Cara Silverman has worked at several big tech companies including MongoDB and Zocdoc, and joined Duolingo last year to lead their Executive Support organization.
In this episode of The Leader Assistant Podcast, Cara talks about growing your career as an executive assistant, managing a team of assistants, and tips for interviewing and being interviewed.
LEADERSHIP QUOTE
I alone cannot change the world, but I can cast a stone across the water to create many ripples.
– Mother Teresa
CONNECT WITH CARA
ABOUT CARA
Starting as an Office Assistant doing basic administrative work to now leading and growing an EA team at Duolingo, Cara Silverman’s dedication and commitment to lifelong learning and both personal & professional growth has propelled her forward. Over the past 15+ years, Cara has taken a lesson from every experience, finding joy and purpose in passing them to others through mentoring, management and coaching.
Cara’s passion for fostering inclusive environments led her to actively engage in Diversity, Equity, and Inclusion (DEI) initiatives. Recognizing the power of Employee Resource Groups (ERGs), she has played a pivotal role in nurturing a sense of belonging and community within the organizations she’s been a part of.
Since finding joy working in the tech space after exploring many industries, Cara has worked at several big tech companies including MongoDB and Zocdoc and joined Duolingo last year to lead their Executive Support organization. She lives in NJ with her fianceé Laura and cats and works in downtown Manhattan.
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EPISODE TRANSCRIPT
00:00:00.460 –> 00:00:05.760
CARA: Hello, I’m Cara Silverman, and today’s leadership quote comes from Mother Teresa.
00:00:05.780 –> 00:00:12.120
CARA: I alone cannot change the world, but I can cast the stone across the water to create many ripples.
00:00:18.420 –> 00:00:25.860
<v SPEAKER_3>The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.
00:00:34.125 –> 00:00:41.025
JEREMY: Calling all Executive Assistants, are you looking for a way to elevate your skills or earn that promotion you’ve been eyeing?
00:00:41.905 –> 00:00:49.565
JEREMY: Nova Chief of Staff’s Online Certification Course provides you with the knowledge and confidence you need to stand out on the job.
00:00:50.245 –> 00:01:04.005
JEREMY: Whether you want to land your dream position or level up in your current role, Nova’s Self-Paced Course gives you hands-on practice doing what Chiefs of Staff do every day.
00:01:04.725 –> 00:01:10.905
JEREMY: Visit leaderassistant.com/nova to learn more and secure your spot.
00:01:11.485 –> 00:01:16.045
JEREMY: That’s leaderassistant.com/nova.
00:01:16.665 –> 00:01:19.245
JEREMY: Hey friends, welcome to The Leader Assistant Podcast.
00:01:19.245 –> 00:01:30.205
JEREMY: It’s episode 261 and I’m your host Jeremy Burrows and you can check out the show notes for this episode at leaderassistant.com/261.
00:01:31.025 –> 00:01:34.225
JEREMY: Today, I’m excited to be speaking with Cara Silverman.
00:01:34.385 –> 00:01:44.065
JEREMY: Cara is the manager of executive support at Duolingo and my wife is always doing the Duolingo language.
00:01:44.085 –> 00:01:53.265
JEREMY: She’s learning Spanish and she’s always, I always hear the little ding in the other room from her accomplishing her little tasks to learn the language.
00:01:53.265 –> 00:01:57.565
JEREMY: So very familiar with that app, but Cara, welcome to the show.
00:01:58.445 –> 00:01:58.985
CARA: Thank you.
00:01:59.005 –> 00:02:00.205
CARA: I’m really excited to be here.
00:02:01.045 –> 00:02:04.425
JEREMY: And what part of the universe are you living in?
00:02:04.445 –> 00:02:09.025
CARA: Yeah, I live in Jersey City, so right outside of New York.
00:02:09.645 –> 00:02:09.985
JEREMY: Okay.
00:02:10.045 –> 00:02:10.925
JEREMY: Are you from that area?
00:02:11.665 –> 00:02:11.985
CARA: Yep.
00:02:12.105 –> 00:02:13.705
CARA: Born and mostly raised in Jersey.
