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Margo SternMargo Stern has landed desirable jobs at several prominent companies – places like Google, Twitter, Facebook, and Peleton.
She has also built multiple content design teams in those same organizations.
Now she’s writing a book to share both her job-hunting expertise and her extensive content hiring experience.
We talked about:
- her work as a the content design lead at Peleton and her prior roles at Google, Twitter and Facebook
- her knack for landing jobs, and her realization that not everyone has that ability – and how that insight led to the book idea
- the foundational elements for a good job search: resume polishing, how to work with recruiters, interviewing, and negotiating an offer
- what a good portfolio should include so that it codifies the job-search story you’re telling
- the importance in her experience as a hiring manager of showing your process and collaboration abilities, not necessarily the outcomes of your work
- how to identify and address the real problems and needs of the hiring manager, which may not actually be included in the job description
- specific questions you can ask to discern the true needs of the organization
- the crucial role of good listening skills and genuine curiosity
- how she deals with affinity bias and other cognitive biases in her role as a hiring manager
- the importance as a hiring manager of including a variety of perspectives in the interviewing and consideration process
- how to negotiate a job offer, set salary expectations, and use silence to advance the process
- the importance in the hiring process of identifying articulating as a candidate the strengths that you have and as a hiring manager knowing what strengths your team needs
Margo’s bio
Margo Stern currently leads Content Design at Peloton Interactive. Before Peloton, Margo built and led teams at Google, Twitter and Facebook. When not in meetings (interviews or otherwise), Margo spends her time hiking up any mountain in San Francisco or petting cats.
Connect with Margo online
Video
Here’s the video version of our conversation:
Podcast intro transcript
This is the Content Strategy Insights podcast, episode number 149. We all love doing our content work, but sometimes – motivated either by our own desire for a change or by layoffs or other circumstances beyond our control – we have to go out and find a new job. At the same time, content managers are constantly adjusting their staffing and hiring to meet their ever-changing needs. Margo Stern has experience on both sides of this system. She’s an expert at both landing good jobs and building great content design teams.
Interview transcript
Larry:
Hey everyone. Welcome to episode number 149 of the Content Strategy Insights podcast. I’m really happy today to welcome to the show, Margo Stern. Margo leads content design at Peloton, an exercise company you may have heard about. She’s also working on a book, which is why I wanted to have her on the show today. So welcome, Margo. Tell the folks a little bit more about your work at Peloton.
Margo:
Hey, Larry, thanks so much for having me on. Yeah, I joined Peloton about a year-and-a-half ago. I joined to lead the content design department that had just started with a couple of people there and now we’ve grown to… I think we’re about eight right now. So both on the e-comm and the product side. I was a very, very avid and dedicated user for a long time and elbowed my way in to lead the team. So it’s been a really great experience and I get to work out of my very cold house in San Francisco.
Larry:
That’s cool. And the way you just said that, this is where your book came from. You said you elbowed your way in. It’s like you’re famous for getting good jobs. You’ve been at Google and Twitter and all the big companies. Talk a little bit about the genesis of this book that you’re working on?
Margo:
Yeah, it’s funny to mention. If there’s something I’m too happy to be famous for, it’s for the places that I worked. Before Peloton, I’ve been at places like Google and Twitter and Facebook, and I’ve had a good time, oddly pursuing jobs. Actually, it’s a downfall of mine too, that if I get a little antsy, I know that I can head out there and interview and have a good time doing it. I came to realize that that’s not the case for everyone. Not everyone likes interviewing and doesn’t really have a great experience doing it. So what I wanted to do is see if I could codify and share the advice that I feel like I’ve been giving and advice that I’ve received over my long career, and make it useful for other people that are out there, either on the hiring manager side or the job seeking side.
Larry:
Yeah, that’s what I’m really taken with that. We talked briefly about this at Confab, and I just love the idea of approaching it from both sides, because you have a lot of success and experience on both sides of the equation. I think we’re the current era, we’re recording this in the Spring of 2023, which is a little fraught time in terms of getting content design jobs. Maybe we should start with the getting a job part of your approach.
