How Millennial and Gen Z Leaders are Changing What it Means to be in Charge
Episode 518 | Host: Emilie Aries | Guest: Amanda Litman
We are changing the leadership rulebook, taking a fresh approach to professionalism and communication.
Every year, more and more Baby Boomers retire, opening up higher-level leadership positions Millennials and Gen Zers rush to fill. (Gen Xers, I know you’re feeling left out, but I promise I haven’t forgotten about you!) This wave of next-gen leaders is bringing a tidal wave of change—they’re ditching old ideas of professionalism, demanding workplaces that reflect their values, and proving that bold and authentic leadership is the new normal.
Amanda Litman is the co-founder of Run for Something, an organization that recruits and supports Millennials and Gen Zers who don’t just want to work for political campaigns—they want to run for office. Her own experience as a campaigner and a leader prompted her to write When We’re in Charge: The Next Generation’s Guide to Leadership. Let’s explore authenticity and professionalism in the modern workplace with Amanda in today’s new episode!
Can you be your authentic self at work?
After co-founding and growing a multi-million dollar operation that—at its peak—had over 60 team members on staff, Amanda was inspired to write When We’re in Charge as a field guide for the modern, next-generation leader.
Amanda advocates for what she calls “responsible authenticity,” which she defines as “being the best version of yourself in service to your goals”—being strategic in your authenticity. And while this might sound calculating, it’s not about faking anything. It’s about understanding that, as a leader, you are setting and modeling the vibe, not reflecting it.
The trick is to get clear on your boundaries, the story you want to tell (and to be told) about yourself, and what you’re trying to accomplish. Then, look for the overlap between your authentic self and these factors. She thinks of it as the athleisure of leadership—you want to be comfortable but still look put together. It’s important to remember that it’s not about right or wrong; it’s about what’s right or wrong for you. And that goes for your literal work clothes, too.
The new version of “professional attire”
Authenticity today often seems intent on kicking every single previous professionalism rule to the curb, including professional dress. What even is “business attire” anymore?
There’s a movement that’s all for showing up to Zoom meetings with full-sleeve tattoos, in your sports bra, with no makeup and your pile of dirty laundry in the background. Amidst these cries for not holding back, Amanda says go for it, but be intentional. Wear whatever you want, but don’t fool yourself into thinking that’s not a choice you're making that will be perceived and impactful. Just like other facets of your authenticity, your outward appearance should suit your leader persona. It can’t be thoughtless.
She gives the example of hopping on work meetings in a casual tank and a messy bun, with minimal makeup. She feels comfortable in this outfit, and she’s being strategic: she’s quietly giving her employees permission to show up how they want at work, bold red lip and crooked ponytail alike.
Your real self vs your full self at work
The emotional component of authenticity is another hot topic these days. Amanda dreams of universal workplace policies that enable everyone to be happy and healthy—but she’s also not trying to be her employees’ therapist or bestie.
It can feel like there’s nothing in between sharing all your trauma and anxiety at the office and tamping everything down until you scream into a pillow after 5 pm. But there’s a middle ground here. Amanda encourages leaders to create guardrails for their teams, not trauma dumping grounds. Make sure they know that if they need time to deal with anything personal, they can have it. And those benefits need to be really clearly defined.
Communicate like a boss
Communication is one of the major shifts being demanded in workplaces run by or employing Millennials and Gen Zers. Dr. Brené Brown said that “clarity is kindness,” that the best thing you can do for your team is to manage their expectations. Amanda concurs. This goes beyond the important point of making sure they know about their paid leave options for health issues. It covers every aspect of the job and the work environment, from the job description onward.
Not knowing what to expect or what is expected of you is so stressful. Younger workers are expressing the need for this approach, and the younger leader needs to clearly lay out all the supports a job has to offer, as well as what it doesn’t provide. You can absolutely hold people to high standards, but those standards need to be defined with precise metrics that are clearly explained multiple times.
If this sounds like a lot of work, it is! But leadership isn’t easy. As Amanda says, it’s your job to spend time figuring out how to transparently communicate with and support your team. It would be so much easier not to care about our employees, but we can do better.
These are the generations set up to transform the future of work: one that upholds good pay, great benefits, dignity, and flexible work weeks so that work can be fulfilling without leaving you soul-crushingly tired on Friday nights. Just imagine what we could accomplish with a world like that.
I want to hear from you! What do you think of how Gen Zers and Millennials are approaching leadership? Do you see yourself reflected in Amanda’s advice? How are you crafting your authentic leadership persona?
Related links from today’s episode:
When We’re in Charge: The Next Generation’s Guide to Leadership
Learn more about Amanda’s work
Connect with Amanda on LinkedIn
Connect with Amanda on Instagram
The Wall Street Journal, The Gen Xers Who Waited Their Turn to Be CEO Are Getting Passed Over
An Election Redesign To Restore Trust In Us Democracy - Tianna Epps-Johnson TedTalk
Episode 466, How Gen X Navigates Career Change
Episode 516, The Power Pause: Rebranding the Stay-at-Home Mom
LEVEL UP: a Leadership Accelerator for Women on the Rise
Build the skills that will take your
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[INTRO MUSIC IN]
EMILIE: Hey, and welcome to the Bossed Up podcast, episode 518. I'm your host, Emilie Aries, the Founder and CEO of Bossed Up. And today I want to talk about how the next generation of leaders is completely transforming what leadership looks like.
