Published on Nov 14, 2022

20 min read

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In this video, Emily Tsitrian, a former manager at Stripe and author of “Make Me the Boss,” takes us through what it takes to be a successful new manager in the corporate world. If you’re a millennial looking for tips on being a successful manager, this video is definitely for you!

We’ll outline everything you need to know to be a successful manager and lead your team to success! We cover a wide range of topics, including the challenges and different responsibilities of being a manager, how to offer difficult feedback, how to manage people who are older than you, how to deliver the performance review of a lifetime, how to use public speaking to create your personal brand and more. These are all essential skills that any successful manager needs to have. By the end of this video, you’ll have everything you need to survive as a millennial manager in the corporate world!



  • 0:00 Introduction
  • 1:18 What’s the difference and what’s unique about being a millennial manager?
  • 3:18 What advice do you have for managing millennials?
  • 5:12 Is becoming a manager a promotion?
  • 7:48 Advice for millennial managers who are managing people older than them.
  • 10:38 Non-linear aspects of career progression and the career progression pyramid.
  • 13:25 Advice for new managers on how to handle those difficult conversations
  • 16:10 Advice on building your personal brand
  • 17:58 What can one manager do to address issues of systemic racism, ageism, and sexual discrimination?
  • 19:52 Advice for women and underrepresented minorities that are either millennial managers or want to become one?
  • 21:58 Besides your book, what other books or resources would you recommend to millennial managers?
  • 24:46 Where could people reach out if they wanted to connect with you?


Vidal: [00:00:00] Good afternoon today. Have with me Emily Tsitrian. She’s a manager at Stripe. Welcome to ManagersClub, Emily.

Emily: Thank you Vidal. I’ve always wanted to be in a club and now I am. And it feels great. So thanks for having me.

Vidal: Great to have you here. So, um, Emily has written a new book. It’s a very interesting book we’re gonna talk about, which is Make Me the Boss.

Vidal: But before we get into that, Emily, could you briefly introduce yourself to the audience?

Emily: Absolutely. [00:00:30] So I’m a year and a half into the current chapter of my career, no pun intended, with the work chapter there at Stripe, but I’ve worked for about 11 years in various tech roles throughout different companies in Silicon Valley. I’d say the past six or seven have really been in a, in a truly a management position. So decided to write the book a couple of years ago when I saw a lot of new folks making some of the same mistakes that I had made and really deciding, why don’t I just write a book with everything I feel like I’ve learned the hard way and put it out there [00:01:00] and see what happens.

Vidal: Great. Uh, So you know what’s interesting about your book is that it has this focus on surviving as a millennial manager. Now there are a lot of other management books out there, even some specifically for engineering managers, but you have a unique focus.

Vidal: What’s the difference and what’s unique about being a millennial uh, manager? I’m like from the previous generation. Curious ,

Emily: And it’s funny you’re Gen X, but Gen X has a lot in [00:01:30] common with millennials and we speak a lot of the same internet languages.

Emily: We talk in memes. Uh, we, We have a lot of kind of dark broody sarcasm between us. So I, I see you. I see you. But what’s interesting is the workforce is changing quite a lot and millennials have often had this sort of this negative stereotype of being really hard to manage, really entitled, not that great at working, but what you’re seeing in the reality of the workplace is the generation that’s late twenties, early thirties, getting up into, even your forties.

Emily: We [00:02:00] are the ones now coming into these. Positions of power and actually taking the wheel in steering corporate America into its next chapter. So I’m very fascinated at that demographic transition that’s happening and some of the values that my generation is bringing into the workplace. But I think it’s a really uniquely challenging experience to be part of this post nine eleven generation.

Emily: Was really the last bastion of not having social media growing up before the internet and yet being suddenly immersed in these tech [00:02:30] roles. And so I think it’s a fascinating corner of the demographic trends of the United States and the world, frankly. And so I wanted to unpack that and it’s, explore that, but write it in the language that millennials understand, which is memes.

