Gabrielle Waxenberg on Recognizing and Empowering Executive Assistants

Jeremy · 0:00

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Speaker 3 · 1:41

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

Jeremy · 1:55

Hey, friends, welcome to The Leader Assistant Podcast. It's your host, Jeremy Burrows, and this is episode 316. You can check out the show notes, as always, at leaderassistant.com. And for this episode's show notes, you can just type in 316. So leaderassistant.com/316. Today, I'm excited to be speaking with Gabrielle Waxenberg. Gabrielle is an, well, she has experience as an assistant, over 12 years of experience supporting CEOs and founders in various industries. But she currently is founder and CEO of the Waxenberg Agency, which we'll dive into that here in a bit. But first off, Gabrielle, thanks for joining. Where in the world are you located?

Gabrielle · 2:45

Thanks for having me. I am currently right outside Boston, originally from the New York, New Jersey area. I've been here now, seven, eight years. Still call New York, New Jersey home, but I'm here in Boston for now.

Jeremy · 3:03

Nice. What's your favorite thing to do when you're not working?

Gabrielle · 3:08

When I'm not working, I really enjoy Broadway and theater. Being from the New York area, always go to Broadway and now here in Boston, see as many shows as I can. I'm on a fun bowling team. Since I moved up here, I joined a social bowling team, me and some friends. We are not good, but it's fun and it's something social to do. As I was discussing with you, I'm a huge Jets fan. Out here, we have the Boston Jets Club, which is probably like an idiom you don't hear very much. I'm a New York fan up in New England, but it's a fun group. We all get together every weekend and watch and I help run that. That's awesome. Now, our season is over, but it was fun for the last few months, all getting together up here.

Jeremy · 3:59

Cool. Well, that's awesome that you do that. Then the bowling thing, I've always loved bowling. I've never really been a great bowler. I've had a couple of days where I've bowled it. I'm like, oh, that was a pretty good day. I remember we used to do, I was homeschooled growing up and we used to do homeschool co-op get-togethers, and we'd go bowling and we'd have an hour and a half time limit, and you could bowl as many games as you wanted in that hour and a half. I remember one time we were doing it and I never tried the spinning or anything. I just bowled as straight as I can. But I remember one time, I must have been, I don't know, 13, 14 years old, and I started off the game with three strikes, and then I think I had a spare, and then I got two strikes in a row after that.

Gabrielle · 4:55

Sounded good.

Jeremy · 4:56

Our time ran out and they turned off everything, and I was so mad. I was like, this is probably going to be my best score ever, and I remember I went up to the counter and I was like, can you print out my score? Because I know I didn't finish the game, but to this day, I don't think I've ever gotten three strikes to spare and two strikes to start off. Yeah.

Gabrielle · 5:17

Like I said, we are not very good. We like to think we are, and then one of my teammates will curse when he gets one pin. I'm like, dude, all scores may be 100, 120, 300. We're not good, but the emotions there.

Jeremy · 5:38

Yeah, competitive nature. Yeah.

Gabrielle · 5:40

Yeah. We have a good time.

Jeremy · 5:41

It's awesome. It's making me want to go bowling, especially in the winter.

Gabrielle · 5:45

I'm going to Boston. I'll take you there.

Jeremy · 5:47

Yeah. It's a great sport to play in the winter for sure. Awesome. Well, yeah. Thanks again for being on the show. Tell us a little bit about your career. How did you end up in the assistant world in your journey back in the day and kind of walk us through a little bit of experiences through that career and then why you ended up deciding to start your own business?