[INTRO MUSIC ENDS]
Like as baby boomer leaders begin to really retire and make space for the next generation of leaders to come behind them, Gen Z and Millennial leaders are rewriting the rules of leadership, ditching outdated ideas of professionalism, demanding workplaces that reflect their values, and proving that bold, authentic leadership isn't just possible, it's the new standard.
Amanda Litman, co-founder and executive director of Run for Something, has been at the forefront of mobilizing young leaders to step up, speak out, and shake things up, both in politics and beyond. Today, we're talking about how the next generation is redefining what it looks like to lead and why the changes that they're driving should have every workplace paying attention. Her new book, When We're In The Next Generation's Guide To Leadership makes it clear that this next generation of leaders is ready to rewrite old rules. Amanda, welcome to the Bossed Up podcast.
AMANDA: Thank you for having me.
EMILIE: I'm so excited to dive into this book because as we were just sharing before I hit record here, you and I share a passion for both leadership and political activism. So tell us a little bit about what made you write this book, in this moment.
AMANDA: So in order to talk about why this book, in this moment, I have to tell you a little bit about myself. I was born and raised in Virginia, oldest of four kids. Went to Northwestern for college, in part because I wanted to work for Barack Obama's presidential campaign. Not a great reason to pick a college, but it's fine. Was hired on his campaign before I graduated, doing online fundraising. Worked for him for a year, worked for the nonprofit that he started for a year, moved to Florida to work on the governor's race, and then moved to New York to work for Hillary Clinton's presidential campaign. I was her email director, so managing online fundraising and volunteer recruitment. And we lost, which was sad.
About a week after Election Day, I'd started hearing from friends I'd gone to high school and college with who were like, hey, Amanda, I'm a public school teacher in Chicago. I'm thinking about running for office. Who do I ask for help? You're the only person I know that works in politics, what do I do? And at the time, if you were young and newly excited about politics and to do more than vote, and more than volunteer, there was no way you could go out and take your call. So I reached out to a whole bunch of people with an idea. What if we started an organization to solve this problem? One of those folks became my co-founder, Ross Morales Rocketto. We wrote a plan, we built a website, and then we launched Run for Something on Trump's first Inauguration day back in 2017 thinking it'd be really small, we wanted to get 100 young people to run for office in the first year.
In the first week, we had a thousand. As of today, we're up to more than 225,000 young people, people all across the country who've raised their hands to say, I want to run for office now what? So over the last eight years, I've been building, along with Ross, up until this year, Run for Something as an organization to recruit and support Millennials and Gen Z, stepping into leadership positions while also leading an organization ourselves and trying to do it differently than any other organization we had seen out there. To think about sustainability, to think about mental health, to think about boundaries, to, you know, run a fully remote organization, which in 2017 was, like, pretty unusual still.
In about 2022, 2023 in particular, when I came back from maternity leave with my first daughter, I started hearing from reporters, questions about some of the folks that Run for Something and helped elect over the last, at that point, six years, people like Mallory McMorrow in Michigan, who had just gone viral for a big speech she made pushing back on one of her opponents. Zooey Zephyr in Montana, the first trans state lawmaker there. Megan Hunt in Nebraska, was pushing back on an abortion ban. The Justins in Tennessee, who were being expelled from the state capitol for fighting for gun violence, safety.
Now, each of those, I think, illustrated something really important and different about Millennial and Gen Z leadership that didn't look like anything we had ever seen before. And as I was reflecting on that and thinking about my own experience trying to find leadership guides as I'd been running this company that really spoke to what it felt like right now, I couldn't find anything. So stupidly, I decided, why not take on another side project? And sold When We're In Charge, which is a first of its kind guide for millennial and Gen Z leaders that really speaks to what it's like to lead now in this moment, in a way that's totally different from the people who came before us.
EMILIE: Right. And just to be clear, this is a book that is not just flat for folks or even really for folks who are looking to run for office. This is really a guide and a practical tactical field guide for anyone who finds themselves leading in their community or very much managing and leading in a professional environment, right?
AMANDA: It's barely about politics at all. I mean it's informed by my experience in politics and I've written a guide on how to run for office. You can, you know, buy that in bookstores too. But this is really about work, about community and about privacy, personal development. I got to talk to more than 130 leaders across a bunch of different sectors. I talked to faith leaders, teachers, doctors, tech executives, media executives, non profit folks. And it was so interesting. The things I heard in those conversations about their leadership styles and the challenges they were experiencing, all echoes of the things I had found myself and the things I'd seen our elected officials struggle with. Yeah, details were a little bit different, but the themes were the same.
