What if leadership didn’t mean overworking your team, sacrificing your mental health, or pretending to be someone you’re not?
In this episode, I’m sitting down with repeat guest, Amanda Litman—founder of Run for Something and author of When We’re in Charge—to talk about how millennials and Gen Z are reshaping leadership from the inside out. We dig into what it takes to lead with empathy, accountability, and boundaries in today’s work culture—and why the old playbook just doesn’t work anymore. From navigating social media and hybrid workplaces to building inclusive, sustainable teams, Amanda offers a refreshingly honest take on how we all can be better leaders, whether you’re managing a team or preparing for your first promotion. This is a conversation about leading with integrity, and doing it your way.
Key takeaways:
Good leadership starts with boundaries, self-awareness, and intentionality.
Amanda emphasizes that being a strong leader doesn’t mean bringing your “whole self” to work or asking that of your team. Instead, great leadership is about developing a leadership persona—a version of yourself that best serves your team and goals. Boundaries aren’t a barrier to authenticity—they’re what make sustainable, compassionate leadership possible.
Gen Z and millennials are redefining leadership norms—because they have to.
Amanda explains that younger generations have inherited unstable systems—crumbling institutions, layoffs, a lack of safety nets—and are rising into leadership with a different playbook. They want transparency, inclusivity, accountability, and purpose from their workplaces. As a result, they’re shaping new leadership models grounded in humanity, clarity, and care.
Burnout is a leadership failure, not a badge of honor.
One of Amanda’s biggest takeaways: if your employees are working 100-hour weeks, that’s on you as a leader. Good leaders create clear expectations, prioritize team well-being, and stop glamorizing hustle culture. Toxic overwork is not a sign of high performance—it’s a system-level red flag.
You can be friendly with your team—but they’re not your family.
Amanda breaks down the blurry boundaries of peer leadership and the dangers of calling a workplace “family.” You can have mutual respect and rapport, but leaders must recognize power dynamics and keep enough emotional distance to make hard calls when necessary. Being a good boss means being human—but not being everyone’s best friend.
Transparency isn’t about oversharing—it’s about trust.
There’s a tricky balance when it comes to being transparent as a leader. Your team doesn’t need to carry executive-level stress, but they do need insight into how and why decisions are made. Thoughtful, values-based transparency builds psychological safety and helps your team trust your leadership—even in hard times.
Leadership lessons apply beyond the workplace.
This discussion draws powerful parallels between parenting and leadership, showing how intentionality, self-regulation, and compassion at home shape how we show up at work. Whether you’re leading a team or raising kids, modeling empathy and boundaries matters—and helps build the next generation of better leaders.
Notable quotes
“You can be friendly with the people you manage, but they can’t be your friends—because you don’t want to fire your friends.”
“If your employees are working 100-hour weeks, that’s a failure on the part of the leader, not the employee.”
“Bad leadership gets us Trump. Bad leadership gets us Elon. Bad leadership gets us fascism.”
Episode-at-a-glance
≫ 01:50 The Impact of Bad Leadership
≫ 04:31 Challenges of Modern Leadership
≫ 15:19 Balancing Professional Boundaries
≫ 22:56 The Only One in the Room: Overcoming Isolation
≫ 28:55 Creating Your Sasha Fierce Persona
≫ 30:21 The Importance of Hiring Good People
≫ 31:39 Leadership Lessons from Parenting
≫ 34:02 Traits of a Good Leader
≫ 42:29 Handling Feedback and Criticism
≫ 46:08 Advocating for Better Leadership
≫ 49:56 Envisioning a Future with Millennial and Gen Z Leaders
Amanda’s Links:
Website: https://www.amandalitman.com/
When We’re in Charge: https://www.amandalitman.com/when-were-in-charge
Run for Something: https://runforsomething.net/
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Meet Amanda
Amanda Litman is the cofounder and president of Run for Something, which recruits and supports young, diverse leaders running for local office―since 2017, they’ve launched the careers of thousands of
millennials and Gen Z candidates and in the process, changed what leadership looks like in America. She’s the author of two books: When We’re In Charge: The Next Generation’s Guide to Leadership, which comes out from Crooked Media Reads on May 13th, and Run for Something: A Real-Talk Guide to Fixing the System Yourself, a how-to manual for people running for office.
Before launching Run for Something, Amanda worked on multiple presidential and statewide political campaigns. She graduated from Northwestern University and lives in Brooklyn with her husband, two daughters, and their sometimes rowdy dog.
Transcript:
Tori Dunlap:
We’ve all had a terrible boss. Here’s how to not be one too. Amanda Litman is the co-founder and president of Run For Something which recruits and supports young diverse leaders running for local office.
Amanda Litman:
If you want to run an effective business, you’ve got to think about how you can build an inclusive environment or your business is not going to succeed.
Tori Dunlap:
Since 2017, they’ve launched the careers of thousands of millennials and Gen Z candidates and in the process change what leadership looks like in America.
Amanda Litman:
A good leader knows that if your employees are working a hundred-hour weeks, that’s a failure on be part of the leader, not the employee.
Tori Dunlap:
She’s the author of two books, one of which we’re talking about to today, which is When We’re in Charge: the Next Generation’s Guide to Leadership, which is out. Now we’re talking today about leadership, but specifically how Gen Z and millennials are changing the game for what the future of leadership can look like, both in organizations and across the world.
Amanda Litman:
Millennials and Gen Z are going to get more and more diverse. Our business places are going to be more diverse, the teams that we hire. It is almost hard at this point to hire a non-diverse team, a homogenous team.
Tori Dunlap:
We get into how to be a good leader very specifically as well as how to relate to others, but maintain healthy professional boundaries.
Amanda Litman:
You can be friendly with the people you manage, but they can’t be your friends, because also you don’t want to fire your friends.
