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Caitlin Jovovich’s EA Cheat Code: The One-Two Punch · CCing my EA Podcast

• 0:00
  Welcome to the CC My EA podcast, where we interview executive assistants about the real tactics they've learned from supporting busy executives.
• 0:06
  This episode is presented by Vimcal EA, the first calendar built specifically for executive assistants. And today, I'm here with Caitlin, executive business partner to the CEO at Jasper. Thank you for joining us.
• 0:18
  Of course. Happy to be here. For people who don't know you, could you share a bit about your journey, uh, up to when you first got your, like, initial EA role? Yeah.
• 0:28
  So I graduated college in, like, the worst time that you could possibly graduate. I graduated in 2010, and, uh, it was like the worst time to graduate because there were no jobs.
• 0:40
  So I graduated with a degree in advertising and was, like, all excited, like, bright-eyed, bushy-tailed. I'm like, "I'm gonna be, like, in Mad Men.
• 0:49
  I'm gonna go r- I'm gonna walk into an agency and be, you know, uh, get my first job like that." And was not the case because we were in a recession and, you know, the, the world was changing.
• 1:01
  And so I went back home after graduating and kept working in the, the retail store that I had been working in throughout college just to make extra money. I had a store visit one day from our VP in corporate.
• 1:16
  They would do, like, surprise visits all the time, and we had a brand new manager. I-- she didn't know, you know, how to lead the visit, so I led the visit 'cause I had been there the longest, and the VP really liked me.
• 1:29
  We hit it off. We just got to chatting, and at the end of the visit, she was like, "Do you wanna come be my assistant?" And I was like, "I don't know what that means, but that sounds like a job, so that sounds great.
• 1:39
  Let's do it." So I picked up and I moved, within, like, two weeks of that conversation, picked up and moved to Massachusetts, where she was located.
• 1:47
  Not where the company was located, but we had, like, a satellite office. Mm-hmm. And just kinda started going from there, and it was very much trial by fire and figuring things out along the way.
• 1:57
  And I was in that for about two and a half years of, like, truly learning and, like, just figuring things out by making all of the mistakes.
• 2:08
  And then I kinda realized, like, "Oh, I actually think I might be good at this." Hmm.
• 2:11
  And continued on in my career and went from, you know, bigger company to bigger company to bigger company, and then, you know, started into the, the smaller, uh, startups, where I was like, "Okay, this is really exciting, and I can actually have an impact in some of these other companies."
• 2:28
  Yeah. So speaking of these other companies- Yeah. [chuckles]... I actually wanted to share this. Ooh. [chuckles] I think these, uh, this is, uh, kinda your career journey as- Mm-hmm... an EA so far. Yep.
• 2:42
  It's interesting 'cause it started out as, like, casual wear, and then you went into luxury, and then you kinda, I think Compass is, like, real estate tech too. I'd love to hear about your EA experience.
• 2:51
  Any common threads between them, and then what were, like, really stark contrasts? Yeah.
• 2:56
  Definitely a common thread of, for the first three roles that I had as an EA, which was, um, American Eagle, Coach, or American Eagle, Michael Kors, and Coach, um, all American brands and, you know, very, very, like,
• 3:14
  corporate. Um, and then going into a little bit more of, like, the high fashion and, like, luxury of Louis Vuitton, being a part of the LVMH conglomerate. Like, it is a, you know, that's, that's such a
• 3:30
  heritage brand, such a giant company. There's a little bit less room for, you know, for change and for impact.
• 3:38
  And then kind of pivoting to something like a Compass or a Jasper, you know, now where I'm currently working, it's, you know, this kind of scrappy mentality of whatever it takes to get it, to get the job done.
• 3:52
  You c- really can, you know, have an impact in what you are working on. You can work on different projects. You can raise your hand for things. You can...
• 4:01
  There's, there's not necessarily a, like, a team or a department for every single thing. Mm-hmm. You can kind of be a part of anything that you want to, as long as you are doing your job well.
