Cara Silverman - Manager, Executive Support at Duolingo

Cara · 0:00

Hello, I'm Cara Silverman, and today's leadership quote comes from Mother Teresa. I alone cannot change the world, but I can cast the stone across the water to create many ripples.

Speaker 3 · 0:18

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 0:34

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Cara · 1:58

Thank you. I'm really excited to be here.

Jeremy · 2:01

And what part of the universe are you living in?

Cara · 2:04

Yeah, I live in Jersey City, so right outside of New York.

Jeremy · 2:09

Okay. Are you from that area?

Cara · 2:11

Yep. Born and mostly raised in Jersey. I've been working in New York for like something crazy, 15 years or something like that. So definitely home.

Jeremy · 2:21

Awesome. And tell us something about yourself personally. You know, your favorite hobby, your favorite song, your favorite movie, anything like that.

Cara · 2:32

Yeah, I am an artist at heart. I'm endlessly creative. I love creating things, making things with my hands, making my own incense, candles, painting, really anything that allows me to have a creative outlet. And I'm also an avid traveler. So I love to see as much of the world as possible. And I set out a goal for myself each year to see at least one new country. But if I can get to three, then I feel like I'm really crushing it at life.

Jeremy · 3:03

Awesome. What's one of the countries you're wanting to visit soon?

Cara · 3:09

Oh, well, I'm taking my fiancee to Belize for her affordability. Really excited for that. We're getting married this September, and we've been talking about honeymoon stuff for next year, and we'll probably go somewhere in Asia. But narrowing down the countries has been very challenging. We want to go everywhere.

Jeremy · 3:31

Cool. Well, congrats, and hope you have fun.

Cara · 3:33

Thank you.

Jeremy · 3:35

All right. Well, let's talk about your career then. What got you into the assistant role?

Cara · 3:43

You know, it's really funny because I never thought that I would be in an administrative role. I kind of fell into it. I took an entry-level job as an office assistant and started diving into work there and realized like, wow, I have a knack for this. I'm really good at organization and reading people and figuring things out. And it kind of took off from there. And I've worked in a lot of different industries with so many different leaders and have realized that I really find it fulfilling. And I love the many dynamics that come along with it, like beyond calendaring, the travel, the event planning, the thought partnership, and really being able to feel and see an impact of the work that I'm a part of. So I found it to be an incredibly rewarding career. And now I've been doing it for so long and it's crazy to reflect on because it just feels like part of my life now.

Jeremy · 4:41

Right. When did you realize, how long did it take as you got into this role for you to realize that, hey, this is a career, this is a long-term profession?

Cara · 4:52

Yeah, I think it was probably about six-ish years ago when I really started to see a growth in it. In the beginning, I didn't necessarily see a career ladder or I saw a lot of people becoming an EA and wanting to step into something else, but not as many career-focused EAs or ones that were becoming managers or anything like that. I also started to see that it started to become a more sought-after role because of the level of involvement and I started to see the shape of being an executive assistant start to shift a little bit. I think part of that shift for me was also the change of industry. I started working in the tech space, which definitely had a much more flexible approach to how they thought about career growth, instead of working in legal or finance or executive search or things that were more restrictive. Once I started taking on more interesting projects and things that really got me excited and I found to be a lot of fun, I was like, I want to do this forever. I love all of this. I think it was for me just finding the right place, the right industry, the right people, and the right groove to really feel like it was something that I could do longer term.

Jeremy · 6:18

Awesome. That's great. I'm looking at your LinkedIn, which I'll put in the show notes at leaderassistant.com/261 for those of you who want to reach out to Cara and say hi. But I was looking and you have a really, really interesting title journey, I'll call it a title journey. So you've got, let's see if we can get this to load. You've got executive support, executive assistant, senior executive assistant, executive business partner, executive assistant and event planner, executive assistant, office manager, and event planner. And then more recently, chief of staff, secretary, board of directors, and then manager, executive support, and senior executive assistant is what your current title is. Is that right?