Margo:
Yeah, absolutely. And to your point, yes, at all those places I worked, I’ve been able to build teams, and so I’ve had extensive experience in the hiring space as well. But for sure, right now, I think the hot topic and what people are concerned about is how do I land a job and how do I make sure that it’s the right fit for me? How do I prepare? What do I need to do to get myself ready, get my portfolio ready, and just get my talking points ready as I head onto the Wild West of interviewing?
Larry:
Yeah. And you shared the outline of the book with me and it looks good. Very comprehensive and very… It looks like the right amount of detail. I used to be a book editor and I’m like, “Yeah, I’d look at this manuscript.” So talk a little bit about how… If you can give us the elevator pitch of the half of the book that’s about getting a job, how that’s organized and how it’s going to help folks? Do what you’ve done so effortless. It seems like it’s been effortless for you, but you’re aware that that’s not the case for everyone.
Margo:
Oh, absolutely. The analogy is failing me right now, but I guess if you go to the ballet or go to the Olympics, you’re like, “Oh, I could do that.” It looks really straightforward and simple. It’s like, “Why can’t I do that?” I think similarly, yeah, I’ve had… Well, I don’t want to say that I’ve had luck. I’ve had luck, but I think it’s also a skill and it’s a skill that can be developed. It’s similar when I talk about content design where people talk about it as being magic with words. It’s not magic. It’s a skill, and that is what I’m going to talk about in the book. I’m glad you had a chance to look at the outline. I’m looking forward to writing the rest of it. I’ve done a couple of sample chapters just to find my voice, but it’s looking good.
Margo:
In terms of the job seeker side, it’s really from the beginning and establishing your foundation. What is the kind of job that you’re looking for? How is your past experience going to inform the next job that you’re going to go after? How does your resume begin to tell a narrative story where the next chapter in that book is your next job? And how to do that with the right amount of detail to tell a good story, but not so much that you end up with a 20-page resume, some of which I’ve seen.
Margo:
So from there, it really takes the progression from getting your resume, getting your materials in order, what it’s like to work with a recruiter, either an internal or external recruiter. What the arc of the typical interviews look like from talking to a recruiter, that first one-on-one with a hiring manager, interview panels, and then all the way down to how to negotiate an offer, which I love. I love negotiating. How to negotiate an offer and also when to know if it’s the right or the wrong job. I’ve been offered jobs that looked really good on paper, but I knew weren’t going to be the right fit for me, and I turned them down even when the offer was really, really compelling because I knew that I wasn’t going to succeed there, and it wouldn’t be long till I would be really unhappy. So that’s it. It follows the arc of that progression of starting to seek a job all the way through accepting or declining an offer.
Larry:
And not to run through the whole book, but that arc makes perfect sense and you get to that point of… And then your favorite part, the negotiation part, but I guess maybe what are the, some just key ideas that people should keep in mind in that first part as they’re preparing? Let me give you one example that comes up. It seems to be an endless point of discussion on LinkedIn and other social media, is the notion of whether or not you need a portfolio and how that fits in. Maybe talk a bit about how to balance, “How much time should I spend on my portfolio, on my job searching strategy, my resume,” all that stuff?
Margo:
Yeah. I know that’s a tough question, and there’s also one like, “Do I need a website?” And I think it’s not bad to have a web presence, and I think it’s not bad to get that work in order. I think what’s really great about a portfolio and getting work samples is that it should show the kind of work that you want to do, and that should be evident to the job, the person who’s hiring. It doesn’t matter if there’s a huge, big national gigantic launch. If there was a really incredible onboarding for a Cooper Scooper app, but it was meaningful to you and you learned from it, then by all means, that’s the work that you should be showcasing.
Margo:
So I think it’s useful, not because someone’s looking for it, but because it helps codify your story and say, “This is the kind of work that I want to be doing. This is where my strengths lie,” and making sure that it’s a match between what you’re looking for and what’s out there.
Larry:
No, and that’s good old content strategy. What stories can I tell that’s going to support my business goal, which is getting a job in this case? Hey, back to the portfolio thing. I’d love to get your thoughts on that because it’s such a common point of conversation maybe from both sides. How important has it been in all these jobs you’ve landed and how important has it been to you as a hiring manager to see a good portfolio?