Tori Dunlap:
As Gen Z and millennials are rising up in their careers, you’re starting to manage people and you need to know how to manage people well. We’re talking about that today. We are so grateful to have Amanda back on the show and this is a must-listen if you work in any kind of structural work environment where you’re part of a team, and an extra must-listen if you are in any type of leadership role. Let’s get into it. But first a word from our sponsors.
Amanda, I have to ask you right off the bat, what does bad leadership lead to and why is it so important to have leaders who are empathetic and understanding, especially in today’s world?
Amanda Litman:
Bad leadership gets us Trump, bad leadership gets us Elon bad leadership gets us fascism. No bad leadership gets bad outcomes. I think bad leadership makes people miserable. I’ve been thinking a lot as I work through this book and talk about this book right now about why it matters in particular in this moment to have leaders who are compassionate and empathetic and boundaried, and I think so much of it is like what would be possible if work didn’t suck? What would that free up for you in your life if your job, which was important and meaningful and well compensated and had good benefits but didn’t drain you of the will to live, that you could leave at the end of the day? How would that make you a better partner, a better parent, a better citizen, a better friend? What kind of space could that open up in your life? So bad leadership means you can’t do any of that, and good leadership means so much more than that.
Tori Dunlap:
I think when we say bad leadership, it’s easy, especially for you and I and the conversations we’ve had previously on the show to go immediately national, global to talk about Donald Trump, to talk about all of that. How do we think about how bad leadership or good leadership can affect us in politics and on a more national or global scale?
Amanda Litman:
I think about this with the politicians we’ve got now who are modeling such bad behavior. How much must it suck right now to work for Trump or Elon or any of these dudes and they’re almost all dudes? How miserable must it be to go to work every day with careening goals and priorities with someone who so clearly doesn’t care if you have a life outside of work, who so clearly doesn’t want to be transparent and open and honest and vulnerable with you?
I think that trickles down. We feel that in our day-to-day life, the pressure and the tension, the way that our shoulders are bunched up and it’s hard to relax. Yes, it’s the atrocities that they’re doing, but it’s also the sense that there is no stability, no structure, no clarity. I think that is one of the things, one of the many things that makes this moment so exhausting is that we don’t have clear visionary leaders at the top who can give us a sense of comfort that we know where we are going and that yeah, there’s going to be road bumps, but at least we have a plan to get there.
Tori Dunlap:
Yeah. Well, and in writing this new book, what was the catalyst for you when we think about current leadership or business books? What did you think was missing from the shelves at Barnes & Noble?
Amanda Litman:
So I think a lot about the last eight years I’ve had running Run for Something, which I started with my co-founder back in 2017 and before that I was managing teams for a couple of years. I’ve been managing teams for over a decade at this point, I’m 35 years old. And I have read, I don’t know, 60 or 70 leadership books in depth of all kinds. And I think much like you with financial information, so much of it is written by old White dudes, people who have social safety nets or wives or partners at home who can provide for them or care for their home life, a lot of military people, and so little that seemed grounded in the actual lived experience of being a leader, especially in being a leader right now. If you go to the Amazon bestseller list of leadership books, it takes you till I think number 10, maybe it depends on the day to find a woman.
It’s usually Dr. Brene Brown, God bless, and you don’t see another one until 20 and almost none of them are under the age of 35 or 40. It’s just so many folks who don’t actually have the lived experience of managing a team, of being online in this moment of having to navigate the demands of millennials and Gen Z in the workplace. So from my experience, I wanted more of that, but I was also facing challenges that I think very few leaders at least of the years past had to deal with. How do you take maternity leave if you’re the boss? How do you post on Instagram if your employees follow you there? How do you think about showing up in the workplace with executive presence when the workplace is Slack or Signal or Zoom rooms? It’s very different ways of thinking about the role of a leader than people had to do even five or 10 years ago.
Tori Dunlap:
I think what anybody listening starts to understand the moment they have managerial responsibility at work is they think shit, I don’t know how to do this. I know how to hopefully be a nice person. I know how to work really, really hard at my job, but I do not know how to lead a team, or I do not know how to get the best out of other people. Is that what you were seeing with a lot of the interviews you did? ‘Cause you did over a hundred interviews for this book and I was one of those interviewees. Thank you for that. But was that what you were seeing is there’s this moment where it’s like, no one’s teaching me how to lead properly?
Amanda Litman:
It is such a challenge, especially in industries where there aren’t formal apprenticeship models where you get promoted ’cause you’re good at the work, you’re not good at leading, they’re not good at managing, and there isn’t that much resources spent doing management training or leadership training. And the management training that does exist feels very divorced from the reality of actually leading, and doesn’t actually get it how it feels to lead, which is what I tried to really talk through so much in the book of the isolation, the loneliness, the vulnerability, the challenges of putting yourself out there. It is so hard.
And that was the theme through so many of the conversations. I know it’s something you and I talked about, something I talked about with folks from across a bunch of different sectors of that this is hard and it feels hard because maybe I’m bad at it when actually that’s not the reason. It’s hard because it is structurally set up for you to fail and you’ve got to overcome that. That I think was one of the themes I heard from so many of the people I talked to, folks from business, from tech, from the law, from medicine. I talk to people who run day camps, I talk to faith leaders, same stuff, different spaces, same stuff.
Tori Dunlap:
Yeah. So maybe let’s split the challenges in two. Can we first talk about the challenges of leading in the world we’re in today? So social media is the perfect example of this. It’s constantly changing, DEI, protecting DEI, all of these things are changing so rapidly. So can you walk me through a couple of those challenges, how they’re showing up for leaders right now more broadly before we talk about why uniquely Gen Z and millennials are experiencing these?
