Episode 21 – Navigating the New Rules of Work: with Alexandra Cavoulacos

We’ve all faced this huge Going Scared moment: job searching. Résumés, cover letters, interviews, networking—it’s draining at best, and gut-wrenching at worst. There are dozens of nuances to navigate in our ever-changing job market, and it’s hard to know how to prioritize our tasks. That why we’re thrilled to have career-building expert Alexandra Cavoulacos on today’s episode.

Alex is the co-founder and president of The Muse, a platform used by over 50 million people a year to find a job, learn professional skills, or advance their careers. She is the co-author of The Wall Street Journal bestselling book The New Rules of Work: The Modern Playbook for Navigating Your Career.

Today’s conversation with Alex is chock-full of job search tips, like how to determine your career values, deciphering if a company is right for you, the best way to get your name in front of the right people, and why you should always have questions for your interviewer.

Going Scared Podcast - Alexandra Cavoulacos


INTRO: Hey everyone, welcome back to The Going Scared Podcast. I hope that you are having a great summer. People have been telling me how they have been listening to Going Scared on their road trips, on their beach laying out times, and still while they’re watching the kids because there’s a lot of kid watching going on right now, I know that. Thank you so much for tuning in.

I wanted to share a review from Megan Donovan. Megan Donovan said:

“This podcast is amazing. With honesty, humor, and depth, Jessica delves into tons of topics with wonderful and relatable guests. I love the mix of business and life and the theme of going scared could not be more perfect to describe the courage of taking a leap into the unknown.”

Thank you so much, Megan. Thanks for all of you who have left reviews. Why do I ask for reviews? Because then iTunes gives me some love, gives the podcast some love. And our podcast is bringing courage to so many people.

So thank you so much for spreading the word of Going Scared and popping on over to iTunes to leave a review.

All right. Today’s guest, super excited about it. How many of us have been through the job search process? Raise your hand. Oh, my word. Talk about a process that keeps you going scared.

Alexandra is the co-founder and president of The Muse. It’s a career platform used by over 50 million people every year to find a job, learn professional skills, or advance their careers. She is the co-author of The Wall Street Journal bestselling book The New Rules of Work. And we chat some about that.

I loved our conversation. We especially get into the interview process. So many tips here. If you are on the job search, or if you think you will be on the job search someday, or you have a son or a daughter that is in the job search, please send them this podcast. It will save them going through a lot of pain.

Alexandra has won numerous awards including Forbes’ 30 Under 30 in Media, Inc.’s 15 Women to Watch in Tech, Business Insider’s 30 Most Important Women Under 30 in Tech. It goes on and on and on.

I think you will find our conversation enlightening, smart, and I know it will encourage you today.


Alexandra Cavoulacos: Co-Founder of The Muse

Jessica: Hey, Alex, welcome to The Going Scared Podcast.

Alex: Hi, thanks so much. Thanks for having me.

Jessica: I’m really excited to talk with you today, both because I love the topic and your life purpose, which is helping others to redefine work, and redefine their own career paths to live a fulfilled life, a life that we’re all meant to live. You have such an interesting background, so before we get into The Muse, tell me a little bit about your own background. Where are you from? Where do you live now? How’d you get to where you are?

Alex: Yeah, happy to.

I am a classic multicultural kid. My father’s Greek. My mom’s Belgian and Hungarian. I grew up most of life in France, outside of Paris, and all of my extended family is in Europe. I grew up there and came here for college, and was very much shaped by the cultural systems and norms in France around what is valuable to study, the pressures to study certain things the way that in the US people can be pressured to take AP classes. For me, it was very much a scientific lean, and I was good at it, and I liked it, so I went down that path. Then came here for college, benefited from a liberal arts degree and background to be able to explore a lot of different things, and discover what I found interesting, even most interesting, what I’d most like to work in.

I ended up starting out doing a lot of international relations-type work in college as my internships, working for the EU and then for the State Department at the Embassy in Paris, and then ended up in consulting. I was at a management consultant at McKinsey, outside of the first couple years after college. Learned a ton there, learned that I love solving hard problems with smart people. That is the one constant. That’s where I met my co-founder, Kathryn, of The Muse. We worked together and launched this company almost, gosh, six and a half years ago now. Just crazy.

I now live in Brooklyn, with my husband and my daughter, and that is really my life. Kind of a whirlwind, meandering path to where I am today.  Which makes sense, in retrospect, but not necessarily in the moment, which I think is true of everyone’s career.

Jessica: You know what? It’s so true.

And I love your story because I also have a background in midwifery and education and real estate, and now I’m the CEO of a fashion brand. So many people today think that there is a linear path to success. There really isn’t, especially if you do want to get out of your comfort zone and off the trail that you were given, the narrative that maybe you grew up with. It’s just so encouraging to know that your background wasn’t exactly linear to what you’re doing now.


Finding Fulfillment with the Right Company For You

Jessica:  Why don’t you give us The Muse 101?

Alex: Yeah. At The Muse, we really want to help people figure out what to do with our lives, and how to get there, and how to find a right fit for them. I think that question of fit is just so critical. There are very few companies that are really bad companies. It’s a question of whether they’re good or bad for you.

There’s actually a lot of places where I personally wouldn’t work but I would recommend a specific friend, "This looks like a great spot for what you value, for your style, for the interests you have." I think really shifting our industry and a conversation towards how we help people find fulfillment and fit in their careers is really what drives us. We work with hundreds of companies. We get 50 million users a year that come to our site to research companies and careers and help find next steps for them, and we also have career coaching and jobs on the site.

