Join Diane Schroeder in the latest episode of "The Fire Inside Her" as she dives into the crucial topic of setting boundaries, especially the art of saying no, and its impact on effective leadership and personal well-being. In a thought-provoking conversation with guest Emily Tsitrian, CEO of Yeeld, they explore the disproportionately low representation of women and people of color in higher corporate positions and the pivotal role of coaching and promoting underrepresented voices in organizations. Get ready to uncover insightful strategies for individual contributors eyeing managerial roles and the unique challenges faced by millennials in leadership positions. With reflections on authenticity, the entrepreneurial journey, and the changing dynamics of leadership, this episode is a captivating exploration of personal growth and professional empowerment.

Emily Tsitrian is CEO and co-founder of Yeeld, a payments consulting company, and is an award-winning author of a management and leadership book called Make Me the Boss. She was most recently the head of Enterprise Professional Services at Stripe, and has spent the past decade leading client success teams across various tech companies. Emily studied economics at UC Berkeley and is based in Chicago, Illinois.

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Make Me the Boss by Emily Tsitrian

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Diane@Thefireinsideher.com 

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Welcome to The Fire Inside Her, the podcast where we explore the incredible stories of individuals who have discovered their inner fire on their journey to authenticity. I'm your host, Diane Schroeder, and I am so grateful that you are here.

Hello, friend. Let's take a trip down memory lane. Do you remember when you got your “real job”? I remember I felt incredibly intimidated by the senior people or the old guys, in my case. I was so worried about impressing them and learning at the same time. I also remember hearing them constantly complaining about my generation, not wanting to work hard, blah, blah, blah. As I grew up in the fire service and became one of the old people, I tried to approach the new kids with more curiosity over judgment.

I wanted to help my people succeed. And the best way to do that is to figure out what they needed. I've had the privilege to work mostly with millennials and Gen X while being in a leadership role. And my mentors were primarily baby boomers. The point of this is I could've really used a guidebook designed for me by a peer to help me navigate that 1st few years as a leader and boss. I had the pleasure of speaking with the inspirational, Emily Tsitrian. We dive into the importance of coaching and providing opportunities for underrepresented voices within organizations, and the unique challenges and perspectives that the millennial generation faces in the workplace, including the emotional aspects of transitioning into leadership roles and the need for self-awareness and support. Emily shares her journey from corporate America to becoming an entrepreneur while I reflect on my experiences leading millennials, and we both agree that the significance of community, self-care, and authenticity is critical in professional roles.

Emily is the CEO and cofounder of Yield, a payment consulting company and is an award-winning author of a management and leadership book called Make Me the Boss, which just so happens to be a book for millennials on how to crush your 1st level leadership and management role. Today, we get the privilege of talking to Emily Tsitrian. And I love her story because she took adversity and turned it into looking out for herself, which follows the advice of my amazing friend, Heather Childress, when you bet on yourself you can't go wrong. And so, Emily, welcome.

Thank you. It's so good to be here. I appreciate it.

I always ask a random icebreaker question. And my question for you is if you could travel anywhere in the world, price is not an option, duration of stay is not an option, where would it be, and why?

Oh, okay. I think I'm going to have to definitely lean on the price as not any sort of a barrier, so I'm probably going to choose, like, one of the most expensive places. I don't know. Maybe the Maldives. Go to Singapore for 3 months, maybe Tokyo. That would probably be my top 3.

Yes. Absolutely. And why do those speak to you?

So, I like places that are a distinctly different perspective history and culture than my own. I think every time we go and travel outside of our comfort zone, we learn about ourselves. We just get new perspectives, and it kind of fundamentally changes us. So, I definitely lean into that whenever I can, and I really like being places where the food is exceptional. So, I tend to travel based a little bit on the restaurant availability.

You are a woman after my own heart. Those are the exact reasons I like to travel, and my best memories from traveling is food. But I do the same thing. I just want to eat.