00:02:13.725 –> 00:02:18.985
CARA: I’ve been working in New York for like something crazy, 15 years or something like that.
00:02:19.005 –> 00:02:20.725
CARA: So definitely home.
00:02:21.685 –> 00:02:22.165
JEREMY: Awesome.
00:02:22.365 –> 00:02:25.525
JEREMY: And tell us something about yourself personally.
00:02:26.205 –> 00:02:30.985
JEREMY: You know, your favorite hobby, your favorite song, your favorite movie, anything like that.
00:02:32.805 –> 00:02:34.445
CARA: Yeah, I am an artist at heart.
00:02:34.525 –> 00:02:36.225
CARA: I’m endlessly creative.
00:02:36.245 –> 00:02:46.605
CARA: 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.
00:02:47.145 –> 00:02:49.465
CARA: And I’m also an avid traveler.
00:02:50.025 –> 00:02:53.165
CARA: So I love to see as much of the world as possible.
00:02:53.185 –> 00:02:57.465
CARA: And I set out a goal for myself each year to see at least one new country.
00:02:57.825 –> 00:03:00.805
CARA: But if I can get to three, then I feel like I’m really crushing it at life.
00:03:03.985 –> 00:03:04.365
JEREMY: Awesome.
00:03:04.385 –> 00:03:07.265
JEREMY: What’s one of the countries you’re wanting to visit soon?
00:03:09.345 –> 00:03:14.365
CARA: Oh, well, I’m taking my fiancee to Belize for her affordability.
00:03:14.845 –> 00:03:16.225
CARA: Really excited for that.
00:03:17.265 –> 00:03:25.105
CARA: 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.
00:03:25.125 –> 00:03:27.725
CARA: But narrowing down the countries has been very challenging.
00:03:28.105 –> 00:03:30.185
CARA: We want to go everywhere.
00:03:31.045 –> 00:03:31.405
JEREMY: Cool.
00:03:31.425 –> 00:03:33.005
JEREMY: Well, congrats, and hope you have fun.
00:03:33.605 –> 00:03:34.125
CARA: Thank you.
00:03:35.105 –> 00:03:35.525
JEREMY: All right.
00:03:35.545 –> 00:03:37.125
JEREMY: Well, let’s talk about your career then.
00:03:37.185 –> 00:03:42.285
JEREMY: What got you into the assistant role?
00:03:43.485 –> 00:03:48.305
CARA: You know, it’s really funny because I never thought that I would be in an administrative role.
00:03:48.325 –> 00:03:49.525
CARA: I kind of fell into it.
00:03:49.905 –> 00:03:58.365
CARA: 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.
00:03:58.385 –> 00:04:02.205
CARA: I’m really good at organization and reading people and figuring things out.
00:04:03.305 –> 00:04:04.745
CARA: And it kind of took off from there.
00:04:04.925 –> 00:04:11.345
CARA: And I’ve worked in a lot of different industries with so many different leaders and have realized that I really find it fulfilling.
00:04:11.465 –> 00:04:28.265
CARA: 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.
00:04:29.065 –> 00:04:32.465
CARA: So I found it to be an incredibly rewarding career.
00:04:32.485 –> 00:04:41.105
CARA: 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.
00:04:41.725 –> 00:04:42.065
JEREMY: Right.
00:04:42.805 –> 00:04:52.065
JEREMY: 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?
00:04:52.725 –> 00:05:04.105
CARA: Yeah, I think it was probably about six-ish years ago when I really started to see a growth in it.
00:05:04.985 –> 00:05:21.005
CARA: 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.
00:05:21.005 –> 00:05:34.625
CARA: 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.
00:05:34.645 –> 00:05:38.145
CARA: I think part of that shift for me was also the change of industry.
00:05:38.165 –> 00:05:56.145
CARA: 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.
00:05:56.985 –> 00:06:05.925
CARA: 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.
00:06:05.945 –> 00:06:07.805
CARA: I love all of this.
00:06:09.265 –> 00:06:18.605
CARA: 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.
00:06:18.625 –> 00:06:20.765
JEREMY: Awesome.
00:06:20.825 –> 00:06:22.505
JEREMY: That’s great.