“Shifting our industry and a conversation towards how we help people find fulfillment and fit in their careers is really what drives us.” Alex Cavoulacos

We’re really trying to have a single destination that helps benefit people in a much less judgmental way than the industry has been. It’s been very judgmental and transactional, I find. You apply, there’s a black hole, you don’t really hear back, or companies are rated on a one to five scale. That’s not really helpful for people who are navigating a nuanced, complicated decision about your career, which is really the majority of where you spend your time. It’s a huge part of your identity, it’s a huge part of your week. Sometimes spending more time at work, oftentimes more time at work than with your loved ones. Getting that right is important, and that’s really our life’s work here.


Knowing What You’re Looking For In a Job

Jessica: How you spend your days is how you spend your life. It is extremely important to enjoy how you are spending your days. What was your ah-ha moment? What’s the problem that you had or that you saw that you realized you had a solution for?

“How you spend your days is how you spend your life.” – Jessica Honegger

Alex: It’s really funny. Just like careers, I think most companies’ founding stories make sense in retrospect, but were always a series of steps.

One of the things I think that was really foundational is Kathryn and I met McKinsey and Company. We were management consultants. We obviously both took the job because we thought we’d like it, we’d learn a lot there. Within even just a couple of weeks, a couple of months, it became really clear that it was a better fit for me than it was for her, and we had a lot of conversations about that. Could we have known ahead of time? Did we even have the information to process and realize that? Doesn’t mean she would have made a different decision, necessarily, but this information asymmetry was actually really, I think, a critical ah-ha moment of saying, "Oh wow. So many people take jobs at companies without actually knowing either what they’re looking for, which is important, or whether this place will actually provide that, which is equally important.”

“Many people take jobs at companies without actually knowing either what they’re looking for, which is important, or whether this place will actually provide that, which is equally important.” – Alex Cavoulacos

I think that was a really big piece, and also a really foundational part of our belief that, really, it’s not about good and bad companies, but about what’s good or bad for you.

“It’s not about good and bad companies, but about what’s good or bad for you.” – Alex Cavoulacos


Discovering Your Career Values

Jessica: I love that because I do feel like people are more looking, when they’re job searching, for a role, than they are primarily looking for the company. Do you find that to be true? And are you switching that on its head?

Alex: Yeah, we see that to be true.

I think there’s two types of job seekers that we’ve seen. Obviously it’s a spectrum that the extreme is, “I’m going to company-first and say where are the places I want to work, and then see if they have a role for me.” Or you have, "I know I want to be a product marketing manager. I know I want to be in sales. Let’s see who’s hiring." Either way, both end up being part of the decision that you’re making.

For us, it’s really important to figure out how do we help get that information to people, regardless of which way they like to process information. It’s a privilege to be able to say, "Let me decide where I’d like to work." If you need a job, if you need a job next week, then of course you’re going to look job-first and role-first, and that’s totally okay. That’s normal.

How can we help you also not jump the gun and take a job somewhere that’s not going to be aligned with your career values, and what matters to you?

What You Can Offer And What You Value

Jessica: Let’s talk a little bit more about that, about career values. Because I know you write about that in your book, The New Rules of Work. I love that because I think that if we don’t know where we’re going, then we just are a bit aimless and then we wind up in a job that we don’t necessarily love. And then we don’t really want to start on the whole job searching process all over again. Getting clarity around your own values and really understanding the values of the companies where you’re applying for is so important.

“Getting clarity around your own values and really understanding the values of the companies where you’re applying for is so important.” – Jessica Honegger

How do you help people identify those career values?

Alex: Exactly. The first part of our book, the first few chapters really focuses a lot on that. I think it’s a process that individuals have to go through, and it’s a step most people skip. They go straight to typing in a job description or title a job search platform somewhere or a job board without thinking about what it is about that role they want, what they’re trying to prioritize.

It makes it harder to get it right if you don’t really do the upfront work and you don’t think about what it is that you want. You can have two people have the exact same résumé, the exact same major and the exact same background, but if one person is prioritizing for prestige, compensation, and stability because that’s what they value, because they have student loans, because whatever reason, those were the three things they want, and someone else is prioritizing flexibility, creativity and autonomy, they’re going to choose different roles at different companies.

I think the big mistake, both the industry and just the way we think about careers, a big mistake I’ve seen is saying, "Okay, my past or what’s on paper should be dictating what I am able to look for" versus saying, "Let me figure out what I want, and let’s figure out what I can offer. Then what does that mean for what I could do next?" Or what kind of company? Two people could go into sales but one person may optimize for higher base compensation, more guaranteed quota, and someone else might say, "I want somewhere that I can travel." Those are just choices. And you do have to pick. You can’t get everything.

Knowing what matters to you, I think, is really an internal process, but also one that you can get a lot of support from by doing research online, talking to other people and figuring out what really you value.

It’s funny, to give one quick anecdote, I remember speaking to someone who recently graduated college, and they were thinking about what they wanted to do. And they’re like, "I’m so excited. I think I really want to work for a startup." Great. Why do you want to work for a startup? Once we really dug in, they didn’t have an answer. The reason they wanted to work for a startup is that that’s what their friends were doing, that’s what was cool. That’s what would look like they were doing the “it” thing right now, in a way that maybe investment banking would have been 20, 30 years ago. They hadn’t thought about, Okay, it’s more likely to have less structure. It’s more likely that I can try lots of different roles and wear a lot of different hats, but I probably will get less training.

They hadn’t thought through all of that, and they were actually someone who really valued clear direction and structure.