EMILIE: Totally. And just to be clear, Run for Something. Your organization that you are spearheading and co-founded is a multimillion dollar operation, right? What, at it’s largest, at its peak, how many people were on staff?
AMANDA: At our peak we're about 65 people, a couple less, we're currently at about 30. We have about a 8-ish million dollar budget per year. We do things very differently. We're eight years into this work. We've had a four day work week, four for three of the last years. We pay people well. We think really intentionally about boundaries. And we've also gone through some really hard times, which I write about in the book. I write about having to do layoffs, I write about making really hard decisions and that's part of leadership too.
EMILIE: Totally. And so I just want to be clear for our listeners tuning in, like you've kind of earned some hard earned lessons of leadership and management. Because I don't often associate what I've seen on campaigns and what I've seen in my political career, my short lived political career, early on, right out of college. That's not what I think of when I think of good leadership and management all the time, right?
AMANDA: No. And this is one of the challenges is like, campaigns and especially political environments are not places where we have time or resources to dedicate to management and leadership development. And it's a real problem because it actually affects the efficacy of our work, which I think needs to be really effective. You know, I was, I was promoted into a management role. I was like, I've never hired or fired anyone. I've never run a team before. And then all of a sudden I was 25 years old and was expected to manage 25 people to raise hundreds of millions of dollars for the presidential campaign. And I figured it out, and I learned some stuff, but I had never gotten any kind of formal training.
EMILIE: And that experience is not unique, right. Like I hear that time and time again, whether it's the nonprofit sector, the political sector, or parts of the private sector too. I think of my lawyers listening in, right? A lot of the organizations that I work with who just, they value the genius, they don't value training and development around leadership. And that is a huge short sighted mistake in my opinion. And so, that's part of what pulled me into launching Bossed Up myself was seeing bad leadership and knowing that we can do better, especially from a progressive lens, right. From the Democratic Party's lens, if we are going to advocate for workers rights, we have to walk the walk as leaders too.
AMANDA: I think that's absolutely right. And I think a lot about, like, what does it mean for our communities, for our democracy, for our families, for our partners, for our friends, if our jobs don't suck? And actually some of that is policy. Like there's a lot of stuff we need to do on a global level, and a lot of that is based on how leaders make individual decisions about how they run their companies, their teams, their businesses. Like, there's so much opportunity for impact here.
EMILIE: Yes. We've wrestled with the systemic versus individualist approach at Bossed Up for years. And you know, everything we do here really focuses on what can I do, what can the individual do, how can I develop my leadership and advocate for change, both where I'm at, what I can influence directly, but also systemically in terms of public policy and collective action. So I think there's a place for both. And you're right to call that out because this book really focuses on what leaders can do, right. And you bring a very fresh approach.
I haven't come across any kind of a leadership development book that feels so timely, that feels so modern. And I want to start with the conversation around authenticity, because something that feels very present for Gen Zers and for Millennials is this belief that we have to be our authentic selves. That anything less than that is superficial or a facade or, you know, succumbing to being some kind of corporate drone or shell of yourself. And what you push back on is saying, look, you got to be strategically authentic. You introduce us to a term, “responsible authenticity”, and basically caution against this advice to just be yourself, especially for leaders, what is responsible authenticity mean, and how did you come across or come to that conclusion?
AMANDA: Now, I would define responsibility authenticity as being the best version of yourself in service of your goals. That can make it sound like it's being calculating or fake. It is not. I'm going to be super clear. My imperative is not to, like, fake it. It is to understand that as the leader, you are the thermostat, not the thermometer. You set the temperature, you set the mood, you model the way you want people to behave. You don't reflect it. And if you aren't really intentional about the version of yourself you bring with you into your leadership role, and I'm going to use the term like at work, because that's where most people's leadership work roles are. But it could be anything. Could be, you know, co-ed, soccer league, could be a campaign, whatever. If you don't really intentional about the version of yourself you bring to work with you, you will undermine your goals. You will set your team up to fail. You will have people, like, wilding out, and you won't be clear why. And it's because you, like, gave them permission, whether implicitly or explicitly, to wild out.
And I think one of the things that I heard in my conversations with Millennial and Gen Z leaders, and every single one, I'd ask them, like, do you feel like you can be yourself at work? Because they would talk about how important authenticity was. They would say, I really want to be, like, an authentic leader. Great. Do you feel like you can be yourself? Almost to a T they would say, well, not fully. One person, quite notably, was like, f*** no, it's just. It's not your team's job to bear the brunt of your full anxieties and problems and burdens. It is your team's job to do their job, and it is your job as the leader to show up in a version of yourself that lets them do that.
EMILIE: Yeah, I think that's really important because we've all been taught, especially us, as you call us, white, middle aged, you know, millennial women, we've been brought up in the school of the gospel of Brené Brown, right? We know that vulnerability is a powerful connection, and we've seen it help people go viral and have major leadership impact. But oversharing is real too, right? Vulnerability in excess is a challenge as well, right. You're not saying to just, this isn't a therapy session. You're a leader who's leading your team or leading a meeting. Finding that balance feels really, really hard to do sometimes. So what guidance do you have for folks in terms of finding the right tack to take?