Right? I know. Anthony Bourdain is just, like, cheering us on right now in spirit.

Absolutely. You know? And I always say when I talk to about equity and diversity and inclusion that the best, quickest way to form a bond in any team is to do it over food. Just bring in your favorite dish and explain why, and that usually is a great conversation starter.

So fundamental to the human experience. I'm right there with you.

I have a question because I know that you wrote a book, and we'll definitely get more about that. But I want to know what inspired you to write your book specifically for millennials as they step into leadership and middle management.

Yes. I think we're going through a huge change in corporate America and just the workforce in general, where the folks that have been largely on the front lines, kind of the line staff, it has graduated into management roles and leadership roles. And in fact, the data shows that most first time managers are about the age of 30, basically, between 30 and 32, and so that is right in the middle of the millennial generation. And I think I'm always fascinated by generational behavior. And I think millennials, in particular, have a very interesting way of relating to the workplace and the values and the expectations that we bring into the workplace, I think, are really unique. And so, I wanted to write a handbook for people of the generation that addressed the whole person, our kind of shared experience given the generation we're at, but also, kind of helped prepare them to succeed and step into this entirely new identity and role, and that's just a way that the entire world is changing.

What a gift to give. I spent over half my life in the fire service. And what I realized towards the end of my career was, yes. There was a clear succession plan and promotional step process. However, there wasn't a lot of, like, here’s how you do it. It was more, this is how I did it, and so they just didn't really speak to obviously, I was a woman in the fire service. That was a very different perspective to begin with, but it just didn't really focus on leaders, and I think we give a lot of attention to upper management, executive management, the C-suite level. We really don't pay attention to the beginning steps of that journey, so I'd commend you on that.

What are some of the generational differences that, in your opinion, from being a millennial yourself and then how to coach, and this is great information for all of us, I think we get a lot of bad information or there becomes, like, this thing that doesn't have to be there because every generation has had their sort of critique or complaining against, and I always laugh because I always tell the boomers, y'all raise the millennials. Everyone has their generational differences. So, back to my question, what are some of them that you recognize?

Yeah. Absolutely. So, to your point about it being, sort of a dearth of support and handbooks for first time managers, absolutely. I've seen that throughout my entire career. Or they're very focused on these sort of lofty leadership things, like, let's read this book about Henry Ford or this expedition to Antarctica, you know, Shackleton. What can we learn from Shackleton? That's valuable, I think, but it's also the reality of, like, okay. You're promoted. Here's your team. You now have these Slack groups. You now have to hire and fire people. How do you do all of that? That's just really missing. And so, I wrote it kind of, like, the to address both sides of it, the tactical and the, you know, leadership and identity exploration. Millennials are very interesting. I mean, our kind of coming of age has been fully bookmarked between 911 and then the COVID-19 pandemic. Like, that was our early adulthood experience.

That's a lot.

It is. It is. And so, I think it's definitely affected our world view. Some things that I think are really encouraging about millennials are that we're very open and almost have an expectation that we're going to talk about mental health. It's something that we bring into the workplace. We're very comfortable, not comfortable, but we tend to be, more comfortable in previous generations and talking and addressing mental health. We are kind of sensitive and anxious, and we definitely speak the language of Gen Z in terms of, like, we like to DM, and we like emojis and memes and sort of Internet culture, but we also do remember what it was like to not have a cell phone and not have the Internet at home. And so, when we work with and manage people that are in Gen X, or even boomers, I mean, there's definitely still a lot of boomers in the workforce. I think that we can relate to those generations with some ease. So, I think that that perspective and experience is really encouraging. And then I think just demographic differences in millennials are that as a generation, the way that we exist in our workplace and communities is very different. And this isn’t a generalization, but the data does support this. We don't tend to be as heavily involved in things like churches or fraternal organizations, you know, the Shriners, the Majacs, like, all those kinds of things that existed in times past. And we also tend to live with roommates longer. We tend to live with our parents a little longer. We tend to get married and have children a bit later in life.