Jessica: I’m laughing. I’m thinking about when we were in our startup days, and I still want to write apology notes to my first hires. Talk about no structure, no career path, no reliability.

Alex: At this point, startups are familiar enough to so many people that you should know that’s what you’re signing up for. People will sign up knowing that’s going to be one of the challenges but that they’re comfortable navigating it. And others will join and really struggle with the lack of structure. I think that’s where both the self-knowledge of what you want and what you value versus just what your friends will think is cool or going to work for a big company because your parents will be proud. That’s a really big factor, what other people think in your career decisions, but they’re not the ones going to work every day. They’re not the ones working. You can work for a big brand, everyone’s like, "Oh that’s so cool that you work with so-and-so brand," but your job might really suck and you don’t like it.

I think really deciding what matters to you is how you can find the right fit and really prioritize what things need fulfilled.

“Deciding what matters to you is how you can find the right fit and really prioritize what things need fulfilled.” – Alex Cavoulacos


You Have a Choice In Work

Jessica: You said not many people actually said and are conscious and aware and do the work to identify their values. What do you think are some of these limiting beliefs that actually prevent people from even doing the internal work that you are proposing is the most valuable thing in the career search process?

Alex: I think one of the things is just the change in the industry, the idea that you have choice in work is kind of new. It’s funny because I’ve spoken about this a few times, but the question of whether or not you get your fulfillment from your job is a newer one.

Decades ago, you’d work from nine to five, but you couldn’t be reached on weekends and at night. There were no cell phones. You had community and family and extracurriculars, all these other things that, for the majority of people, is where they got their fulfillment and their self-actualization. Work was work. That’s what it was. That’s fine.

When work takes over so much more of your life like it does now—you’re much less likely to be disconnected, you’re more likely to be working more and more hours, working on vacation, thinking about work in the shower, doing more intellectual work as well, that’s shifted in terms of the way the digital environment has changed—it’s more important to get fulfillment from work.

I think our parents and our grandparents didn’t necessarily go through the process of saying, "What is that I want, and why?" We don’t have role models for it. If you do, you’re very, very lucky, but you’re not the majority.

I think that’s one of the big transitions from a cultural perspective that’s not actually generational. There are people in their 40s, 50s, 60s today who still want to work and are asking themselves for the first time, "What do I want?" They just started in a career path and that was it. They’re like, "Well, I started as an accountant, so I become a senior accountant, but I run the accounting department and that is what I will always do." Then whether they’re laid off or they have a decision to make a career transition and whatever it is, they have a moment where they ask, "Do I actually want to be an accountant anymore? Why did I ever become an accountant? Maybe it’s because I actually loved working in the details, and now that I manage, I don’t get to do that anymore."

Those are the things that I think are exciting for me that it’s intergenerational. It’s at every level of the workforce, is people really trying to think about how they can have impact in a way that matters to them.

Jessica: Yeah. It’s so interesting because at Noonday, we work in about 13 different countries, and we are working in countries that are forty, fifty years behind where America is now. We’re working in India, where you do absolutely follow in the footsteps of your great-great-great-great grandparents. I just got back from Vietnam, where it was a fourth-generation horn artisan. And there isn’t that sense of, How can I have purpose in my job and be fulfilled and passionate? But there is such satisfaction and dignity for the workers because they’re working in environments where the unemployment rate can be 80%.

I struggle a little bit on the flip side here in America. We are creating job opportunities. We are a social entrepreneurship company, and so we have created thousands of jobs for women across America to have flexible incomes and really live with impact.

I find sometimes, having this conversation with my team members at Noonday, and we talk about this idea of purpose, which our company is completely purpose driven. That’s a primary reason why people really want to work at Noonday. Then I also am all about grit, and I know that you’re not going to love your job every minute of every day.


Accepting The Good & Bad Days At Work

Jessica:  How do you coach people to hold this tension of finding purpose, but honestly sometimes your days just suck at work?

Alex: Absolutely. I think that’s funny. There’s nothing in your life that’s always good. Nothing. Maybe sleep. Sleep is always good.

Jessica: Sleep is always good.

Alex: I think that there’s a question around shifting too far into the “follow your bliss, find your passion.” I think it does a disservice to people.

Jessica: Do you think that there has been a shift? Because I do sometimes feel like there is this almost perfectionistic mentality of, No, there can’t be a bad day at work.

Alex: Yeah, I think there has been. I think it’s coming back more towards the middle.

I think it’s started with “work is work,” and then it went towards “work should be your all fulfilling thing.” Really, it’s somewhere in the middle, where you should do something that fulfills you, but there will be good and bad days, there will be hard times. There’s challenges that you will be glad you went through and challenges you will be not glad you went through and you would avoid if you could go back in time.

I think one of the most useful, for me, one of the most useful parallels with careers is actually thinking about finding a life partner. When you go out and you’re dating, if you don’t know what you’re looking for, it’s very hard to find them. If you’re doing really superficial, like, “I’m looking based on looks,” you’re going to have a lot of failed dates because that isn’t actually the foundation for the majority of people of a successful relationship. It’s just the first glance.

Just the same way how well-known a company is or how sexy their offices are is actually just a superficial first look at what an actual culture or an employee experience is like. Similarly, with any relationship, there are good and bad things. There are hard things. You have to work at it.

I adore my husband. He’s not perfect. He’s perfect for me, but he is not perfect. I am not perfect either, and so I think that it’s a big thing when I think about careers is it’s the same trade-offs. There are things, whenever people decide to get married or commit to a partner, that you know you’re signing up for also their weaknesses and their gaps and their failings. But those are ones you’ve decided you’re okay with. The things that really matter to you, you found in them.

