739 Emily Tsitrian:

Founding a company and leading it as it grows is one of the most vulnerable, things you can do– and often it can feel isolating, because invariably and necessarily the demands on you as CEO to get results from your team … can get in the way of being liked. My guest today – Emily Tsitrian (Citrun) is an expert in team management and author of the new book Make Me the Boss, and she shares her secrets on how to get the best out of your team without losing yourself in the process.

MELINDA

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’ve lived and breathed the ups and downs of starting and growing businesses as a 5-time serial entrepreneur, right now the interactive podcasting app Podopolo. So wherever you are listening to this, take a moment and download Podopolo so you can discover other great podcasts around what interests you and your friends, and follow Wings there so we can take the conversation further with your questions, perspectives, experiences, and advice for other female founders at whatever stage of the journey you’re at! Because together we’re stronger, and we soar higher when we fly together.

Today we change it up a bit to interview an expert in team management who has spent the past 10 years growing and leading teams in technology. Emily Tsitrian (Citrun) leads the professional services team over at the payments company Stripe, and she has a new book out called Make Me the Boss, with important tips for entrepreneurs, CEOs and team leaders who may be stepping into this role for the first time, or want to polish up their leadership skills.

Business is all about people, and no company ever succeeded without a great team.

So, what makes a great team? And what makes a great team leader?

Today we talk about what it takes for a founder and CEO to inspire, mentor, lead and grow a team that drives the results you want to see in your business, the common mistakes most female CEOs and team leaders can make, and how to balance the innate desire to be liked with your necessary objective to enable success while assuring accountability of individual team members and aligning everyone on mission and culture.

Emily Tsitrian is a passionate manager who has made it her mission to ensure up-and-coming leaders have the encouragement, knowledge and tools they need to succeed, whether as first-time founders or team leaders in corporate.

Emily’s nontraditional approach to management has seen her grow a tech team from scratch at a start-up before their Series A financing all the way through their acquisition by AutoDesk. She says her experiences as a manager have helped her unlock the secrets of effectively communicating and empathizing with others – and involves knowing how to build and maintain great relationships and have meaningful and important conversations. Her passion for combining these skills with real world knowledge and situations puts her in a unique position to provide genuine, relatable, and ‘un-stuffy’ words of wisdom to new leaders who are looking to find their place at the table.

Emily recently released her management guide, Make Me the Boss, to guide new managers and leaders through some of the most exciting (and weirdest) aspects of their new jobs. She also has a podcast called manager.flow, where she speaks with other business leaders and entrepreneurs about their experiences, what they have learned, and how they continue to make a difference.

She’s led a consulting division to win ‘Team of the Year’ twice. She was also a featured speaker at the Lesbians Who Tech – Pride Summit, and in 2017 her leadership efforts were highlighted in the New York Times for her work bringing tech into the construction industry.

Let’s put on our wings with the inspiring Emily Tsitrian, and be sure to download the podcast app Podopolo so we can keep the conversation going after the episode.

Melinda Wittstock:

Emily welcome to Wings.

Emily Tsitrian:

Thank you. It’s so great to be here, Melinda.

Melinda Wittstock:

Well, I’m excited to talk about your new book, Make Me The Boss. So entrepreneurs have to grow teams and make sure those teams are working well and efficiently and delivering results. Take me through your biggest epiphanies that you’ve learned along the way, leading and growing teams in tech and also all the things you’re doing at Stripe.

Emily Tsitrian:

It’s a really good question because I do think that founders and entrepreneurs sometimes struggle here when it goes from the skillset and the energy and the approach that’s required to bring a vision to life in a company structure, to then hiring, growing, and nurturing a team for the first time. And often those are two really different things that the same individual is doing. And I think a lot of founders and first time entrepreneurs trip up a bit in trying to apply that same approach to what does it take to launch a company and a brand and get funding and paint this vision to now what is the actual execution of hiring and managing, leading, coaching, firing. And so I wrote the book for anybody whose taking management on for the first time, but I think that there’s a lot of overlap with first time people managers just in a tech or corporate space, and founders and entrepreneurs who are developing a team and their identity as a people manager for the first time.