00:06:22.525 –> 00:06:29.745
JEREMY: 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.
00:06:30.625 –> 00:06:40.925
JEREMY: But I was looking and you have a really, really interesting title journey, I’ll call it a title journey.
00:06:40.945 –> 00:06:43.565
JEREMY: So you’ve got, let’s see if we can get this to load.
00:06:43.805 –> 00:06:56.745
JEREMY: 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.
00:06:57.245 –> 00:07:09.945
JEREMY: 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.
00:07:09.965 –> 00:07:10.425
JEREMY: Is that right?
00:07:11.425 –> 00:07:11.845
CARA: Yes.
00:07:12.185 –> 00:07:12.965
CARA: Yeah.
00:07:12.985 –> 00:07:15.905
CARA: So the chief of staff role is a board that I’m on.
00:07:17.565 –> 00:07:20.525
CARA: It’s, it’s specifically in the ERG space.
00:07:20.985 –> 00:07:32.285
CARA: 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.
00:07:34.045 –> 00:07:38.665
CARA: But yeah, currently I am the, the manager for executive support at Duolingo.
00:07:38.685 –> 00:07:45.285
CARA: I joined September of last year and I’ve been really, really loving it so far.
00:07:45.305 –> 00:07:48.405
CARA: It’s really nice to work somewhere that’s mission driven.
00:07:48.425 –> 00:07:53.825
CARA: I feel like I’m working somewhere that’s trying to help people and create accessible education.
00:07:53.845 –> 00:07:56.025
CARA: But yeah, it is interesting.
00:07:56.045 –> 00:08:04.945
CARA: 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.
00:08:06.365 –> 00:08:12.585
CARA: Like executive business partners, I feel are more depending on the company, of course, because I feel like it’s all pretty subjective.
00:08:12.625 –> 00:08:23.125
CARA: 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.
00:08:23.145 –> 00:08:32.305
CARA: 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.
00:08:32.325 –> 00:08:34.345
CARA: I have information that I can share with people.
00:08:34.985 –> 00:08:40.625
CARA: 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.
00:08:40.645 –> 00:08:44.545
CARA: I’m like, oh, everybody knows this, you know, and they’re like, oh, wow, that’s really helpful.
00:08:44.565 –> 00:08:45.345
CARA: I’m like, oh, is it?
00:08:45.445 –> 00:08:46.125
CARA: Okay, good.
00:08:47.205 –> 00:08:54.585
CARA: And I, you know, I found it really rewarding to be able to to share those experiences with other people to help them grow.
00:08:54.605 –> 00:09:01.005
CARA: And I started mentoring a little bit and coaching a little bit and realized that I really love people management.
00:09:01.025 –> 00:09:06.845
CARA: I find it just to feel really good to help others excel and help others shine.
00:09:06.865 –> 00:09:11.485
CARA: And you know, being a part of their journey, I find really rewarding.
00:09:12.985 –> 00:09:13.365
JEREMY: Great.
00:09:13.385 –> 00:09:27.565
JEREMY: 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?
00:09:27.585 –> 00:09:27.645
JEREMY: Thank you.
00:09:33.395 –> 00:09:35.975
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00:09:36.915 –> 00:09:44.595
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00:09:45.215 –> 00:09:56.735
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00:09:57.415 –> 00:09:59.635
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00:10:00.395 –> 00:10:05.355
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00:10:11.627 –> 00:10:12.507
CARA: That’s a great question.
00:10:12.527 –> 00:10:21.807
CARA: I would say to really think about people management of like, there’s so many parts of it that does feel good.
00:10:21.827 –> 00:10:34.207
CARA: 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.
00:10:35.207 –> 00:10:50.607
CARA: 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.
00:10:50.627 –> 00:10:55.027
CARA: I think that that’s something to keep in mind.
00:10:56.267 –> 00:11:01.087
CARA: Really thinking about why you want to be a people manager is important.
00:11:01.947 –> 00:11:03.047
CARA: Is it a title thing?
00:11:03.127 –> 00:11:04.507
CARA: Is it a compensation thing?