And so, I think all of that has resulted in we tend to have a higher amount of social connectivity and expectation for social connectivity in the workplace. And so, when you transition as a millennial from being, you know, a young person in your 20s living in a city, most of your friends are from your workplace, to all of a sudden that you're a manager now and you can't really be friends with your team and you need to kind of rethink how you exist there, I think that's particularly hard for us. I think we are uniquely suited to raise to that challenge, but I do think that that is distinct with millennials that I have observed time and time and again.

That is incredible feedback, so thank you for sharing. I loved leading millennials. It was my favorite demographic or generation to lead, partly because I'm a Gen X-er, and I'm towards the end of the Gen X movement, but still, I'm stuck in this like, sometimes I felt like I was stuck in this hell of, I have to stay in my job forever and ever and ever, and I never leave because that's what my parents did. And when I learned, when the best information I got for millennials and really understanding was, your generation has been raised, like you just said, in a very trauma informed generation. You have not known a time where you didn't have access to tragedy. We're seeing the whole thing unfold, whether it be 911 or Katrina or, you know, the COVID pandemic, like you said. So, you just have a very different view of the world, which I think is a gift because you do talk about mental health. And the social, you know, the acceptance and the, you know, community and the culture of, there just seems to not be as much stigma around, you know, gender or identity or culture backgrounds. You know, I always say we're the problem. It's the older generations that really create a lot of that problem in the workspace. There's just so much to learn from that, and I just think that's a beautiful way of putting it. And we all struggle going from that buddy to boss, and I never thought of it in that perspective that it's because it's such a huge social connection. And that's really hard to learn how to have difficult conversations and lead with love and be, you know, all the things that go with being a manager. So, I just think that's fantastic. Now how did you get from where you started in your career to deciding to be an entrepreneur and writing a book?

Yeah. You know, it's kind of funny. I actually never thought that I would be an entrepreneur or CEO. I very much, like a lot of people, I enjoy the structure of corporate America. I love working for really big companies. I love going from, you know, manager to director to VP. And so, I kind of saw myself, you know, continuing to climb this ladder. And I'd really found kind of my part of the Tech worlds that I was really good at and enjoyed. But I like so many people in the past 2 years, was laid off from a company that I really loved and a job that I really loved, and it really, sort of rattled me to my core. And I think this is, you know, I'm not unique in saying that it was, you know, definitely a traumatic experience. And so, I think the initial reaction was, how can I make sure this never happens again? And, really, the only way to do that is to be one of these crazy entrepreneurs. No boss. But in reality, it was basically a combination of, okay, I can see that there is a very real opportunity with this unique skill set that I have, and the timing is right for this. I very much believe that to be true. It was then finding a cofounder that I was compatible with because knowing myself, I know that I work best in teams and groups. And then in the 3rd of it was talking to a lot of what I will call my personal board of advisers. And I think everybody should kind of have this where, you know, it's people you've worked with, maybe you don't work with them anymore, but they kind of know you as a person and as a professional. And I asked them, A, is this a good idea? And, B, please be brutally honest with me. Do you think I can do this? And it was a resounding yes. You can do this. And so, at that point, it kind of became like, why would I not do this? Got to try it. A big risk, but fails, and at this point, it's not going to fail. But if it fails, so what? Going to fail business. Okay. Learn from it. Move on.

Yes. It's so easy to say that as, you know, I'm relatively new in the entrepreneurial world too, and I'm like, oh, wow. That's just a hard and fast rule if you want to survive and keep growing. You have to accept that failure is part of it. And you just figure it out and move forward, you know, in our fast, quick gratification society and all the ads that pop up, be a millionaire, and, you know, six weeks, follow my program, whatever, that kind of can alter your expectations of really just how hard it can be. And I think it's just so wise to, yeah, ask people and believe in yourself that you can do it, and the so what attitude is fantastic. How do you take care of yourself? What does your self-care routine look like? Because I do know it can be really exhausting, and it can be lonely, and it can be frustrating, and that's all before launch, when you're an entrepreneur and when you're running your own business and a CEO. So, how do you make time for yourself and prioritize that?