Cara · 7:11

Yes. Yeah. So the chief of staff role is a board that I'm on. It's, it's specifically in the ERG space. So I'm, it's a voluntary thing and we help to connect different strategies and ideas for ERGs at different companies to kind of lean on each other with resources and suggestions. But yeah, currently I am the, the manager for executive support at Duolingo. I joined September of last year and I've been really, really loving it so far. It's really nice to work somewhere that's mission driven. I feel like I'm working somewhere that's trying to help people and create accessible education. But yeah, it is interesting. I've had a lot of different titles and there's definitely a lot of overlap of similarities, but certain things that are definitely different. Like executive business partners, I feel are more depending on the company, of course, because I feel like it's all pretty subjective. But for me anyway, the executive business partner was more, you know, in line with strategy, working closely with the CEO and, you know, kind of like diving into different things in that way. In becoming a manager and a team lead, I, you know, it was one of those aha moments of like, wow, I've been doing this for a long time. I have information that I can share with people. Like, in just having conversations, which I never like really thought about that way, because I would just like talk to people about certain things. I'm like, oh, everybody knows this, you know, and they're like, oh, wow, that's really helpful. I'm like, oh, is it? Okay, good. And I, you know, I found it really rewarding to be able to to share those experiences with other people to help them grow. And I started mentoring a little bit and coaching a little bit and realized that I really love people management. I find it just to feel really good to help others excel and help others shine. And you know, being a part of their journey, I find really rewarding.

Jeremy · 9:12

Great. So what's your best number one tip for the assistants listening who would like to manage an executive support or executive assistance in the future? Thank you.

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Cara · 10:11

That's a great question. I would say to really think about people management of like, there's so many parts of it that does feel good. The part that I've had or that I had some struggle with in the beginning were like those difficult conversations, because you always want to be encouraging people and telling them good things. But when it comes down to the constructive feedback or the areas for development, those conversations are hard and you think about it, you're like, oh, I could do that, and then you try to do it and you're like, okay, I need to practice this a little bit more. I think that that's something to keep in mind. Really thinking about why you want to be a people manager is important. Is it a title thing? Is it a compensation thing? Is it the work itself that you find to be exciting? Because people management can be very challenging. I know some people who have gotten into it who have been like, yeah, I actually don't really like this and I don't want to do it. That's okay too. But I think really spending some time developing what that means for you and figuring out why you're making that choice I think is really important. For me, I always just want to be the kind of manager that I've always wanted. I just want to keep it real. I want to help people grow and really just be part of that growth. The other thing too is to think about as well, being an executive assistant by itself is hard. There's a lot of things that we're juggling and navigating and figuring out on a day-to-day basis. Taking that IC work, that individual contributor work and pairing that with people management, it does intensify your workload. That is something to think about too, to see how you feel about going in that direction. Yeah.

Jeremy · 12:24

Did you ever have that or was there a period of time where you're like, oh man, what did I get myself into? Related to the workload.

Cara · 12:35

There were moments for sure. When I was in a previous role and the team was growing really fast, and I tripled the team in hiring, and there was a moment where I felt like a full-time recruiter. I was managing or supporting one of the busiest executives in the company. I was already managing a team of three, and then I was hiring for three roles at the same time, and it was a lot. It was a lot, and it was one of those things that I'm like, oh my gosh, did I bite off more than I can chew? Is this how it's always going to be? But in moments of chaos like that or moments when things just feel really crazy, I'd remind myself this is just a now craziness. This is going to be crazy for the time being, and things will sort out. And they did, but it's a little hard to think of that right away or feel that right away when you're deep into it. But I'm also one of those crazy people who thrives in chaos. So it also depends on how you function, how you work, and what makes the most sense for you.

Jeremy · 13:54

Totally makes sense. That's awesome. Thanks for sharing. And I think that there's a lot of assistants who, like you mentioned, I've even interviewed some on my show where they're like, I tried managing a team and it's just not for me. And then yeah, there's assistants listening here like, oh, I think that would be fun to manage a team. So yeah, thanks for sharing that. So what about the growth? So, you know, there's career growth as far as your role, you know, Cara as an assistant, as a manager of executive support function. And then there's also the, it's kind of the two sides to the coin, your growth, but then also helping your team with their growth goals. So talk to a little bit about, you know, to the growing your career as an assistant, you know, from your experience.