Emily: And it’s, talking about contemporary heroes and leaders like Lizzo and Nicki Minaj. We’ve heard a lot about Henry Ford and what he did, and there’s certainly lessons there but we need a fresher take on what does it really take to lead at influence and make a.

Vidal: I think that’s great.

Vidal: Your book is super interesting. Like, I love [00:03:00] the illustrations in the book, the memes, kind of the sassy kind of aspect to it. So it is, it’s very different than most other managing books I’ve seen, so I agree with you. It, Henry Ford is not in this book. Um, since, Since we’re talking about, you know, millennials.

Vidal: Alright, let’s just go to this. What advice do you have for managing millennials right? What are the nuances of that?

Emily: Yeah, so millennials and in fact, Gen Z, who’s coming to the workplace, [00:03:30] we really relate to our employer and our work very differently than previous generations. The fabric of society is shifting in a way where people expect and need so much more out of their workplace than we ever have before.

Emily: So participation in things like churches, synagogues, fraternal organizations, social clubs uh, that whole has very much decreased and people are having children later. They’re living with [00:04:00] roommates longer. There’s also a lot of weird economic inequality and going on and a lot of awareness about.

Emily: Climate change and systemic racism and so I think when we’re managing folks that are other millennials, I think it’s very important to acknowledge the reality is that we are in a different world and a lot of those same workplace or trying to figure out what motivates people.

Emily: Tropes are just gone. People do need so much more from their workplace and frankly from their manager, which is part of why it’s you represent so [00:04:30] many things now to the team that you manage, and so you have to create some distance and space there for yourself to gracefully adjust into this new position of influence, but also just acknowledge that it’s the reality and so the stakes are higher.

Vidal: Okay. Interesting. Yeah. You refer many times in the book to becoming a manager as a promotion. So let’s talk about that for a minute. Cause I’m gonna disagree with you a little bit. I think that a [00:05:00] lot of people may see it as a promotion, but it’s really a totally different job.

Vidal: It’s like being a soccer player and now you’re the soccer coach, right? It’s not exactly the same, but what are your thoughts on that? Do you disagree?

Emily: Yeah. And actually you make a really good point because I think in very technical fields such as engineering org charts do tend to be flatter.

Emily: And the promotion into a a you know, an engineering manager, an EM, is not necessarily rife with huge new perks and company expense [00:05:30] cards and all of a sudden I’m now. Pushing all the levers and making all the things happen. And I think that’s the trend that I’m seeing too, just in the valley in general is organizations are becoming much flatter.

Emily: And so I. I, I think traditionally the idea of like, All right, I got promoted and I’m the boss. Now that idea is gone. That’s in the past. But I would disagree with the idea that it is not a net new transition and acceptance of power and influence, whether it’s perceived or real. When somebody [00:06:00] becomes a manager of other human beings, the responsibility that is on your current plate.

Emily: Exponentially bigger than when you were an individual contributor and there’s parts of my book where I give people a Cliff’s Notes or a cheat sheet on how to navigate that as an individual contributor. You probably have never thought about what happens when someone on my team has a death in their family and they’ve got a big deliverable coming up.

Emily: What happens when I receive a [00:06:30] complaint about harassment from a vendor that they worked with? What happens when all of a sudden somebody resigns or has to go out on leave and so there’s all these kind of situational things that you probably have never encountered, but the need for you to really step up and embrace and manage those things while keep the business humming along is much greater.

Emily: And so maybe it’s not a promotion in the traditional sense of the word, but it certainly is. Expansion of duty and responsibility and the impact that [00:07:00] you will have on your team members and on your company.

Vidal: Oh I agree. I agree totally with that. Now it’s not just responsible for yourself, You’re responsible for a whole group of people, their careers. I mean, You could tank the whole team if you’re a bad manager, right?