If I ever am fully able to answer that question, I will write another book and come back on your podcast. I certainly don't have all the answers, but I can give a few tips that have really helped me personally over the past year or so since I've been doing this. So, I think at the beginning, I definitely had that kind of, like, go fast and break things and the Silicon Valley inspired mentality of, like, you got to just, like, rage every day and, like, grind on weekends and sometimes I do. I definitely do that sometimes. But realizing that, you know, burnout is probably not the best way to build a multibillion-dollar empire. That's just the reality. And so, one thing that I did, I think, pretty early on after I realized, I was exhausting myself every day is, I very intentionally found a community and a network of other entrepreneurs and female founders specifically in the town where I live now, which is Chicago. Lucky that it has a very strong founder and entrepreneurial mindset, and it was almost instant that I felt connected to other people that were going through some of this, not just the tactical of, like, what CRM tool do you use, but the more social of, like, how do you feel when you, like, have a bad day or you make a mistake or you start to doubt yourself? And that really changed how I related to it and that, you know, going from being part of a big company, lots of people to being, like, mostly alone, with the, you know, couple employees of your company, that filled a lot of the gaps and also, you know, gave me a sense of community and, you know, even friendships that have made the entire experience feel more complete and fuller.

Well, you answered my other question too because I focus a lot on community. And I believe that the pillars to, you know, really being your authentic self is through community, taking care of yourself, and leadership. And a lot of women, I find I wouldn't say they struggle with leadership. They struggle identifying themselves as a leader because of this idea that we have in our head that you have to be a CEO or you have to be something different than you are when, really, we are all leaders leading our own lives, and, you know, it doesn't really matter what your role is professionally. It's how you attach yourself to that role, and showing up to lead in the best way possible. So, yes, community is everything. I'm still looking for my community in the entrepreneurial world out here in Colorado. So, I'm glad to hear that it's successful for you, and it gives me hope that I will find that as well. Because it does. It's just that communication that not everyone understands. It's really hard to find that camaraderie amongst peers.

Little tip is Instagram. Figure out what are the hashtags. What are all these people doing on hashtags and find them. Yeah.

I need more millennials in my life. This is where my age gets me. This is about being a Gen X because we're just so solo. Like, we got this. We can figure it out. We don't need anyone else. Like, it's really hard sometimes to be of this generation. So, what is, like, 1 piece of advice or maybe 2 pieces of advice that you would give to someone, a millennial, who just started that leadership role. Like, what's one thing you can say if you start doing this right now, right away, that will make the transition so much easier.

Yeah. So, in terms of people management, one of the first things that I think is really critical and actually, a lot of people miss is a stakeholder map. So, when you're an individual contributor, I think it's very easy to figure out who are your stakeholders. It's your customers. It's your colleagues. It's your, you know, peers in other departments. That actually is generally about true. But if you look at, like, an org chart of your company, just move it up a level. And then look at, like, what's my stakeholder map now? So, we're talking about heads of department that your team works cross functionally with. We're talking about within the customers you used to work on, who are the executive sponsors now of those companies who are maybe the C-suites or the VPs or the people you need to be mapped to. And if you look up your leadership chain, your manager is probably somebody that's more like a middle manager, and so you need to think about managing up a little bit differently, but also knowing who your skip lines are. Who is, you know, ultimately the VP or the SVP, putting yourself in a position where you can be an effective leader in representing your team by creating those relationships. It might feel a little bit selfish to go out and say, hey. I would like to meet you. I'm the head of this department, but you actually have to do that. That is part of your job is to be establishing your own leadership brand for yourself.