00:11:04.767 –> 00:11:08.687
CARA: Is it the work itself that you find to be exciting?
00:11:09.847 –> 00:11:13.627
CARA: Because people management can be very challenging.
00:11:14.627 –> 00:11:23.087
CARA: 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.
00:11:23.847 –> 00:11:24.847
CARA: That’s okay too.
00:11:25.047 –> 00:11:37.427
CARA: 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.
00:11:37.847 –> 00:11:42.647
CARA: For me, I always just want to be the kind of manager that I’ve always wanted.
00:11:42.667 –> 00:11:45.887
CARA: I just want to keep it real.
00:11:45.947 –> 00:11:52.527
CARA: I want to help people grow and really just be part of that growth.
00:11:54.847 –> 00:12:00.407
CARA: The other thing too is to think about as well, being an executive assistant by itself is hard.
00:12:00.987 –> 00:12:07.087
CARA: There’s a lot of things that we’re juggling and navigating and figuring out on a day-to-day basis.
00:12:07.507 –> 00:12:16.727
CARA: Taking that IC work, that individual contributor work and pairing that with people management, it does intensify your workload.
00:12:17.147 –> 00:12:23.127
CARA: That is something to think about too, to see how you feel about going in that direction.
00:12:23.927 –> 00:12:24.267
CARA: Yeah.
00:12:24.287 –> 00:12:30.807
JEREMY: Did you ever have that or was there a period of time where you’re like, oh man, what did I get myself into?
00:12:32.167 –> 00:12:33.307
JEREMY: Related to the workload.
00:12:35.667 –> 00:12:40.067
CARA: There were moments for sure.
00:12:40.107 –> 00:12:50.807
CARA: 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.
00:12:51.267 –> 00:12:56.147
CARA: I was managing or supporting one of the busiest executives in the company.
00:12:56.167 –> 00:13:05.147
CARA: 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.
00:13:06.067 –> 00:13:11.187
CARA: 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?
00:13:11.187 –> 00:13:12.847
CARA: Is this how it’s always going to be?
00:13:14.487 –> 00:13:24.587
CARA: 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.
00:13:24.847 –> 00:13:30.167
CARA: This is going to be crazy for the time being, and things will sort out.
00:13:30.547 –> 00:13:39.047
CARA: 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.
00:13:41.227 –> 00:13:44.367
CARA: But I’m also one of those crazy people who thrives in chaos.
00:13:44.787 –> 00:13:54.107
CARA: So it also depends on how you function, how you work, and what makes the most sense for you.
00:13:54.127 –> 00:13:56.807
JEREMY: Totally makes sense.
00:13:56.827 –> 00:13:57.307
JEREMY: That’s awesome.
00:13:57.327 –> 00:13:58.187
JEREMY: Thanks for sharing.
00:13:58.207 –> 00:14:07.327
JEREMY: 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.
00:14:08.847 –> 00:14:13.327
JEREMY: And then yeah, there’s assistants listening here like, oh, I think that would be fun to manage a team.
00:14:14.607 –> 00:14:16.247
JEREMY: So yeah, thanks for sharing that.
00:14:16.747 –> 00:14:22.027
JEREMY: So what about the growth?
00:14:22.207 –> 00:14:31.707
JEREMY: 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.
00:14:33.227 –> 00:14:41.627
JEREMY: 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.
00:14:41.647 –> 00:14:49.947
JEREMY: So talk to a little bit about, you know, to the growing your career as an assistant, you know, from your experience.
00:14:51.287 –> 00:14:59.167
CARA: Yeah, I think one of the biggest learnings that I had was recognizing that my growth was in my control.
00:15:00.687 –> 00:15:06.167
CARA: And in the beginning, I’m like, I’m just going to do my job really well and everyone’s going to see it.
00:15:06.247 –> 00:15:08.047
CARA: They’re going to be like, you should do this.
00:15:08.047 –> 00:15:09.407
CARA: This is what you’re meant to do.
00:15:10.067 –> 00:15:13.047
CARA: And I was just waiting for that moment for a while to happen.
00:15:13.067 –> 00:15:15.027
CARA: I’m like, I’m crushing it and doing so good.