Amanda Litman:
Yeah, so social media is a good one to start with. A lot of the branding, like the books I would read beforehand would assume that you had built a personal brand without ever being online before. They’d be like “Start a Facebook page, go to LinkedIn and update your personal websites.” It’s like “My dudes, I’ve been on Facebook since I was 15. I’ve had an email address since I was six. I have been thinking about personal brand building since I had to set up an AIM message to attract my crush in high school. What are we talking about here?”
And I think especially leaders right now are acutely aware that every Zoom could be recorded, every email could be screenshot, every private Google Doc could be going viral in a Reddit thread that you don’t know anything about. The transparency that people demand out of companies, the way that they can leave a Yelp review or a Google review on a business, they are doing the same thing, but they’re employers. So you got to be so intentional about how you show up in all of these spaces, and to make sure that the story of you that you’re telling on Slack, on Zoom, on your personal Instagram account is unified. And that is a challenge that the leaders before us didn’t have to deal with. You mentioned DEI, and this is sadly, I think one of my hottest takes in 2025. Segregation is bad, DEI is good.
I’m like, it is a-
Tori Dunlap:
Crazy that that’s a hot take, but it is yeah.
Amanda Litman:
I know, it is. I mean think it’s really important to say it straight up, diverse and equitable teams are good for business. They’re also a moral good. They’re also a lived reality. Millennials and Gen Z are going to get more and more diverse. Our business places are going to be more diverse, but teams that we hire, it is almost hard at this point to hire a non-diverse team, a homogenous team because that’s just not how populations work anymore. So if you want to run an effective business, you’ve got to think about how you can build an inclusive environment or your business is not going to succeed. And we’re seeing this, there’s a reason that Nike’s like best performing ads of the last six months have been about women’s sports, Black women in basketball directed by Malia Obama, so inspiring, so beautiful and so lucrative for them.
We’re seeing Target’s numbers go down as they abandon DEI and Costco’s numbers go up. It matters to do this and it matters to do it right, and I think that is often the challenge that leaders today are facing is that what is the right way to run a diverse and equitable environment.
Tori Dunlap:
So when we’re thinking about leadership for millennials and Gen Z, can you talk me through the things that set those two generations apart in leadership, but also the unique challenges they might have?
Amanda Litman:
Yeah, I think for millennials and Gen Z in particular, it’s thinking about how the institutions that we used to imagine to exist for us are no longer there. We have seen financial crises, the pandemic, the elections, layoffs after layoffs after layoffs. There is not the same kind of safety net for your career that I think our parents or grandparents could have relied on, at least in the grand scheme of things. Obviously all generations are not a monolith. There’s generalizations here, but generally speaking, we know that our work cannot love us back.
So that really changes your relationship to it and as a leader it changes your relationship to your team and the kind of environment you want to build for them. I don’t want to work a hundred-hour weeks. I don’t want my team to work a hundred-hour weeks. I want to have a life outside of work. I want my ambitions to be for my job, yes but also for so much more than my job. I want a life bigger than my job and I want an identity bigger than my job, so how do I set that up? How do I build that? How do I operationalize that so that that’s possible?
I think one of the biggest challenges that millennial and Gen Z leaders have is that we are managing our peers that millennials and Gen Z have very different demands out of the workplace. They want more transparency, more accountability, more insight into decision-making. They want work to provide more for them to think about the big tech companies that would offer laundry services and workout classes and free food in the cafeteria, and all of that was really just meant to keep you chained at your desk or at the office to do more.
You think about the flexible work environments that people want. All of this is totally reasonable in many ways to want, but then the onus becomes on leadership to be so clear about what they can and can’t provide. I think that’s one of the challenges that for millennials and Gen Z, both as leaders and as members of team to be so on the level about what is the responsibility of the workplace and what is the responsibility of the employee. And as I argue in the book, to be so generous and expansive about what the workplace can do within the constraints of what is meaningful or reasonable for a workplace provider. Things like compensation, healthcare, benefits, clear definitions of success and failure, good team environments, inclusive team environments. We should be as generous of an employer as we can be and also be so boundary about what is and is not the responsibility of leadership.
Tori Dunlap:
After the break we talk about some of the sticky parts about being a leader, including how to create boundaries with coworkers and some of the simple tactics Amanda uses to create a leadership persona, which is one of my favorite takeaways of the episode. Stay tuned.
Did you see the clip that went viral of Emma Grede on the Diary of CEO podcast? She got ripped a new one for basically saying “Work-life balance is not the responsibility of a company or a leader and it’s the responsibility of the employee.” And of course I think it got ripped out of context because if you listen to the whole episode, I actually think she’s right where she’s like, “Assuming you’re a great place to work and you offer good compensation and you offer good benefits and you offer all of the things, it isn’t my job to actually manage your life outside of work and it shouldn’t be my job.” I don’t know how you felt about that clip too and if you listened to the whole episode, but it feels kind of like what we’re talking about.
Amanda Litman:
Yeah, I think the way that she phrased that was the utmost artful way of doing so, but I-
Tori Dunlap:
Yeah, definitely.
Amanda Litman:
The onus is on leadership to create the guardrails so that people can have the latitude to run their lives the way they want to. I think the problem is that so many companies don’t. They ask so-
Tori Dunlap:
Oh, absolutely.
Amanda Litman:
They treat people like shit and the thing that I want to push for is it has to start from the top, but if the top is bought in so much more is possible. So much more is possible.
Tori Dunlap:
Something that I really want to talk about because anybody who’s listening right now who’s in any space of leadership, whether that’s just managing one person, whether that’s managing a whole team, I think the peer to peer versus leader to subordinate position that starts getting really messy, and it’s something even I had to learn as someone who employs people around my age, sometimes older or more experienced, that was really difficult because I like and respect all of the people I work with and I think we are friends, but at the same time I am their employer. So how do you find how they manage or how good leaders manage that relationship where yes, we can be friends or friendly, but ultimately there is still a power dynamic here?
Amanda Litman:
Yeah, the number one red flags in the US, people are like “My workplace is a family.”