• 4:10
  I am curious if there's anything you've picked up from the more heritage brands that still applies in your current, more scrappy roles. Yeah.
• 4:23
  I love, and maybe this isn't necessarily from those bigger, more established brands, but, uh, this could just be me being type A, but I love a good process. I love a good, like, really well-structured
• 4:39
  system and process that there are, like, steps to follow.
• 4:43
  There's something about a playbook that just makes me so happy to be able to, like, anniversary something and just be able to follow it, and kind of almost like a set and forget.
• 4:55
  Um, when you're in a big company, those processes have to exist because there are so many people.
• 5:01
  Move into a more entrepreneurial, scrappy environment, and everybody's trying their own thing, they're seeing what works, and you're having, like, a little bit of, like, duplicative efforts in different departments or orgs and, you know, you have one person trying it this way and one person trying it that way, and at the end of the day, it's like, "Okay, well, whose was better?
• 5:19
  And did we even know that each other was doing this exact same work?" Is there, like, a specific example? There's a couple.
• 5:26
  There's one, for instance, when I was at Compass, we had this, we had so many people within the office of the CEO. We had a chief of staff. We had an exec comms.
• 5:35
  We had myself, I was the senior manager of, you know, exec operations. I had EAs reporting to me. We had somebody that handled internal comms that reported into the exec comms. We had social media.
• 5:47
  It was a bunch of different things. And we, at one point, it was like, "Okay, there's so many people here now.
• 5:54
  We need really specific swim lanes, again, so we're not duplicating any efforts because there's so much going on and we're all moving so quickly."
• 6:02
  So it was kind of putting together this, like, office of the CEO 101 playbook of, like, here's what this role does and here's what that role does, and kind of putting it in a more, like, here's what...
• 6:15
  We used to have this, um, I'm sure they still use it there, it's, they would always say SPOA, single point of accountability. Like, who is the SPOA for this task? Who is the SPOA for that task?
• 6:24
  And then we would have, like, the backup. If I was no longer able to take on this task, either I was out or there was a point I went on maternity leave, who was going to be taking that on?
• 6:34
  It was, like, a very easy, almost, like, cut and paste of this person moves into this spot.
• 6:39
  It was like a flow chart, and it just made it so much easier to be able to have this playbook of, like, almost, like, looking- You know, down the line being like, "Okay, that's the person."
• 6:50
  I always say this in, like, whenever I would start a new job, I would always say, "I'm not happy until I'm the catch-all drawer," until I am, like, the person that people go to for absolutely everything, because that's when I'm, like, really comfortable in a company or with an org.
• 7:04
  But once I'm there, it's like, okay, now we have to clean out this drawer and organize it and get it into the little buckets where like, you know, the junk drawer in your kitchen where you're like, "Okay, we have all the pens, and we have, like, random paperclips, and we've got all these other little, like, organized buckets of things."
• 7:18
  That's when I really, really like a process. Uh, in all your experience throughout your different EA roles at different companies, I am curious if you have a EA cheat code that you've learned. Play to your audience.
• 7:32
  I come from a family that's very much in the theater world, and you always, you hear that a lot in the theater world, like, you know, if you're, if you're, you know, you got a dead audience, you have to play to them specifically or, like, pick one person, or if you have, like, a really, you know, loud, riotous audience, you're gonna really feed off that energy.
• 7:49
  But as far as, like, you wanna play to the specific people that are in front of you, and you wanna make sure that you are tailoring your communications and that, those moments to them.
• 8:00
  And I, anytime that I have had to get anything over the line with very little authority, I have used my communication skills, my EQ, to be able to read, how is this person best going to receive this information and be able to respond in a way that I kind of need them to?