00:15:15.047 –> 00:15:17.647
CARA: Why is nobody just like giving me promotions?
00:15:18.447 –> 00:15:32.427
CARA: 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.
00:15:33.347 –> 00:15:35.847
CARA: And I realized that I had to be more intentional.
00:15:35.867 –> 00:15:40.607
CARA: Like I had to go into the conversation with my manager being like, this is what I want.
00:15:40.967 –> 00:15:42.387
CARA: This is where I see myself.
00:15:43.407 –> 00:15:45.407
CARA: Here’s where and here where my gaps are.
00:15:45.427 –> 00:15:50.327
CARA: And I started figuring out like how to make a development plan for myself.
00:15:50.627 –> 00:15:55.587
CARA: And I still do it now because I’m very committed to lifelong learning.
00:15:56.207 –> 00:15:59.427
CARA: No matter like what stage of growth I’m at, there’s always more to learn.
00:15:59.447 –> 00:16:13.967
CARA: 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.
00:16:13.987 –> 00:16:23.067
CARA: 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.
00:16:23.787 –> 00:16:28.887
CARA: So one piece of advice that I give people on my team is to keep a brag book for yourself.
00:16:29.767 –> 00:16:41.967
CARA: 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.
00:16:43.567 –> 00:16:53.247
CARA: And it’s an ongoing conversation to have, but you are the leader of that conversation and you have full ownership in that.
00:16:53.287 –> 00:16:55.847
CARA: And for me, that was a big aha moment.
00:16:56.627 –> 00:17:07.827
CARA: 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?
00:17:07.867 –> 00:17:13.467
CARA: Do you want to be a career EA forever, or do you see this as a stepping stone into something else?
00:17:13.987 –> 00:17:20.787
CARA: And just being really prescriptive about what their own goals are, so I can figure out how to best support them.
00:17:21.747 –> 00:17:26.327
CARA: Because if somebody wants to be a career EA, that doesn’t mean like, okay, the coaching stops here.
00:17:26.347 –> 00:17:31.687
CARA: That just means like, all right, well, what skills do you want to enhance?
00:17:32.047 –> 00:17:35.207
CARA: What areas do you want to learn about that you could find interesting?
00:17:36.387 –> 00:17:54.907
CARA: 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?
00:17:54.927 –> 00:17:57.367
JEREMY: That’s great.
00:17:57.387 –> 00:18:11.767
JEREMY: 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.
00:18:11.787 –> 00:18:21.027
JEREMY: 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.
00:18:21.487 –> 00:18:24.667
JEREMY: We think you should do this.
00:18:25.467 –> 00:18:30.327
JEREMY: Very much a self-managed role in a lot of ways.
00:18:31.087 –> 00:18:32.427
JEREMY: That’s great.
00:18:32.447 –> 00:18:33.047
JEREMY: Thanks for sharing.
00:18:34.087 –> 00:18:36.627
JEREMY: You mentioned you felt like you’re a recruiter for a while.
00:18:38.627 –> 00:18:43.407
JEREMY: What tips do you have for both sides of the interview process?
00:18:43.427 –> 00:18:57.867
JEREMY: 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.
00:18:59.467 –> 00:19:12.207
JEREMY: 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?
00:19:13.087 –> 00:19:14.807
CARA: Yeah, that’s a great question.
00:19:14.827 –> 00:19:33.507
CARA: 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.
00:19:34.467 –> 00:19:37.227
CARA: So I think that that is a really important thing to remember.
00:19:39.667 –> 00:19:40.847
CARA: Interviews are interesting.
00:19:40.967 –> 00:19:48.427
CARA: 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.
00:19:48.447 –> 00:19:51.507
CARA: It’s a lot of pressure.
00:19:51.527 –> 00:20:00.847
CARA: 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.
00:20:01.527 –> 00:20:11.767
CARA: 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.
00:20:12.867 –> 00:20:28.727
CARA: 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.
00:20:29.187 –> 00:20:36.107
CARA: 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.
00:20:36.547 –> 00:20:39.827
CARA: And making sure you weave that into your conversation.