Tori Dunlap:
Family.
Amanda Litman:
Not a family, not a family.
Tori Dunlap:
Not a family.
Amanda Litman:
Nope, can’t fire my family, which sometimes I would like to. Can’t fire my family. And I think that is such a lame excuse to paper over bad behavior for treating people like shit.
Tori Dunlap:
Absolutely.
Amanda Litman:
And I think the thing you named is that you can be friendly with the people you manage, but they can’t be your friends because also you don’t want to fire your friends. I think that is one of the things that makes leadership so lonely is that the folks that maybe you came up with or your colleagues that you’re now responsible for, you have to maintain some kind of emotional distance and you want to be collegial, you want to be a human, you want to have honest and authentic relationships with them.
So the tension between those two things, that’s the tension of next generation leadership is I want to be friendly but I can’t be their friend. I want to be human, but also I have to make decisions that are about the care for the whole, which sometimes compromises care for the individual. It’s fucking hard. And the thing that I came back to in so many of my conversations is like how do you network in this moment? How do you build relationships with other leaders outside of your workplace? How do you find a mentor or a thought partner? How do you do it when it’s often the mechanics that people use to network before no longer exist, as one of the challenges of remote workplaces, which I think are still net good, but have their own separate limitations? So many people brought up to me group chats, which I think is really fun.
I was like, “Yeah, of course it’s a group chat or a Facebook group.” One person who became a partner in a law firm in Chicago was telling me that her number one networking space was a Facebook group called SYR Moms, and it was where she was in conversation with other moms who were lawyers across the country, and they would refer business to each other. They’d talk about their different practice issues, they’d talk about the challenges of being a working parent. She was like “The other 85-year-old partners at my firm do not understand when I talk about how I got this business from someone on Facebook. It’s incomprehensible to them.”
Tori Dunlap:
Are there practical ways that we can think about setting boundaries as leaders, where we can still show up as the cordial friendly version of ourselves, but also knowing we sometimes have to bring the hammer down? How do we navigate that?
Amanda Litman:
Yeah, I talk about this in the first part of the book about responsible authenticity, which is how do you be yourself would be the version of yourself that’s actually what your team needs and what your mission or your goals need. Because I think that’s often the challenge of leadership is you get to this point, you’re like, “I’m great, I’m the boss,” but it’s actually not about us. It’s not about us, it’s not about us, it’s about our team and what they need. So you got to have real deep self-awareness and introspection. You need have your mental health care for, have your needs outside of work cared for, build a community around you to care for yourself. Know what it is that your team needs of you, what version of you do they need. I think you think about managing someone directly. You often ask them, “How do you like to receive feedback? It’s not how do I like to give it? It’s how do you like to receive it?”
The same is true with how do you think about how you set up, show up in the workplace to best present for them, and then what’s the overlap between the two? And I talk a bunch about how to create a leadership persona, which to some people feels like you’re talking about faking it or wearing a mask or not being yourself. No, I’m talking about being the best version of yourself to accomplish your goals. And the hope is that that leadership persona is as close to possible to who you are as a person, but a little bit of distance can be good ’cause it allows you that freedom to make the hard decisions. And when you get criticism, which if you are a leader and you are standing for something, someone else is not going to like it, it gives you a little bit of space to deal with that criticism and take the good faith stuff as feedback, and the bad faith stuff as a haters going to hate.
Tori Dunlap:
You and I talked about that with the social media section of your book too, where the person that you’re hearing on this podcast right now or the person that you see on Instagram is me, but it is not the full me. And I think a lot of people understand that but are also shocked by that of like, “Oh, does that mean she’s living a lie or she’s inauthentic?” And it’s like, no, I have to keep a degree of separation for my own safety, for my own mental health. And it sounds like we have to kind of do the same thing as leaders because yeah, if you show up as the fullest version of that is potentially a liability and it’s also, I don’t want to ever fire people. That’s not true to me is to make somebody else feel badly, but sometimes I have to do that for the benefit of the whole in the collective. So can we talk about the Beyonce versus the Sasha Fierce of it all? How do you separate without it feeling inauthentic?
Amanda Litman:
I think influencers and people who have built public personas online are such good examples of the tactics that we can think about, because if you think about what does an influencer do, it’s inspiring their followers, their community to take an action. Ideally it’s doing something good or buying something and not cyber bullying other people on the internet, but it’s trying to get people to take an action and that’s what leadership is.
So if you think about the tactics that someone who has created an online persona has done, it’s the visuals, it’s the language, it’s the audio, the music, the tones, the word choice, it’s the way in which they engage with others online. Are you in the comments? Are you tagging other people? Are you re-sharing and remixing? That vernacular of an influencer’s brand building can be applied to the workplace and I think especially for folks who are in flexible or hybrid work environments where so much of their interaction is over Zoom rooms and Slack chats, it can almost feel parasocial. It’s not quite parasocial in that there is a two-way relationship here, but I can so clearly carefully curate the relationship that my team has with me that it’s parasocial adjacent.
So being really intentional about all of it, I think that that’s the theme of so much of this is there’s not a right way or a wrong way to show up as a professional anymore. That’s one of the beauties of so many women and people of color and LBTQIA folks taking power in this moment is that we’ve blown open the model of what it could look like. The scary part of that is that you sort of have to shape it on your own, and you have to decide how you want to show up as a leader and then be so thoughtful about that presence.
Tori Dunlap:
One thing I wanted to talk to you about is the feeling that so many of us have had of being the only one in the room, and especially when you’re the only one in the room as a leader. So I’ve had this experience of being the only woman in the room, but then also the youngest person in the room and having a better or a higher job title than the other people in the room. For folks of color, being one of the only Black or brown people in the room. If you’re queer being the only… How do we navigate either feeling the imposter syndrome, feeling the oh someone is going to… It just feels very isolating to be the only one in the room, especially when you’re in leadership. So have you ways in your interviews that people have navigated that?