AMANDA: I think it starts with self awareness, like really know who you are. And it seems like such woo woo b*******. And I chafe against the woo woo. But to really know yourself, like, know your boundaries, know the story that you want to tell about yourself, that you want other people to be telling about yourself, know what you're trying to accomplish, which again feels really obvious. But you'd be surprised, often people like, well, actually, I don't know what my goal is here. And then what is the overlap between those two?
You know, I think the thing that makes this particularly hard for people in this moment of the way that work culture functions is that the tools that we use to communicate with our employees or our teams are the same ones we use to shoot the s*** with our friends or send emails to our grandparents, or coordinate with our kids teachers. The boundaries are so blurred, even like, we're talking to each other in our homes. You are seeing the candlesticks for my weekend dinner. Yeah, it's all my workbooks, but also some of my husband's psychology books behind me. This is my life. You're getting an insight into my home. And that is like an exposure that people didn't have into our personal lives in the same way up until a couple years ago. So the leaders that we take our cues from, like, don't have good examples for it.
EMILIE: Exactly. And 2020 really changed everything, right? Like, you've been building this culture from the beginning of Run for Something which precedes the pandemic. But this became a leadership imperative without any real guidebooks out there as of 2021, when so many particularly white collar workplace environments, like, went virtual. And so there's sort of like a, there's like a voyeuristic aspect, right?
AMANDA: Mhmm. I mean, I know whenever I see, whenever I see pictures of anyone's home, like famous online, I'm always like, zooming in to see what's on their bookshelf. Always. [LAUGHTER]
EMILIE: Yeah. And so like you're, you're bringing this strategic communications principle to the conversation here, which is so important because I talk a lot about strategic communication on this podcast, which is know your goals and know your audience. Sharing your breakfast smoothie recipe only makes sense if it furthers your goals and meets your audience where they're at, right? So I think there's a good kind of walkthrough you do in the book in those early chapters of saying, okay, let's get really clear, not only on what is authentic to who you are, but does it serve a brand that you're building? Does it serve that leadership persona that you're building? You make a great reference to athleisure, like a metaphor there. Can you share that with our listeners?
AMANDA: You want your leadership persona to be something to, like, be the equivalent of athleisure. You want it to be comfortable, but you want it to look good. Like, you want it to present the professional vibe that you were trying to go for while also still feeling true to yourself. Like, you don't want it to be scratchy, like a wool suit that doesn't fit, but you also don't want to be sloppy, like the raggedy shirt that has holes in it, because that also is going to undermine the story you're trying to tell.
You know, the thing that I really try to hone in on is that because the rules around professionalism have changed, the definition of professionalism has changed because the way that leadership looks like, quite literally, women, LGBTQIA people, people of color, people of different kinds of backgrounds, it literally looks and feels, and sounds different. The rules that we used to be able to work from no longer apply. The new rules are not this is right or this is wrong, but rather, this is right for me and what I'm trying to accomplish or wrong for me and what I'm trying to accomplish. And you have to, like, know those things in order to find the answer.
EMILIE: And there's also, like, a commitment to that, because I think you make it an interesting comparison to being lost in the mall. This is such a mom thing, right? But, like, if your 3 year old is lost in the mall, you do not want them running into every store trying to find what they're looking for, which is us, right? You want them to stay in one place and we will find them. And there's something similar to that when it comes to building your leadership persona, right? If you're trying to stand for everything, you're trying to appeal to everyone, it doesn't really work, does it? There's no commitment there.
AMANDA: And I think this is true in politics. It's true in leadership. It's true and based in art. If you are trying to be a people pleaser, you will please no one, and you will lose your sense of self and your sense of vision. Like, to be a leader is to take a stand.
EMILIE: Yeah.
AMANDA: Yeah. They can smell it. You can smell the insecurity. Like, it. It reeks of b*******, and it doesn't work. Now, the flip to that, I would say is like, it invites haters. Because when you take a stand for something, not everyone likes it. And balancing that is, you know, one of the many tensions of leadership.
EMILIE: Yeah. Well, you call yourself someone who can be a b**** at work. What is that like from your vantage point? What's it like to be hated, Amanda?
AMANDA: You know, I never. It's funny you ask that question. I. It. Most of the time, it rolls off my back, which is a good thing. I can be a b****. But I'm also usually a strategic b****. I feel like I do. I've always, like, if you need me to yell at someone on your behalf, I am not happy to, but, like, I'm happy to because it's in service of our mission. However, I do think it's really important. Like, the places where people hating me has gotten to me is when the thing that they are hating me about is a thing I also hate about myself.
