going in the wrong direction. I hear way too many leaders say things like, well, I'm looking for leadership positions at innovative companies that are doing something good for the world.

And that is a huge red flag to companies as well as people. Like if I told you that right now, if you could help me land a job like that, you would have no idea what job that is. It brings up absolutely no ideas. So that's the thing is you need to get crystal clear on that so that the companies and people in your life can place you. This reminds me of things I've heard in sales

where you talk about having your niche or target market and people get really wishy washy or really vague and it's like, I work with women, but sometimes men, and it's like, eventually you get to the point where you're like, okay, so you work with people who breathe, right? Like, and then I don't believe that you're any good at any of what you are doing because you're

not clear, crisp, done, as you mentioned. So I think that's phenomenal advice. So I guess what are some of the mistakes that you see job seekers making and some of the things that you talk about in Reverse the search that we should know about if we're either thinking about heading in that stage or we're in that stage. Absolutely. So let's say we know what we want. Okay? The next thing you do, and this is the advice you'll likely get from your friends and family, is they'll say, Nicole, just keep applying. Go to apply a bunch of things. The job search is a numbers game. And I'm here to tell you it is not.

I have so many clients and I walk through it in reverse the search of how it's really, you know, I'll have, I've had a client who went from applying to 500 places to then completely switching his strategy to job shopping. And then at about, he applied to about six more places, got interviews at 40% of them, six. And so it's really misguided to think that we need to blast more and now more than ever, because with AI, job seekers are blasting out more resumes. They're even using tools that are applying for them. And it's very clear on the employer side what's happening.

And so you are further just getting lost in these digital filing cabinets, which are applicant tracking systems. And you're really not standing out at all. This is not the same thing, but it's an endorsement of what you just said. We get a lot of pitches and the AI pitches could not be any more obvious. We started basically responding back, this is clearly an AI pitch and will not be considered. It's so obvious when somebody hasn't put themselves or their time or their energy into something as important as a resume. So if the answer isn't sending as many applications out

as possible, as you call it, the spray and pray method, which I love, if that doesn't work, I guess my question is around, should you set up some practice interviews or some practice conversations for opportunities that may not be the ones you're the most excited about or your top opportunities before you go and sit in front of those ones you really, really want? Is there any value to that or is that just potentially mess with your confidence?

I always tell my clients and my audience, never turn down an interview, even if it's something you are not super excited about. Now of course, if you are burnt out and you don't have the time or whatnot, that's up to you to decide. But to put yourself in that situation, to essentially get a free mock interview, essentially like putting yourself in that situation of testing yourself, getting your blood pressure up a bit, seeing how you think on the fly. I think there's tremendous value there

because one huge mistake that job seekers make is that they'll prepare for the interview, they'll write down all their answers to the top interview questions, and the very first time they ever hear themselves answering these questions is in the interview of a role they want. And that is something where it's like this, this interview could determine the rest of your future, your happiness, your financial wellbeing.

And we are essentially flying by the seat of our pants. You're absolutely right. You need to practice before you actually get into that championship game. Okay. Now, interview skills can feel at the very least rusty, if not something maybe we don't feel all that good at in the first place, it can feel like an uphill battle. Are there still a lot of these common questions that you're gonna get in every interview? And if so, how do you answer them in a way that's both truthful and has you stand out?

Because I always use the example, nobody's ever told me in an interview that they're not, everybody always says they're hardworking, right? Nobody's ever once said, oh, I'm kind of lazy. I mean, it would be refreshingly honest, but verbalizing how hardworking you are does not separate you from everyone else.

Everyone's doing that. So how do we answer these common questions in a way that's both truthful and makes us stand out? Nicole, I'm so glad you said that because that's the way we've been taught to interview is, and you even see it on people's resumes, seasoned, hardworking professional, you know, who is creative and blah, blah, blah, right?