Emily: It’s a very hard the stakes are very high when you make a hiring decision for a manager. It’s very hard to unwind.

Emily: Um, so, so, Yeah, totally agree. And let’s say you’re in sales, for example. You’ve got your book of business, you gotta sell 1 million a year. You inherit a team of five people. Now your [00:07:30] number is not just the 5 million, but it’s actually now 6 million because you’re gonna be exponentially higher.

Emily: And it happens like that overnight for most new managers, which is why I wrote the book is, it takes a few months to adjust to.

Vidal: I got. Yeah, totally. Yeah. Your scope, your influence is definitely much larger. Alright. Since we’re talking about generations like what’s your advice for millennial managers who are managing people older than them?

Vidal: People who are maybe Gen X or baby boomers? Cause they be very awkward perhaps.

Emily: Yeah, it was [00:08:00] actually very awkward the first time that I did it, and I don’t know why, but I think it was because I had somebody on my team who’s I knew their children were like, closer in age to me, than I was to the and so I, I just felt kinda okay.

Emily: In this, in terms of life experience, I still need to deeply respect that you have more than me. And even though I am in this position of honor and privilege of leading you during this chapter of your career, there are still so [00:08:30] many things that you can teach me from the years of experience that you undoubtedly have in your career in your.

Emily: Hard won life lessons. The nature of people, the nature of business relationships there’s lots of gems there so don’t be afraid to have that learning. Really be mutual, but also think that you’re actively doing a disservice to that person if you shy and tiptoe around the fact that it is now your.

Emily: Again, to lead them in this chapter of your career, you owe that to them. And it’s not showing [00:09:00] any, It, it’s actually very disrespectful if you don’t step into that with position of grace. So some of it’s a mindset adjustment, but there’s also some very tactical things and there’s this kind of stereotype about millennials, which I joke about in my introduction, that we don’t really like to take phone calls.

Emily: We preferred to group texts. You can’t hide behind Slack with your older team members. You’ve gotta call them. You’ve gotta have in person time. That is just one of those generational tropes. And stereotypes that is true if you are millennial managing [00:09:30] Gen X and baby boomers. Don’t be afraid of the phone.

Emily: Like meet, meet folks halfway, where. Their generation’s communication style tends to be and then, of course just being mindful of things like team events. Is everybody really gonna enjoy acts throwing, or is everybody really gonna get that meme that you, that you posted from every kind of different generation and walk of life?

Emily: So being a little bit more sensitive to things like that but also enjoying the time that you have because it, it will be transitory every relationship and situation we’re in changes and [00:10:00] so you’ve been given this gift of getting to lead somebody um, with more experience than you through this, this chapter that you have.

Emily: So, enjoy it.

Vidal: I think that’s very well said. Clearly you’ve thought about this a lot and I like how you recognize their experience and you’re trying to also meet them where they are too, which is great. Totally. You have a cha I like the titles in your book a lot. I think they’re very clever.

Vidal: And so one of is delivering the performance review of a lifetime, and I love that phrase. So a couple [00:10:30] things in that chapter. One is, a lot of people are interested in promotions and you talk about this non-linear career pyramid. Could you say a little about the non-linear aspect of career progression and the pyramid?

Emily: Absolutely. So performance reviews are, I think, a very special time that you get to really deeply influence and impact somebody’s experience and ability to grow. And also just self-awareness of where [00:11:00] they are, importantly in relationship to where they wanna be. I think the worst performance reviews are where it’s just, here’s a laundry list of.

Emily: And here’s all the bad feedback that I’ve gotten about you, and here’s all the good feedback, and you’re just Okay, like thanks and you owe it to your team member to share, Yeah. Could have done better here than, I’m not saying hide that or sugar coat it, but where I think the value add is as a manager is helping that individual visualize their career journey in relationship [00:11:30] to.

Emily: The company, the industry and the environment around them, and also where they want to go. And so if somebody is angling for the promotion which is, I will say common amongst, the kind of newer folks in the workforce. But not really understanding what that means and why that’s important to them is you’re again, doing that disservice.