Amanda Litman:
Yeah, being so clear-eyed about how the scam is structural in this regard, you feel like you don’t fit in because you don’t and it’s not, that’s not a personal feeling. I remember talking to one woman who was describing to me her challenges finding a mentor and she was a young Black woman in Hollywood and she was like, “Every mentor I’ve ever had has been a White dude and they would give me advice about, ‘I’ve tried this project and I failed, but then I was able to make a documentary out of the failing and so you’d like, it’s fine.'” She’s like, “Jim, that doesn’t work for me. I don’t get to fail the way that you do.” She would say-
Tori Dunlap:
I don’t get second chances.
Amanda Litman:
I don’t get second chances.
Tori Dunlap:
I get one chance, maybe not even that. Yeah.
Amanda Litman:
If we’re lucky. And she said to me, she was like, “So I take that advice with a grain of salt and I’m also so not bullshitting myself about what opportunities are available to me or not available to me, because of what I look like and who I am.” So many, and I think this is true, especially for people who have been the first or the only, have been so thoughtful in finding joy in bringing up others with them. The amount of people I talk to who said the thing that they get the most meaning out of in their work is mentorship, especially of women and people of color, of how can I make sure that, well, I might be the only one right now, that’s not true forever?
Tori Dunlap:
What happens if your leadership style is then questioned? If you’re the only woman in the room and your leadership style is questioned by men did you feel… I imagine you felt like that at some point in your career, but how do you respond in a way that is going to navigate that with grace while also setting boundaries?
Amanda Litman:
This is where confidence is your key to know that-
Tori Dunlap:
Yeah.
Amanda Litman:
Well, confidence in yourself, but also just if you’re right, you’re right. I remember my co-founder over the years was this incredibly equitable guy Ross [inaudible 00:25:42], was one of the most thoughtful feminist men I’ve ever had the opportunity to work with. We would go into meetings occasionally with men in politics and they would address their conversation entirely to him and Ross would be so thoughtful about like, “Oh, Amanda should speak on this, da da da.” We would share equity there. But it really ingrained in me If I want them to listen to me, I have to speak up. I have to own the fact that I’m in this room because I deserve to be in this room. I have put in the work, I have proven that what we are doing matters and if I don’t speak up for myself in this moment, they’re not going to give me another chance to do so.
It is exhausting and that actual exhaustion is what I think in many ways makes next-gen leadership so hard is like, man, they don’t have to think about this. They don’t. This came up even with members of Congress I spoke with, spoke with a number of millennial women in Congress who would tell me how much time did I spend in debate prep thinking about vocal fry or my up speak or how my suit would look on camera. The men who I was debating with didn’t have to think about this shit.
Tori Dunlap:
I mean I think about that even in my work a lot, of the way I present myself. I don’t love getting all made up. I think for me it feels like a waste of time. I don’t love it, but I know I have to in order to present myself in a way where people will take me more seriously. And that is the experience I think of every single woman, is I don’t want to have to do all of these things and spend all of this time worrying about things or worried about my presentation, but I have to perform my gender in a certain way in order to be taken seriously. And that’s a lot of mental and emotional energy before you even have focused on how do I do my job well.
Amanda Litman:
I talked with this woman, Tiana Epps-Johnson who runs the Center for Tech and Civic Life. She’s like a democracy hero. It’s a nonpartisan group that does all kinds of work around election administration. She has raised half a billion dollars maybe to protect elections. She’s an icon and she told me how she always fundraisers wearing big gold hoops, she’s a Black woman. She said, “I wear big gold hoops and I put my hair in a headband, got my hair in a knot on the top of my head.” Because she said she once had a mentor who told her that wearing big gold jewelry was tacky and low class. She was like, “Fuck that. I’m showing up as me and I’m proving that that doesn’t stop me from doing the job done.” She has this amazing TED Talk it’s worth watching where she’s on stage with her Doc Marten boots and her skater dress.
She’s like, “I’m making the case for defending democracy exactly as who I am.” She was describing the challenge of that is that it requires immense bravery. She was like, “I think I find the bravery to do that ’cause I am playing a role and playing a character of brave Tiana who is paving the way for other people to do it this way too. And if I think about it as role modeling, if I think about it as what I can do to make it easier for others, that gives me the strength to do it.” I love that mentality.
Tori Dunlap:
Well, and it’s back to what we were just talking about. I think you’re exactly right that one of the best things anybody listening can do as a leader is to create the Sasha Fierce to your Beyonce. What is the version of you that shows up slightly differently than you might show up in your relationship to your partner or your friends or your family? Because it requires a different set of skills. It requires a different version of you. It can be you, but it is a different version of you.
Amanda Litman:
One person described to me as my Tuesday self versus my Saturday self. Both are me, but my Tuesday self shows up to the board meeting not ready to mess around. My Saturday self is home with my family and my dog and my pillows and having a good time. That doesn’t mean I’m not me, but how do you do that authentically? And that wasn’t a thing that the bosses we’ve had in years past had to deal with, because they could just show up as the worker bee or the robot boss, which that’s not what our employees want and that’s not what we want. I think that’s the challenge.
Tori Dunlap:
I love the idea of the Sasha Fierce you that comes into work. Feel free to let us know in the comments if you’re listening on Spotify, if this is something you’ve tried or have a plan to try. When we come back from award with our sponsors, we’re talking with Amanda about how to be a good employer and also what leadership looks like outside of work, especially for instance, as a parent. We’ll be right back.
You said in an interview that you recognize that “talent is a product”. Can you talk more about that?
Amanda Litman:
Yeah, people are what make the work happen. If you can hire good people, everything gets easier. And I think by this, with the work I do at Run for Something which is recruiting candidates to run for office, you think about a political campaign, the ads are better, the organizing is better, the message is clearer when the candidate is good, when the person doing the work is good. Anyone who’s ever had to hire knows how difficult it is and when you get it right, oh, what a relief and when you get it wrong, oh my God, what a headache.