Cara · 14:51

Yeah, I think one of the biggest learnings that I had was recognizing that my growth was in my control. And in the beginning, I'm like, I'm just going to do my job really well and everyone's going to see it. They're going to be like, you should do this. This is what you're meant to do. And I was just waiting for that moment for a while to happen. I'm like, I'm crushing it and doing so good. Why is nobody just like giving me promotions? And, you know, I started learning and taking some classes and listening to different, you know, talks and about people who have like really focused on their career growth. And I realized that I had to be more intentional. Like I had to go into the conversation with my manager being like, this is what I want. This is where I see myself. Here's where and here where my gaps are. And I started figuring out like how to make a development plan for myself. And I still do it now because I'm very committed to lifelong learning. No matter like what stage of growth I'm at, there's always more to learn. There's always things that are changing and being able to recognize what those things are in order to take your next step is really important and communicating that to your manager because managers want to know how they can support you. You know, we only see a fraction of the story, especially with executive assistants, because there's five million things that people are doing behind the scenes. So one piece of advice that I give people on my team is to keep a brag book for yourself. Write down those quick wins, those projects that you're really proud of, the ways, the goals that you set for yourself, and the work that you're doing to kind of align with the goals that you're setting for yourself. And it's an ongoing conversation to have, but you are the leader of that conversation and you have full ownership in that. And for me, that was a big aha moment. For growing my team, I asked them the same questions of what makes you happy, what fulfills you in your role, where do you see your future going? Do you want to be a career EA forever, or do you see this as a stepping stone into something else? And just being really prescriptive about what their own goals are, so I can figure out how to best support them. Because if somebody wants to be a career EA, that doesn't mean like, okay, the coaching stops here. That just means like, all right, well, what skills do you want to enhance? What areas do you want to learn about that you could find interesting? What type of projects are your executives working on that you want to get more involved in and being able to zoom in on areas that are not necessarily tied to promotions or title changes or things like that, but different skills that you can continue to build or different areas that you can learn more about?

Jeremy · 17:54

That's great. I love what you said about, earlier you mentioned that you're expecting people to notice that you're doing great work and then like, oh, here, and it's very similar with professional development. It's like, oh, you can't just sit around and wait for your HR team or your executives to say, hey, we're going to let you do this to develop this year. We think you should do this. Very much a self-managed role in a lot of ways. That's great. Thanks for sharing. You mentioned you felt like you're a recruiter for a while. What tips do you have for both sides of the interview process? If there are assistants listening, looking for work, and currently interviewing or trying to get the rest off when it comes to having those interview conversations. Then on the other side, if there are people like you who have to interview and recruit and hire other assistants, what are tips on that side too as an interviewer?

Cara · 19:13

Yeah, that's a great question. I think it's important for everybody to remember that interviews are too way street and going prepared into them, knowing like, okay, this employer is going to be asking me things, but there are things that are important to me that I want to make sure that I get out of that interview. So I think that that is a really important thing to remember. Interviews are interesting. I have some friends that hate them like so much because you're on the spot, you have to talk about yourself, you have to be clever, you have to be charming. It's a lot of pressure. And what I like to try to do is try to remove the stress from it and say, I'm just having a conversation with a person. And sure, we're going to be talking about this job that maybe I'm going to get hired for, but trying to approach it in in a casual way, but coming with a lot of preparation. So it's important to do your homework on the company, on the role, and specifically really going through the job description and taking out some of those bullet points of what they're looking for and tying that into your own experience. So you can say, all right, here's three bullets that they mentioned, and here's three things that I did that tie into these different things. And making sure you weave that into your conversation. So I always go to interviews with notes on one screen or half of the screen or whatever that I'm able to make sure that I'm hitting those points. And the other part of it is they're probably going to just ask you something that you're not prepared for. And it's important to just be honest. Just take a deep breath beforehand because I've seen a lot of very nervous people. And I think just taking a moment to just go in and just clear your mind, I think, can be helpful. Being a hiring manager, I mean, I kind of look for the things I mentioned, right? Like I look for people who have a really strong grasp on the role that they're applying for and really have like an understanding of what it entails, and then can kind of walk me through, you know, their journey, their own goals, and kind of how that mirrors what the job is that they're looking for. So, you know, before I joined Duolingo, I was very interested in the job, so I did a lot, a lot of homework. I watched, you know, their UConn videos. I was, you know, reading articles about them. I was like, I did a lot of homework, and I was like dropping quotes in there. Nice, nice. That I found the opportunity to show, like, I, you know, I was paying attention, and they really did appreciate that, you know, and I think that those, those details, they do matter. Because also during this research, you might find something and be like, actually, like, I don't want to work for this company for whatever reason. So it's also for your benefit as well to really get to know, you know, where they're at, like what they do, what matters to them, so that you can be just comfortable and prepared. Because I think if you're also more prepared, you're going to just be a little less anxious, because you're going to have, like, some stuff in your back pocket that you're able to, you know, bring with you.