Emily: So if somebody wants to be a director, we want to be a vp. It’s But what does that mean? Is it the money that we’re angling for? Because we can, I can [00:12:00] work with you to strategically set up your career in a way that maximizes income is. The opportunity to have influence and impact, because let’s go down that road and what does that influence and impact really look like?

Emily: Is it because you’re actually in the wrong job and you wanna go down this path? So really helping them because you will have more, you’ll have more understanding of what’s going on at that company than your team members. And so you need to kind. Help them frame what it is [00:12:30] they’re doing, why it’s matters.

Emily: Here’s where I see the company going, and here’s how we can best set you up to go in that direction together. That’s where that real value add comes in. And so if you help people visualize. Strategically planning their career with the positive and the critical feedback coming in alignment with that, you can deliver a really highly valuable performance review that will in fact make your team member pretty excited to, to go on that journey with you in, in, in many cases.

Vidal: [00:13:00] Totally. So since we’re also talking about new managers, so one thing like giving a performance review that’s like, “Hey, you’re doing great. And here’s your promo. Congratulations.” That’s not so hard. We’re a lot of managers to earn their pay is when you have to give the performance to, it’s I have some bad news for you.

Vidal: I have some, some feedback I have to give you that’s maybe, not what you want to hear, or you didn’t get the promotion that you wanted. So do you have advice for new managers on how to handle those difficult conversations? [00:13:30]

Emily: Absolutely. It is one of those things that is your job to do it, and so you have to embody that.

Emily: This is not necessarily a personal thing. This is literally, it is in my job description to deliver this information to this person at this time. They deserve it, and if I do not do it, I am disrespecting them. You cannot control how they will react to it. [00:14:00] You can use tactics that I talk about in my book aligning on the safe space indicating that you are very much, in their court, you want to see them succeed.

Emily: But if you have some news or some feedback to give, that is not going to land well. You owe it to them to be direct, to be factual, and to give them the space they need to absorb it in the way that they’re gonna absorb it. if somebody is having a very bad reaction to it. So let’s, they start crying.

Emily: [00:14:30] They, things, they go into a kind of mental state where you’re not gonna have an effective conversation. You need to recognize that, take a pause, come back to it the next day. That is something I’ve had to do more than a few times. It’s not necessarily the most fun, but you also need to recognize.

Emily: We are no longer able to have an effective conversation about this. And you also need to be able to, Set that aside because creating a wall around the space where you’re having that difficult conversation is another [00:15:00] skill to then go on and function the rest of the day. As managers, it’s not just I give a bad performance review, my team member’s upset, I’m gonna go home and watch Netflix and recover for the next day.

Emily: No, you may have a customer escalation to deal with the next hour, or you may have a great performance review the next hour, and you need. Happy and excited with that team member in kind of that same, two hour time period too. So creating walls around it and being not necessarily dry and transactional, [00:15:30] but just being direct and delivering the message in the way that respects, that the person absolutely deserves to hear it and needs to hear it.

Emily: And it is your job to deliver it is my best.

Vidal: I like the way you speak about respect. You’ve mentioned that a couple times in your answers, right? That’s your job to do this. And if you don’t do it, you’re disrespecting the the direct report cuz you didn’t give them the feedback or you didn’t, do whatever.

Vidal: So I think that’s a very nice way of thinking about it. I wanna touch on you also talk in the book [00:16:00] about the importance of building your personal brand and specifically public speaking. I know that’s a challenge. A lot of people are engineers are like introverted, they’re not good at public speaking.

Vidal: Do you have some advice on, building your personal brand?

Emily: Absolutely. So I, I think having a personal brand. One of the most important things that you could actually do for your career and personal branding. I don’t mean be somebody that’s got a huge LinkedIn following or that’s, got all this great like Google search result.