00:20:40.187 –> 00:20:49.207
CARA: 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.
00:20:50.767 –> 00:20:55.207
CARA: And the other part of it is they’re probably going to just ask you something that you’re not prepared for.
00:20:55.227 –> 00:20:58.847
CARA: And it’s important to just be honest.
00:21:00.247 –> 00:21:05.267
CARA: Just take a deep breath beforehand because I’ve seen a lot of very nervous people.
00:21:05.287 –> 00:21:12.367
CARA: And I think just taking a moment to just go in and just clear your mind, I think, can be helpful.
00:21:13.587 –> 00:21:20.967
CARA: Being a hiring manager, I mean, I kind of look for the things I mentioned, right?
00:21:20.987 –> 00:21:38.767
CARA: 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.
00:21:40.947 –> 00:21:47.347
CARA: So, you know, before I joined Duolingo, I was very interested in the job, so I did a lot, a lot of homework.
00:21:47.367 –> 00:21:49.667
CARA: I watched, you know, their UConn videos.
00:21:49.687 –> 00:21:52.287
CARA: I was, you know, reading articles about them.
00:21:53.067 –> 00:21:57.087
CARA: I was like, I did a lot of homework, and I was like dropping quotes in there.
00:21:57.107 –> 00:21:59.067
CARA: Nice, nice.
00:21:59.327 –> 00:22:09.047
CARA: 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.
00:22:09.067 –> 00:22:17.047
CARA: 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.
00:22:17.567 –> 00:22:29.047
CARA: 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.
00:22:29.067 –> 00:22:38.287
CARA: 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.
00:22:38.887 –> 00:22:47.607
JEREMY: 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.
00:22:48.067 –> 00:22:51.807
JEREMY: But when I do public speaking, it’s like people are like, well, how do you go up and whatever?
00:22:51.827 –> 00:22:54.007
JEREMY: And like, I’m just super prepared.
00:22:54.027 –> 00:23:07.067
JEREMY: 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.
00:23:08.187 –> 00:23:09.807
JEREMY: So that definitely helps in the interviews too.
00:23:09.827 –> 00:23:30.807
JEREMY: 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.
00:23:31.047 –> 00:23:32.907
JEREMY: What’s the riddle you like to ask?
00:23:34.367 –> 00:23:35.267
JEREMY: You never know these days.
00:23:35.287 –> 00:23:37.027
JEREMY: There’s a lot of crazy interview stuff happening.
00:23:37.907 –> 00:23:41.087
CARA: And I do try to switch it up as well.
00:23:41.447 –> 00:23:50.267
CARA: 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.
00:23:50.767 –> 00:23:59.387
CARA: 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.
00:24:00.327 –> 00:24:12.467
CARA: 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.
00:24:12.487 –> 00:24:22.507
CARA: And just kind of creating a real life thing that happens and seeing how the assistant would respond to it.
00:24:23.107 –> 00:24:27.967
CARA: Walk me through your thought process and how you solve for this.
00:24:28.167 –> 00:24:30.147
CARA: What are the suggestions that you come up with?
00:24:30.947 –> 00:24:32.047
CARA: How do you approach this?
00:24:32.067 –> 00:24:36.027
CARA: And then after you figure that out, how do you communicate those changes?
00:24:36.047 –> 00:24:43.047
CARA: And I think that kind of gives a full picture of the start to finish problem solving.
00:24:44.067 –> 00:24:57.047
CARA: 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.
00:24:59.147 –> 00:25:00.307
CARA: So that’s one example.
00:25:00.667 –> 00:25:03.767
CARA: And another one could be tied into event planning.
00:25:04.687 –> 00:25:15.407
CARA: 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.
00:25:16.147 –> 00:25:30.207
CARA: 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.
00:25:32.727 –> 00:25:39.327
JEREMY: Do you try to send those scenarios ahead of time so they can come prepared?
00:25:39.347 –> 00:25:41.107
JEREMY: Oh, yeah.
00:25:41.447 –> 00:25:43.067
CARA: Yeah, that’s more of like a take-home.
00:25:43.447 –> 00:25:43.887
JEREMY: Gotcha.