And the bottom line is- Detail-oriented. Yes, detail-oriented, collaborative, you know, cross-functional leadership, whatever it is. And you said exactly what the hiring managers are thinking is that I don't believe you, or at least I'm willing to believe you given more data points. Like just saying it is not enough. And so I actually recommend both on your resume and in your interview to

essentially use no adjectives, like never describe yourself. Now, of course, if you spot on, ask me, Madeline, you know, what, what is, how would you describe your work style? I might give you a quick description, but guess what I'm doing afterwards? I am giving you an example of, if I say my work style is highly organized and regimented, maybe I pull up a document of showing how organized I am with building out all of my content and all of my work with my clients. Maybe I give an example of,

well, let me tell you about what happened this morning. And now you as the interviewer are saying, I believe her. I could see myself working with her because talk is cheap. Whether it's a family member, friend or furry companion joining your summer road trip, enjoy the peace of mind that comes with Volvo's legendary safety. During Volvo Discover Days, enjoy limited time savings as you make plans to cruise through Muskoka or down Toronto's bustling streets. From now until June 30th, lease a 2025 Volvo XC60 from 1.74% and save up to $4,000. Condition supply. Visit your GTA Volvo retailer or go to Volvo cars stop see a for full details So I guess then if we go back to this concept of job shopping and mutual fit

How does the person looking for the job? flip the interview or have it so that they're also Interviewing the potential employer and having them answer some questions. Let me give you a few different strategies that your listeners can use here, because it's really this idea of making the interview into a conversation. And interviewers report that they enjoy interviews

that feel more like conversations, because it feels more like it's a coworker, like you're experiencing this person on more of what it it feels more like it's a coworker, like you're experiencing this person on more of what it would be like to be in a meeting with them versus this strange abnormal dynamic. And so a few different ways you can do this. The first is you can often sometimes end your answers with a question. So let's say you ask me, well, Madeline, why should I hire you?

Which is a very common question. And I say, well, Nicole, a few things that I've noticed about the role that you said is X, Y, and Z, correct? Yes, okay, so that's what you're looking for. So based on my background, I have A, B, and C. And then I go, but Nicole, did I get that right? Is that what you're looking for?

And is that, when you've been talking to me, is that how you see me in this role? And you say, well, yes. Or you say, well, no, not, well, one of the things that the reason I interviewed you is because of this, and now we're talking about the role. Now we're having a dialogue. And a lot of making the interview into a conversation

is having done your research, having being a student of the industry so that I can converse. And even if you bring up something of, yeah, and I currently have 10 direct reports and I go, hold on Nicole, that's a lot of direct reports. Are you overloaded right now? Is there additional head count to go under you for more managers? And now we're dialoguing again, right? So really just utilizing your critical thinking

and even just doing that one thing of just when they ask you questions, sometimes flip it, don't overdo it in an unnatural way. But that's a great way to get it rolling. Yeah, I feel like getting people talking and getting it to feel like a conversation is a masterful skill because that's gonna carry over in the actual job. Being collaborative, being curious, being you know pointing out things, connecting

dots. These are the types of skills that I would want to see in real time and you're basically just demonstrating it. Outside of salary, which is I think where most people's brains go to, salary, maybe structure of time worked and where you're working and things like that, what are some other things that we should be looking for to determine if an opportunity or company is the right fit for us. So when you are choosing your target companies, you won't quite know if the role is right just from looking at the company, just from reading their mission statement,

even reading their Glassdoor reviews, those can often be misguided. Usually it's just the most disgruntled people posting on there. And then, you know, you know, maybe HR team. So, you know, you, you have to go with generalizations, right? Of for me, I was someone who I looked at my skillset and what gets me going. I am kind of like a, I'm like someone who loves to build processes and I really don't mind ambiguity and I love really deep learning. So in my career, I focused a lot on more of those growth stage companies versus really large companies where my role would be narrow.

I've met tons of people who they would bang their head against the wall for the craziness of that type of company and want structure. So first of all, look at yourself and look at these kind of big things. You know, if you don't mind things moving a little bit more slowly, public sector could be good. If you, you know, want something a little bit more collaborative, maybe look for more of a flat organization, whatever it is. Okay. So you just have to get these understandings of these industries and types of companies under your belt. Next, it industries and types of companies under your belt. Next, it mostly comes down to the questions you ask both in the actual interview and then speaking with people at companies. One thing that I've done for every offer I've accepted in my life is I get references for the company. So, you know, one of my past job offers,

I get the offer and I go on LinkedIn and I find people who were previously employed at that company. So no, no attachment anymore. They can say whatever the heck they want. And I contacted them and called them up. I did this all myself. I didn't have to have the company give them to me.

And I asked them, how did you like working there? And I asked them specific questions and they would give it to me. And I asked them, how did you like working there? And I asked them specific questions and they would give it to me unfiltered. And so you can do things like that. A lot of people don't think to do things like that but then I spent years of my life working in that company. And so it's so important that we're making these intentional steps.

