Amy Tilley on Workplace Grief, and Managing a Team of Assistants

Amy Tilley · 0:05

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

Jeremy Burrows · 0:13

Hey friends, welcome to the Leader Assistant Podcast. It's episode 394. You can check out the show notes for this conversation at leaderassistant.com/394. Today, I'm excited to be speaking with Amy Tilley. Amy is executive assistant to the CEO, and we're really just going to jump right in and have a great conversation. So, Amy, welcome to the show.

Amy Tilley · 0:45

Great. Thank you. It's a pleasure to be here.

Jeremy Burrows · 0:48

Tell us, what part of the world are you in and what do you like to do when you're not working?

Amy Tilley · 0:53

I'm actually in the suburbs of Chicago, a lifetime Midwest girl. And when I'm not working, I'm outside all the time. So, I am hiking, biking, playing in the dirt, all that kind of stuff. So, I get out of the office and I get outside most of the time.

Jeremy Burrows · 1:11

Love it. Love it. And Chicago is similar to Kansas City where there's some really, really nice weather for a few weeks in the spring and a few weeks in the fall, and then it's kind of pretty extreme.

Amy Tilley · 1:26

But Yeah, exactly. Yeah, exactly. We're kind of in the Sahara Desert right now. It's about 110, I think, heat index right now.

Jeremy Burrows · 1:34

Yeah, it's about, it's about the same in Kansas City. In fact, my air conditioning broke a couple of days ago and I was like, I didn't really notice it at first. I was like, it's kind of warm this morning, but it's 100 degrees out. So, you know, and then like a couple hours later, I was like, man, it's really warm in my office. And then another hour later, I was like, all right, something's not right. So I walk over to look out the window and I was like, oh, my air conditioner is not moving outside. So I was like, all right. But anyway, it's fixed now. Ready to rock. I'm not sweating too much in this conversation. So we should be good to go. Well, Amy, thanks for being on the show. Let's jump into your story. Tell us a little bit about how you ended up, you know, becoming an assistant.

Amy Tilley · 2:19

Yeah. So it's, It's a wild story. It's one that I'm always excited to tell 'cause I ended up in a field I didn't think I was gonna end up in. But I started, oh my gosh, like 20-some years ago, really. That's scary to say. But we had just moved. My husband, daughter, and I had just moved. And on 9/11, I had faxed over a resume to a trucking company because I hadn't had a job prior to moving. And a couple days later, and that was, I faxed it by the way. So for those that don't know what a fax is, we didn't just email things back in the day. But, you know, and I got hired and it was one of those where I had enough, I think, experience within, I would say, the assistant world with what my background was, hired there. And from there, Within about a year or two, I was supporting the CEO. We made another move to the Chicago area because of my husband's role. And I just, I stayed within the profession and I've been blessed because from that point on, I've always sat next to a really amazing CEO, no matter which organization I was with.

Jeremy Burrows · 3:34

Awesome. Awesome. Well, what, what has been, and maybe early on in your career too, what drew you to this, this role as you got into it? Made you excited about it?

Amy Tilley · 3:48

Yeah, I always knew, even growing up, I always knew that I wanted to be in leadership. Like, I love leading people. I love coaching, mentoring. I— it's, it's kind of been a part of me, I think, my whole entire life. But interestingly enough, I don't think I ever wanted to be the final decision maker in anything. So being an assistant put me really at a high level where I could have lifelong learning. Whether it was business, whether it was food and beverage or transportation or whatever. And it just, it motivated me to stay within, within the field because I felt like I was able to be a leader, but I didn't have to make those hard decisions. And I think that sometimes that sounds kind of funny, but I love sitting at the top, just not having the responsibility of the top decisions.

Jeremy Burrows · 4:36

Yes, I'm actually, that's actually probably one of my favorite parts too. It's like, You know, you kind of, you're in the know on all the different things that maybe not very many are in the know of, but you also don't have the complete full pressure of being the top dog, if you will.

Amy Tilley · 4:56

Yep. Yep. I love it. I do. I just, I feel the field has such amazing individuals that, you know, the number of people I've come in contact with or hired or whatever, there, it's just, it's a, it's a great It's a great network of people.