Gabrielle · 6:13

Yeah. Well, I think like many assistants, it's not something I went to school for or was looking to do. I kind of, as people say, fell into it. I actually went to school for hospitality and casino management. My first job was at a casino, doing that, and from there, working in hospitality, which I think a lot of assistants started in hospitality. Yeah. In the casino management field, it was a very finance-based career. I then went into finance, like entry-level stuff, APAR. From there, I'm still doing finance in a legal company, and from there, I worked my way up in that legal company. I became head of finance, head of billing, and then there was the scheduling and coordinating, and then I started working there, and then became head of that, and then I oversaw a few departments, and then, in fact, I became the office manager, and then it was a small office, and then I was overseeing people, became a manager, and did this, and then I was the right hand to the VP in the office, and it was just doing those basic EA tasks, but I wasn't an EA, I didn't know what an EA was, and I was doing that. When I left that company, I was burnt out. I was 23, 24, working 24-7 in this legal company, and I just needed something that wasn't as much, and I ended up going to this actually pet food manufacturing company, mainly treats they made, and I took a job as an EA to the CEO. I can't even remember how I got this job or why I was even qualified, you know, just from what I was doing at this legal firm. And I was there, I think, only a year, but I really enjoyed what I was doing there. And so from there, I just started looking at other EA jobs. And that was kind of the start of my EA career. And then from there, technically that was a manufacturing company. I kind of just did everything. I was in IT sales, I was in banking, I was in another legal firm, I was in healthcare. Just everything, as you know, like EA, you can kind of transfer those skills to any industry. It doesn't need to be specific. Then when I moved to Boston, the Boston landscape is very pharmaceutical, biotech, healthcare. So since I've been in Boston and I became an EA, it was mainly in the healthcare. I was with Fortune 4 Company, Aetna, CVS, very large, obviously 300,000 people, and then some startups. Boston's also known for their startup cycle of all the MIT, Harvard, all of that, very startup heavy. So I've also worked for some startups here. About, I would say, two years ago and more, I've always thought about having my own thing, but never really did anything about it. One of the startups I was in did very well. We got unicorn status, we were valued at 1.1 billion, we went through a series C. I had shares, we did very well. That's the hope for everyone when they're working in a startup. My CEO left who I was working for and had the opportunity to stay, but he was the one I was working with, he was the one I had the relationship with, and I said, you know what, he's going to go, I'm going to go too. I said, this is my opportunity, let me see if I can start something now. I'm young, I'm not as young as I thought I was, but I'm going to start it now. If I don't do this now, I'm always going to kick myself in the butt, but let's do this. You know what, if I fail, if it doesn't work, I can always go back to work, but this is my opportunity, these are the signs, I'm going to do this now. I decided to start my own Fractional Assistance Company, and we have different branches. It's not just Fractional Assistant work, I'm also doing recruiting for full-time EAs for those companies that still want that, and I'm also doing coaching for EAs, confidence coaching, interview prep, resume rewrite, LinkedIn, all those things. So there's three branches to what I'm doing here. But the main goal was one, obviously, work for yourself, that's the American dream, who wants to do that? And I was burned out from, it's not a 40-hour job, an EA, you're working 24-7, when you're working for C-suite and board members and founders, it's around the clock and I was on call at all times. I didn't have a social life. When I put myself into work, I put myself into work. So my life was their life and a lot of that's my fault, but I felt I needed to do this. I was getting paid very well and I was doing things. I loved my job, but that was my life and I needed to find a better balance. Now, instead of working for one principal, 70, 60, 70 hours a week, I split my time and I'm doing a lot of different things. We also have subcontractors that sub out to other people. It makes for a better dad and I'm the boss. I report to myself and it's a different relationship now. The EA's that are going are doing the same work, but they're business partners. It's not their boss. They're a business partner. There's an SOW about what you're going to do, and it's just a different mentality going into it now. I just think it's the breath of fresh air.

Jeremy · 12:14

That's awesome. You've mentioned fractional EA. How do you think that varies in your experience from maybe just contracted virtual assistant? Does that make sense?

