Ciara Trotman on Forming Professional Relationships and Career Paths for Assistants

Ciara · 0:00

My name is Ciara Trotman, and today's leadership quote is, I will not lose, for even in defeat, there's a valuable lesson learned, so it evens up for me. Quoted by Jay-Z.

Speaker 3 · 0:19

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

Jeremy · 0:34

Are you tasked with ordering food for your office? Let me tell you about Easy Cater. With over 100,000 restaurants to choose from nationwide and 24-7 customer support, Easy Cater helps assistants like you and me succeed at work and makes our lives easier. Visit easycater.com/leaderassistant to find out more. Hey friends, welcome to The Leader Assistant Podcast. It's your host, Jeremy Burrows, and it's episode 254. You can check out the show notes at leaderassistant.com/254, leaderassistant.com/254. Today, I'm very excited to be speaking with Ciara Trotman. Ciara is an executive assistant, has been an executive assistant with a career spanning 20 years in corporate finance and big box technology. I'm very excited to jump in and chat with her. So, Ciara, welcome to the show.

Ciara · 1:38

Thank you for having me, Jeremy.

Jeremy · 1:41

What part of the world are you in?

Ciara · 1:43

I'm in Brooklyn, New York.

Jeremy · 1:45

Brooklyn, nice. I was in New York City a month ago or so with my family, took my boys and my wife for the first time. Oh, nice. It was a fun little three-day trip.

Ciara · 1:57

Yeah, I'm sure it was pretty loud and exciting.

Jeremy · 2:03

Definitely. What's your favorite thing to do on your weekends?

Ciara · 2:10

Really just hang out with my family. I have a 10-year-old niece who is 10 going on 25, and she's just really exciting and we usually just watch a lot of good movies, cook some good food, really just enjoy loving on each other.

Jeremy · 2:27

Awesome. What's one of the better movies you guys have seen lately?

Ciara · 2:36

Nothing spectacular, but we're really excited to see Wonka.

Jeremy · 2:40

Oh, nice.

Ciara · 2:41

Quality break.

Jeremy · 2:43

Good deal. Sounds like a plan. Well, what got you into the whole executive assistant world?

Ciara · 2:49

Oh my goodness. Funny story. My father was an entrepreneur. He was a sports photographer for the New Jersey Nets eons ago. And so I started working for him as my summer job. And I noticed he had a couple of gaps in his corporate structure. So I offered to fill them and I bargained for my payment of my bike. And just said, if I can do a great job for you over the summer, will you get me a bike and will you, you know, do something about my allowance and getting increasing it? And so I was able to actually not only begin my executive assistant career with him, but I also retained my first international client with his business at 12. So it just kind of, you know, that's where the spark started for me.

Jeremy · 3:43

Nice. Well, how did you end up with the international client? Was that, was that like just an inbound thing for the business, or did you have to go reach out to people? How did that happen?

Ciara · 3:56

Yeah, really interesting. He was working with the US-based publications for the most part, and he was starting to expand his services overseas, but had a major communication barrier. And so I did some quick recon, went to the library, and, you know, just looked for a couple of key greetings and things that I could say to open a meeting and start a conversation, and maybe jump in to interpret negotiations from point to point. Nothing too heavy, though, but the effort made really resonated with the client. And so because they were so impressed with the amount of work that was done, and they obviously could tell that I was a child, they were just like, this is adorable, this is great. And so they wanted to get in business with my father. So he was able to secure his first international publication in Spain, and then I believe one in Italy behind that.

Jeremy · 4:49

Wow, that's great. That's some initiative for sure.

Ciara · 4:53

What a kid, right?

Jeremy · 4:55

Yeah. So then, okay, so then as you grew up and got into the corporate world, did you just enjoy that type of work? Is that what you sought after? Did you, I noticed in your bio, you mentioned event planner as well. When did you kind of get into that? Or has it always been part of your assistant roles?

Ciara · 5:21

It's something I enjoy doing, and I'm very passionate about event planning. So in one way or another, I've always kind of invited that or offered that service, even if it was just a mindset. I approach my desk job as an event and try to just bring some excitement to the day-to-day. And I think because of that, my manager kind of flagged me for my first opportunity with corporate finance and said, you've got something unique here, why don't you give it a shot? And there are a lot of aspects of executive assistant work that do lend itself naturally to event planning. And it was just a match made in heaven. And I just kind of went full throttle in those places.