I write about this later in the book about how in order to guard yourself against the haters, to protect yourself from the criticism, you have to arm yourself with a suit of your integrity. Like, you have to know that you made decisions in line with your values and your ethics in service of your goal. That's what helps you sleep at night when people critique you. And I get hate, my therapist told me I get yelled at on the Internet more than any one of his patients. I was like, what a fine compliment. [LAUGHTER] But I know that I'm right, and I know that I'm right and being strategic. When you know that and when you feel like you can feel it in your body, when it's not right, when you are right, the criticism doesn't, it bounces off you a little bit more. It only breaks through when it speaks to something that I also kind of agree with, where I'm like, oh, actually, I wasn't. I wasn't in line with who I am. That wasn't true to me.
EMILIE: Right. And like, there's also a redemption narrative that can feel scary to walk down, but also kind of part of the, and granted specifically in politics, that part of the leadership practice nowadays, it's like finding, like, the way forward when you did mess up as a leader, when you were acting out of alignment with either your values or your organizational values, like, when there is hypocrisy, people will call you out about it and how you choose to handle that, I mean, maybe that's a topic for another book, but it is not easy.
AMANDA: No. And I think about it a lot as comparable to, like, millennial parenting trends where, you know, right now one of the big things is repair. Like you're gonna yell at your kid. Everyone yells at their kid. I promised myself I wouldn't be a yeller, but I have a two and a half year old, so occasionally I'm a yeller. And it's not about the yelling that does harm. It's the repair that makes it worth it. And thinking about that as applies in the workplace, like, you need leaders who can repair.
EMILIE: Yes, I love that. And you know, the direction I thought you were gonna go in is when you open the book, you say, look, Millennials and GenZers, first of all, we're like the most therapized generation to date. We are breaking cycles in every direction, right?
AMANDA: All over the place.
EMILIE: Like, that s*** is hard. Whether it's in how we're practicing leadership in wildly different ways than it's been practiced in the past, or parenting or being a partner or just like anything, like gender expression and identity and like just being open minded, man, there is a lot that we're doing. Of course we're going to make mistakes along the way. If we're trying to pave new paths and create new models of leadership, you are going to mess up. And so figuring out how to repair is just as important.
AMANDA: I forget where I heard it, or read it, or who said it to me, but I distinctly remember someone noting that the first model for leadership most people have in their lives is a parent. And that's where you learn how to be a boss, is from your mom or dad or the grown up in your life. And that really stuck with me because the things that we are trying to do differently at home with our kids is the same kind of stuff we're trying to do differently at work.
EMILIE: Totally. And my listeners, I'm currently doing my annual community survey and 50% of y'all are not parents. And I'm hearing the feedback from my listeners already. They're like, can you cut it out with all the references to parenting? And I'm trying, I really am, but there's so many parallels. And not to like, patronize or paternalize the relationships at work because they're, we are not a family, as you write in the book. Like, that is not what a professional relationship is. My god, are there some comparisons? Even Brené Brown's books are now about leadership and parenting, right? Like the philosophies really do transcend so many different arenas.
AMANDA: And you know, I think in particular, even if you're not a parent, like, it is so useful to think about that skill of self regulation and to think about, like, actually shutting the f*** up is always free and always available to you in many contexts. And the ways in which you're interacting with your friends, with your peer groups. It's the same thing, same skills.
EMILIE: Yeah, absolutely. That emotional intelligence, first rung on the EQ ladder is super, super helpful. Also, I identify so much with you. As I was reading that section, I was like, are we the same person? This is wild.
So you mentioned earlier that the very nature of professionalism has changed, and I agree completely. I'm curious what you make of leadership presence or executive presence in the conversation today. Notably, the cover of your book has two hands. You know, doing the classic business handshake, one covered in ink, the other one with blue painted fingernails. Like, what it looks like to be a leader has changed, but it doesn't mean that what you look like and how you present yourself doesn't matter. So what's your thought on that aspect of leadership?
AMANDA: That's such a good way to put it. It is that, like, you can have tattoos and blue hair and crazy fingernails and huge earrings and, you know, crazy makeup and wear leopard print. And it doesn't mean you're not professional, but it does mean you are telling a very specific story about yourself. It's, like, worth being precise here. Not everyone has access to the same kind of story. I talked with leaders of all different races, classes and backgrounds. And in particular, a number of the black women I spoke with talked about the way they're so thoughtful about self presentation, about how they wear their hair, how they wear their earrings.
I talk with Tiana Epps-Johnson, who's the head of The Center For Tech And Civic Life, a true icon who told me how she specifically dresses to sort of undercut this idea that you have to look a certain way to be a black woman. In her role, which she raises, I don't know, half a billion dollars for democracy in Las Veers has done a great TED Talk. Google her. She wears her hair in a bun on the top of her head at the time, big gold earrings, in part because someone told her to wear big gold jewelry while fundraising was tacky. She was like, f*** them, I'm gonna do it my way. But I think that's a choice. That's a very specific choice. I think it's the right one for her, and it suits her. It suits the way that she approaches her work and the attitude that she brings. But it is not, it’s not haphazard. I think that is the mistake people make is they think that it can be thoughtless when it needs to be incredibly thoughtful.