When you think about an employer, it’s a less long-term commitment, but I think it’s the same approach is actually very, very useful. Saying the things that are non-negotiable for me that are really important, they have. That may mean that they don’t have this or this or this, and that’s something I signed up . . . I think the most important thing is if you sign up knowing.


Honesty In An Interview Is Key

Jessica: Let’s talk about when you were going through that interview process. I know you are running a vastly growing company, so you’re probably interviewing people, or I know you have people that are interviewing people now. I think it’s interesting to think your entire company is built on this idea of helping people find the right careers, and helping companies find the right people.

How has that helped you become a better president in your role as you go about hiring people for The Muse?

Alex: Yeah, I mean I still interview all the time. I don’t do it to be the final decision maker unless the person is, you know, reporting to me directly.

Jessica: Right.

Alex: But I like meeting people who are going to join The Muse, and building the relationships from the beginning.

I think what I found is that having that honesty is really useful in conversations. Obviously, you’re both trying to like impress each other to a certain degree. It’s kind of like dating, right? You’re not going to be like "Hey, this is me in my pajamas on a weekend." But I’m not going to pretend to love art if I don’t, you know? I’m not going to be like "Yes! Poetry slams are my thing," if they’re not, because it kind of gets you into trouble down the line.

I actually had breakfast with someone this morning who could have . . . you know, I was exploring a role I’m probably going to post soon. I was introduced to them, and as they described what they liked, I was able to say, "You know what? It sounds like what I’m looking for is totally the wrong thing, because it’s going to be x, y, z, and you said you actually don’t want something that’s that.”

That’s amazing we figured that out in the first conversation.

Jessica: That is.

Alex: Let’s not waste each other’s time. That being said, we both got a lot of value out of it. I can now keep an eye out for things within The Muse or outside The Muse that might be a good fit for this person, where they would actually thrive. They can keep an eye out for people who might be a good fit for me and the role I might be hiring for. But why pretend?

I think the worst thing is when someone says, "Oh, and this is what I’m looking for," and you’re like, "I can offer that."


Interview 101 Part 1: Preparation & Research

Jessica: So let’s give an Interview 101, if you don’t mind, because I have definitely been through some hard interviews with people and I’m like "Oh my gosh, your mama didn’t tell you some basic things!"

Give us an Interview 101.

Alex: There’s obviously different steps of the interview. But once you’ve applied and you hear from a company, I think that some of the most important things are:

1. To prepare, right? And make sure that you’re coming in knowing what you’re signing up for. So if you could find out who you’re interviewing with, it gives you a little bit more context.

2. Research the company. Look at what’s at least publicly available information. You need to do less of that during the early stages. You should do more of it as you continue down the path, so that by the time you’re in the final round, you have a really good sense of the company and the role, and you can ask informed questions.

I’ll give you an example of something that might not be the best impression: if you’re in a final round with me, for example, and ask, "So how did you start The Muse?"

Jessica: Oh my gosh.

Alex: It happened.

Jessica: Painful.

Alex: Probably one in three interviews that I do. And, that information is highly Googleable. It’s not a bad question, I will answer it. Of course, and I’m happy to have a conversation. I’m happy to have a conversation around it.

But the interesting thing to me is what it signals is you were curious about it, but didn’t look, didn’t do any effort, didn’t do any research. You didn’t take initiative. And if it’s a role where that’s important, I will take that into account.

And it’s interesting, because the much better question to ask is "I was looking up how you started the company and heard that you moved to San Francisco for the accelerator and Y combinator. That’s so interesting. What was it like?" That you’ve done the research, that you’re inquisitive, and maybe it’s something that you particularly care about. So I think that’s where, one of the things I’d say for interviewing is don’t forget the prep. People think about prepping their own answers. But prepping the questions are just important.

“People think about prepping their own answers. But prepping the questions are just as important.” – Alex Cavoulacos

If someone says, "Do you have any questions for me?" And the answer is no, that’s not a great sign.

Jessica: No.

Alex: If you interview five different people and you say, “Yes, I’ve actually met with a bunch of folks that got all my questions answered," that happens, that’s normal. But if you don’t have any questions, you have to be interviewing them as much as they are interviewing you to find that fit. So going into it with that head space and really believing that is important.

And not being afraid to ask the questions that matter. You know, if you really, really care about flexible work, some people will be scared to ask and say "I’m not going to ask if you have a flexible work environment, because if you don’t, maybe you’ll disqualify me." If you only want to work somewhere with a flexible work environment, you should want them to disqualify you if it’s not an option.

Jessica: That’s so true.

Alex: You should disqualify them, right? If it’s the only job on the table and you need a job tomorrow, I understand and obviously you should be using your discretion for these things. But the idea that, "Oh no, I might be out of the running." But wait, maybe they should be out of the running for you. So really putting that mindset towards it I think is really important.

Jessica: So prepare, don’t just think about your answers, think about the questions that you want to ask: what else?

Alex: Thank you notes, follow up . . . you know, you notice it. You certainly do the more . . . especially depending on the role that you have if you’re going to be interacting with clients, if you’re going to be writing or communications in any way, I find it really useful to see what people apply.

I’ve certainly interviewed some great people for our sales team who write amazing follow-up notes, and I’m like, This is exactly the kind of thing that I want them to sending our clients after doing a call. It shows me that they were listening, they brought up little nugget, they sent me . . . "Oh and this article that I read made me think of you and the part of our conversation we did x, y, z." It’s actually showing me their skills in their thank you.