Jeremy · 22:38

Yeah, it's when I, when I speak, you know, I'm an introvert, and I can put on my extroverted hat if I need to. But when I do public speaking, it's like people are like, well, how do you go up and whatever? And like, I'm just super prepared. Like, I just prepare, prepare, prepare, write out everything I'm going to say, practice it, practice it, until I'm just like super confident, like, oh, I could, I could go give this speech in front of thousands of people because I'm so prepared. So that definitely helps in the interviews too. What's your favorite question to ask that may not be like, like if you're the interviewer, what's your favorite question to ask, assistants, that maybe it's not like a super common one, but maybe it's a fun one, maybe it's a test or a, you know, a riddle. What's the riddle you like to ask? You never know these days. There's a lot of crazy interview stuff happening.

Cara · 23:37

And I do try to switch it up as well. One thing that I do with candidates that kind of move it a little further into the process is that I do send them situational questions. And those questions are really thought provokers that tie into like what it is to be an executive assistant and how their thought process works. So that could be something along the lines of, okay, this executive needs to travel to four cities in one week, but currently has a board meeting here. And just kind of creating a real life thing that happens and seeing how the assistant would respond to it. Walk me through your thought process and how you solve for this. What are the suggestions that you come up with? How do you approach this? And then after you figure that out, how do you communicate those changes? And I think that kind of gives a full picture of the start to finish problem solving. It also shows me how resourceful someone is or their level of detail orientation or different things when we think about the very broad spectrum of problem solving. So that's one example. And another one could be tied into event planning. The EAs, a lot of EAs, most EAs these days, but especially at Duolingo, plan a lot of different events, whether they be offsites or dinners or team building or anything like that. So I always throw in a question to kind of show me how somebody walks through their thought process for event planning and the questions that they ask and how they make sure that they're set up for success and have everything that they need.

Jeremy · 25:32

Do you try to send those scenarios ahead of time so they can come prepared? Oh, yeah.

Cara · 25:41

Yeah, that's more of like a take-home.

Jeremy · 25:43

Gotcha.

Cara · 25:44

For like, I'm trying to think of like a good on-the-spot interview question that I ask on like live, and the ones that come to my head are more of the traditional ones. I know there's one question. I'm not sure if this falls into the category of one of the typical ones, but I always find it very interesting to ask about a challenging personality type that somebody has worked with, and what made that person challenging, and how they navigated that to create a strong working relationship. I find that really interesting, especially in terms of being an executive assistant, because there are challenging leaders out there, and people have different ways of communicating and operating. So it's interesting to me to hear an example that ties to that.

Jeremy · 26:31

Love it. Well, thank you so much for sharing. I know there's people listening right now that are on the job hunt, and I can just hear them jotting down note after note to help them prepare for their interview process. So thanks for doing that.

Cara · 26:48

Yeah, happy to.

Jeremy · 26:49

So okay, so what's maybe a funny or interesting or crazy story throughout your career as an assistant where you saved the day or where your executive at the time asked you something to do something that was just out of left field or anything like that? Is there any sort of nugget that you're like, hey, if I write a book someday, the story has got to be in it for the assistance of the world?