Jeremy · 6:13

What's your number one tip for those who, their CEO or their executive calls and says, hey, I need you to plan this event? What's your number one tip?

Ciara · 6:23

My number one tip is start early and design that budget early. And just make making sure that you're talking to your executive team about what they're hoping to accomplish with the event. Because more than just throwing a good party or a good social experience, you want it to be able to tie back to a business need. When people walk into the event, they should know why they're there on many different levels, except to just enjoy yourself. And it kind of it centers the purpose of the event.

Jeremy · 7:01

Good tip. Good tip. So let's let's talk about then maybe what was throughout your career as an assistant, what was maybe your most challenging time or or maybe the most difficult thing that you've faced as an assistant?

Ciara · 7:22

Oh, Jeremy, we could be here all day. I've had a lot of unique challenges throughout my career. I think the first one was just understanding how I wanted to show up to the space. And second, of course, is establishing a great relationship and a good rapport with your executive team. And then if I'm being fully transparent, just jumping the hurdle through corporate politics as an African-American woman, you know, it is a very real thing that happens, and it is very, very challenging. Managing imposter syndrome along the way are some things that kind of crop up that you didn't see coming. And it really just requires you to push through in a very nuanced way to manage your career.

Jeremy · 8:16

Interesting. So tell us a little bit more about the office politics and maybe how can we as assistants navigate office politics?

Ciara · 8:31

Office politics are tricky. They're unique to one's environment. I think in my own experience, I have always been raised with the mentality of being a worker bee, just put your head down, work really hard, and eventually by magic someone will notice how hard you work and just reward you. And that's not how it works at all. So much later on in my career, I kind of relented to the mentality of you have to form relationships. As much as you don't think about that, and yes, a good work ethic is very important, but also establishing some key relationships with decision makers, with managers within your team to just be able to say, I'm showing up as more than a doer. I'm a team player as well. Really changed the narrative for me and kind of changed my reality as well.

Jeremy · 9:33

Nice. So how have you seen that corporate, or forming those professional relationships? Do you have tips on that? Like is it, hey, you know, I'm going to grab lunch with this colleague and just talk shop or ask them about their personal life and try to just build that rapport? Is there kind of certain boundaries in those professional relationships based on the org chart and where you fall and all that kind of thing? Is there any tips that you would have through your experience?

Ciara · 10:09

Absolutely. I think first and foremost, executive assistants have a very unique position and that we are the human being in the equation. Most people are just doing cross-functional partnerships or managers are talking to their directs and their skip levels, but they kind of lose the humanity in that situation. And I realized that one of my specialties was just being a confidant in that space. And some of the things that I did for my managers, I started to apply them to myself. When you onboard a new executive, the first thing we do for them is coordinate meet and greets. Who should they be talking to? Who should they be connecting with? And who are we putting in that what I'd like to call their phase five? Who are they always going to be connecting with and talking with and meeting with? But I noticed I wasn't doing that for me. And here I am a key right arm in that situation. So I put it into work. During my first 30 days, I looked at the chart of the org chart and said, who are the people closest to my manager? I need to meet with them. I need to do coffee intros and just let them know that I'm here. I'm part of the team. I'm going to be working closely with my executive, but I'm also a resource, an open door, a safe space for you as well. I was really diligent about following up. I made sure that whenever I saw people, I was always reaching out, friendly, made a joke or two. Just people understand me. Then I developed curiosities about what they did in their professions. I always asked about, what is it that you do? What are you passionate about? What are your pain points? Let me think about that. Then I used that information to be very strategic with my manager about pointing out how his or her organization runs on a broader scale and tying those things back. It put me in a great place to be a true eyes and ears to the org. In that process, I have been branded as a strategic partner. I would say when I think of myself and where my career is going and headed and currently is, it's a true strategic partner.

Jeremy · 12:36

That's amazing. So I love what you said about being curious, because I've talked about that all the time as far as what makes a good assistant. Well, you got to be curious. You got to go, oh, well, how do we do this? And how can we figure this out? And even curious about the industry and just general curiosity of what's going on in the macro environment. But I love how you specifically brought that curiosity skill set into relationships and being curious about your colleague and what they enjoy doing and what their skills are and what their passions are. So that's a great, great tip.