So thinking about every interaction you have is part of the package, not just the moments you’re in the room with an interviewer.

And finally, I’ll also add this, it’s relevant to that: Every person you talk to at the company, every interaction you have is part of your interview. The person at the front desk, if you’re getting a glass of water, and really using that as an opportunity to see what the company is like, what the culture is like, are they really friendly?

“Every person you talk to at the company, every interaction you have is part of your interview.” – Alex Cavoulacos

When we were smaller, we didn’t have anyone at the front desk, and it’s funny because our company’s really friendly and really nice. So, people would come in for an interview, be sitting at the front, and like eight different people would come by and be like, "Hey, can I get you a glass of water while you’re waiting?" Without knowing. But it told them a lot about the kind of place we were.

So both use it for clues about what the company’s like and the energy. But also remember that you’re presenting yourself as a candidate, no matter what. So, if you’re sitting there charging your phone, having breakfast, looking really sloppy and like you just ran in from the subway, take a second. That’s an impression you’re making.

Actually, one more. This is actually a hiring pet peeve that a lot of people have but don’t talk about: do not arrive really, really early. If you are, like, thirty minutes early, go to a coffee shop around the corner and arrive five to ten minutes early. But most companies aren’t really equipped for you to just sit around at the front, and you can actually add a lot of stress to the hiring manager when you arrive super, super early. But do plan so that you’re not arriving late.

Jessica: That’s really good advice because we are a small, I mean, we have fifty employees and when someone does arrive early, and our office space isn’t huge, so it is a little awkward you know, with someone just hanging out for a really long period of time.

I love this advice.


Interview 101 Part 2: Answering & Asking Questions

Jessica:  Okay, tell me: what are some of your like favorite questions to ask in an interview. I know that it changes from role to role, but what’s sort of your money question that you always ask?

Alex: I think for me I really like questions that dig into specific projects, actually. What was a project you were really proud of, and tell me a bit about it. It both tells me about what they choose, what makes them proud. Sometimes we have folks who say "I had this project and it was really challenging. The fact that we turned it around is why I’m proud of it." Others, it’s the reach it had.

So it not only tells me about the work they did, but also what energizes them, which there’s no right or wrong answer, but it’s really helpful for me. If someone joins the team and I know they’re really energized by recognition, or by client impact, that actually helps me be better as a leader and a manager if they’re reporting to me directly. It also helps me learn about their communication style. Do they get super into the details, do they talk big picture, do they talk about process, do they talk about ideas?

So I think a lot of questions like that can really help you just get to know someone. I think the best questions don’t have a right or wrong answer but give you a window into the kind of person, the kind of colleague this person would be for you.

[insert quote]
“The best [interview] questions don’t have a right or wrong answer but give you a window into the kind of person, the kind of colleague this person would be for you.” – Alex Cavoulacos
[quote time stamp begins:  28:22]

And in any team, I think you need a mix of skills. If everyone’s the same, not just demographically, also demographically, but if everyone’s super idea-generating, sort of machine-type people—if nobody has process or execution orientation, that team’s going to struggle. So I also think about team building as a whole, about what underlying skillset might this team benefit from: data orientation, process orientation, really great EQ, interpersonal skills, whatever that might be to make the team whole. So that is a question that lets me get to that.


Interview 101 Part 3: Networking

Jessica: So let’s talk a bit about networking cause you said earlier these résumés often go into a black hole and we get hundreds of résumés for every position that we post.

What is the most effective way to get your name in front of the right person? Because I think a lot of people just send their résumés out to twenty different companies in town and aren’t necessarily going that extra mile to make that personal connection.

Alex: That’s a great question.

“Networking” is also a word that makes a lot of people really nervous or scared. It feels like a hard thing to do if you don’t do it day-to-day. But, I think reframing it as “relationship building” is actually really helpful. Like, that’s all it is. You’re not going to meet a stranger and say "Here’s my résumé. Please pass it on." You’re trying to build authentic relationships with people that could now or in the future lead to something beneficial for either one of you.

“Relationship Building (Networking): You’re trying to build authentic relationships with people that could now or in the future lead to something beneficial for either one of you.” – Alex Cavoulacos

When it comes to the actual application portion, what I usually recommend to people, and this is something for people who apply to college, you often think about your sort of safety schools, your target schools, and your reach schools, right? And you have a spread because you have things you’re really excited about that you’re less sure about, and so you think it through.

I think when it comes to applying for jobs, most people only apply to their reach. "I’m going to work for Coca-Cola or like IBM," and you’re like, "Great, maybe, but also what are the other options out there?” So when you think about the jobs that you’re applying to, whether it’s sort of reach, targets, or safety, or whether it’s more priority, like based on your excitement level, I think it’s important to have a top tier that you’re willing to invest more in. You’re spending more time. You’re crafting a customized cover letter. You’re seeing if you have connections. You’re looking on LinkedIn seeing if, Does anyone I know, know someone who works there? And then I’m asking them "I saw you’re connected with John at IBM. Do you know him well enough for you to be comfortable passing on a short recommendation? I applied to x, y, z role."

Those are all things that you can do. If you’re doing them for all the jobs you’re applying to, it feels overwhelming and then you don’t do it for any, which I think is the biggest mistake people make. I think it’s much better to say, "These are the ten jobs I’m really excited about," or the five, whatever number this week or this month, and, “I’m going to actually write a custom cover letter.”

About 45–50% of hiring managers care about cover letters. It kind of sucks because you don’t know. It’s a one in two chance. Fifty-fifty. Is the person going to read it or not? Are they going to care about it or not? But for me, there are people we have interviewed based on the strength of their cover letter alone.