• 8:18
  So one, uh, an, a specific instance that I can- Mm, mm, mm... share. Yes, please. So [laughs] we, uh,
• 8:26
  I was on a team at one point, and there was, there was kind of this, like, dynamic where if ideas came across, like they were just kind of like thought up off the cuff or even if they were great, it felt like there maybe wasn't enough either backing or buy-in, or they weren't well thought out enough to make it, like, past the CEO or past like, it wouldn't get, like, the green light.
• 8:51
  Mm-hmm. So we started doing this thing where the team would kind of get together beforehand and almost, like, workshop a few things. Like, "Wait, I have a really great idea for this meeting.
• 9:00
  We're all gonna go in," and I started calling it the one-two punch, and I'm like, "Okay, you say this, and then I'm gonna say this, and then they will go, 'Yeah. Actually, I really love that.'"
• 9:10
  And it was this kind of like, it didn't feel so manipulative, but we were all sitting there collaborating and almost, like, poking holes in how our executive would see things ahead of time, and kind of almost like, we almost, like, tricked ourselves into be- just working smarter [laughs] not harder, and, and mitigating all of the risk ahead of time, but figuring out a way that, how did they need to hear it- Mm-hmm...
• 9:35
  from us in the smartest way?
• 9:37
  How could we present it the best that they would, one, be able to receive it, be able to absorb it, and understand, you know, the end game without all that kind of like workshop-y feeling in between and feel like we're just kind of spewing nonsense?
• 9:53
  So we kind of honed this practice, and it was like, "All right, you wanna one-two punch this when we go in?" And it was like, it became this, like, well-oiled machine of, "This is how we're gonna do this."
• 10:04
  It doesn't necessarily have to be with other people.
• 10:07
  I think if you think about who you are talking to, how they communicate, how they absorb information, and how they best receive things, like, you have to figure that out if you wanna get anything over the line, and figure out who you are, almost like who you're selling a product to, whether it's executives or business partners, and, and make those, you know, make those slight tweaks and adjustments as needed, and being able to know when to make those adjustments.
• 10:34
  Are you able to share, like, a specific details about, like, one specific meeting where you guys were trying to get this very specific idea across, and so person A said this, person B said this?
• 10:47
  At one point, we were doing, uh, like a, a social media push, and we wanted to get, we wanted to, to get something out there that wasn't, like, super popular, but the team really felt that it was a great push because down the line, like, we were playing the long game.
• 11:05
  Down the line, we had something that, okay, in three months, this is really going to make sense. So let's do this now, and then we can call back to it in three months.
• 11:15
  And it kinda didn't really fit in the strategy of that social media push that we were doing that day.
• 11:20
  And, you know, a lot of times with executives, it's like, if it's not right in front of you right now, especially with something as, you know, the minutiae of social media, it's, you know, this is like, it's not, it's not super strategic in that moment, but we felt really strongly about it, the team.
• 11:36
  And so we were like, "Okay, here's what we're gonna do. I'm gonna go in, and I'm gonna be like, 'You know what would be a great idea?'" And then the other comms person was gonna be like, "Yeah, that's a great idea."
• 11:45
  And then the chief of staff, who was a highly trusted person, was like, "You know why that would be great? Because in three months we're gonna be doing this."
• 11:53
  And I go, "Yeah, and then when we do post that, we can call back to this and then re-share it." And it was this whole thing that we orchestrated where it was really just like we had had a quick conversation about it.
• 12:03
  We were like, "That's actually a great idea, but we don't think that's gonna be, like, really bought in," because this, every thing that we pushed out had to be, like, the best post, and this wasn't necessarily, like, gonna get the most likes or the most, you know, it wasn't, like, the sexiest post that we could have pushed.
• 12:20
  But it was going to be worth something later down the line. So it was this kind of like, we're gonna go in, lay the groundwork, plant the seed,
• 12:30
  water it a little bit with this one being like, "Ooh, I love that," and then the real heavy hitter was gonna come in and, like, bat clean up. Mm-hmm. And say, "Love this. Here's why." And we got it over the line.
• 12:41
  Where normally, if, like, I had just gone in and said, "I think we should do this," it would've been like, "Mm, I don't really like that." And it would've died right then and there. Yeah, really curating just the energy.