EMILIE: Yes. And I kind of. I like how it. You're underscoring the risk inherent to those choices, right? Like, you can play it safe, and there's no shame in that, especially if you feel like you don't have the privilege to take risks with your appearance. And yet, if you really think about who you are, what your goals are, and who your audience is, you can also choose to take a risk and see if that pays off. Like, there's iteration involved here. You don't need to stay stuck, static. And as someone who started Bossed Up with a platinum pixie haircut and now has long, naturally brunette hair, like, you can transform your brand. I remember feeling very locked in to my brand. And then 2020 hit and I couldn't dye my hair for a little while, and I was like, f*** it, okay, we're letting go of that, of that era. And that's fine.
AMANDA: I think it is so powerful and so scary at the same time to note that the old rules no longer exist, which means we get to write our, we get to write them new. And that is an opportunity and also so freaky. Like, you know, I can think of any time I get an invitation that has a dress code. And like, what? What's business casual mean in this context? Who the f*** knows anymore?
EMILIE: Well, you're based in New York, right? And I'm in Denver, and I call it Colorado Casual. Nobody here knows that business casual in Colorado is not business casual in D.C. or New York. And in fact, I had a colleague come in from DC, the DMV area, and my god, he looked overdressed, right? Colorado casual is. Is, uh, the business casual here is cowboy business casual, and I'm here for it. But no one here even knows that it's different. So it is. It is funny. Like, I love a Priya Parker Art of Gathering book. I love being intentional about setting expectations around dress code, etc. But knowing that there is a lot of subjectivity, it can be open to interpretation also matters.
AMANDA: Which is why, like, as the leader, what you do and how you show up and how you present yourself is so important. You have to bring it full circle here. Like, I often will join work calls with, like, a tank top, sports bra hair, and a messy ponytail. Yeah, some of that is because I have two little kids and I'm tired in the morning and it's not that important to me. But I also want to give permission to my team that they don't have to put on a full face of makeup to get ready for work in the day. That if they want to show up as themselves, whatever that means for them, they can. If they, and I say to them, like, if you feel better with red lipstick on at work, great, do it. I'm telling you, I feel the most like myself in this outfit today. And that is how I'm going to be present.
EMILIE: Totally. Well, let's talk about setting up a workplace that works in a fresh and modern way. Because you're alluding to some of the norms of your workplace that you've created very intentionally. And I, norms is such an organizer word. You probably will appreciate that more than most, right? But you write people should be their real selves, not their full selves. And you're talking about sort of at work and in the workplace. What does that mean?
AMANDA: You know, I think in particular this will resonate with you as an organizer. We sometimes ask people to bring their trauma, their psychic pain, their anxieties with them to work. And work is not the right container for that. It is not the right place to deal with all of your mental health problems, your physical health problems, your social life, your civic engagement, your political engagement. Even your political job is not always the right place for your political engagement.
Work is, at it’s core, an economic transaction. My company pays people to do things. I think that work is meaningful. I think it's important. My job as the employer is to make it as well compensated as I can afford with the best benefits I possibly can. A place where they have dignity and boundaries and have time to do the work and the resources they need to do the work and also time to step away from it and be real people outside of it. That is my job as an employer. My job is not to provide them a social life or to be their therapist.
EMILIE: Yes, I knew you were gonna say that. But what do you say to the pushback? I could just hear a listener saying, I would love to check my mental health at the door, but I'm coming to work today and I'm gonna have a mental breakdown. Like, what do I do with that? You know, and how can I. You're not arguing that people should try to check their personal life at the door, right? It's something different.
AMANDA: No, it's that my job as the employer is to create the guardrail so that if you need to take the mental health day, you can. So that if you, and we say this to our team constantly like if there's something going on for you where you need to step away, you can do that. Like here's the process to ask for that time. Here's you know, it's fully paid. Here's if you need more than a day or two, here's how you do that. Here's what's available to you. Here's the employee benefits we have for you. Here's how our healthcare covers as much as, you know, mental health care as we can. Here's how our compensation allows for you to have that time.
EMILIE: And you're not going to be derided for taking that time.
AMANDA: No, you are going to be celebrated. We're going to say thank you for telling us like, thank you for saying that this is something you need. Thank you for asking for help. Here's what we can do to get to give it to you.
EMILIE: Yeah, and some of those norms and sort of like rules of the road in your workplace you emphasize right from the job description on to onboarding and like expectation setting which if there had to be any lesson in leadership I've learned for the past 12 years, it's like everyone thinks they're being clear with their expectations. You're not, odds are, you're not. Like I've seen so many leaders who I've worked with, who I'm like you are being so unclear. So how do you get clear from the get go and why does that matter when it comes to establishing how your employees, like, what your employees can expect from you?
AMANDA: You know we talked about Dr. Brené Brown earlier. Her line of like clarity is kindness is the best possible thing you can do for your team is to manage their expectations about what you can reasonably deliver. Starts with the job description, with the hiring process, all the way through to onboarding, constantly repeating yourself, being really clear about what you can and can't provide. Even if people don't like the answer, they know the answer. That is like such a relief for stress. You know, again I think about kids or my dog, you know, the stress that comes from them is the same stress that comes from my team when it's unclear how this is going to work. Like what is the container that we're trying to create together. We need to know the rules of the road.