Emily: Things like you should [00:16:30] probably think about stuff like that too at some point. But your personal brand is really how people experience you and how they talk and think about you when. In the room. And so developing your career is certainly one piece of it, but also developing as a comprehensive human being is actually gonna make you more impactful in developing your career as well, because you’ve got interesting things that you can do and learn about and talk about with people in a professional setting outside of just the work.[00:17:00]

Emily: So I would say that public speaking is actually one of the most important skill sets that a new manager needs to master. Whether it’s being able to deliver a really compelling vision in a team meeting, or it’s representing your team at an event where to, company all hands and getting them to think, Wow, that’s my boss.

Emily: She’s pretty cool. I’m glad to work for her. That’s one of the. The greatest hacks I think there is to developing that report and that respect [00:17:30] with your team. It’s something you can practice and get better at if you’re not naturally good at it. And by the way, introverts make incredible public speakers because they’re very intuitive.

Vidal: I think that’s great. You also talk about dismantling systemic racism, and you have an incredible story. You’re share in the book about time that you volunteered to prison and then what happened afterwards.

Vidal: So I wanna touch a little bit about this topic. So I’ll just start. What can one manager, especially [00:18:00] a new millennial manager even do to deal with all these issues of systemic racism, ageism, sexual discrimination, all these kind of things?

Emily: Yeah. This is where I actually think millennial managers have a little bit of a, of an edge here and a superpower.

Emily: We are conditioned by an environment and our general experience of life in 2020 and, the Black Lives Ladder movement to be hyper aware of these [00:18:30] issues and as a generation it’s. It’s very important that our workplace is a place where we can express those values. So what can a new manager do?

Emily: Let’s first think about the impact, or rather the lack of impact that many investments have had over the past decade or so in dismantling systemic racism, especially in the tech industry. Microsoft, these large companies have invested millions of dollars in trying to correct some of these issues.

Emily: They have amounted to [00:19:00] very little. And so what a new manager can do is not necessarily go down that path and instead think about personal impact in the ways in this sphere of influence that you have. So it’s everything from ensuring that you’re mentoring. Everybody with the same level of intent.

Emily: Ensuring that you’re really broadening your hiring pipeline, ensuring that your personal professional network is not just the people you went to college with, or not just the people you [00:19:30] worked with at your last company, but is truly a diverse set of professionals from many different backgrounds so that they can enter into your hiring pipeline and eventually go on to get promoted within your company.

Emily: So I actually think the impact is pretty huge.

Vidal: All right. Do you have any specific advice for women and underrepresented minorities that are either, millennial managers or that want to become one?

Emily: Absolutely. So women [00:20:00] and other underrepresented minorities. I think also Have a bit of a superpower in that we have had to be because of circumstances, coalition builders in the way that we access power and the way that we promote our ideas within the workplace, in the community.

Emily: Because we don’t necessarily come from this sort of pre-canned set of personal networks. We can actually leverage our ability to gather people around us and get people. Aligned with your point of view pretty [00:20:30] fluidly. And so I would say lean into that. You don’t have to emulate the management style of the person that doesn’t look like you and doesn’t come from your community and doesn’t share your values, but is clearly very successful over here be who you are and bring that strength into your workplace.

Vidal: Say a little more about coalitions. I’m curious what you know about that.

Emily: Yeah, of course. So that can be a very tactical way to do it. I’ll give you an example. If you need something done in another part of your company that enables you or your [00:21:00] team, rather than taking a heavy handed bull in a China shop approach that I’m the leader of this department and you’ve gotta do.

Emily: Get people convinced that’s the right way to go. So leverage your ability to create relationships to, campaign to. Call in, warmth in favors on people that you really need to do things to make you and your team successful. And so that’s what I mean around building, building more of those coalitions.

Emily: Not so much the top down, but the, Hey, let’s all [00:21:30] move in this direction together because I’ve invested some time and some warmth in these interpersonal relationships.