Jeremy Burrows · 5:13

So what, what about your progression then? How, you know, you've, you've worked in a lot of different— it looks like even different industries and such. Yeah. What was the path that kind of brought you to where you're at today?

Amy Tilley · 5:29

I would say so. It's the path that I ended up at the height of my career is I got to work for a company for 13 years, immediately started with, you know, like supporting the CEO. CEO, the CFO, and then I ended up taking over the admin team. And at the time, it was a very small team. The organization was still smaller, and I was able to build an amazing career over 13 years as they grew, as I grew, and having, you know, I think a leadership team behind me that helped me grow. And so the progression was I got to start to very slowly, but yet through growth of the organization, build an amazing admin team. So I've got— I got my leadership background, right? I got, I got the chance, in my opinion, to lead a best-in-class admin team that I felt was like the best, the best in the world. They were such an amazing group of people. And it took me— it took 13 years, I think, to get to the point where then I was able to say, I built this great team, I worked for this great organization, now it's time to move on and start to experience something different. I'm, I'm learning that kind of like, you know, when you buy a pair of tennis shoes and you're a runner, you can only wear them so long before the tread wears out and you have to buy a new one. It's kind of like that, that, that for me. So then I went to another organization. I had a great, a great run there. Same thing, supporting the CEO. But, and I'm sure as we'll start to talk later in, in our conversation, um, a little bit of grief hit with the departure of a 13-year career? Am I doing what I want to do? And then I took a little bit of a gap and went into a completely different industry that I had never worked in. And I call that my recovery year. And that was because the people there were so wonderful.

Jeremy Burrows · 7:19

Hmm.

Amy Tilley · 7:19

And they grew me in ways I never expected to grow personally and professionally. And that brought me to where I am here. And I'm back in the, in the, what you would call it, the food and beverage industry. I'm supporting an amazing CEO. And it's been a great 20-year career to put me where I am today. But the reason I am here today is because of every step that I took within my career.

Jeremy Burrows · 7:40

Yeah. Well, tell us, I'm really curious. We'll get into the topic of workplace grief here in a minute. But I'm really curious about your time leading an administrative professional assistant team. So give us your— well, so there, you know, there are different structures like you lead the team, but they still directly report to their executives and they do the performance reviews with the executives, but you're still kind of managing the team. And then there's another structure where it's like, no, you're actually doing their performance reviews and you're their direct supervisor. And then they support, you know, they're assigned certain executives. What was the structure for your situation? And tell us some of the lessons learned and maybe best practices during your time? Because I know a lot of people reach out and say, hey, do you have any episodes on the topic of administrative team management or leading a team of assistants? And so it's always an interesting topic to get into.

Amy Tilley · 8:45

It is an interesting topic. And I think it's an interesting topic too, because as the assistant world changes and morphs, you know, You have some people that are really excited to be a part of a team and report into another assistant. And then you have other people that really just want to report into their executive. And that's a personal preference. And when I interviewed, I always started with that. This is how we lead our team. You know, your preference is you, you do what's right for you. Our structure was the entire admin team that was locally based, um, reported to me. So at the peak, I believe I had 9 direct reports, 10 direct reports as we continued to grow.

Jeremy Burrows · 9:23

Okay.

Amy Tilley · 9:24

And I did everything. I did their performance reviews, they reported directly to me. I decided who supported who. I was, I was blessed to have a leader behind me that allowed me to do that. But the entire leadership team from the CEO down, that structure is what worked for us as an organization. And I think that's one of the most important things too, when people are looking at doing some kind of structure like this, it has to be right for the organization that you're in. Sometimes it's not. a good fit. For us, it was a good fit. So for us, I had— I was able to run my team. We actually felt like we were our own department. What I was very cautious on doing is making sure that the assistants and the executives that they supported knew I was there to mentor, coach, and grow them. But how they supported their exec was on them. That relationship was always separate. I did not micromanage and say, you have to run a calendar this way. you have to do an event this way. That relationship still was built between your executive and your assistant.

Jeremy Burrows · 10:29

Mm-hmm.