Gabrielle · 12:27

Yeah. I don't like to use the word virtual assistant. When people hear that, they assume offshore, international, this and that. I use the word fractional assistant. Most of it is remote. There are times when travel is needed. If there is a big off-site, a big board meeting, sometimes they want somebody in person for logistical reasons, or there's trouble. There was an event that had to go do that was a big to do with a lot of important high-net-worth individuals, and I flew there to handle, to make sure everything was okay. But most of the work is done remotely. So that word virtual is okay. It's just when a lot of people hear that nowadays, they assume it's this offshore, and I want to get away from that. Not that there's anything wrong with that, it's just a different level of service that we're providing than an offshore company. There's also the cultural differences of someone's going to call and say, hey, can you make sure we get a five-star restaurant that has a private room that has this, that has that, and you want to know about, is there a valet parking? Where can they do this? Where can they do that? That somebody that's familiar with certain cities are going to know that or someone, and I'm making this up, if you call a virtual system in the Philippines, just doesn't know the nuances of America and of this, and do they know what downtown New York City is like on a Saturday night, around the holidays in December, that's going to be chaotic and that GPS tells you it's going to take 20 minutes to get there, that's going to be an hour and a half drive, and you have to leave this much time and parking and this and that, and there's just certain things that people don't know in different cultures. So that's why I stray away from that, and there's obviously also the compensation differences between offshore and American, obviously, vast. But what I'm noticing is, is there's still those companies, and I would say, in my experience, what I've noticed, the larger companies are still going with full-time EAs, but a lot more of these startups and these more tech companies are doing more fractional, they don't need full-time, and they need certain more assistance. There's also a difference between tactical assistance and strategical assistance. Some people just need those, I need help with scheduling meetings in my email and do this, and other people need more help with board initiatives and stuff that they're doing on that level. There's so many different levels of help that we can help with, depending on those people's needs.

Jeremy · 15:15

Do you have a team that you work with? Do you have in and out finding people, or do you have a few full-time people that work with you all the time and that hire out of these different clients?

Gabrielle · 15:29

It varies. They're all subcontractors, they're all 1099. Some want full-time work, some only want part-time work. Depending on the clients, of course, we match them accordingly. I have a couple that work full-time with multiple executives. For instance, I have one that has three, and so with those three, she works full-time hours, but with each of them fractionally. I have another one who she only wanted to work a max of 20 hours a week, has young kids at home and didn't want to work the full-time hours. She works with one client, she has about 10 to 15 hours a week, and that's the max that she wants. To her, she's full-time, that's done. It really depends on the individual. They stick with the same clients, of course, unless some contracts are open-ended, some are a three-month contract, some are I just need it for a project, we're doing it off-site. Can you help us plan this and do this? We're having a huge company party, there were holiday parties going on and things like that. We have a 500-person company, can you just do this? Something like that might take a month or two to handle. But most of our contracts are open-ended, where it's just assistants until they either want to close the contract or modify the hours or something like that.

Jeremy · 17:01

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Speaker 3 · 18:01

Nice.

Jeremy · 18:01

Awesome. So that's great. Congrats on getting that business set up and going. You mentioned you do some training and stuff. What are your thoughts on advocating for assistance in different organizations? Like, hey, you need a full time, you need a strategic assistant here, or even empowering those assistants to see themselves as strategic partners. Yeah. Any thoughts on advocating for and empowering assistants?