Margo:
Yeah, I think it goes both ways. I think it is important to show work that you like to do. I think it’s important to tell a good story, and it doesn’t matter to me if it’s in a really shiny, beautiful, customized website that has your name in the URL, or if it’s just like, “I’m opening up my Figma files to show you what the problem is that I was trying to solve.” I think the important thing is that it’s work you care about, and that, again, it tells a story. “This is the problem we were trying to solve. These are the constraints we are working in. These are some of the problems we came across along the way, and this is how we solved them.”
Margo:
And maybe if there was an impact. I know at a lot of these really, really big companies, some of which I’ve worked for, the work doesn’t get shipped or gets sunsetted, or it doesn’t have the impact that it was intended. Or you may not even have the metrics to show. I, for one, am less interested. I’m more interested in why this was meaningful to you? Why you’re showcasing this work? Even if it’s like, I worked on this crazy audit that I felt a sense of accomplishment about and is the kind of work that I want to be doing in the future.
Larry:
And that notion of it seems like more about the process than the product…
Margo:
Oh, a 100%.
Larry:
Yeah, that makes sense. And I don’t want to project the problems of the whole industry on any one job candidate, but we are notoriously bad at describing our work, right now, what does content strategy even mean, or content design or UX writing, the differences? I guess the thing I’m getting at there is how precise do you need to be in your language about describing this? Or does this get back to that process thing, about just showing what engaged you and what you did?
Margo:
Yeah. First of all, I hope that at someday we’ll be able to answer the question of what is content design after 150 episodes? Maybe that’ll be your 150th. But yes, we want to be specific about language choices, but also, what I look for as a hiring manager is showing them that you’re passionate about something, that you’re really interested in solving the problem and what you contributed to it. And that doesn’t necessarily mean I wrote this word or I named this thing. Talk to me about the naming process. Talk to me about who was in the room or how you drove collaboration, everything that goes around the decisions that you made. Sometimes, but not necessarily your focus solely on the impact of those decisions. I like to hear how people work together. I like to hear how people take initiative, drive things forward. I like to understand the story behind the screen, I guess.
Larry:
And that story, obviously you have all your experience to draw on to craft that story, but how much does it need to match up bullet point by bullet point with the job description or with other… Because a lot of this is going to come out also in interviews, I assume. I guess, how do you organize your anecdotes and your stories to support the whole mission?
Margo:
Yeah. I think the more you learn about a job, the more you understand what is the problem that they’re trying to solve? What is the gap in their hiring right now or the gap in their team right now that they’re looking for? Job descriptions aren’t a recipe. Job descriptions are also pretty templated, and many companies use the same job description for the approximate role and may tweak a thing here and there. So even though a lot of thought should and does go into job descriptions, I don’t think it should be viewed as a checklist that you need to hit all the boxes. I know when I’m a hiring manager, I get an opportunity to post a job. I’ll take a once over at the old job description and make sure it mostly works, and my intent is to get it out the door because if I have an open role, I want it filled yesterday.
Margo:
So I probably won’t, I never have an entire job description if I’m looking to fulfill a job right away, but like I said, I think as you get to understand the role better, the company better, the team, the hiring manager, you can start to piece together, “Oh, they’re looking for someone who has this particular experience or this particular strength.” And then I think it’s about crafting your story or responses to fill in that gap. So what you really want to be driving towards consistently is, “I am the solution to that problem.”
Larry:
And you talked a minute ago about trying to identify what’s the gap in your team right now, or what’s your core need? I’ve tried to infer that from the outside in prior job hunts and things, and that can be hard. Can you talk a little bit about how you discern that? Do you talk to other people at the company? Tell me more about how you figure out what to identify that true need that the hiring manager’s trying to fill?
Margo:
It’s definitely a conversation, and I think there’s no harm in being direct. I think the common question that I hear people ask is, “Why is this job open?” Or, “What kind of person will be successful in this role?” I think those are hard questions to answer. I think better questions might be what is the gap in core strengths that you’re looking to fill? Is there a particular project or knowledge area that would be really useful for this job? Is there a particular experience that you’re looking for or would be useful or applicable in this role?