Melinda Wittstock:

Oh gosh, a hundred percent, because most founders start out, it’s just them and their idea. And then they have to persuade people to work for them for free. And then the company grows. It needs different people. It goes through all these different stages. So I’ve built five of them. You learn along the way and you make a lot of mistakes along the way. So why don’t we talk about it from that first stage where you’re building your team from that very beginning and what are the biggest mistakes do you think most people make and what could we do better at that stage?

Emily Tsitrian:

Absolutely. So one of the biggest mistakes that I see first time people leaders making is this feeling that now that they are the boss of people, their absolute God given mandate is to fight like hell for their team and represent them and beat down doors and be a bull in a china shop representing that team and the needs of that team. And that’s what we call managing up. And so a lot of first time leaders will really burn themselves out in the first six to eight months doing exactly that and really failing to build bridges amongst their peers and mapping out who their peer stakeholders are. So the art of managing down and being able to negotiate the upward pressures of the team and the downward pressures on the business. And let’s say you’re a CEO, maybe that’s your board of directors who you feel you’re accountable to. And finding that happy medium it’s tough.

And so I think taking it a day at a time and recognizing that you are no longer one of them, you’re just not anymore. You have to honor that power and that influence that you have to both produce results for your company and really represent the needs of your company, but also be that trusted guided leader on your team and somebody that’s feeling like is advocating for their needs. It’s a tough balance and it takes a while. And I still struggle with that. I think 10, 11 years into my personal management career, but it’s a mindset that can feel a little bit isolating at times.

Melinda Wittstock:

Oh totally. I know that feeling, because there’s a moment where you’re part of the team in a way, but you’re not. And the pressures on you as the CEO and the founder are totally different. And I think a lot of founders expect their team to be entrepreneurial like them, but they’re not, if they were, they would be founders and, or to understand all the different things that are going on. So definitely I know in my case, I have a board of advisors for that. I have personal advisors, mentors and how I am with the board and figuring out who you’re being in all these cases while still being your authentic self is a tricky one.

Emily Tsitrian:

It is. It reminds me a little bit of that Mean Girls character, the cool mom. Your employees don’t need a cool boss, they need an effective one. And that will mean some days that you are not liked. And I think as women, we really struggle with that. This innate desire to be liked, whether it’s socialized or part of our nature. I think that’s up for debate a bit, but being able to recognize that you’re not really you to your team, you represent something and people are going to have complex feelings about you because of what you represent, and that’s okay. That is the hat and the role that you are playing when you step into this new identity. Does that make sense?

Melinda Wittstock:

Yeah, it totally is. Well, this fear of not being liked is existential for women. I think we’re so relationship focused and that we were acculturated to people please. And so then when we’re in a situation where we, A, have to deliver bad news, or B hold someone accountable, or when there’s the team doesn’t want to do something that’s absolutely vital for the company and you as the founder, you’re at this 30,000 foot level so you can see all the connective tissue of the whole organism. You can see the why, but not everybody else necessarily can. And so sometimes you’re going to have to make an unpopular decision. So talk to me about how in the leadership context, you’re able to persuade, cajole, force, you have all those tools in your arsenal to get the results you need from your team. Do they just need to understand the, why?

Emily Tsitrian:

I think that’s part of it. And I will say that I think all human relationships are like these trust banks, not just in the workplace, in our personal life too. And so there are moments that are these magic moments I call in your first six to eight months. And frankly, it’s when somebody on your team makes a mistake that you can help them fix or you can cover for them. And in that moment, your team member is very vulnerable and coming to you with a mistake or a problem or solution. And you’re able to really course correct, take it on the chin and get them to that spot where they’re feeling good and confident. That then is a deposit in your trust bank, because the very next day you may say, “Hey, team member, I know this is going to be rough, but I need you to change the course of your day to go work on project A to project B. We’ve had a shift in priorities.”

And without having to explain all the context, there’s already that synergy of knowing that, okay, because you had my back last week, I’m going to have your back today, boss, and we’re going to get through this together. I will say, Melinda, I think you’re absolutely right that women have some proclivity of struggling to be liked. But on the flip side, I do think that we and other underrepresented minorities are just naturally very good at building coalitions. Some of that I think is because we’re coming from positions and communities that have no other choice.