Ciara · 13:14

And, you know, if I may add something else to that, I sort of put myself up as a tribute, if you will, to be the one that would fall on the sword for them. You know, I always say, like, if there's a question you want to ask and you're just shaking in your boots about it, pass it to me. You know, I'm in a great position to be green, to not really know everything about everything, so I can ask your question for you. And just having that extra added layer of trust so people knew that they could maintain their professionalism and they had someone fighting for them in the background really went a long way. It also helped me quite a bit in learning to lose the fear of walking in certain situations or conversations that may be a little bit above me. Instead of wasting the time being fearful about what I don't know, I jumped in blindfolded and just said, hey, I'm going to ask the question, you know, and be a driver for truth and always making sure that whatever we're doing, we're getting to the root of that situation. And sometimes that just means asking a tough question.

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Jeremy · 15:11

Yeah, that's great. I love that. And it's like, it's almost like you could be, it's like good cop, bad cop in a way, where it's like, oh, you know, you're gonna go over and you're gonna ask that hard question and take one for the team. So that's awesome.

Ciara · 15:24

Absolutely. It's what us Brooklyn girls do.

Jeremy · 15:28

Nice, nice. Well, let's talk a little bit about career paths and what you've seen in your career and what you, you know, there's always that question of, what do you do as an assistant? Or the also one of the more common questions I get, and I know a lot of assistants get is, you know, what are you going to do next? What, you know, like, okay, you're an assistant, that's great. What do you want to do after that? So how do you wrestle with the career path idea for assistants? And what's maybe what's your career path hopes and dreams? And then what do you think is, are a few good options or maybe just one good option for assistants?

Ciara · 16:14

I have so much to say about it, but I know you have a time limit on your show, so I'll try to put it down. I am super passionate about this because I've seen through the years, and I've heard a lot from my colleagues about what a dead-end executive assistant work can be. And that's largely because it takes a special or specific type of person to be an executive assistant. And we really get in the weeds about our work and the people that we work with that sometimes we can nurture too far to the left and not worry about ourselves. We're the first people we forget all of the time. And so for that, again, I've allowed the hurdles that I've faced to make me braver to really kind of forge my own path because I've looked for it, I've asked for it. I've had terrible career conversations where I just failed epically. And then I've learned you can't always ask for the things you want, you have to sometimes create it, demonstrate it, let it show up, let people live with it. And then when they realize that there is value in this, they're ready for a different kind of conversation. So while I'm not putting that forward as a concrete game plan, it's definitely something to consider. I've also tried to just be organic to the things that I do well and just keep doing those. Being unafraid to ask a tough question made me a disrupter. A lot of things that were done just because I questioned, I challenged, I pushed back on, and it can be very efficient. So I think of my career, I'm always going to authentically show up as a disrupter and a strategic partner. And I will never relinquish those two things. And while, again, I'm in the boat with a lot of other executive assistants where the path is not always clear, I'm definitely working to kind of split it somewhere between a chief of staff and an assistant. I think that's the organic progression for me.

Jeremy · 18:40

So then like you see the strategic partner and disrupter as one of those, you know, chiefs of staff, if you will, skill sets. Is that kind of what you're...

Ciara · 18:52

I think to be an effective chief of staff, you really have to be able to look at the broad picture and the small picture. You can't lose either vision, and you really have to have that in mind to drive a strategy forward and understand what it takes to build the steps for the strategy to live. So I think executive assistants have a lot of those qualities baked into what we do and who we are, and it seems like a natural transition. Or at least I hope it is.

Jeremy · 19:27

Yeah, yeah. Well, this has been a great conversation. Just a couple more questions if you're cool with it. So, you know, there's perception versus reality. Like what's an EA, you know, like, you know, those memes where it's like, oh, this is what my mom thinks I do, and this is what people think I do, and this is what I actually do. And so what's an EA's real job?

Ciara · 19:58

Ruler of the world.

Jeremy · 20:01

Done and done. She said it. She said it.