Jessica: I know. For everyone listening, Noonday loves cover letters please.

Alex: The Muse does too, and we actually say it. We’re like, "Please submit a cover letter so we can get to know you." We don’t put it in there just for fun. We put it in there because it tell us so much about you and it’s an opportunity to stand out.

I think that’s the thing: with every application, there’s opportunities to stand out. Sometimes it’s making sure you’ve read all the instructions. The number of times people apply without having read the instructions and not including . . . like it tells me a lot about your detail orientation because a job that needs detail orientation, you’re not even applying right. How can I count on you to do the job right?

Where can you stand out? Did you apply the way they said, doing the things they said? Did you take the opportunity to customize the cover letter, if it’s a job that you’re excited about? Did you check if you have connections?


Building the Relationship Before You Get the Job

Alex:  Do you follow the company on social, if you’re on social media? It’s actually one of the things I’ve also seen be really successful is we post for x, y, z role that we’re opening and someone comments back, "I just applied, I’m really excited." Our social media manager will pass that on to our hiring team. There’s different moments where you have a chance to do that, so I think it’s thinking about your application holistically. And if you have a network, obviously tapping into it is really important. I think what’s hard is a lot of people just don’t have the network.

Jessica: Mm-hmm.

Alex: And that feels harder. Other people have this big leg up that you don’t have, so don’t forget that social media’s a great equalizer. You can actually message someone directly. If there’s a product role you’re really excited about, you can actually message or tweet at the head of product of that company and be like, "Hey I saw you were posting for x, y, z. I’m really curious how you’re approaching this problem." They may or may not answer. They’ll probably see it. But if they do, you now have a connection.

“Social media’s a great equalizer.” – Alex Cavoulacos

Even better, start following them and engaging with them ahead of time, right? And then building those relationships before you meet them. It’s like anything else, you’re not going to go to someone who’s not a friend and ask for a favor, or you shouldn’t. But you can ask friends for favors. That’s really what networking is: professional friends that you can both go and ask for favors, and they can say yes or no. But the impact you have on them ahead of time is the strength of the recommendation you’ll get.

Jessica: So true. It’s just building that relationship ahead. I think two people get worried that networking is all about this exchange of favors, but if you go into it with the intention of relationship, really with no strings attached, eventually you can ask a favor and you know that it’s coming from the right intent. I think that’s really powerful.


Smart Recommendations

Alex: One thing I’d also say is a mistake a lot of people make is thinking that any recommendation is a good one. If someone I don’t really know asks me for a recommendation that I can’t vouch for, because essentially that’s what a recommendation is. It’s saying "Hey, can you vouch for me?" And if they don’t know you well enough to vouch for you, or if they’ve had . . . I’ve had people I’ve had poor working experiences with asking me to vouch for them. It’s not a great choice, right? You might not want that recommendation, or it might not be valuable.

Now there’s a different question you could ask, if you don’t really know me well, saying "Hey, would you be comfortable passing my application on?" That’s not a recommendation, that’s me saying, "Hey, there’s this person that I’ve tweeted back and forth with a few times. I don’t really know them, but they wanted to apply. I just wanted to pass it on." That can help you at least get an eye on your résumé for a company that maybe doesn’t look at every single résumé. We do, for the record. A lot of companies don’t.

I think the flip side is if you’re like, "Hey, please recommend me." And they feel uncomfortable. They pass it on, but it’s kind of a lukewarm recommendation, you could also be hurting your application. So being really thoughtful about, Is this person actually able to vouch for me? That’s what I’m asking them to do? Or am I hurting the relationship because I’m asking too much of it? It’s part of sort of this calculus, I think—

Jessica: It’s a dance.

Alex: It’s a dance.

Jessica: It truly is.

Alex: Exactly.


Creating a 3-5 Year Plan

Jessica: So your whole book is The New Rules of Work, obviously comparing to some sort of former rules that we used to live by. If you were to write this book in five or ten years, how do you see this landscape continuing to change?

Alex: Yeah, I think it’s one of the things that’s changing the most, and continue to change, is the options on the table are just wider and wider. You can now work in cryptocurrency. That was not the thing before.

Jessica: That’s so insane.

Alex: Ten years ago, there was no such thing as a social media. Then it was an intern position. And now there are people who are at the executive level who have a decade of skills, almost, working in an analytical, strategic, creative role that did not exist beforehand.

So I think one thing we talk about in The New Rules at Work is that you really need a 3–5 year plan, not a 10 year, 15 year, what I want to do in my entire career plan, because you cannot possibly visualize what the future options will be.

If you know, I want to be a heart surgeon, it’s all I want to do, amazing–that’s fantastic. But it’s okay if you don’t know what you want to do forever. But if you know in the next 3–5 years, I really want to look at this experience, or learn this skill, or be in this industry, that’s sufficient. Because so much is changing and how we connect from one path to another, I think is still being defined.

“It’s okay if you don’t know what you want to do forever. “ – Alex Cavoulacos

You mentioned earlier working with people in other countries that have certain different workforces. One of the things that was the biggest shift for me, coming from France to the US–France is shifting now, but you know, 15 plus years ago–it was really linear. If you start in this field, your options are in this field. It is a limiting–you make a choice, and you close doors. If you continue to go down that path, and the hallway has all the doors are closed, and you just keep going down the path.

I think going through college with a liberal arts background; actually being able to change my major, take different classes, was the first time I experienced choice in that real way. And what’s interesting is, it’s both an incredible thing to have, and it’s also very hard.