00:25:44.767 –> 00:25:53.667
CARA: 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.
00:25:55.327 –> 00:25:56.747
CARA: I know there’s one question.
00:25:56.747 –> 00:26:14.167
CARA: 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.
00:26:16.247 –> 00:26:26.507
CARA: 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.
00:26:26.967 –> 00:26:31.147
CARA: So it’s interesting to me to hear an example that ties to that.
00:26:31.167 –> 00:26:33.607
JEREMY: Love it.
00:26:33.627 –> 00:26:34.827
JEREMY: Well, thank you so much for sharing.
00:26:34.847 –> 00:26:46.687
JEREMY: 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.
00:26:46.707 –> 00:26:47.507
JEREMY: So thanks for doing that.
00:26:48.007 –> 00:26:48.827
CARA: Yeah, happy to.
00:26:49.767 –> 00:27:10.767
JEREMY: 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?
00:27:10.787 –> 00:27:21.067
JEREMY: 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?
00:27:22.347 –> 00:27:28.007
CARA: You know, it’s so funny because there’s probably 6 million of those moments and trying.
00:27:36.127 –> 00:27:41.307
JEREMY: To pinpoint any of them is challenging because they all kind of slide together every day.
00:27:41.487 –> 00:27:50.807
JEREMY: 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.
00:27:50.827 –> 00:27:53.527
JEREMY: And so I’m kind of putting you on the spot here, but no, it’s fine.
00:27:54.327 –> 00:28:02.007
CARA: 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.
00:28:02.727 –> 00:28:11.367
CARA: I used to work somewhere where I was taking over support for two leaders that nobody on the EA team wanted to support.
00:28:11.747 –> 00:28:15.687
CARA: And one of them was like, well, you can’t ask him questions.
00:28:16.127 –> 00:28:18.207
CARA: And I was like, what do you mean I can’t ask him questions?
00:28:18.227 –> 00:28:19.867
CARA: They’re like, you can’t ask him questions.
00:28:19.887 –> 00:28:22.667
CARA: And I’m like, I don’t know what to do with this information.
00:28:23.367 –> 00:28:29.347
CARA: And then, you know, the other leader, you know, the team was like, you know, we don’t like working with her.
00:28:29.467 –> 00:28:34.767
CARA: She’s condescending, you know, there’s, you know, her approach to things is just not respectful and this and that.
00:28:35.307 –> 00:28:38.227
CARA: So I was like a little nervous at the beginning.
00:28:38.247 –> 00:28:40.147
CARA: I’m like, okay, so I’m taking on these leaders.
00:28:40.167 –> 00:28:41.127
CARA: I’m brand new here.
00:28:41.467 –> 00:28:42.687
CARA: Don’t know what’s going to happen.
00:28:42.707 –> 00:28:44.227
CARA: I’m going to figure this out.
00:28:45.127 –> 00:28:53.507
CARA: 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.
00:28:53.667 –> 00:28:58.547
CARA: 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.
00:28:58.567 –> 00:28:59.907
CARA: So then he’d be upset about it.
00:28:59.927 –> 00:29:00.947
CARA: And I’m like, well, that makes sense.
00:29:01.567 –> 00:29:19.447
CARA: 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.
00:29:20.667 –> 00:29:23.667
CARA: And I found that to be like a huge learning.
00:29:23.687 –> 00:29:26.247
CARA: I was like, I actually really love working with both of them.
00:29:26.247 –> 00:29:28.507
CARA: I don’t know what you were all thinking.
00:29:30.287 –> 00:29:31.567
CARA: Did they ask for crazy things?
00:29:31.747 –> 00:29:32.427
CARA: Sure.
00:29:32.847 –> 00:29:47.827
CARA: 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.
00:29:48.907 –> 00:29:52.087
CARA: It was October and this was an event for 400 people.
00:29:52.107 –> 00:29:56.067
CARA: I was like, all right, you have a venue, right?
00:29:56.087 –> 00:29:56.907
CARA: They’re like, no.
00:29:56.927 –> 00:30:02.147
CARA: I’m like, oh, well, we should probably figure that out.