Margo:
Being specific about that and trying to dig in a little bit more. I find those generic interviewee questions, not only to be hard to answer, but not really coming up with useful or actionable responses.
Larry:
So as you talked about that, I’m thinking back to the outline and then the sample materials you provided. You talk about having a lot of questions ready because you don’t want to… But now I’m wondering how you pick which ones to ask? Does that make sense?
Margo:
Absolutely.
Larry:
I guess this comes back to another thing you talk about is the importance of listening. I’m going to guess that might be the answer.
Margo:
Yes. I think it’s both. Well, so in terms of the questions, oh, yeah, be generative, come up with so many questions, and here’s a sneak trick. You can ask the same question to different people. If you’re in multiple one-on-ones, ask them all the same question because you might get different answers, and it might be really interesting to compare and contrast what they’re coming back with. A question like, “What keeps you up at night?” Is one I always like to ask, or, “What is the thing you’re most excited about in the business right now?” I have someone who always asks in interviews, “What motivates you?” And I always find that to be really, really revealing.
Margo:
So I think there’s like, yes, you want a list of generic questions that you can ask anyone. And then I think through the interview process, you might want to find out specific things. If there’s red flags that are coming up, if there’s something that feels ambiguous, ask about it. If there’s something you read about in a blog post that seems worrisome to you, ask about it. You don’t want to put your interviewer on the spot, but I think you’re wanting to find out about them just as much as they wanted to find out about you.
Larry:
Yeah, that’s it. And as you say that, I’m picturing how to craft those questions so it’s interesting enough to elicit the information you’re really looking for, but to also not throw them a softball, but to ask it in a way that it’s an interesting little balancing act you’re talking about there.
Margo:
Ask questions you genuinely want to know the answer to. Don’t ask questions you think they want to have asked of them. This is an exercise in curiosity. This is an exercise in finding out, I don’t know, if this is going to work for you. And I think the more curious you are, the more interested you are, the more you listen to the answers, and I’ll just wait for the person to stop talking so you can ask another good question, the more you’ll understand about the company, and I’ll honestly make a good impression.
Margo:
My point of view about interviewing is that it shouldn’t feel like an interrogation. No one should feel like in the hot seat. It ideally, and in my best experience, it’s been two people who have a lot in common or maybe have nothing in common, connecting about something and being genuinely curious about one another and about the work and about the space. And then it’s just a conversation and you get that feeling. You walk away from a good interview thinking, “I want to spend more time with that person. I want to work with that person,” that get you excited about the potential of working in the future.
Larry:
That’s interesting to think about. The optimal outcome might be that, over answering any particular question about how you would do the job well, but more just like, “Oh, I really would like to spend more time with them.” And that could work from both sides, the hiring manager or the candidate. Right?
Margo:
Absolutely. And just to flag, a sense of people not relying on their bias or, I know Dave Dylan Thomas, I’m channeling him right now. I know there’s a very specific bias that he would say of confirmation bias or affinity bias. You look like me. You have the same background. We work at the same company. And so I’m not necessarily saying I’m looking for someone that I like the words “culture fit” are bad. It’s more about do we connect? Are we energizing one another? Is this something that would make my work better?
Larry:
Yeah. And you mentioned Dave in the notion of biases. How do you keep that because… And that notion of common ground and affinity for one another. A lot of that is based on familiarity, but there’s so much benefit to diversity in every aspect of business. There’s just so much evidence for that. How do you balance, I guess, mostly from the hiring side, I guess in this case, that, “Oh, they’re just like me?” And whereas maybe you want to be looking for somebody different from you. Have you dealt with that as a hiring manager?
Margo:
I deal with that as a hiring manager every day. Absolutely. I think affinity bias is really hard. I was in an interview recently where… I went to a very small, strange high school in Los Angeles, and it turned out that the candidate had also gone to that very small, strange high school, and I could see us immediately going down the path of talking about that experience. And it was actually in the context of a panel setting, and I didn’t want to bias that conversation. I didn’t want to bias my perception of her. So I cut it off and changed the subject really quickly to make sure that that didn’t seed into… because I was also a hiring manager running the panel. I didn’t want other people to perceive that as like, “Oh, this is someone that Margo has a lot in common with. I bet she’s going to want to hire her, this candidate, so let’s make sure that we treat her in a particular way.” So yes.