“[Choice is] both an incredible thing to have, and it’s also very hard.” – Alex Cavoulacos

There’s a paralysis of choice. It’s easier to say, "Well I committed to accounting, so, now what kind of accounting do I want to do and what kind of company?" It’s just fewer questions to have to answer. Saying, "Okay, well, I started in sales, but I could continue in sales, I could go to account management, I could go into business development. I actually like writing, maybe I could be a freelance journalist." All those are options.

People change their careers dramatically. They’ll go from being lawyers to being bakers, right? There’s so much you can do, and that is a hard thing. I think it’s caused a lot of anxiety in the workforce. A lot of people are still struggling for their paths.

And so one of the things that I hope, when you’re looking 3–5 years ahead, that it will be so much more common, and people will have heard so much more about these winding career paths we mentioned at the beginning.

There’s very little that is linear, and it doesn’t have to make sense in the moment. You don’t have to justify it. And every skill set you develop, every experience you have is building towards something. And maybe you’re the best possible journalist ever, because you started in accounting, and you actually have this amazing detail orientation that lets you be a great investigative journalist.

Jessica: Hmm

Alex: I talked to someone who was a lawyer who wanted to become a therapist but was really nervous about explaining it.

I was like, “Look, there’s so many parallels. You are used to dealing with sensitive information. You are used to working with clients, who may or may not be demanding. You handled all the process that comes with working with clients, sending invoices and time tracking and scheduling and all those things. And you’ve had to ask questions to get the right answers from people. There’s way more overlap than you realize, and all these transferable skills are real.”

I’m hoping people will be much more understanding of them than they are now, both hiring managers understanding how to apply transferable skills, but also individuals realizing what their options are.

Jessica: I love that, but I think that really goes back to the interview process as well. It’s that if you’re able to sort of lift your eyes up and sort of see the metanarrative of your life. What has been a common thread? Guaranteed, yes, there are common threads throughout all sorts of careers, because the one consistent thing you’re bringing to your different jobs is yourself. And I think being able to sort of describe that narrative is really powerful in an interview process.

“There are common threads throughout all sorts of careers, because the one consistent thing you’re bringing to your different jobs is yourself.” – Jessica Honegger


Consistency In Career

Jessica:  On that note, I am curious: it used to be like red flags, “They change jobs every year.” When would you consider the "red flag" now? How often are people changing jobs? What’s your sort of tolerance level for that?

Alex: Yeah, I think part of it depends what industry you’re in, what function, right? You see a lot more change for people who are in start-ups, where maybe it’s the company that no longer exists rather than them leaving the company.

For me, it’s more about patterns. If they spent 9 months somewhere and then they were somewhere for a few years, then it wasn’t the right fit for whatever reason. If I see 9 months, 8 months, 6 months, is it that they’re not good at their job? Is it that they keep picking the wrong place, don’t know what they’re looking for? What’s happening? It doesn’t mean they don’t necessarily interview if the skillset is right, but it’s a flag to get into.

And some people are good about proactively talking through it. Like I know I’ve jumped to a couple different roles, there was a series of circumstances here that, you know, we can talk through it, but sometimes it’s an indicator that this person has performance issues. And if you don’t address it then, that may be the underlying impression you’re giving on your résumé.

I think I’m also seeing people not know how to sort of bridge the gap between different things, so for example if they freelance and took about a bunch of different projects and it just looks really fragmented. But if it’s really freelance you can say, “The past two and a half years I freelanced, here’s examples of clients and projects.” Versus, “I bounced around three months at this company, two months at this company.” I think a little bit of it is also framing, but that would be one of the red flags, is the pattern. What patterns are you showing that might not be indicating what you want them to, and are you addressing them?

Jessica: So job searching obviously is a nerve-wracking process—it can be, it can be. We can all reframe it to really think about it as such an opportunity and the opportunity to discover really what you’re created to do in the world. But I find it is a time of a lot of fear.


Tackling Common Job-Seeking Fears

Jessica:  What are some of the fears that you see are most common in your users? And how do you help them move through those?

Alex: I think the first one is, not knowing what they want to do, actually. It’s that first step.

The number of times I hear "I want to leave what I’m doing, but I don’t know what I want to do next." That fear that either you won’t figure it out or that you’re going to be stuck doing what you’re doing, I think that’s a very real and palpable one. What we recommend on The Muse and articles that we have and also in the book, The New Rules of Work, is really taking control of, at least of having a process and a next step.

So you don’t know what you want to do next, it’s taking the time to think about your career values. If you have your career values, but you’re not sure what job fits them, i’s having informational interviews with people for things you find interesting. I remember when I was still at McKinsey as a consulting the city about 2 years in. All my friends really needed was a 2-year program, and I’d been offered to stay on for a third year, and I liked it. I liked it, but I felt like maybe, I had this FOMO (‘fear of missing out’), right? Should I be leaving, everyone else is leaving. and I decided to do a bunch of informational interviews. And I had conversations with a bunch of folks.

One of them, I remember, was a branch manager of a large, a well-known company. And her job sounded so sad. I asked her about her role, and she said, "Yeah, I need to change the shade of red on the T-shirt, I need to get 20 sign offs." And I said, "Oh, got it, this is not for me." And it was just this really clarifying moment: that things that sound cool from the outside all have their good and bad, and that I was a bad I was not willing to compromise.

So I think that’s one of the big things I push people, we push people, is to not just take the outside glossy look, but to actually learn a little bit more about what it’s about.