Cara · 27:22

You know, it's so funny because there's probably 6 million of those moments and trying.

Jeremy · 27:36

To pinpoint any of them is challenging because they all kind of slide together every day. When I was writing my book, I had a friend of mine who had written a couple of books and he's like, you know what, just write down stories, just anytime you think of a story, write it down because you never know when you're going to be able to use it. And so I'm kind of putting you on the spot here, but no, it's fine.

Cara · 27:54

This is slightly different than what you asked me, but there's one thing that pops out into my head, which was a very big learning moment for me. I used to work somewhere where I was taking over support for two leaders that nobody on the EA team wanted to support. And one of them was like, well, you can't ask him questions. And I was like, what do you mean I can't ask him questions? They're like, you can't ask him questions. And I'm like, I don't know what to do with this information. And then, you know, the other leader, you know, the team was like, you know, we don't like working with her. She's condescending, you know, there's, you know, her approach to things is just not respectful and this and that. So I was like a little nervous at the beginning. I'm like, okay, so I'm taking on these leaders. I'm brand new here. Don't know what's going to happen. I'm going to figure this out. And what I realized was that people were intimidated by this one executive, which is why nobody wanted to ask him questions, because they would just yes him to death. And then he would expect things to be done because people told him that they would get done and then they wouldn't get done. So then he'd be upset about it. And I'm like, well, that makes sense. And I started realizing that there was a huge disconnect with certain perceptions that some people have about certain leaders just because of their own working styles or the way that they interpret body language or tones of voices or things like that. And I found that to be like a huge learning. I was like, I actually really love working with both of them. I don't know what you were all thinking. Did they ask for crazy things? Sure. Well, so the craziest thing that I can think of was not actually from an executive directly, but I was asked to plan a company holiday party or take over the planning for the holiday party. It was October and this was an event for 400 people. I was like, all right, you have a venue, right? They're like, no. I'm like, oh, well, we should probably figure that out.

Jeremy · 30:02

They're like, oh, when is it? Oh, it's next week. Yeah.

Cara · 30:05

400 people in New York City, Christmas time. Cool. I work through the weekend to make it happen, and find venue options, figure stuff out. After I negotiated a place down, I was raised by a salesman, so shout out to my dad. But I negotiated them down to the budget. I put together a proposal. I was so proud. I went, I'm like, look what I did. They're like, actually, we're cutting the budget in half. Oh, wow. I know. I was like, okay. I'm going to make this work. At that point, I was very committed. I was very like, we're going to make this happen some way or another. It did happen and it was wonderful. But it was definitely one of those moments that put all of your resourcefulness, patience, grit to the test. You try to make something happen.

Jeremy · 31:06

Did you go back to that venue and negotiate down again, or did you have to find a different option?

Cara · 31:11

I had to find a different venue. I basically got them down to the lowest that they were.

Jeremy · 31:16

Right.

Cara · 31:17

Which is why I was so proud because that was already beyond.

Jeremy · 31:21

You learned some good negotiation skills that you, I'm sure, have used in your career since.

Cara · 31:31

It was a reminder that you just have to roll with things. You know what I mean? Changes are going to happen, budgets are going to change, teams are going to shift, things are going to be crazy. And I feel that executive assistants feel that in a much more profound, different way than a lot of other teams do because we're supporting the people who are overseeing a lot of these changes. Yeah.

Jeremy · 31:55

You got to embrace the process.

Cara · 31:58

Yeah.

Jeremy · 32:00

Awesome, Cara. Well, congrats on a great career, and thank you so much for taking a few minutes to share your story with us. Is it okay if people reach out and say hi on LinkedIn?

Cara · 32:13

Yes, of course.

Jeremy · 32:15

Well, again, for those listening, leaderassistant.com/261, you can check out the show notes there and get linked to Cara's LinkedIn, and say hi and reach out and connect with her. So it's been a pleasure speaking with you, and I wish you all of the best, and it's fun working in the tech world. I work in the tech world as well, and it's always fun speaking with an assistant in the tech world. So yeah, thanks again for being on the show.

Cara · 32:52

Yeah, thanks so much for having me.