Amy Tilley · 10:30

And that was— that is something to this day when I talk to people about running admin teams that I think is so, so, so important, is your role as a leader is to coach, mentor, and grow, but you have to allow those relationships between the assistant and the executive to form naturally and organically. And we did it, we did it right. We, we, it worked so well for us at the organization.

Jeremy Burrows · 10:54

That's awesome. I, I love the— it's some— it's such a hybrid thing, uh, generally. But, you know, I personally, as an assistant to the CEO, I would not want to have kind of this other supervisor dynamic. Um, but I also know other assistants who, you know, support C-suite executives and they're like, no, I really like having that other because, you know, a lot of the times assistants, we have to self-manage and a lot of assistants don't want to have to do that.

Amy Tilley · 11:32

That's very true.

Jeremy Burrows · 11:34

So yeah, it's, it's, it's cool because there's no like right or wrong way. You know what I mean? Like it's, like you said, it depends on the organization, depends on the executives, depends on the assistants. What was the most challenging situation or just in general part of leading that team? You said about 9 or 10 or so?

Amy Tilley · 11:56

Yeah, 9 or 10 at my peak. So I had all of the assistants and then I also had the receptionist for our front office. And then depending— and on top of that, I was also the office manager. So I managed our— I managed 2 offices, our local one and then one that at the time we had in Boca Raton, Florida. The biggest challenge, honestly, was when we would bring new leaders in that had come from a different structure with their assistants. So for example, when we brought in, um, I think it was either a president role or a senior VP role, they had had their assistant. They had one assistant, it was only theirs, and they did it exactly how they wanted. There was not— a team where, for example, if somebody was gone, they were their backup. Or, you know, they— we followed all the policies and the procedures of the organization, and they couldn't, like, sideswipe that, you know, because that was how we ran the team. So the hardest part was almost onboarding new executives into how we, we manage the team, um, because they do report to me. Most of the time, once they realize that they don't have to deal with PTO, they don't have to deal with performance reviews, they don't have to deal with any dysfunction within the team, or where, you know, 2 assistants aren't getting along, or they don't want to do that, and that all fell on me, this— they slowly, eventually, everybody got on board and realized that, again, for us as an organization, it just worked really, really well.

Jeremy Burrows · 13:31

Love it. Love it. Well, Is there any, any kind of final tip for those assistants who maybe want to develop into that role where they're, you know, leading the team or leading or moving into a role where there's an opportunity to lead a team of assistants?

Amy Tilley · 13:51

I think the biggest thing I tell people is make sure if it's something that you want to do, that it is something that you'll get the buy-in from the leadership team at the organization, at the organization you're at. First off, I'm a huge proponent for growth within our roles, whether it goes into leadership of another team, whether you decide to completely upscale to achieve a staff role. Fully on board with the growth opportunities that we have. When it comes to developing an admin team, it's so important to make sure that before you just jump in and go to HR or your boss and say, I want all the admins to report to me and I want to manage them, Make sure you get that buy-in from the organization. Make sure you get some type of leadership training ahead of time. It is not as easy as having people report to you. There's so many leadership dynamics that as assistants, we sit and watch in the background with the leaders we support. Once it sits in your lap, it's a whole different ballgame. So, you know, start that conversation with those that you support or those that, you know, are technically your direct manager, and, and then build it from there. And if it's something that doesn't work there and you really, really are passionate about it, find a company that does utilize it that way, or find those of us that have done it. Reach out and say, you know, what do you think, or how would we do this, or do you know of other companies that do it this way? Um, that's probably the best advice I would give somebody that's really thinking they would like to have that kind of a structure.

Jeremy Burrows · 15:25

Yeah, that's great. That's great. And I actually, shameless plug here, my friend Tara Sims just launched a course called Administrative Management Accelerator. So she talks about that whole process of like, hey, I gotta look into that, lead the team and the different structures and all that. So I'll link to that in the show notes at leaderassistant.com/394 for those interested in checking that out. That's fabulous.

Amy Tilley · 15:52

Somebody doing something like that is fabulous.

Jeremy Burrows · 15:54

Yeah. Awesome. Well, tell us a little bit about the— let's talk a little bit about workplace grief.

Amy Tilley · 16:00

Mm-hmm.