We have to create coalitions for the issues that matter to us because we’re not the represented minority in the space that we’re in. And so I think leveraging that collective power of underrepresented voices to join together, to bring people alongside you with a particular vision or mission, that’s really powerful. And I think it’s really something we’re missing out on with the fact that the powers that be in the higher echelons of the company to companies today are still not fully represented of women and other minorities. We’re getting there, but it is-.

Melinda Wittstock:

Yeah. the other thing too, is balancing the authority and having the confidence to step into that authority while at the same time leveraging things like our intuition and our natural empathy, all these things that are very archetypically female, and using those to build, I like the word coalition where you’re uniting people in a collective mission. I think that’s very powerful. I think women are very naturally good at that. As long as we do have that confidence and authority, and aren’t constantly second guessing ourselves and whatnot. And really using those skills to empower our team.

Melinda Wittstock:

One of the things, Emily, that I’ve found, just working with so many female founders as a mentor or through my own entrepreneurial experience building all these businesses is that we have a hard time sometimes even with the hiring, because women tend to look at it, oh my God, it’s an expense. And what if I can’t meet payroll? So we tend to hire too slowly and then hire people to do things rather than as an investment of the return that you’re going to get on that person.

And if you’re not clear about what return you’re expecting from that team member, then they’re not going to be clear on it and they’re not going to succeed. how do you get that balance between empowering people and not micromanaging them but also holding them accountable.

Emily Tsitrian:

100%. I put in my book entire chapter on hiring, because it is one of the most, if not the most critical thing that a people manager does. And it’s also the hardest thing to unpack. You’re going to make a lot of mistakes. You’re constantly making mistakes as a manager. That’s part of it. You learn what doesn’t work and go the other way, but it’s hard to undo a hiring mistake. And so there’s possibly a temptation to be a bit more risk averse and think about, okay, what is the profile of somebody that I feel really confident is going to do well in this position and what’s needed? And the danger there is we sometimes back into unconscious bias when we do that. So as a hiring manager, it’s really important to think about what is the skillset and the nature of the person that is going to best compliment me if it’s your first hire and you’re needing somebody to be that counterpoint.

So what are the skills that I don’t have that this person’s going to be bringing to the table? Or what are the skills or the background that the team doesn’t have? Let’s say I’m hiring a marketing team. And I’ve got a lot of people from really traditional schools of marketing and ad space and normal channels that we’ve all heard a thing about, but I haven’t hired anybody that has really cracked the social media code or somebody that perhaps has military experience. Let’s just to take a segment of the population. So I think team building and thinking about what are the skillsets that actually are lacking rather than what is a carbon copy of what I know works is very important. And to your point about micromanaging, this is probably if you were to pull a hundred people about, what’s the most annoying thing that your boss has ever done? 99 of them will say micromanaging.

So don’t do it, but how do you not do it? So here’s how I have found works really, really well is you help somebody understand how to make a decision about the work that they’re doing and the many thousands of decisions they’re making every single day about the work when you’re not there, because they clearly understand the guiding principle and the framework of what you’re trying to accomplish. And so if somebody was to apply that framework that you’re aligned on and think about how do I guide my work today in alignment with that, then there’s no need for you to micromanage. And in fact, the time that you spend with them can be much more focused on vision building, relationship building rather than this transactional tactical update that sometimes happens in a recurring one on one.

Melinda Wittstock:

A hundred percent. What do you think the cause of micromanaging actually is? What’s going on there psychologically that makes someone want to micromanage to begin with?

Emily Tsitrian:

I think it’s often a reaction to imposter syndrome, which we all experience frequently in our careers. And I actually have a whole chapter in my book about how to unpack it and work with it, but it comes from this fear of not being effective. And so where can I flex? Where can I power up my effectivity as a leader, as a founder, as a manager. And it’s to tighten your grasp of control of the work that is right in front of you. That is going to fail. Even in the short run, if you’re able to produce a really exceptional result or help somebody take the quality of their work to the next level, you still haven’t taught them how to do that themselves.

And so you’re actively not investing in their ability and growth to do it just as you would’ve done it or ideally even, better because that’s why you hired them. You never want to be the smartest person in the room, I think I’ve heard that a lot. That’s very, very true here. And so it always rubs off on me, a deep seated insecurity that is manifesting in this need to really tighten your grip of control. And it’s not good. It’s not good when you see it.