And then the second addresses a little bit more of that social emotional problem. So, because you can no longer really be friends with the people on your team, right away later you can, I think, once you really establish yourself as their boss. But because you do have to lean out of a lot of friendships and, you know, you can't really gossip in the workplace anymore. Like, you're a boss now. You can't do that. You know, you're going to know how much everyone makes, and you're going to know their disciplinary stuff. Like, you can't. You should find other people that are in a similar position, preferably outside of your company. So, this is where LinkedIn can be very helpful. Find people that have your title at a different company and reach out to them and establishing that relationship to be able to kind of be in it together and maybe replace some of those previous connections that you had in your own team, I think, is really critical to getting a good self-awareness check and knowing that other people are going through the exact same thing, because I promise you, they are, and it's going to feel very lonely if you don't do that pretty intentionally.

Oh, that is such sage advice, and I've seen that happen. And I think it's also really okay to normalize that you have to grieve that loss. Even though it's exciting that you're getting promoted and you're in a new role, you still have to grieve the loss of the relationships and the different dynamics between you and your coworkers. It's even okay to say that. Like, this really bums me out, and here's our new role moving forward. It's not necessarily a bad thing. I just think it's important to recognize it and give yourself space to do that, to just accept that the change is happening. And it's interesting because I really like to focus on the middle managers and kind of, like, when you're stuck in the middle. And I always say, it's storm clouds above you, alligators below you, because now you're further from your people and you're closer to the top, but you're, like, in this really awkward middle, and we really don't focus much at all on the middle. And that's, you know, where I saw a lot of deficits in the fire service and just, you know, the more I work with other organizations that, man, the middle managers are another, like, big step. It's like going from middle school to college and the expectations. So, I think what you said is perfect. Establishing those relationships. You know, putting yourself out there might be perceived as selfish, but it's not. It's smart. And relationships are key in any organization. Regardless if you're private or public sector, it's really important to establish those.

It is. And your relationships with your team are very important, but I think sometimes millennials over index on that. It is okay to be the boss. It is okay if people don't like you. It is also okay if you make a mistake. You will.

Yes. Yes.

It's not your job to not make mistakes. That's not why you were hired. And so, that can be very awkward as well is transitioning into that mindset. And I think if you expect that you're going to be great at the job right away, you're going to be setting yourself up for failure. Nobody is great at something the 1st time they do it. They just aren't. So, you know, your 1st 4 to 6 months they’re going to be a steep learning curve, and that's okay. That is why your company is investing in you. And to your point about kind of grieving the loss, I mean, I kind of write in the book, like, it extends even outside of your career a bit. I think in your personal life, especially if you're hiring manager, you're going to see a lot more people requesting, like, coffee chats or catch up and asking, like, can you, like, send in this referral? Do you know anyone that's hiring for this? And I think just entering that with a little bit of grace and realizing that you're now in this position of power to be able to really influence people's careers and connections and network and maybe not saying yes to everything, that's something to get used to as well.

That boundary, no, is a boundary. No is a really important boundary to set as you start in that leadership, you know, journey. It's an important boundary to set in life in general, but especially when you're starting to because if you say yes to everyone, you will be saying no to others, especially yourself. And then it's hard to unwind that. It's so much easier to start with a firm boundary, and then back off as you get more comfortable in the role than it is to just be, like, you know, try to please everyone. Would you say that's a generational, like, thing to millennials? Is it a gender thing? Is it just, like, that people kind of pleasing, yes, we can make this happen, or is it just a human thing?

Yeah. I've observed it more, I think, with women and other minorities. I think that we are somewhat socialized in a way to baby top rock the boat, and that's potentially why we see just such a huge drop off of women and people of color if you go up a corporate ladder. I mean, by the time you get to the Fortune 500, I think there's, like, one black CEO. Not sure how many women. Yeah. So, I'm not an expert in that. All I know is my experience and what I've studied.