Margo:
And then also when reviewing resumes as a hiring manager saying, “Oh, they worked at this company. I know that company is good,” or, “I don’t know any place that this person has ever worked, they must not be good.” So I think as a hiring manager, continuing to check yourself to make sure that you’re aware of all the biases that you have, good and bad. There might be a particular company where, “Oh, only terrible people work in X industry. I would never hire someone from them.” You have no idea. You have no idea why someone took a particular job, what they might’ve found interesting in that moment or what they learned in that space.
Larry:
Yeah, that’s interesting too, and what you just said makes perfect sense. But there’s also the… I’ve found in many experiences that making that transition from learning something that makes perfect sense to actually embodying it in your day-to-day practice. Do you have any gut checks or self checks around checking your biases as you go through an interview?
Margo:
Absolutely. This is something I picked up at Facebook, that was part of our process that when we were in a hiring review, so we’d go through the interview process and we were going to assess our candidates and say, “Do you have any biases?” And it would be just a very quick checkpoint, and that could be, “Do you have any biases about this candidate?” And that’s something that I’ve taken with me in every interview that I’ve done when me and the panel are discussing any particular candidate. I’ll ask and I’ll always concede my own good or bad.
Larry:
Yeah, that’s so interesting that. Is that a built into you review at the end of an interview process or after a panel, you’ll have a debrief about, “Hey, I just want to check in” on those things you just mentioned?
Margo:
Exactly. And that’s more speaking to a place that has a particular process. My usual hiring manager process is last few companies I’ve been at, there’s a recruiter screen, then I speak to the candidate, to the hiring manager, and then moving into a panel or a cross-functional review. And that usually looks like some kind of work review or presentation from the candidate, and then one-on-ones with each individual person who is in that panel. And then the panel and I will debrief and go through and make a decision.
Margo:
So it’s pretty structured but that’s not always the case. Sometimes I’ve worked at places where I’m the singular manager making the decision. I’ve actually done that for short-term contract roles where I don’t have the time or luxury or necessarily need to go through the whole robust process. It might be just a talk with me. But yeah, I’m constantly checking myself and saying, “What are the biases? What am I looking for? Am I also biased by my own need to fill this role?”
Larry:
An urgency bias?
Margo:
Yeah, urgency bias, sure. Where it’s like, “Oh, am I…” Yeah, I’ll agree to that term, but, “Am I compromising? What am I compromising on?” Because I have this urgency bias, and I’ve had that backfire for sure.
Larry:
So just figuring out ways and probably on both sides of the equation, but more on the hiring side to just check those biases.
Margo:
Yeah. I think it’s more than bias. I think it’s also, sorry, impulse control. My husband will confirm. I have pretty bad impulse control when I get excited, and when you have these initial exciting conversations with someone, you want to be like, “Oh, we can just skip the whole process. They’re great. It’s fantastic,” and get them in. But it’s important to have a bit of process to get other people’s opinions depending on what the role is, depending on the candidate.
Larry:
You’re reminding me, years ago when I was a textbook editor, I edited a book about bureaucracy, and the book I had signed was The Case Against Bureaucracy, but another author had written a book, The Case for Bureaucracy, and you’re making that case right now that you have procedures and policies and things in place to check all these tendencies and biases.
Margo:
Yeah. It’s not for the sake of slowing things down, but I think it is for the sake of really considering diverse perspectives. I think the other thing to consider is who’s going to be working with this person and making sure that those cross-functional people are feeling that same chemistry that I am? I’m a particular personality. I respond to certain different people. Other people may rebut them, and no, I wouldn’t want to work with that kind of person. So making sure that they’re bought in as well.
Larry:
Interesting. And we’ve talked a lot about preparation and a lot about interviewing and that. What about when you get to that point of negotiation? Tell us about your experience, I guess, again, from both sides, especially as a job seeker?
Margo:
Yeah. I more have it from a job seeker perspective. From a hiring manager perspective, I tend to have less visibility there and have to leave that to the finance and recruiting teams. So I don’t have as much visibility there but from a job seeker perspective, love negotiating.