00:30:02.167 –> 00:30:03.227
JEREMY: They’re like, oh, when is it?
00:30:03.247 –> 00:30:04.067
JEREMY: Oh, it’s next week.
00:30:05.607 –> 00:30:05.827
JEREMY: Yeah.
00:30:05.847 –> 00:30:08.087
CARA: 400 people in New York City, Christmas time.
00:30:08.107 –> 00:30:08.487
CARA: Cool.
00:30:12.567 –> 00:30:19.667
CARA: I work through the weekend to make it happen, and find venue options, figure stuff out.
00:30:20.047 –> 00:30:24.727
CARA: After I negotiated a place down, I was raised by a salesman, so shout out to my dad.
00:30:25.587 –> 00:30:27.927
CARA: But I negotiated them down to the budget.
00:30:27.947 –> 00:30:29.227
CARA: I put together a proposal.
00:30:29.247 –> 00:30:30.467
CARA: I was so proud.
00:30:30.487 –> 00:30:33.367
CARA: I went, I’m like, look what I did.
00:30:33.387 –> 00:30:36.587
CARA: They’re like, actually, we’re cutting the budget in half.
00:30:36.987 –> 00:30:37.627
CARA: Oh, wow.
00:30:37.987 –> 00:30:38.407
CARA: I know.
00:30:38.427 –> 00:30:40.347
CARA: I was like, okay.
00:30:41.087 –> 00:30:42.167
CARA: I’m going to make this work.
00:30:42.907 –> 00:30:44.807
CARA: At that point, I was very committed.
00:30:44.827 –> 00:30:48.827
CARA: I was very like, we’re going to make this happen some way or another.
00:30:48.847 –> 00:30:52.587
CARA: It did happen and it was wonderful.
00:30:53.047 –> 00:31:02.427
CARA: But it was definitely one of those moments that put all of your resourcefulness, patience, grit to the test.
00:31:03.087 –> 00:31:05.847
CARA: You try to make something happen.
00:31:06.447 –> 00:31:11.347
JEREMY: Did you go back to that venue and negotiate down again, or did you have to find a different option?
00:31:11.367 –> 00:31:13.247
CARA: I had to find a different venue.
00:31:13.447 –> 00:31:16.527
CARA: I basically got them down to the lowest that they were.
00:31:16.527 –> 00:31:16.947
JEREMY: Right.
00:31:17.487 –> 00:31:21.707
CARA: Which is why I was so proud because that was already beyond.
00:31:21.787 –> 00:31:29.807
JEREMY: You learned some good negotiation skills that you, I’m sure, have used in your career since.
00:31:31.727 –> 00:31:34.047
CARA: It was a reminder that you just have to roll with things.
00:31:34.087 –> 00:31:35.327
CARA: You know what I mean?
00:31:35.347 –> 00:31:40.887
CARA: Changes are going to happen, budgets are going to change, teams are going to shift, things are going to be crazy.
00:31:40.907 –> 00:31:52.687
CARA: 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.
00:31:54.787 –> 00:31:55.187
CARA: Yeah.
00:31:55.607 –> 00:31:57.627
JEREMY: You got to embrace the process.
00:31:58.167 –> 00:31:58.567
CARA: Yeah.
00:32:00.347 –> 00:32:01.087
JEREMY: Awesome, Cara.
00:32:01.107 –> 00:32:08.447
JEREMY: Well, congrats on a great career, and thank you so much for taking a few minutes to share your story with us.
00:32:10.267 –> 00:32:12.927
JEREMY: Is it okay if people reach out and say hi on LinkedIn?
00:32:13.527 –> 00:32:14.347
CARA: Yes, of course.
00:32:15.847 –> 00:32:33.787
JEREMY: 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.
00:32:33.787 –> 00:32:43.407
JEREMY: 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.
00:32:43.427 –> 00:32:49.687
JEREMY: I work in the tech world as well, and it’s always fun speaking with an assistant in the tech world.
00:32:49.707 –> 00:32:52.407
JEREMY: So yeah, thanks again for being on the show.
00:32:52.887 –> 00:32:54.167
CARA: Yeah, thanks so much for having me.