Melinda Wittstock:

I think women sometimes tend towards it because we’re such inherent perfectionists. Perfectionism comes up on this podcast over and over and over again. I think at the root of that is often fear. It’s part of the imposter syndrome. So it has to be perfect and that then translates into, it has to be done my way. And someone else, I’ve come to the conclusion, I don’t really care how people do it. It’s the result. It’s the why. It’s the what. It’s the when, it’s not really how.

Emily Tsitrian:

100%, 100%. And if you were not actively surrounding yourself with people that are better than you and can use something as their leader, your company’s going to plateau [inaudible 00:17:48].

Melinda Wittstock:

Yeah. It’s impossible to do it all. So this is why we always talk about hire your weaknesses, double down on your strength. So it means a self-awareness in what is it that only you can do and do really well. No one else could do, focus on that. And then there’s a whole bunch of other things that you can do really well, but someone else can also do really well. And then there’s the things that you’re meh, or actually you suck at, or you hate, you’ll hire those things. And then you trust the person and give them the guidance as to what the milestones and metrics and things are. But I think that, that whole control thing it can be hard for women to let go and just learn how to delegate even. I see a lot of businesses struggling there and it strangles them. You can never become even a million dollar business if you’re operating that way, you’ll always stay small.

Emily Tsitrian:

100%. Yeah. It’s not a growth mindset. And speaking of growth mindsets, another really important thing that I see frequently first time leaders making is not actively investing in your own growth, both as a person and a professional while also operating the business.

Melinda Wittstock:

Oh, vital. I couldn’t agree with you more. We joke on this podcast all the time that if you want therapy, just become an entrepreneur, because the situations that are out of your control, in your control, unexpected things, whatever, all the challenges that are invariable every day, there’s something new. There’s always a challenge. And how you’re reacting and how you’re triggering is a real clue as to what you have to release or let go of to get to another level of, I guess you could call it personal growth or personal development, or consciousness even makes you a better leader. So being aware of those things, but it is therapeutic to be an entrepreneur.

Emily Tsitrian:

It’s incredibly vulnerable. I think it’s one of the most vulnerable things that humans do. And you’re exactly right, who you were at the kitchen table as a child in your family dynamic, that is going to inform how you show up in your workplace, how your family dealt with conflict. That’s going to be so deeply embedded in you and-.

Melinda Wittstock:

So true. Oh my goodness, that’s so true. I just think of myself. I will be a little vulnerable here. I had two older brothers that are eight and 10 years older than me. So it was always a struggle to be heard and to be taken seriously and all that kind of stuff. And I see little glimmers of that in, because it ends up being your deep subconscious fear. And so you’re basically your life is being run by a five year old child. 80% of us are operating from our subconscious minds. So getting more and more awareness of that, letting that stuff go. It is not even you, it’s just something that without a frontal lobe view that made a belief about yourself.

Emily Tsitrian:

Oh yes, it’s so painful. It’s so painful. But again, that growth is powerful. And with power, acknowledging that you are in a position of power is what’s really critical to unlock your potential. And what I tell people is you’re not the perfect leader. No one is, but you’re the perfect leader for the moment. This is a very unusual time in human history. There’s a weird economic situation. There’s social dynamics that are changing in the workplace and all around us, the experience that you have coming into this is perfect for what is needed and what is being asked. And yes, that does mean your growth and your humility and the inevitable mistakes that you’re going to be making.

Your first mistake is going to feel so much worse as a people leader than it may have ever done as a worker, as an individual contributor. And you get better at that with time. But this is where I do think women have some superpowers here in not being so afraid to make a mistake. And yes, there’s the battle with perfectionism certainly, but having a little bit of that humility and recognition of, okay, that decision I made, that was the wrong decision. Okay. Let’s move forward. What did we learn? How do I set up structure around me to not go down that path again? That’s really, really powerful.

Melinda Wittstock:

I want to talk to you about running tech teams though, specifically.

Emily Tsitrian:

Sure.

Melinda Wittstock:

And this is where, if you’re a non-technical founder and you are trying to tell a tech person how to do something, or it’s maybe what you want, but you don’t really understand all the intricacies of what that means, and you have tech teams that could build a Toyota, which might be sufficient or a Maserati, which might be the thing, because there’s so many different ways to get to the result that you want. And so in that context, I see so many non-technical founders or even semi-technical founders making a mistake that results in what I’ll call malicious obedience, where the teams say, okay, we’ll do it your way. And then your way actually sucks, because you didn’t know all the intricacies of building tag.