• 12:52
  Mm-hmm. Kind of reminds me of when performers will- might, like, plant their friends in different parts of the crowd. 100%. And so, like, it sounds like- Yeah... it kinda gets the crowd going.
• 13:00
  Well, there's another one in case that one's not, like, super clear that I can give you that just came to mind- Uh-huh. Okay... that's also, like, very low stakes. Yeah.
• 13:07
  So we had a, uh, we had an off-site recently, and one of the people that I was planning this off-site with is a, like, a photographer.
• 13:17
  And one of the ideas we had for swag was these cameras that somebody found on one of their vendor websites that had this really cool, like, very specific style of film that you actually had to go get developed.
• 13:31
  It was, like, a very high-grade film in these disposable cameras. It's not your generic, like, what you would get at the, at the drugstore.
• 13:38
  We were like, "How cool would it be if we branded every one of these disposable cameras?" And it was like, "Create your own memories with these. Give them to us at the end.
• 13:47
  We'll get them all developed, and then we'll push out all of these cool pictures, and it'll kind of be fun for everybody to not have this, like, instant memory," like the instant gratification.
• 13:55
  It was more of, like, this moment that would be really fun, as opposed to we were thinking of, like, you know, swag. Our CMO was like, "No, I don't wanna do that," because why are we spending...
• 14:05
  It w- it was gonna end up being, like, several thousand dollars. She was like- Yeah... "Why are we gonna have all this money spent on something that we're gonna throw away?
• 14:12
  That doesn't feel like we're giving them anything." I was like, "Okay. What if we don't position this as swag? Let's reframe this."
• 14:21
  We're pitching it to the CMO, who needs a story told, because this is the person who's telling the story for the entire company. Let's reframe it and share it as an activation.
• 14:32
  Let's share it as, you know, this isn't swag. It's not something that people are going to take home with them. We're using it as an activation instead of this, like, big experiential thing.
• 14:41
  Everybody will scatter them around the tables. We'll grab them at the end of the meeting, and then we'll bring them to the off-site event later that evening, like the nighttime event.
• 14:50
  People will take pictures in the evening. We'll grab them again, bring them the next day. Nobody needs the same camera twice. It doesn't matter.
• 14:57
  Everybody just grab a camera, take pictures, because the ultimate result that we want is just a ton of photos. Mm-hmm. And after I...
• 15:05
  So I had kind of re-pitched it, like reframed it and pitched it to her as an activation, not as a take-home piece. And she was like, "Yeah, that's fine." She's like, "All right. That sounds good."
• 15:15
  And it was just, it was the quickest answer. Mm. And everybody was like, "How did we get this over the line?" Like, all of a sudden now the cameras are back on the table.
• 15:24
  We just needed to slightly reframe, because I knew things that were non-negotiables for her was throwaway swag and wasting money. An activation is not tangible for the most part.
• 15:37
  Like, if you're doing something experiential, usually not something that you can take home with you.
• 15:42
  But, you know, the memories and the, the camaraderie and whatnot, that's something that, you know, we want our employees to leave feeling really good.
• 15:51
  And also, we would get photos, and we weren't gonna hire a photographer. We were like, "Great. Two birds, one stone." Mm-hmm. "No photographer. You guys are the photographers."
• 15:58
  We made it, we doubled down from there, and we were like, "You be the paparazzi this time, and you take the photos. Take whatever photos you want," and gave them, like, challenges and stuff.
• 16:08
  So we made it into this, like, really fun, uh, like, common thread throughout the week, and people loved it. It ended up being, like, one of the biggest hits that people were like, "Can we anniversary this every year?"
• 16:19
  It just needed to be sold in the right way, and we needed to know- Mm-hmm... who we were selling it to. What is the most abnormal task that you've accomplished on behalf of your exec, um, or maybe your proudest moment?
• 16:31
  Oh. [laughs] Those are two very different things.