Hiring good people and making it so it’s a place they want to stay and do their best jobs, do their best possible output is transformative. And I think we know that retention costs for businesses, it can cost up to three times someone’s salary to fill an open role between the lost time of having someone doing the work and the time to recruit and the hiring efforts and then onboarding. It’s expensive to be somewhere crappy to work. And that is my reminder to business leaders in this moment who are like, “Why should I run a good workplace?” How can AI or all this crap that might make it a shitty place to be? It is bad for business to be a bad place, to be a bad employer.
Tori Dunlap:
To connect this to leading in families you touch on this connection between different generation parenting styles and how that can lend itself to these alternative leadership styles. You say how “The first leader most people encounter in their lives as a parent or guardian.” Can you touch on that connection? How does our leadership blend into our parenting and then our parenting into leadership, and how does this affect the leadership ability of future generations?
Amanda Litman:
This is so personal for me ’cause I wrote this book, I had a one-year-old and I was pregnant with my second daughter, which was stupid.
Tori Dunlap:
She’s like, “Never again.”
Amanda Litman:
Never again in many ways. But I have a toddler now and an eight-month-old by the time I [inaudible 00:32:29] a little bit older, but two little girls. And the experience of managing a toddler’s self-regulation, at home we use Daniel Tiger episodes and you count to four and you’re roar when you’re mad. At work it’s a meeting agenda, it’s taking a beat before you speak in a meeting. It’s the same kind of self-regulation. Honestly, if I could bring Daniel Tiger to work, I would because pretty compelling. I think those same kind of ways in which millennial parents in particular are trying to break the cycle of our parents. I am trying to think about how I show up for my daughters in a way that is so different in many ways than my parents showed up for me.
Not that they did it right or wrong, but that I don’t ever want to talk to my girls about their bodies. I don’t ever want to scream at them, stop crying. I want them to have emotional literacy. I want them to have comfort with who they are. I want them to feel safe in this home so that they can be themselves. Similarly, at work, I want to create an environment where my employees can show up and be their best selves, and also know that there are boundaries to what work can provide for them. It is such a different way of understanding the role of parent and the role of boss. And it was a thing I heard in so many of my conversations, especially from people who already had kids, which was the re-parenting I have to do to myself so that I show up differently for my kids is making me a better leader at work.
Tori Dunlap:
What are the concrete things, maybe give us two or three that separate a good leader from a bad leader?
Amanda Litman:
A good leader knows that if your employees are working a hundred-hour weeks, that’s a failure on be part of the leader, not the employee. That the employer has a responsibility to set up really strong guardrails for when work has to happen, how work happens and what success looks like. And then the employee has the freedom to make the decisions on how they use their time. So that’s point number one. A good leader is themselves in the workplace but not their full self, and they don’t ask their employees to bring their full self to work with them either, because work is not the right container for your full self. Work is the right container for your work self and it should be a welcoming container, an inclusive container who that work self is should be expansive, but you don’t need to bring everything to work with you ’cause it’s not fair of me to ask you to do that. It’s not fair to the workplace to be the container for it.
So the third thing that a good leader can do is reasonable transparency. I think this is a challenge especially in this moment because sometimes people are not prepared to take everything you want to show them, but you should be able to give enough information and insights that people can have a certain amount of accessibility into what’s going on. They can know how you’re making your decisions even if you can’t always let them have input onto those decisions. I think this is one of the tensions that come in with managing millennials and Gen Z where people want agency but they don’t want the commensurate accountability. As a leader, I have both of those things. I am both in charge and also I’m responsible for what happens and if things go wrong, it’s on me.
You got to balance those things and that I think is a sign of a really good leader that knows how much to let people in, and how much to show that I’m making decisions based on my values and you know what those values are, you know who I am as a person so you can trust me to make these decisions. And I think that trust, when we talk about authenticity, when we talk about being yourself a workplace, all of that is in service of building trust and creating psychological safety, which then allows people to do their best work and get you good outcomes. Brings us full circle.
Tori Dunlap:
I think that’s one of the hardest things I had to learn as a leader is actually that transparency piece, because there have been concrete times I can point to where I was like I was not transparent enough, and then there’s other times I can point to where I was like I was way too transparent.
Amanda Litman:
Too much, yep.
Tori Dunlap:
Way too transparent. And I think one of the biggest pieces of advice I can give to leaders, especially if you’re leading the company, you’re the CEO or you’re in the executive level is like you’re there to handle executive level problems and that is your job. It is not the job of somebody who is working in your team underneath you to stress about executive level problems.
So there would be times we were having very transparent conversations about revenue and there’s certain people we want to have those conversations with, but there’s other people that think they want to know that, but then they have the executive level responsibility for something that is not on them. So I think it’s finding what feels like the right level of transparency, both in your values but also realizing that there are certain things that you are responsible as a leader to carry that the rest of your team does not need to worry about. I am worried about everybody’s livelihood. That is not my responsibility to pawn that off to my employees. My responsibility is making sure every day that the company is making enough money to support my team. They shouldn’t have to stress about that in the same way that I do.
Amanda Litman:
And it is a problem if they are, that means that we have failed as leaders. I’ve been in those shoes when I had some tough years and it is so tempting to want to unload all of that to be like, “No, look, see, these are the XYZ things happening. This is why this is a problem.” You can’t.
Tori Dunlap:
You can’t.
Amanda Litman:
And the impulse to want to be transparent and know that actually it does not serve them. It is not a clarity that would be kind to provide.
Tori Dunlap:
Yes.
Amanda Litman:
Now the clarity that is kind to provide is like here’s who I am, here’s who I’m thinking about these decisions, here are the constraints in which we’re making them. Here’s how this happened.