Emily Tsitrian:

Oh man. Yep. That sounds familiar. I like your phrasing though. That’s interesting to me, but yeah, I think that creating tech companies, which is, every company is a tech company to some extent now, but there’s always going to be that trade-off between speed and long-term infrastructure viability. And so it’s very important that your technical team and your technical leader are really in lockstep with your business leader and your operational leader to understand what are the trade-offs of these really important technical decisions that years down the road are going to be incredibly difficult to rewrite or to rearchitect. So understanding what those decisions mean and what are the potential consequences are really important. And especially in a company’s early days and especially when maybe you’ve got cash for a year or two. To find your market fit get those first customers. So what sort of trade-offs do we need to make, but it’s definitely a complex one.

Melinda Wittstock:

Oh man. Absolutely. For sure. So when I think of say someone like Steve Jobs who talked about the difference between A players, B players, C players, or whatever on a team. If you’re hiring A players, these are people who are defined, they’re self-starters, they are motivated, they’re aligned, they’re really excellent. They’re always want to do better, achieve more. Those type of people only want to work with other people that are at that same level of operating from a zone of excellence or genius.

And if you hire a B player, the B player, who’s not necessarily as genius or as competent or whatever is more likely to feel, yeah, kind of a fish out of water is more likely to want to hire a C player. And so it’s the bad apple theory. You have one bad apple in a team and what that does for morale or whatever. So what do you do in that context? So you have a team that’s operating really well. It’s at its zone of genius, but you hire someone who’s not the right fit and it starts to impact morale. Have you had that happen to you? And what do you do in that circumstance?

Emily Tsitrian:

Yeah, I have, I think that every new people leader will encounter this at some point. And first of all, I want to be clear that from a human perspective is different from a work perspective. So none of this is a value judgment on the people as people, it’s really looking within a workplace dynamic. I also think that where you’re at in your life and what you’re experiencing can influence if you’re showing up as A player, a B player, a C player. So I think that there is a little bit of nuance here and what’s going on in this person’s life that’s impacting this. I guess it would challenge your description and possibly Steve Jobs’ description of A players only want to work with A players a little bit. And here’s why. I find that to be very true in the creative side of technology. People that are highly passionate, very engaged and really brilliant, absolutely they light up, they do their best work when they’re in a room and they’re in a team with other just exceptional individuals.

The reality of a workplace is that there is this whole bucket of yucky work that just has to get done. And when I think about, we sometimes call that the keep lights on, it’s like the day in, the day out, the grind. B players have a higher tolerance for showing up and executing that work with high quality in a way that can sometimes really facilitate A players being enabled, in that they can focus on some of that more like let’s move the business forward in this really focused way, because we have other people that either who they are, or how they’re showing up is more in the, all right, this is a job and going to do the job, I’m going to do the job well, but I’m not showing up every day to disrupt the industry, disrupt this space.

So I think a mix of A and B players in my experience is that optimal mix. And the other thing with A players is, this happens I think, there’s a stereotype about gen Z and millennials that you want to get promoted really fast. I think that’s true. A players, if they don’t see substantial career progression, either in salary, title, reporting chain, whatever that means to them pretty quickly, they can sour on the experience more quickly. And the reality is you can’t promote everybody once they’ve been there for two years, you just can’t do it. The slots are far and fewer between. And so I think if you have an entire team of A players, you sometimes end up with a bit more churn, tension, competition that can sometimes dabble on the toxic side because you’ve got so many really ambitious, hungry people that want to see meaningful career progress very quickly. Does that make sense?

Melinda Wittstock:

Yeah, it does. It’s a balance, because the other aspect of it too is really great A players often enjoy or tend to be more generous mentors as well. I’ve always found that if you want to learn something, find out who’s already done it before you and was really great at it. Ask that person, hey, how did you do it? And they tend to be much more generous than you’d expect.

Emily Tsitrian:

And so how do you scale their craft and their genius? Yeah, that’s a million dollar question right there. Do you make the managers? I don’t know. I don’t know. Sometimes you do.