• 16:35
  [laughs] Um, I think probably one of the things that I am proudest of was somehow figuring out how to throw together a, like, a IPO la- or an IPO party, like a celebration, on listing day during COVID when it was still, like, very much, like, social, social distancing.
• 16:58
  There were... You still had to get permits for things to be X amount of people in a certain space. We also had this moving target of when, uh, when our listing day would be.
• 17:07
  We only had a handful of people that were under the tent, so I couldn't talk about it with anybody.
• 17:12
  I had very few resources that I could actually go to, and I think it was, it was just, like, the one ask that I had from my exec was make it great.
• 17:21
  I was calling vendors and being like, "Hey, I may need to have a party here for 50 to 75 people, which I know isn't allowed. How do I make that happen?
• 17:30
  Also, it might be on Tuesday, but it also might be on Thursday, but it could be Wednesday also." Mm-hmm. "I need you to reserve those days. I can't tell you why, and I can't tell you for who, but can you do that?"
• 17:40
  And I couldn't go there in person, 'cause I was about 175 weeks pregnant, and we somehow, I somehow found a contact that had... This didn't even exist at the time. I don't know how it existed.
• 17:52
  Somebody had, like, a proprietary invention of a rapid PCR test, so we knew it wasn't, like, just your gen- like, general rapid test for COVID.
• 18:01
  It was a rapid PCR, and we were able to do those at the door, and I was able to promise the establishment that, like, we could guarantee that nobody in the building would have COVID. [laughs] Mm. Um, we figured that out.
• 18:14
  We were able to get, like, with retaining, you know, fees, we were able to hold a couple of venues. Somehow it worked out. We had a successful listing day, and then about four days later, I, uh, had my son.
• 18:28
  So it was, [laughs] it... Somehow we pulled it off. That was one of those things where it was like, "I don't even know how to make this happen, but I guess we'll figure it out." [laughs] And you did. Yeah. Somehow.
• 18:39
  Zooming out, this is our last question for you, but what have you found to be the most fulfilling part of your job? Ooh. I still really love the, like, untangling knots.
• 18:50
  I'm always, like, called back to a former executive that had, um, y- there was this print hanging in their office, and it, it was that quote of, you know, um, like, nothing's impossible, and, like, it was the way that, like, possible's in the word impossible.
• 19:06
  Mm-hmm. And it was like, it s- it was so annoying, 'cause they would always point back to it.
• 19:11
  Anytime I feel like I'm such a wet blanket for all of my execs that I've ever worked for, where I'm like, "Actually, we can't do that because of finances and because of the funding and this, and, like, finance is never gonna approve it, and also timing," and they're like...
• 19:24
  They would point to that, and I was like, "Ugh." And then I would pull it off and be so annoyed with myself, because I'm like, "Now they're gonna think that I can make magic happen."
• 19:32
  And time and time again, somehow everything still gets done. And oddly enough, as annoying as that is, that's still really fulfilling at the end of the day.
• 19:41
  But it's that feeling of when the invisible becomes visible in the sense of, like, like nothing has fallen through the cracks and everything has gone, like, pretty smooth, and everyone is just, like, kind of humming along about their day, and you kinda look around and you're like, "Look at all this just moving along.
• 19:58
  This is great." [laughs] "Look at you guys just living your lives. I love this." [laughs] It's just kind of... It's still so fulfilling and so, um... It's just still, like, you know,
• 20:10
  it's this, like, like, joy and annoyance relationship, but it does really, like, fulfill me at the end of the day. Well, that's it for this episode of the CC My EA Podcast. Thank you, Caitlin, for coming on- Mm-hmm...
• 20:22
  and sharing your tactics and stories. Uh, if you liked this episode, subscribe to CC My EA for more practical EA stories and tech tips.
• 20:29
  Uh, and if heavy calendaring is part of your role, check out Vimcal EA, the first calendar built specifically for executive assistants. See you next time.