And so, I know that a lot, I believe that a lot of the foundation for what ultimately creates a lot more equity and a lot more prosperity, frankly, happens in that kind of 1st layer of individual contributor to manager. So, we need more women. We need more people of color being coached and then getting that 1st shot at management and leading a team. And I think that would make a huge amount of difference. And, ultimately, in my opinion, I think that's where the company really happens is on the front lines. It's not really in the executive. That's where, like, you know, big company decisions happen, but the day to day, you know, fulfillment of the mission is frontline management.

Absolutely. I could not agree more. Now what advice would you give to someone who's considering taking that next step to becoming a manager? That first level of leadership and management, what would you tell them to do to prepare for it?

So, there's many things that individual contributors can do to even assess if that's something they would like to do. Not everybody should, and not everyone should. And it's entirely possible to have a lot of career growth and a lot of, you know, other sort of accolades going on at individual contributor path. So, there's very specific things like, if you have a new team member volunteering to be their onboarding buddy or, you know, person that kind of coaches them while they're learning, that's a little bit of management light. The second is if there is some cross department or cross functional initiative that's looking for an owner, raising your hand and volunteering to take that on because that is going to give you experience in giving people orders and direction, which even as a manager, yeah, you can give orders and direction, but you really can't control if people do it. And the time that you spend with individual people, it's maybe 30 minutes a week, and they have to figure out what to do for the other 39 and a half hours they're going to be working. So, getting into some kind of cross functional leadership role when you're driving an initiative or something that's, you know, outside of your direct team will give you some sense of, do I like to do this, and do I have the influence or can build the influence to get people to do a thing that needs doing? And so, that's a really good management light.

And then I also recommend asking managers at your company what it's like to be a manager at that company. They will probably be pretty honest with you. And not all companies have a great environment for managers, and I do think that that should be part of your decision for the very first time. If you go and become a first-time manager at a company where the experience isn't great for frontline managers, you might not have super easy time getting into it, or it may just not be the right timing. So, I would have that conversation pretty openly with your direct manager and also with other managers at your firm.

That is great advice. I could not agree more. And I think, also, I would add to that, if you're really good at your job and people like, coworkers might be like, oh my gosh. You're so good. This position's coming up. You should apply for that. It's still going through those steps to take that self-assessment because not everyone, like you said, is cut to be a manager or a leader. And just because you're really good at one thing doesn't mean you're going to be excellent at something else, so it's really got to be a personal decision of what you want and acknowledge that and kind of own that, which is really, you know, a lot of self-reflection. And maybe you try it and, like, you know what? This was not a fit for me, and there's no shame in that. That is okay. At least you tried and recognize that maybe not this time, to your point, the timing.

Timing is everything. They say basketball is a game of inches, so are promotions. You know, if you're up for promotion and someone else, maybe they've been at the company 2 weeks longer than you or something like that. So, you know, go for it next time.

Awesome. Well, Emily, thank you so much. I do have 1 other question for you before we end our lovely conversation, and that is, what is your favorite part about being an entrepreneur so far?

So, my favorite part of being an entrepreneur is being able to pattern, recognize, pivot, and take calculated bets in a really unencumbered way. That's something that is very hard to do within a large company. You're always kind of fulfilling someone else's mission, and you can have a lot of agencies and a lot of direction within your scope of influence. But ultimately, being an entrepreneur, the ability to triangulate and make decisions quickly and move forward with the information that you have in front of you is pretty unparalleled, and I'm really enjoying that aspect of it.

That is one of the best answers I've heard, so thank you so much. And I will link your book and all your contact information in the show notes. Thank you so much for taking the time to chat with us today.

Thanks for having me. It's been a great conversation.

Another great conversation. Thank you for giving the valuable gift of your time and listening to The Fire Inside Her podcast. Speaking of value, one of the most common potholes we fall into on the journey to authenticity is not recognizing our value. So, I created a work book. It's all about value. Head on over to thefireinsideher.com/value to get your free workbook that will help you remember your value. Until next time, my friend.