Melinda Wittstock:

It gets into character of people and your culture as a company, what your values are.

You can publish your values on your website like everybody does and your mission and all these things, but how do you operationalize these things? And what’s the responsibility of the founder, I guess, and the CEO and the management team to really be able to consistently walk their talk. Easier said than done on that. So if you say integrity is one of your highest values, well, how are you in integrity and when are you out of it? And are you aware that you’re out of it for example?

Emily Tsitrian:

Yeah, absolutely. If you have somebody or group of people on your team that don’t have that integrity of accountability and an honesty, and frankly… Let me start that one over. If you have individuals on your team or group of people on your team who maybe they are high performers, but they don’t necessarily demonstrate that fundamental character stuff, ownership, honesty, integrity, accountability. It’s not going to work out. And so for me, that is the clearest sign that somebody’s not going to be a fit, if I see behavior or indications that this person is unwilling to take that accountability and shown the way that I can trust them. Once that trust is degraded, it’s very, very hard to pull it back. Now you might also have what we’re characterizing as a C player who just is not like, the skillset is not a right fit or it’s just, they can’t take the feedback in action on a way. You do have to make a change, but I would argue that, that is the hiring manager’s area right there.

You need to seriously look at your hiring process because that individual should never have been hired in the first place. And that’s on you. So as a hiring manager, you really need to take that very seriously when that happens, as far as what have we missed in our hiring process that we weren’t able to screen for this and set somebody up for success. And it is not doing them a kindness to keep them on. You don’t want to be at a job where you’re failing, or you don’t have the fundamental skills. You’re not beating the bar. No one wants that. And so being able to have that really honest realization and show them the respect and dignity of severing the business employment relationship, it’s an important thing that’s got to be done, but if you don’t do it and you don’t do it in time, your A players and your high performers will leave the team, because they want to be part of a high performing team. That’s just human nature. So it does have to be done. And it’s really tough, but it’s part of the job.

Melinda Wittstock:

Yeah. So it’s the Google mantra of hire slowly and fire fast. I remember a long time ago, previous startup of mine, we had, I would describe someone as a B player. And I remember I was speaking at Harvard and I was at Logan airport and just waiting for my plane. So I was thumbing through Harvard Business Review books in Logan airport. And I just opened one up about teams and it just opened to this page that said, if you have someone who’s just not really performing, they’re like they’re okay, but they’re not great why you should fire that person. And I was really quite shocked and scandalized by it, but it was talking about the context of morale and how that saps the team.

And it was really, to me at the time, it was a really radical idea. But the more I thought about it, the more I thought, oh, okay, because we weren’t really performing as well. Our growth had slowed down and it wasn’t really clear what the cause of it was. I, after some soul searching made the decision to let go of this person. I thought my whole team was going to hate me, that I was going to be the proverbial B word. I was worried about not being liked, all this kind of stuff, all this stress, but I did it. And I swear to God within hours, everybody on the team was coming into my office, thanking me.

And what was interesting is I learned from that, is they were just assuming that I really liked this person or I thought this person was great. So they weren’t really giving me honest feedback about what was really going on. And so sometimes, you can get so isolated as the company grows that you don’t really have those information flows, you don’t really have a clear idea of what’s actually really going on. And it was a really interesting lesson mean. Have you encountered that before too? Where it’s just not, someone’s not egregious, they’re not really screwing up, but they are in the sense that they’re really sapping morale or they’re just not walking their talk, or they’re not providing the kind of leadership that people want.

Emily Tsitrian:

Oh Melinda, 100%. Yes. And your experience resonates a lot with me. Have been in similar positions of making that decision and been thinking, oh, this is going to be such a shakeup. People are going to be really, they like this person and that this is going to be a big issue. And it turns out my intuition was actually right that-.

Melinda Wittstock:

Exactly. This is where we have to get better at trusting our intuition, because we know. And I think over the years, all the people sadly that… Because firing is a terrible thing. It’s really scary and awful and you feel bad, but every single time I’ve done it, I’ve always asked myself afterwards, why didn’t I do this six months ago, or a year ago, or a month ago or whatever. And it’s always instantly better the minute that it’s done. And I knew, but what was it? Was with all the fear or whatever that stops you from taking action. The minute you have that, I guess it’s some intuitive divine download.