Tori Dunlap:
Here are the ways you can contribute to goals.
Amanda Litman:
Here’s the feedback loops. And I write through this in such concrete detail of how to think about modeling decision-making models, how to think about talking through them and explaining them, the tensions of transparency. But it is not everyone’s job to be worried about the things that the boss is worried about. It’s the boss’s job and that’s what the money is for.
Tori Dunlap:
Yeah, yeah, exactly. So you interviewed over a hundred people for this book. Can you share a few of the most impactful stories you’ve heard?
Amanda Litman:
I could do this for hours. It’s so fun to get to talk to folks. I remember speaking in particular to Marshall Hatch who’s a pastor and a faith leader out in Chicago. We were talking a lot about the challenges of thinking about your work as a calling. Chino is a resident for a lot of people who do passion work, whether it’s in faith or nonprofits or public service or I think you think of your work as a calling to really educate women about the power that financial literacy can have, and what happens when that consumes you, what happens when you’re getting lots of different calls? He at the time we were talking was about to have another kid, and what does it mean to want to be a different kind of dad than he had had, and show up differently for his family and not having great models for that?
It was such a fascinating conversation and I loved hearing it in particular from someone whose work was so deeply grounded in his faith and also his commitment to his family, both his parents and his kids. I love talking to this woman who ran a summer camp in North Carolina up in the mountains. We were talking about inclusivity and how to create environments that were welcoming, and she was saying that one of the challenges that they had was they wanted to create a camp for boys that was really expansive and how it understood masculinity, especially for little boys. She was like, “If you want to send your kids somewhere, your son somewhere where they’re going to come home with painted nails and that upsets you, then this is not the right summer camp for you.” And that’s okay. That doesn’t mean that we have to be for everyone. To be welcoming and inclusive does not mean needing to be for everyone.
It means being for the people you are for and knowing that to be inclusive you got to be a little exclusive. You got to draw the lines somewhere. I’d say the last person actually… I say I loved talking to you for this book Tori, because I think it was such an illuminating conversation would blow up your spot a little bit about the way in which you deal with negative feedback online, and the red lipstick and leather jacket that allows you to perform as Tori without giving all your full self away. I think about that a lot and the way that it can feel when there’s a hundred comments under a video can feel like a hundred people screaming you on the street, but it’s a drop in the bucket in the grand scheme of the impact, and staying focused on that impact allows you to stay focused through the work.
Tori Dunlap:
It was really fun talking to you and honestly a fun little therapy session for me. And yeah, the a hundred people thing, I’ve talked about it on this show before, but I think that what folks might not understand is, and we all have, even if we don’t have millions of followers, we all have a version of this where we get told 95 lovely things. Just those five seem really, really heavy and it’s very easy to ignore the other 95. But also the 95 are extremely overwhelming. And I think that’s unique for somebody in my position where the metaphor I give is I was walking down the street and a hundred people yelled at me and 95 people yelled nice things and five people yelled horrible things, one that five is going to be awful, that’s just going to be rough. But it’s still an overwhelming thing to have a hundred people yelling at you.
And I think for somebody, again, running a public facing business or who is a public person, that might be a unique thing that the average person does not experience. But we all experience a version of this where we get a lot of feedback and we have to determine what feedback is actually valuable, what just feels hurtful and not constructive at all, and how do we parse through that. So that actually leads me to a question I have for you too, which is how do we receive feedback in a way that doesn’t devastate us if we care so deeply about the work we’re doing?
When we come back, we’re wrapping up our conversation with Amanda, including how to overcome the need to be liked as a leader and how to advocate for your needs within leadership if you’re not a leader yet. Stay tuned.
Amanda Litman:
I think about this guess through the lens of my work in politics, which is if the most popular politician in the world would have a 70% approval rating. That doesn’t happen anymore, a 70% approval rating, that still means 30% of people don’t like them. And that reminder that if you are doing a good job and you are standing for something and you are staking out a vision, people are going to disagree with you and some of them are going to disagree with you really loudly, and some of them are going to disagree with you in a way that is personal and pointed and shitty and sometimes in a way that feels dangerous. And it’s worth naming that for a lot of folks that can put their physical and emotional health at risk. In the book I make the case for arming yourself with a suit of your integrity.
If you know that you are making decisions with the right goals in mind, that you have a clear values framework that you’re using to work through them, especially when you have to make the hard calls, the feedback doesn’t get to you, ’cause you know did the right thing. The point when the feedback gets to you is when you know they’re right. And I think about the decisions and the things I’ve messed up over the years, and I write the book a ton about the ways in which I have messed up. It’s when I know that I put ego or myself or feelings above the work or above the bottom line. If you are in service of your integrity and your goals, yeah feedback is always helpful. A lot of feedback is a gift, but a lot of feedback is not a gift or it’s the gift in the form of shit being left on your doorstep. You can ignore it and that I think really helps think about the thick skin that you need to build when you’re in charge.
Tori Dunlap:
Yeah, I think especially for me a couple of years ago, I’ll add to what you said that for me the feedback that hit hardest was sometimes, yeah, I knew I could have done that better, but it was often the thing that I myself was insecure about. So it was especially a couple of years ago, and I always think about this, but any conversation about I’m not doing enough as a White person was always something that hit really close to home because that’s always what I’m worried about. And I think before I had the tools to manage that feedback in a way that was healthy, it felt so acute because it was something that I was secretly scared of, that I was secretly nervous about, was that I wasn’t doing enough or that I wasn’t showing up enough in the right way. So I think that that is also where the feedback feels sometimes really personal is it’s because it’s the thing that you are self-conscious about too.
Amanda Litman:
Yeah, and it’s like whether or not it’s right, that’s the thing that I’m beating myself off about as well. Did I make that decision? I gap a lot on the internet about politics and if I say something that I might wish I had said it differently and oh, if I said it actually this way, it hurt our relationship with a partner or hurt a funder like, ah. That insecurity about it is what makes that feedback so hard to hear. It sucks.