Jeremy Burrows · 16:01

You know, there's— it always seems to be, you know, everyone's busy, obviously, all the time, but like, it always seems like it's in those moments where it's like, oh, things are really crazy at work. And then it just hits you like someone's, like, you know, There's recently been a few instances where my colleagues had personal matters come up and, you know, it's just like, it's just the nature of life, right?

Amy Tilley · 16:32

Yeah.

Jeremy Burrows · 16:33

But whether it's someone that has a stroke or someone passes away or maybe it's, you know, not as serious, if you will, but like you were mentioning, just grieving that career That long-term role that you had and moving on to another place in another position was kind of a tough situation to manage. So talk through your journey with that. And, and yeah.

Amy Tilley · 17:01

Yeah, you know, grief is one of those words that I don't think has really entered the workforce well. I think there's a lot of hesitation with grief just because, you know, Whether you look at it as the 5 stages of grief or you look at grief as being something that's 100% emotional. And, you know, we're still trying to work through emotions within the workforce. What happened with me was a couple of things. First off, I realized after I left a career of 13 years and made a change, I had to accept the grief that I went through. I mean, one of my— one of the gals that works for me, who to this day is still one of my best friends, had worked for me for 12 of those 13 years. Members of my team that I left had worked for me for—I mean, one of them was eight, and the others were like five. I had—I don't think I had anybody at the time that I left under five except for—for one. So for me, I wasn't prepared for—I had the joys of starting the new job, of moving on, and then I did not expect to kind of get slapped in the face with, oh my gosh! I left these people that I had worked with for so long. So I had gone to lunch with a—with a gal that I worked with, and we were talking about it. And why this has really come to be a little bit of a passion of mine is what I also didn't think about was on the backside of it was the grief that they went through when they were left behind. And that was a phrase that she lived. So you left me, we were left behind.

Jeremy Burrows · 18:28

Mm-hmm.

Amy Tilley · 18:29

I'm like, oh my gosh. As we got talking about it, I realized what I don't think we do well in leadership, or we don't do well as, as organizations, especially for assistants, and especially as I can only speak From, you know, supporting a CEO is we have relationships with so many, so many people, and some long-term, some short-term. But we're not good at accepting when those people leave that there's a grief period. You know, oh, we have, we have their cake, their cupcakes, their coffee on Friday. Thanks. Bye. Thank you for putting a 2-week notice in. And then Monday, assistants are supposed to just come back and start their day like nothing happened. And, and that's where I'm trying to wrap my head around how do we support specifically assistants with the grief of people leaving, of assistants who leave roles, especially if they're long-term roles and the people that they've left. But to your point too, also, again, as assistants, we're kind of expected to work with whatever happens daily, immediately when we have coworkers that pass away, when we have family members that pass away. Again, We're allowed a little bit of a short period of time, and then on Monday morning come back and it's like nothing happened and you have to show your face. And I think it would be so beneficial if maybe we started to do more check-ins, or maybe we started to have those conversations with individuals that said, hey, are you doing okay? I know that you had a great relationship with X and now they're gone, and now this other person's coming into the— To the departures and the arrival of people and the grief that the assistants go through.

Jeremy Burrows · 20:14

Yeah. Yeah. What, what was, as you were going through that process, what were some simple things that helped?

Amy Tilley · 20:23

Um, number one, I continued to talk to a lot of people that I you know, had worked with. Um, I still coach and mentor a couple of them. Um, you know, honestly, it was, I think, accepting— I do say it was going a little bit through some of the, the 5 stages of grief, some of it even being anger of like, why on earth did I leave? I should have stayed. What was I thinking? Um, but then on the flip side, being so excited about, you know, what my future looked like. Um, For those that were coming to me that were also grieving, you know, we had those conversations and I still was able to uplift them. So I think you need to be able to find somebody that you continually, whether it's a coach or a mentor, that you can talk through those situations with. And, you know, I just also had to, I guess, kind of pull my big girl pants up and said, you know what, you had a great career, you met great people, they don't have to be gone forever. And, you know, just take the positive and move forward. And that's how I think that's how I personally dealt with it. But I do know that, you know, there's still, you know, people that deal with it differently.