EMILIE: And we need leaders to define success. Like it is not unsuccessful to take a mental health day, if I know what I'm driving towards, what my metrics are, are for success, what my, you know, what my performance, how my performance is being evaluated. Like, that level of clarity is such a gift to give to your team. And that's what people all want. So that we know we can deal with our ailing elderly dog and know that I'm still okay because I'm on track to deliver on deadline.
AMANDA: And this is not to say don't hold people to standards of excellence, absolutely hold them to standards of excellence. But define what excellence means. Define it in numbers, Define it quite qualitatively. Tell them what excellence is and is not. Like, be as precise as you can. And I understand why leaders are often hesitant to do this. Like, you don't want to feel like you're micromanaging or, you know, maybe you don't really know it when you, until you see it or until you don't see it. But you know, that's leadership is to do that. It's like, have that vision.
EMILIE: And it has mental energy involved and that's your job, like as a leader. And you begin the book with that differentiation between leadership and management that I find myself repeating on this podcast and elsewhere until I'm blue in the face, right? But like, we're not just talking about managing benefits and expectations and giving feedback. We're talking about having a clear leadership vision. Here's why we are doing this, here's where we are headed. And that is the leader's job to articulate over and over and over again, right?
AMANDA: It should be boring to you as a leader, but for your employee, the 10th time you say it might be the first time they hear it.
EMILIE: Yeah, I love that. I'm gonna steal that. Wow, I feel like I could talk to you all day. I want to get at one critique that I'm sure you've gotten from older leaders, right? Your book really doesn't hold back when it comes to critiquing the baby boomer generation. And I wonder where Gen Xers first of all fall in, in your psyche around leadership and management. But what kind of flack are you getting from older leaders who feel like you're talking about the average age of folks in the Senate, which is pretty old and you know, so many people are retiring soon, that last generation of boomers is on it’s way out. So, you're almost like, eager to get these GenZers and next gen leaders into positions of power and authority. And trust me, I'm eager to as a millennial manager myself. But what do you say to the boomer who feels pushed out, who feels that it's ageist to slander their leadership style first?
AMANDA: I hear you loud and clear. You are not being shy about it. You know, part of it is I'm being intentionally provocative in service of strategic communication. Like, I want to paint an illustration here. And I think it is not biology, is not ageist. Like, we're living in a world where it is not a personal failing, that older folks don't quite have the fluency with the communication tools of the moment and don't always have the ability to like, understand what emojis to use in slack to convey the exact feeling they're trying to get across or even like, how to use slack at all.
And so many of the folks I talked to for the book brought up, you know, up until I took on the position as partner, we still had to print out everything and put bring it into the boss's corner office every day so they could read it like, in hand because they didn't understand how to use the attachment on their email. No generation is a monolith. There are good leaders and bad leaders of all ages. And there are absolutely older leaders who can adapt to this new moment. But I really appreciate actually, I just got an email this week from someone who very kindly wrote it in Comic Sans, which I love, telling me how it said, I'm a boomer in Canada, I read your book. At first I was a little taken aback, but I realized, like you, you're saying these things that once I realized it, oh, I actually do really trust that institutions will be there for me. Oh, actually, I do kind of stigmatize a conversation around mental health. And I never thought about those as like, not even bad or good things, but just like, things. And once I've heard it, you're right, I do need to think about this from a fresh lens.
EMILIE: That's amazing.
AMANDA: It was so kind.
EMILIE: You've converted. You've made a, you've made a evangelist out of a skeptic. That's pretty powerful.
AMANDA: You know, and as for Gen X, you know, one, don't be mad at me. Blame the boomers. But I'm saying there's actually a Wall Street Journal article a couple weeks ago about how more and more companies are going from boomer executive to millennial executives, skipping over Gen X entirely, one, because they're much smaller. But also, that's not the future. And like, I'm not the one to be mad at there. I'm just, I'm not.
EMILIE: Gen X gets so left out. I feel like Millennial had such good branding. Honestly, we all, we all took the branding classes.
AMANDA: And just the scam is structural, as they say.
EMILIE: As they say, yes, the scam is structural. I love that. I had a friend who's a millennial recently say to me that her grandmother was very anxious about getting through the airport security line. She was getting ready to drop her off at the airport and they spent about 30 minutes talking through the mechanics of how it was going to work. And she said, grandma, have you ever thought about your anxiety? Have you ever thought that you're maybe more of an anxious person than the average person? And her grandmother very casually replied saying, anxiety is just something your generation made up. [LAUGHTER]
And so it is kind of funny to hear Gen Zers and millennial leaders like this next gen leadership class, as you call them, we are absolutely changing the norms around what it means to be a professional, what it means to have a professional operation, what it means to be a good boss, right? And in that same breath you're saying that doesn't mean I'm your therapist, right. I'm your manager, you have mental health and that matters. And I want to accommodate and not solve for that in my relationship to you. And so I do think you, you present a really powerful boundary there. But that's something that next gen leaders really need to hear because we can and some of us do overcorrect.