Gabrielle · 18:34

Yeah. Earlier in my career, I didn't speak up, I just hung out in the background, and I didn't really feel like there was anyone in the company, whether it be HR, my direct supervisor, that even really spoke up for me. I also noticed that a lot of the times within these companies, there's training budgets, there's L&D budgets, and making this up, the marketing team or the finance team, they would go on maybe a day off site, the whole team, and they would have a team retreat or a team learning thing, or they would be allowed to go to a conference and learn something, could be a payroll thing or some kind of marketing thing. But EA's never did it. There were no conferences, or even if there was a training, you'd be like, we're not spending money on that. It always seemed like they were pushed to the side, and there was nobody advocated for them, and there really were no trainings, one even dedicated to them, and if we found something, the money could be used better somewhere else. The L&D and training money didn't go to them, and they sometimes, not always, depending on the company, they weren't really part of department. Maybe you were the marketing EA, but you weren't part of the marketing department. Sometimes the EAs were part of their own group, and so there was an administration department, whatever it may be. And it always frustrated me because a lot of EAs felt like they were stuck. Once you got to a certain level, if you were an EA to the CEO, where do you go next? You're done. There's nowhere else in the company unless you wanted to not be an EA anymore, and then go do something else. And these were a lot of thoughts that when I spoke to EAs, they all felt the same way too. I'm at this pinnacle, and now I'm done. What? Do I become a Chief of Staff, but I don't really want to be a Chief of Staff? That's a totally different job? Do I have to be a project manager now because that's kind of the only realm of an EA? Or I'm done now, and that's it. And I've also seen where a lot of EAs are, if their boss leaves the company or something happens, sometimes they're out of a job. They're linked to that person. Someone who takes over their job, had their own EA comes. But so a lot of times, they're not their own person, or they're just this extra body in the company, and there was no one there for them. And it happened with me. I've had almost, I think it was three or four times in my career, where my C-suite exec moved on, and I was just gone because, what now? They're eliminating his position, so bye, because there's no open EA, but something like that. And so as I got older, and I got my voice, and I started speaking up, sometimes it wasn't accepted as much. I could be brash. I started seeing some of the younger EAs come in, and feeling like a big sister to them, and saying, this isn't acceptable. I was seeing what was happening. And I would kind of, I don't want to use the word mentor, but kind of feel like I was mentoring them, and saying, don't let this happen to you. Speak up now. Don't get into this position where I feel like I'm stuck now, but you can make these moves quicker. And I saw some changes. And then I got involved with the Admin Awards, which was a huge recognition for admins and help advocating for them. And when I first got involved with them, I was very, I guess the word's queasy about it. Admin, they don't want to ask their bosses for a letter of recommendation, any money, can you do this for me? Because half the time, we end up doing the thing anyway. We write the letter of recommendation. I have to write my own thing about me. I have to do this. So it was weird. But I had a great relationship with my boss at the time. This was that same company where I said he thought Unicorn Tadis. And I said to him, hey, I want to ask you two things and pick one. And it was kind of a, you know, I didn't know how to do it. So I figured if I gave him two options, maybe he'll pick one of them. And they were both for me. So it was kind of like a weird thing. And I said, hey, can you either write me this nomination and do this thing because I was nominated or, and at the time I was sitting on a charity, and he knew, like, I was very philanthropic and doing things, would you and or the company donate to my charity and putting on this event? So do you want to give me money personally or would you write this? And he was like, well, which would you rather? And I was like, and I was very honest with him. I was like, well, I hate asking for things myself. So I'd honestly rather you donate to the charity. And that's what I said. And he was like, you know what? I think I'm going to do the nomination. And I think the company will still dominate to the charity. And he was so nice about it. I was actually shocked that he did both. And in hindsight, it was like, both things were really no big deal.

Jeremy · 23:45

Right.

Gabrielle · 23:45

Like I wasn't asking him to donate a million dollars. You know, I was asking him for something little. And he wrote the nomination, which I had never seen. And I ended up being nominated. I became fine as I didn't win, which was fine. But the act of doing all that gave me so much confidence as an EA and just a person. And he gave me this voice to say to admins, don't be scared to do this. Don't do that. Yeah, some executives might say no. You might be scared. But if you are a good admin and you have that relationship with your boss, one, if you're scared to ask them, you are not working for the right person. If you don't have a good enough relationship where you can't even simply ask for a recommendation, you're not in the right workplace, and that is not a good work environment for you. And the worst end, it's not, the worst that can happen is they're going to say no. And you have to work on your relationship with your boss. I always say working with someone as an EA, I mean, that is one of the closest relationships. I know their families, I know their kids, I know you're social, I could steal your whole identity. Like, I know everything about you. You should, for the most part, know almost everything about me. It's one of those closest relationships. I know some of my execs closer than my sister or my parents. Like, I know they're ins and outs. So if you can't be that vulnerable to ask them one question, there's something a little wrong with that relationship there. Again, you may not want to ask me in your first three months of working with them, but I mean, as you get comfortable with them. And so since then, I've just been advocating, I've been working with the Admin Awards, and some of my dear friends who I know are a little scared and timid, I've seen them come out of their shell. Some of them, I got into the Admin Awards, we've nominated them, and just to see them kind of stand up and be that person and see them change as admins, they become better admins, better workers, and more of this community, I think is amazing.