Larry:
I think a lot of people don’t.
Margo:
I know.
Larry:
So I would love your tips on this.
Margo:
Yeah, and a lot of women don’t do it. A lot of women feel… I also have a conspiracy theory/theory that this leads to the ongoing pay gap is because women don’t ask for what they deserve and they don’t negotiate because they feel like, “Oh, if I ask for too much, if I’m too bold, if I’m too assertive, they’re going to take it away from me.” And I think that might not always be the case with men to make a broad generalization. I love negotiating because once the offer is in, now we can start. Now we ca start a conversation to make it worth it for me, to make it worth my time.
Margo:
So my tips in terms of negotiation are this. Step one, negotiate. An offer is an offer. It is an initiation. It is the beginning of a conversation. So if you accept a first offer, you’re doing yourself a disservice. And as someone recently pointed out to me, you’re doing a disservice to everyone else in the industry, because if somebody is going to take a low offer, then that means that may set the band, the pay band for that particular role, for that particular level. So if you’re not negotiating, if you feel uncomfortable negotiating for yourself, think about that you’re also negotiating for everyone who may come after you. So step one, negotiate.
Margo:
Step two is to get a reasonable idea in mind and then add 5% or 10% because you don’t necessarily want to counter with what’s reasonable because they’re going to come back and come back with a counter offer. That’s probably going to be less. So give yourself a little bit of wiggle room to come back to something that you’re comfortable with. So something that you would be happy accepting.
Margo:
The third thing, and this is I think the hard thing for, I’ll say it is for women is to make the offer and stop talking. And this isn’t to say the women talk. Make the offer and you don’t need to justify it. You don’t need to explain why your worth is that much. You don’t need to divulge your past salary. You don’t need to divulge how expensive a city you live in. That is what you’ve decided is the number that works for you. So you put it out there and you stop talking.
Larry:
That’s always a powerful tool, and it’s one that especially, I don’t know, there’s something about… Content people always have something to say. Maybe that’s part of it too, I think. But hey, Margo, I can’t believe it. We’re already coming up close to time. These conversations always go way too quick. But hey, before we wrap up, is there anything last, anything that’s come up in the conversation that you want to elaborate on or just is on your mind about job hunting or hiring?
Margo:
Yeah, I think the whole idea for this book and then the philosophy behind it is something that I’ve talked a lot about in previous Confab talks, and really what has defined my career trajectory and informs a lot of the career coaching that I do when I get an opportunity to do it. And the idea is that finding a new job or hiring someone is really based, and I think management too, feels like it’s based on strengths on identifying and being really clear about what are your strengths as a designer or as a content designer? As a hiring manager, maybe finding the strengths that are lacking in your team or area where your team could flex a little bit more. And about connecting what a particular job seeker needs to what a candidate has. So being able to identify what those strengths are. Maybe for some people, it’s more copywriting type writing. For some people it’s getting into audits. For some people it might be more technical writing. Some people like speaking, some people may not like speaking.
Margo:
There’s all different kinds of ways to do content design and knowing which are the ways that you love to do content design and seeing how that fits with what someone’s seeking. I generally ask three pretty regular questions when I’m doing screening interviews. I ask people to tell me about their journey in content design, how they got to where they are. I ask them what are the content design tasks they love to do, where they feel super in the zone about? And then what are the content design tasks they don’t love to do or that they feel happy when someone takes it off of their plate? And those can be really revealing to me. Those are the three questions I always ask because it speaks to that idea of identifying your strength and knowing what it is that you’re coming there to do.
Larry:
Nice. That’s perfect. I love a nice concise list of things to do at the end. Hey, one very last thing, Margo. What’s the best way? If folks want to follow you online or connect. What’s the best way to stay in touch?
Margo:
Yeah, I’m WordStern everywhere. So on the Instagram, on Twitter though, I’m spending less time there like we all are. I think on LinkedIn, I’m just Margo Stern, it’s all phonetic. But yeah, I’m in all those various and sundry places.
Larry:
Great. I’ll put that in the show notes as well.
Margo:
Cool.
Larry:
Well, thanks so much, Margo. I can’t wait for the book.
Margo:
Oh, yeah. I hope it turns into a real thing.
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