The other fear, I think, is just when you’re interviewing. It’s fear of rejection. And that’s hard. Unfortunately, resilience is something you need to develop over the course of your life. Some people are forced to develop it sooner, others don’t. Some industries, obviously if you’re in sales you hear no all the time, or if you fundraise you hear no a lot more, you develop that muscle. But getting comfortable with how you bounce back from rejection, I think, is also really important, so that fear doesn’t paralyze you as you’re applying for jobs.

“Getting comfortable with how you bounce back from rejection is also really important, so that fear doesn’t paralyze you as you’re applying for jobs.” – Alex Cavoulacos

Jessica: Yeah, and I think that for someone walking into an interview that’s already fearful of rejection, I mean, you feel that energy, you know? It’s important to really set your mind on what’s possible instead of already counting yourself out, in a way.


Entrepreneurs Can’t Stay Comfortable

Jessica:  So what about you? This podcast is all about going scared. Entrepreneur, new author, how are you continuing to live on your growth edge?

Alex: I think one of the pros and cons of being an entrepreneur is you don’t have a choice. You are pushed to that edge, you cannot get comfortable, that is not an option set on the table.

My co-founder Kathryn and I joked since the early days that our job is to grow faster than the company. And when the company’s growing fast, then we got to grow even faster. So some of that is investing in yourself, it’s taking the time, making sure you’re self-aware, asking for feedback, processing and building from that feedback. We do 360 interviews twice a year, and Kathryn and I get reviews as well, and we get reviews from our peers and, of course, direct reports, from our executive team. But we also do a companywide survey. It’s our performance and our style impacts every single person here. So that’s amazing to read and you’re like, Great, I’m so glad, I’m killing it here, and other stuff you’re like, Ooh, yeah, they’re right. I really need to work on that. I think that makes sure that you have a mirror that’s showing you some of the things that are impacting others.

I also encourage a lot of entrepreneurs to get a coach or to think about coaching. I think it’s done much more often than it’s talked about. Executives in general and entrepreneurs in particular, we’re just like anything else, elite athletes have coaches. They sometimes have food, sports, and mental coaches, all separate people that are helping them be at their peak performance. And when you’re trying to do elite performance in the business world, not having someone else there to help you grow, particularly when you don’t have a real boss—obviously we’re accountable to our board and our investors, we’re accountable to our team, we’re very serious about being accountable to our users, our partners, and our clients. But there’s no one who’s sitting me down to say, “Alex, these are your goals this month. Here’s some feedback for you.” You don’t get that when you’re an entrepreneur.

So making sure that you create a place that’s free to hear what you might need to work on and then get support in growing there, it’s been the best thing that I’ve done to make sure that I keep growing to be the best leader that I can be.

Jessica: I love that comparison with just an athletic coach. There’s no athlete that doesn’t have a coach, so why shouldn’t an entrepreneur have a coach as well?

I think sometimes when you’re starting out, maybe you’re scrappy and there’s not a lot of money on the table, I think you can go out and create coaching for yourself too. We’ve been able to hire an executive coach recently, and it is next level, but it can be really expensive.

I just want to encourage listeners to go get the help that you need. You can form your own brain trust, you know. It doesn’t have to be paid.

Jessica:  And by the way, Alex, you are like hello, the most amazing career coach! I’m so excited about all of the information that you just gave, so much value. I can’t imagine how much value you are offering via your website, and your articles, if I got so much out of a 45-minute podcast. So how can we come and make you a part of our brain trust? Where can we find you?

Alex: Yeah, absolutely. So I’m on Twitter @acav, it’s relatively active there, themuse.com or @themuse on Twitter. We have over 10,000 articles covering all sorts of topics, so if you have career question themuse.com/advice is where I would start, and search there. We have questions on how to deal with your manager, how to manage for the first time, how to negotiate a raise, how to prepare for a performance review, how to give feedback, receive feedback. We have a whole community in the discussion section. We recently launched where you can actually ask questions and hear from the community, as well as our experts for things like productivity or being stuck in a rut. So knowing that there’s all those free resources.

And then, obviously the book, The New Rules of Work, for those people who, especially like a little more time to process and a bit more of a taking you by the hand and going A to Z. We do have these 10,000 articles and website, but you have to sort of pick and choose and make your journey. In the book we really go from Part 1: How to Figure Out What You Want. Part 2, How to Get It, Interview, Cover Letter, all of that good stuff, Negotiation. And then Part 3 is once you have the job, setting a good foundational strength to show you’re successful. So those are all options.

I think you’re right, what you said before about peer mentorship, online resources, there’s a lot out there. It’s an amazing world we live in with the access to information that we have. Knowing that you are not alone in your career and your struggles, you are not the first person to go through what you’re going through and you will not be the last, and there’s a solution to it. The worst thing you can do is just stay stuck.

Jessica: I love that, absolutely, and we are all about getting out of our comfort zones and moving towards a life of purpose by leaving comfort and going scared.

This has been awesome. Thanks so much for joining us today, Alex.

Alex: Thank you.


It’s Okay to Ask For Help in Your Job Search

Jessica: That was such a great conversation. I loved how we ended and how Alex just reminded everyone that none of us are alone. No one’s alone. I know that we can feel alone, but I want you to know that that is a lie. There are people out there who want to show up for you, who want to help you. It just sometimes takes reaching out and asking for help.

My recommendation to you is to go and find the help that you need, whether it’s online whether it’s—I loved her peer counseling recommendation, lunch and learns—go find the information. The connections and the people that you need if you don’t have something right now it doesn’t mean you’re not going to have it even a week from now. Go do that thing that you need to do.

Thanks again for tuning in on today’s episode. Find me over on Instagram. Tell me what you learned, and I will see you back next week.