Jeremy · 25:50

That's awesome. That's great. Yeah, and I think that even your point about asking and then them saying no, I think even the act of putting yourself out there and asking can give you confidence.

Gabrielle · 26:04

Oh, yeah. The scary part is the unknown, right? There's so many things I'm scared of, and once I do it, I'm like, oh, that wasn't that big, but it's the anxiety.

Jeremy · 26:13

Exactly. Cool. Well, what is maybe one of your favorite parts about the assistant role in your career? Maybe one of your favorite tasks that you've accomplished or just a general element to your career in working as an assistant. What's maybe your favorite thing that you've done or your favorite aspect of it?

Gabrielle · 26:45

Let's see. I don't know a specific task, but for me, maybe a lot of you see this. I'm a little OCD crazy, but for me, even in my personal life, like I make to-do lists, what do I got to do this weekend, my errands, my this, I love crossing off my lists. As an EA, I constantly have a list like 20 things right here, and there's constantly more come, but I love just crossing off, and I still use paper and pen. I know there's monday.com and all these things that you can electronically use, which I have, but I double it up and I do it on paper and pen, because I love crossing off when I do things, and at this level of support that I'm providing, there's just like a million things to do every day. And so my lists are crazy long, but I love crossing it off. And I know I get such satisfaction out of that. I know it sounds very nerdy, but-

Jeremy · 27:48

No, I'm married to a list person, so I get it. I get it.

Gabrielle · 27:54

But do you get getting those lists from her?

Jeremy · 27:56

Well, yeah, I'm like, I don't want to write lists. I just want to do the work and not put it on a list.

Gabrielle · 28:03

See, but I'm also visual, so I have to see everything I have and then know what's most important, right? Not everything's urgent. People say it is. So then other things get added, so I have to switch it up in the line of where it goes, so that not everything can get done in a day, right? So you got to figure out when to do it.

Jeremy · 28:22

Awesome. Well, Gabrielle, thank you so much for being on the show. To wrap things up, what is the best place or where is the best place for people to reach out to you if they want to learn more about your agency or your training and all that jazz? What's the best place for people to find you?

Gabrielle · 28:42

Yeah. So I think the quickest and easiest is always LinkedIn, Gabrielle Waxenberg, and I have LinkedIn for the Waxenberg agency, and obviously for work. From there, you can get all my works up. I have public, so everyone, when you hit the contact info, you can see my work e-mail and all my socials, LinkedIn, Instagram, X, just The Waxenberg Agency. You can find them everywhere. Then from there, you can get to my e-mail on my website, which is The Waxenberg Agency, and contact me in any way.

Jeremy · 29:13

Perfect. Well, I will put the links in the show notes for sure at leaderassistant.com/316. Thank you so much again for being on the show, and congrats on a great career as an EA and as a business owner now, and thanks for the work that you're doing to recognize and empower assistance of the world.

Gabrielle · 29:36

Thank you so much for having me. I really appreciate it.

Speaker 3 · 29:48

Let's review on Apple Podcasts.

Jeremy · 29:57

GoBullos.com Hey friends, my best-selling book The Leader Assistant has a companion study and discussion guide to go along with it. It's called The Leader Assistant Workbook. Now you can buy the Kindle ebook version of The Leader Assistant Workbook on Amazon, or you can go to leaderassistantbook.com and get a printable PDF version of the workbook. This version has all the space and margin in between the questions that you can write your own answers and take notes with. So it's a great way to print it out and keep track of your discussion and study guide notes. Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.