AMANDA: And I think that is the tension here. And it's the thing I kept coming back to throughout the drafting process. At one point my editor was like, you need to stop talking about how hard it is. It's like, no, but it's really hard. All of this is so hard. You have to care for your feelings and your self regulation and your team's goals and their regulation and like, model the behavior you want to see and also give feedback when it's not quite what you want to see. And also like, deal with all the externalities of the world that is crumbling around us. And you know, it is so challenging. And I think it's really important to name that it's hard because otherwise people think like it's a personal failing and it's not.
EMILIE: Yes. Particularly in a moment of anti-work and anti-girlboss energy, which I always think of as just like a pendulum swinging. I just had Neha Ruch on the podcast talking about how she's rebranding the stay at home mom and how people love a trad wife versus girl boss, you know, simplification of womanhood. But in this era of anti-work, anti-capitalists, like billionaires shouldn't exist. Which I fully agree with. Like, what you're talking about is the challenge of being a good leader. And a good boss in this moment is also kind of a thankless one, right? Nobody really pities you because you represent this, like, thing that people are disappointed in. Like, institutional scams.
AMANDA: It would be so much easier not to care. I think about this every day. Like, it was so much easier to just not care and to just be an a****** and run a hostile work environment and be like, we're gonna get s*** done at the expense of everything else. I do not give a f***, I don't like it. If you don't like it, you can leave. Like, I do care that people feel good about the work that they do. And I think the world would be better if more bosses cared.
EMILIE: Yeah. Even if it's not innate, right. Like, I think in my worst, I'm like, get it done. And I have a sense that might be you too, right? Like, at your worst, uh, your most exhausted, tapped out. You know, we can be like, excellence oriented. You admit in your own book that you celebrate everyone else taking vacation and you, I think your loved ones had to drag you to a vacation two years after you came back from matleave, right?
AMANDA: Yeah. We're back in that fight again, for what it's worth.
EMILIE: Uh oh. And so it is. It is hard to care because you need to also model that balance in and of itself for your team.
AMANDA: Yeah. And I think it is really important to do it. Even though it's hard, like, it's worth it, because very occasionally, not even very occasionally, pretty often, I reap the benefits of it myself. Like, we're talking on a Friday. For what's worth, Friday’s are not work days for me. I went and had breakfast with a friend. I read a book for a little while. I, like, took a bath. Fridays are days off. And that is such a gift that I have given both myself and my team that allows us to do this work for the long haul.
EMILIE: Yeah. Let's end there, actually. Because you open the book saying that this is not reflective of the current status quo. This is an aspirational book. And you paint a picture of the future of work and what it could be. What do you envision for workers everywhere?
AMANDA: I imagine where jobs are well paid, compensated with great benefits. No, it's ideally a world where we have better system wide support networks, family, paid leave, all those kind of things. But jobs where people are paid well, cared for, have dignity, can show up and know what they need to do to get the job done well, have bosses who care about their well being, but also about holding boundaries for how much they're responsible for that well being. I dream of four day work weeks for everyone or as much as is possible, flexible scheduling, flexible work environments so that people can be full people outside of work. Because I really, I do, I beg the question constantly. What if your job didn't leave you soul crushingly tired at the end of the day? What might be possible for you as a partner, as a parent, as a friend, as a citizen? Like, how could you better show up for your village, your community if you weren't so, so wiped? I think, you know, anything could be possible to that end.
EMILIE: Absolutely. So for those who want to make that a reality, where can we get our hands on a copy of your new book? And where can we learn more about you and keep up with all the great work you're doing?
AMANDA: So When We're In Charge is available wherever you get your books. If you like the sound of my voice. I narrated the audiobook and it's all those places plus on Spotify Premium so you can get it there too. You can learn more about me at AmandaLitman.com I do a weekly substack. I'm also just like yapping my mouth on all the different social media platforms. So wherever you are, if you search me, you'll probably find me.
EMILIE: Awesome Amanda, thank you so much for being here today.
AMANDA: Thank you for having me. This was really fun.
EMILIE: For more links to everything Amanda and I just talked about, head to bossedup.org/episode518, that's bossedup.org/episode518. And now I want to hear from you. What do you make about how Gen Z and millennial leaders are approaching leadership differently? Do you see yourself in some of the advice that Amanda just gave? Or are you a Gen Xer who feels perhaps left out of this conversation entirely? If that's you, by the way, see the episodes we've done on Gen X in the workplace because we want to shine a light on you and not make you feel so left out too. But regardless of age, authenticity and leadership matters for all of us. So how are you strategically crafting an authentic leadership persona? What does that look like and feel like in a day to day practice?
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Let's keep the conversation going as always after the episode in the Bossed Up Courage Community or in the Bossed Up Group on LinkedIn, my inbox is always open so DM me or email me at emilie@bossedup.org and until next time, let's keep bossin’ in pursuit of our purpose, and together let's lift as we climb.
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