Jeremy Burrows · 21:31

Yeah. Yeah. Well, thanks for sharing. Just switching gears a little bit. I would love to hear your experience with and, you know, coming back to leading a team as well, but professional development and Just growing within the administrative field. How have you, you know, treated that in your career? And then even just how have you helped your team develop and keep growing?

Amy Tilley · 22:03

Yeah, it's— I might get a little dramatic here. Just be prepared. This is a big one for me. I think professional development is probably one of the most important things that you can do for any assistant starting at the beginning of their career, especially like if they're supporting directors, you know, all the way to vice presidents, senior vice presidents, people that want to go into the C-suite. What I struggle with is I don't feel that there's enough there that organizations give assistance. I feel like sometimes we are treading our own water and that if you, especially if you're a new assistant and you don't have a big network or you don't know how to go onto LinkedIn and connect, I mean, I've I've been connected to you for years, right? This is the first time we're actually having a conversation, but you started putting your content out there, so I started following you, right? And so you start to see all of that, and then everybody starts tagging everybody, and it's so important. But where I struggle is that I do not feel that professional development within the administrative field is there from leadership. I just don't.

Jeremy Burrows · 23:12

Mm-hmm.

Amy Tilley · 23:15

I had to do my own. I did, I did my own. I took a number of college courses, um, because they didn't fit into the organization's college reimbursement plan, you know, like—

Jeremy Burrows · 23:25

Yeah.

Amy Tilley · 23:26

That wasn't covered, right? So it was out of pocket. Um, I took a year-long coaching class, so I was a— I had a certified ability to be certified as a coach, executive coach. I didn't do it because I wanted to be an executive coach. I did it so I knew how I could manage my admin team. who was supporting the executives.

Jeremy Burrows · 23:42

Right.

Amy Tilley · 23:42

Again, on my dime. Because it didn't fall into criteria that's there for professional development for assistants. I was successful when I took over and really kind of put my foot down on needing professional development to get their internal leadership courses taken. So I did do 1 or 2 of those internally. But for my team, I felt like I gave them more professional development because of what I learned on the background, because leadership is so important to me. But anytime I could get them into any courses, any classes, anything like that that I could get organizations to approve, I was having them take it, take them.

Jeremy Burrows · 24:20

Love it. Yeah, it's tough because, you know, some people, they think that their organization doesn't support and then they ask and they're like, oh, sure. Yeah, you know, exactly. But then some people, they've been asking for years and, you know, hitting a brick wall. So. Yeah.

Amy Tilley · 24:37

And I will say to this too, that if you don't have— if you aren't somewhere where you can get the funding or things that are needed for professional development, the one thing to always ask, and I'm a big proponent of this too, is ask if you can at least have a mentor. Ask if there's somebody within leadership that you don't support, that's not part of your team, that you can have like a mentor or an internal coach. Because I think that that makes a huge difference. And it also, again, opens huge doors. Especially for like networking.

Jeremy Burrows · 25:09

Love it. Well, Amy, thank you so much for taking time to share your story and your wisdom from your great career. Is there any last, last words you want to share with assistants listening?

Amy Tilley · 25:21

I would just say, I hope that everybody that's listening really, really embraces the role and listens to themselves and projects their career the way that they want it to be for them. That's probably the biggest thing I would love to say to everybody.

Jeremy Burrows · 25:38

Awesome. Well said. Love it. Well, check out the show notes at leaderassistant.com/394. I'll put your LinkedIn and looks like you've got Substack and Instagram. Reach out to Amy and say hi and connect. And yeah, we really appreciate your time and Hopefully we can connect in person someday.

Amy Tilley · 26:02

Absolutely. Absolutely. I'm a Chiefs fan, so I'll be down in Kansas City sometime soon.

Jeremy Burrows · 26:06

Okay. Well, hey, you get me tickets, I'll go to the game with you. That's not— no big deal.

Amy Tilley · 26:11

I'll save you a seat.

Jeremy Burrows · 26:13

Love it. Love it. Well, thanks again. And yeah, keep leading well.

Amy Tilley · 26:17

Thank you. Have a great day.