I mean, I love that as a suggestion, like what a great way to find out the real deal. And yeah, you kind of have to take certain things with a grain of salt if they're no longer there, but to actually hear from people, because like we were saying earlier, how nobody ever says they're kind of lazy in an interview, the flip side is no leader or company is ever like,

oh, we have a pretty toxic culture. Again, refreshingly honest, but nobody says that. So everybody always talks about how great their culture is and their leaders and how much development or whatever it is that they're selling. So getting that information from somebody who doesn't have any skin in the game, I think is phenomenal advice. So where and how much does negotiation come into play? Because as women, I think we've been told a lot that women are less likely to negotiate or they're not necessarily as good at it,

though I don't think the research supports that. But where do negotiations fit in? And if so, like, how do we do them well? One of the things that I've seen as far as negotiation goes, and I think that it actually plays to a lot of strengths that women have is if you go into a negotiation highly collaboratively, because the way I teach negotiation and I help men, women, you know,

whoever get tens of thousands of dollars in salary increases, if they are introducing it in a collaborative way, they are going to get bigger money. And there's even a study I talk about in reverse the search where they looked at negotiations and they didn't measure what was said in the negotiation. They just measured the social indicators of rapport building. And the more rapport that was built, the better the offer for the candidate in the end. And so that is a really freeing idea,

I think to a lot of women and people in general. And so there's two things that need to happen. First, before you even talk a single word about money, the pre-work is you being an irresistible candidate. That is why my clients get usually really top offers out of the gate is because they're positioned as a high value candidate, an irresistible candidate, this job shopper from the beginning.

So that's why it all builds on each other. But let's talk about when you're actually talking about money. So really always starting with gratitude, right? Oh, thank you so much for this opportunity. I'm so excited. The company is giving you an offer and they want to feel like

there's a chance you'll accept it. If you come across cold or whatnot, they're like, I don't, I'm not vibing here. This is weird. It's like a weird, weird shift. They want to feel, they want to feel chosen equally by you. Um, and then being specific about your asks and saying a lot less. Now, this is something people struggle with is really make a statement. The roles that I've been interviewing with have been more with a salary of 180,000. Is

there a way to make up the difference? I don't have to go on and on about here's the data and here's why I think I should do this and all that kind of stuff. Sure, if they ask for more information, you can do that. But I think really just having that collaborative conversation where it feels less like a ping pong match and more like you're rowing in the same direction. So I'm one of those people who fills those awkward silences too quickly. I tend to over say. And so again, phenomenal advice is to make it a statement and then shut your pie hole, right? Like no matter how uncomfortable it is, stop talking and let them respond and react without giving away too much or saying to providing too much information. Yeah. And yes, and you can hear in the way they respond if that statement was too high, right? If I said,

you know, is there a way to make up a difference to get to 180,000? And they go, Oh, yeah, well, let me talk to the manager and let me see. But if they're like, Whoa, I don't know. And I, you know, you can then have the opportunity to walk it back up like, well, yeah, that's, that's what I'm seeing from other companies, but I'm really flexible for the best overall fit and package. Right? So it also gives you an opportunity that don't walk it back until you're actually hearing the reaction. Yeah. Okay. So I want to talk about some of the things being an irresistible candidate. What are some things that we need to have, be, focused on in order to be and become that irresistible candidate.

So here's the reason why there's so many examples in the book of my clients and people I've helped that are career changers that are landing more offers than people who have the perfect experience. And that's because the way you win from your resume all the way to the offer stage is not based on what you've done in the past. It's about the company picturing you in their future. So if you can come into the interview and also show this on your resume, which I walk through it very detailed in the book of how to do this, of showing that I, I can

solve your challenges. I understand what those are and I can solve them. That is music to the company's ears because they are again, they're, they're, it's very risky to hire someone. And it's one thing to say you've done something, but for then that person to say, no, I clearly understand you and how to solve this. That's the transformation that so few job seekers make, but it makes all the difference for a company. I'm really glad that you said that because it does feel very risky and very scary. And there's frankly not much that's more costly to a company than making a bad hire. And we do have a tendency to look to our past to try to sell ourselves. So what are some

ways that we might be able to find out about what the company cares about and how we might fit in the future? Like to me, there's a research element of this. What are some things that we can look at or look to to begin to prepare ourselves to position ourselves as somebody that this company does picture being part of their future? Absolutely. In my courses and all of that, I do teach a very specific interview prep, which is actually not very long. I think people actually sometimes over research companies. And so there's very specific things you can research. But even if, you know, if you Google certain things and all that, get some background about the company, that's fine. Now, what I really want you to do is first start with this job description. Okay? Read between the

lines of what they want you to do. You know, onboard new customers and help them meet their goals. Okay. I'm reading that and I'm thinking, what are the goals of these customers that they have to reach? How is onboarding currently done? What is the best, what makes onboarding better? Is it if it's faster? Is it if it's more tailored to the person? Right, so now I'm thinking of all these questions.