Vidal: Oh, I see. Okay. So these are like coalitions, just like other people in the. Then not necessarily in that group that you’re in, but you’re, instead of moving by yourself, you’re trying to move with these other people like together.

Vidal: Exactly, Yes. Got it. Got it. Emily, besides your book what other books or resources would you recommend to [00:22:00] millennial manager?

Emily: Yeah, absolutely. And thank you for mentioning my book. It is Make Me the Boss and certainly I would recommend the book . Thank you. Thank you. I have a bit of an unusual take on this question.

Emily: There are some incredible leadership books out there and a simple search on Amazon or will give. Some of the best ones. I actually really encourage people that wanna develop their management leadership skills to, to read fiction as well. And think about [00:22:30] fictional leaders in a way that what is it that, that you want to emulate that they do?

Emily: What is it that they’re doing that you wanna make sure you don’t do? It could be characters on TV shows. It could be Star Trek. It could be. Moran, Dr. Miranda Bailey on Grey’s Anatomy. Yeah. Yeah. And I think more truth can be said in fiction than nonfiction sometimes. And so I think with fiction or with nonfiction, we sometimes fall in the trap of thinking that many historic leaders are very important.

Emily: [00:23:00] Sometimes when you go down the path of watching fictional characters or reading about fictional characters that have leadership qualities I think you could actually get a lot from that.

Emily: A little bit of a strange response, but that’s what I always say.

Vidal: No, I think that’s a cool resp I should hear the second person I’ve interviewed who’s who said someone else recommended they like to read fiction. So there’s definitely some truth to that. I’m curious, do you have any like fiction that you find particularly inspirational for leadership?[00:23:30]

Emily: Yes. I recently. Binge watched Grey’s Anatomy. I’m Grey’s Anatomy, slightly afraid to say this, but there’s this really important episode where one of the residents who we followed through the entire series becomes the chief of surgery. And she, she comes in with this kind of bull in the China shop mentality.

Emily: We’re changing this, we’re changing that, we’re changing that classic first time manager, right? Classic. You always see it has a really terrible first [00:24:00] day. Make some very bad decisions, very bad things happen, and immediately thinks. This is not for me. I can’t do this job. And then her mentor kind of speaks with her and says, No this is the job.

Emily: The job is to make mistakes. And it’s in the learning where that magic where that leadership happens. So it’s a, eating some humble pie. I think many first time managers I would say probably all have experienced that day. Maybe it’s your first day, maybe it’s your first week. But really understanding that that’s just the journey of it. So [00:24:30]

Vidal: yeah, you’re definitely gonna make a ton of mistakes as a new manager. I know I did. And um, Emily, it’s been great to have you. You’ve been very generous with your time and talking with me today. And the listeners of Managers Club. Where could people reach out if they wanted to connect with you?

Vidal: Learn more about being a millennial manager or

Emily: anything. Yeah, absolutely. So I’m fairly active on LinkedIn. Please come on over and follow. I also have a [00:25:00] website, You probably need to get this in the show notes cause it’s a little, little podcast. I’ll put it,

Vidal: I’ll put it

Emily: there. I’ll put it there.

Emily: Thank you. But yeah, I have a, my own podcast as well which is linked out from there. And I enjoy speaking with managers at various points in their careers from all different kinds of industries to see what we can glean from each.

Vidal: I, you know, I think it’s a great idea, . Yeah, I know, I

Emily: know. It’s a great idea.

Emily: I might have, you might need to have you over on my side of the fence here. It’s,

Vidal: It’s a great idea. I, I, I love talking about the [00:25:30] managers street. You always, you learn something, right? It’s every time, it, every time. Because I think, um, we’re all dealing with a lot of the same problems. It’s just the names of the characters are slightly different.

Vidal: Again, Thank you so much for being on, I look forward to speaking with you again in the future. So

Emily: Emily, absolutely. Thank you so much.

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