Ciara · 20:05

That's a fact, people. I think our real job is we mirror everything our executive team does. And we make their ideas happen in real life. And while I'm not speaking to an actual running a corporation, it takes true leadership to do that. So I won't undermine that process. But I think it speaks to what we do to really be able to just walk in the door and get that broad picture and be able to, in real time, respond to keep the pieces moving forward in order for them to be able to accomplish that free and clear. So it's about thought, leadership, true partnership, being able to be crystal clear again about the vision from the bottom to the top and the top to the bottom, and then really have an understanding of the organization and how it actually works, what's right about it, what's broken about it, who are the people who should be in those conversations versus who shouldn't be at a specific moment in time. Those are the things that it takes to just really be a great executive assistant. And so while I hear a lot of people saying, oh, I'm a true right hand, I hate that expression because my executive has a right hand, his or her own. They don't need me to be a right hand. They need someone to like pick things up on their own and run with it. And so I think that's what I focus more on. Like you do your job, I'll make everything else happen while you're away. And when you come back, I have all of the answers that you need. That to me is a partnership. A good one.

Jeremy · 22:01

Yeah, totally. Love it. Well, what do you think about AI? What's your like 60 second, you know, elevator pitch, cocktail hour answer to the AI replacing assistants and all that?

Ciara · 22:17

I think, first of all, the AI photo enhancements are top tier because they don't look better. But I think AI is worth delving into. I haven't finalized my thoughts on it, but it's a natural progression. The world changes, technology changes, and I'm just at a place where I'm staying open minded and open to learning more about it. I've seen some quick ways that it makes my life a lot easier. And I think if we look at it from a perspective of it's just another tool. Before we had BlackBerrys, now we have iPhones. iPhones are so much more efficient. They have so much more that they can offer. So AI could probably fit the bill like that for us now if we just keep an open mind about learning what it actually does and where it's going to go. We're in charge. We have to create AI. It didn't create itself. So as long as we're the makers, we're always in a position to drive how that looks and feels.

Jeremy · 23:23

Well said. That's a great elevator pitch for AI.

Ciara · 23:27

Thank you.

Jeremy · 23:31

What about diversity and inclusion for assistants? I asked my guests on the show what topics they would like to talk about and to wrap up our conversation, I would love to hear your thoughts on DEI. I don't really know any specific questions that I necessarily want to ask right now. I'm just curious to hear your thoughts on it.

Ciara · 24:00

That's a mouthful. And I'm super passionate again about this space, again, specifically because I'm an African American woman. I'm also a Caribbean American woman. I live in New York, which is the melting pot. So I've been accustomed to world culture all my life. I'm not surprised by or shocked by anything, but a lot of people around me are not. So it's a natural thing for me. I think DEI is important because it helps the greater ecosystems to understand how it shows up in real life. Things that may not be an issue for you can be an issue for someone else. And the simple example is a tall person never has a problem reaching the top shelf, but a short person would. So it benefits the tall person to understand, hey, I'm 5'1, I'm always going to need a ladder. So if you can be empathetic to something like that, then you understand that my experience is inherently different than yours. It's not something we need to spend a ton of time focusing on if it's real or if it's valid, because it is. And that's not where the work in that process is. The work is now let's understand the different nuances and the many different layers of diversity, equity and inclusion, that those words are very different. They mean very different things, and we have to dig into that. And it just doesn't include someone's race. It's ableism, you know, physical, sexual, it covers the gamut. And it's also a new area for a lot of corporations, so we need to give ourselves some grace in wrapping our minds around learning about it and really, truly integrating it into corporate culture.

Jeremy · 26:00

That's well said. I love the analogy, you know, of the example of the tall person versus the short person. You know, I'm tall. For those listening, I'm 6'2.5. I'm the one that's reaching up in the top shelf for my kids or my wife or whatever, but that's a very simple yet powerful example to kind of describe it. So thanks for sharing that. That was great.

Ciara · 26:24

No problem. And I'll be looking for you anytime I need to reach something.

Jeremy · 26:29

There you go. I got you. I got you. Awesome. Well, Ciara, thank you so much again for being on the show. What's maybe the best place for people to reach out if they wanted to say hi?

Ciara · 26:40

That's awesome. Yeah, you can find me on Instagram or you can find me at LinkedIn. LinkedIn is probably my preferred because I love meeting people and chatting and all the information is there so we know where we can pick up a conversation.

Jeremy · 26:55

Perfect. Well, I'll put your LinkedIn URL in the show notes at leaderassistant.com/254, leaderassistant.com/254. Ciara, thank you so much. Have a great rest of your day and it's been a pleasure speaking with you.

Ciara · 27:11

Thank you so much. This was a blast. Highlight of my week.

Speaker 3 · 27:25

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