I'm bringing all these questions to the interview if I'm not finding the answers online. I'm also, if it's more of like a customer success role, I'm asking their customer success a question when I'm on their website or walking into their store and asking, right? I'm experiencing it myself. And so you have to start thinking more critically. I might also go and read their other job descriptions because you could see what the other people on the team are working on too. It's a whole cornucopia of insights there. So even if we're just looking at their job board, we can get those things where at least it's starting us

to get the right questions to ask in the interview. And if a company hears you coming into the interview, asking those types of questions, I just said, they're gonna go, you know, you're right. Our time to reply on our website is quite long compared to our competitors and blah, blah, blah, right? And you are now seeming more like a coworker than some Joe Schmo off the street

who's just looking for any old job and doesn't really seem like the right job. Totally. And even if you don't know the answers, asking the questions related to the job description helps me as your future employer think, you know, this person's really trying to figure out how to be good at this job. They're trying to figure out how to win, how to succeed.

And that certainly helps when I think about thinking of you as part of our future, right? Like this person wants to do a good job. Okay, Madeline, for somebody tuning in who might be thinking job shopping sounds too good to be true, especially when you think about competitive markets or those times where your confidence isn't so high or where you feel like the rug just got pulled out from under you, what would you say to those people who might be fighting against that desperation feeling to stay focused on job shopping? I would say job shopping in the past was a really nice bonus of something that you could focus on to really attract some of the best opportunities and more opportunities. I would

say now it's a necessity. The job market is too competitive to where you now must be a job shopper if you really want to compete. The reason being is the online boards right now of applications are as noisy as can be. So you cannot just be falling into the crowd. If it's comfortable, it's crowded. So you need to be finding alternate ways to stand out. And second of all, I know a lot of your listeners, if they've been through an interview process, probably anywhere within the last year, they might have been through a process where the company was really slow to hire, or they got to the end and hired no one at all. For the reason of right now in this economy, in this job market, companies are having that fear we were talking about of,

ooh, I don't want to make the wrong decision. We only have a certain number of head count and we have to be really careful. And so now you must be that irresistible candidate. You must be that person where they go, I actually don't have a hesitation about Nicole. I know she's going to be wonderful in this position. And so job shopping is now, like this is the time to do it.

And the faster and sooner you master this skill, the more that you are never going to miss another opportunity that could be life-changing. Right. And I'll reiterate what I said at the beginning. This is an ongoing life skill, you know, so books like yours reverse the search that help walk through the actual tactics

and all that I think are super helpful. So to the listener, if you or anyone you know is wanting to develop this skill or needing to develop the skill, a reminder of the book is called Reverse the Search. Uh, Madeline's website is madelineman.com. You can find her on social media at the Self Made Millennial, and we'll put the links to everything in show notes. But Madeline, thank you for this important work

that you're doing, especially right now, when it does feel very competitive and very convoluted and all that. So I so appreciate your time today and teaching us how to develop the skill. It's been my pleasure. Okay, friend, here's what I'm walking away with. Job searching isn't just a box to check or a painful process you white knuckle your way

through. It's a skill. It's a strategy, a muscle you can build and strengthen so when the time comes, you're not scrambling. You're shopping. You're showing up to the job market knowing your worth, knowing what you want and not settling for less. Because being good at your job is awesome, but being great at getting the job, that's

power. That's agency. And whether you're actively looking, thinking about making a change, or just trying to recover from a career curveball, this episode is your reminder. You're not begging for a seat at the table. You're deciding which table is worth sitting at. Get clear, get strategic, and for the love of all things caffeinated, stop sending out 100 generic resumes

hoping somebody picks you. You are not a fit for everyone, and everyone isn't a fit for you, and that is the point. So here's to shopping, not settling. Never thought I'd say it, but in this case, shopping is absolutely woman's work.