Tori Dunlap:
So when we’re thinking about our position, if we’re not leaders, how can we mirror this leadership style up or advocate for better leadership in our current spaces?
Amanda Litman:
I love this question, it’s something I’ve been thinking about a lot. If you’re like mid-level, even more junior, I think really being clear about what you can demand of your employer, you can demand clarity. It is totally reasonable to say, “Hey, you are asking me to do this. Can you define what success looks like?” “Hey, we have a code of conduct that feels pretty vague. It just says don’t be an asshole. Can you tell me what your definition of asshole is and what my definition of asshole is, so we can make sure we’re speaking the same language here?”
You can do that in a way that is respectful, but you can do that in a way that serves the ultimate team and sets everyone up to succeed. The other thing I would say, especially in your more junior space in your career is start building the muscle now of how you want to show up online in Slack on Zooms. Build the persona that you want to have when you’re in charge now so that when you are in a position of power, you don’t have to make it up as you go. ‘Cause if it becomes more of a habit today, it’ll serve you better down the road.
Tori Dunlap:
I will also give advice to anybody who is more junior that you will have moments where you let yourself down or you let your team down or you didn’t show up the way you wanted to. And sometimes the only way you figure that out is through going through it. Like, “Oh, that didn’t feel good in my body. I made somebody feel like shit today and that was on me.” Or “Yeah, I didn’t follow up when I was supposed to and the project didn’t get done on time. Okay.” Or “I didn’t figure out what was the clear objection of success from my leader.” So those moments are sometimes, often all the time very uncomfortable in the moment, but they’re a hundred percent how you learn and please take those as learning opportunities. Don’t just sit in a spiral of shame of going like, “Shit, shit, shit, how could I have done this,” And then not learning anything from it. You’re allowed to be disappointed in yourself and you’re supposed to use that disappointment to make sure that something changes in the future.
Amanda Litman:
I think about it like weightlifting where if you want to get stronger, if you want to be better, one, it might hurt yourself from time to time, but two, there’s going to be a little soreness as part of that growth. The muscles are going to hurt and that’s part of the process. Growth is uncomfortable, discomfort is in service of a better ending. And the flip to that is much like with weightlifting, you got to rest. You’re not going to rise to power if you’re working yourself out around the clock.
Tori Dunlap:
The other weightlifting metaphor I’ve heard too is that weightlifting makes you stronger, but it makes you feel weaker while you’re doing it and that’s what growth is.
Amanda Litman:
I love that. Yeah.
Tori Dunlap:
Is like there’s so many things in our life that vulnerability makes you feel weak in the moment but actually makes you stronger. There’s so many versions of this that feel really uncomfortable in the moment, but ultimately make you stronger, better, more empathetic, but you don’t get any of those things unless you do the thing.
Amanda Litman:
And the only way out is through unfortunately. My hope, and I think if you read the book and you come away with it is that at the very least you will only make new mistakes. Don’t repeat the mistakes that you and I have already made, that the leaders coming up now should try and only make new ones ’cause we’ve already learned from the old mistakes, and hopefully you can try and avoid them.
Tori Dunlap:
Yeah, so I mean with that, my last question for you is how does a world full of Gen Z and millennial leaders look? How does the world change when all of us are in charge?
Amanda Litman:
I love this question because I think it looks so beautiful. I think it’s so expansive. Imagine the kind of person you could be for your friends, your family, your partner, your team if you could show up to work, know what is expected of you, know how to engage and then leave it at the end of the day. Imagine a world where millions of business business owners were able to pay people well, give them good benefits and healthcare, provide for their mental health as much as reasonable at the workplace, could create an inclusive environment but also didn’t demand them that they burn themselves out and then your team could go home and be present. It could expand and transform our relationships with each other, with our jobs, with our communities, with our government if every space we were in was more compassionate, more humane and more boundary. I think millennials and Gen Z are going to save us, one because we have to, but also because I-
Tori Dunlap:
We have to.
Amanda Litman:
… I think we have it in us to do it. We are the hero generations ready to take over and I’m excited for it.
Tori Dunlap:
Amanda, I said this to you the last time you were on the show, but you continually inspire me and are one of my favorite people to listen to because I always walk away a more interesting, better person. Plug away. I am so excited for your book. I have a copy downstairs. Please tell people where they can find it.
Amanda Litman:
You can get When We’re In Charge wherever you get your books. It’s in hard copy, e-book and audiobook, which I narrated so you’re can listen to me yap on for a couple hours. And you can find me online at amandalitman.com as of a Substack that I’m doing amandalittman.substack.com and all the other normal social platforms where just yapping and posting away.
Tori Dunlap:
Thank you.
Amanda Litman:
Thanks Tori.
Tori Dunlap:
Thank you to Amanda for joining us. Both of her episodes of Financial Feminist are so helpful. She wowed me the first time we met, which was to record that first episode. I believe it’s episode 34, all about how to save democracy, which feels especially relevant right now. So I would really recommend going back and listening to that episode with her if you enjoyed this conversation. You can get her book, When We’re in Charge wherever you get your books. Thank you as always for being here, Financial Feminist. We appreciate you subscribing and sharing the show. Only a small percentage of people do both of those things and we love when you’re outliers. So thank you for supporting the show. We’ll see you back here very soon. Have a good day. Bye.
Thank you for listening to Financial Feminist a Her First 100K podcast. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/quiz for a free personalized money plan.
Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino. Audio and video engineering by Alyssa Midcalf. Marketing and Operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First 100K, Kailyn Sprinkle, Masha Bakhmetyeva, Sasha Bonar, Rae Wong, Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Meghan Walker, and Jess Hawks. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting our show.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