Emily Tsitrian:

Yeah. We have this instinct that we’re so deeply empathetic, that’s probably why we’re leaders, that we want to avoid the pain that this will cause somebody. But at the end of the day, we’re agents of the business and we are responsible for the work of the business and of the team. And so you have to actively put that at the front of your mind is what is my core responsibility. And if I fail to make this decision, I’m actively failing many, many other people in a much more severe way over time than the individual pain that will be felt in this decision to separate this individual.

Melinda Wittstock:

So what a wonderful way to look at it, because that’s the thing, you’re responsible for the entire organism. And so if one person is ultimately hurting the company, you’re hurting the livelihoods of all those other people, I think that’s really good perspective, really good perspective. I could talk to you for a lot longer. So tell me about the process that made you write your book, because you had all this experience, 10 years with all these tech teams, startup companies, companies of different sizes, really managing growing, leading teams and now professional services at Stripe. What was the aha where you said, okay, enough, I got to write the book?

Emily Tsitrian:

Yeah. So my journey to management was at a very early stage startup. Pre-series A, 20 person, really one of the founding employees of the team. And that’s how I think a lot of people get into their first management career is they just happen to be an early employee or a founder. And all of a sudden, boom, you’re growing a team, you’re growing a function, you got to learn these very tactical things. So I learned a lot of things the hard way. And many years later, a friend of mine had recently got promoted and asked me if I had any recommendations for how to really thrive in that first six month period. And I just had this burst of inspiration, that was the book you need doesn’t exist yet. And I should write it. I’m going to write it.

So I basically spent three years taking everything that I learned and that I experienced new managers around me going through and adapted it to a more modern audience. I referenced people like Lizzo. It’s not the business books of the past, it’s much more modern and updated. I use memes the language of the millennial, because the population of people that are starting companies and that are taking on management roles, it is millennials. And so I wanted to meet people where they’re at and having a fun, approachable, sassy, funny book that they could relate to and could also really, really help them feel empowered about this major life change that is happening.

Melinda Wittstock:

So I would be remiss if I didn’t ask you about the latest, big thing post COVID, which is the quiet quitting. Have you noticed this? Is this phenomenon something that happens at Stripe or elsewhere? Because for a while there was the great resignation. Okay. And then there’s all the balance of how do you run remote teams or hybrid teams, come back to the office, not, is all of that. How does the management style change? And now we have this quiet quitting issue.

Emily Tsitrian:

Yeah. I think it’s a phenomenon that I am not personally seeing it in my corner of the world, but I can see where it’s coming from. I think people are really renegotiating, what does my job mean to me? COVID had a very powerful effect on a lot of people rethinking, what are their priorities in life? What do they really want to be doing? Followed by this period of, we called it the great resignation. I think it was honestly a lot of women leaving the workforce too, which is very concerning to me for a multitude of reasons.

And I think what we’re experiencing now is younger generations who have, the past few years have been rough. And are thinking about, do I really want to spend the next 50 years staring into a nine by 13 inch thing of pixels? And so in order to make this job meaningful and fulfilling to me, I need to have some boundaries now. Is quitting the right way to go about it? No, but I think it’s indicative of a larger shift that’s happening and a conversation that needs to be had, which is what does gen Z and millennials really care about in a job? And what do employers need to be thinking about as they welcome this new generation of people into the workforce? So it’ll be interesting to see how it plays out.

Melinda Wittstock:

So Emily, I want to make sure that everybody knows how to find and connect with you, but also, of course, get your book. What’s the best way?

Emily Tsitrian:

Absolutely. So my website is Emilytsitrian.com. You’ll probably need to get that from the show notes, because it’s a tough last name to spell, but-.

Melinda Wittstock:

We’ll make sure. So don’t drive off the road trying to… It’ll all be there. And so you’ll be able to be able get the link.

Emily Tsitrian:

Absolutely. Yeah. I’m fairly active on LinkedIn and you can find my book, Make Me the Boss, wherever books are sold, Amazon, Barnes & Noble, Apple Books, or your local independent bookstore.

Melinda Wittstock:

Well, congratulations on the book. It’s amazing. Thank you for putting on your wings and flying with us today.

Emily Tsitrian:

Thank you so much for having me. It’s been a great conversation.