annie croner round 2 leader assistant podcast

Annie Croner is the founder and CEO of Whole Assistant, an online platform & community, formed to provide a positive place where assistants can go to transform their lives and level up their careers.

Annie was originally on this show back in 2019 (Episode 26), and I’m excited to have her back! As a heads up, this episode is a bit out of the ordinary. How? Well, not only do I interview Annie in this conversation, but she also interviews me. So much for keeping myself out of the spotlight, eh? 🙂

Annie and I talk about burnout, boundaries, confidence, automation, and detaching your worth from your work. Enjoy our conversation!


First be a leader of yourself. Only then can you grow to lead others.

– David Taylor-Klaus


Annie Croner Leader Assistant Podcast New


Annie Croner is the founder and CEO of Whole Assistant, an online platform & community, formed to provide a positive place where assistants can go to transform their lives and level up their careers. Annie has made it her focus to help assistants achieve their goals and manage everything on their plates, while finding freedom from overwhelm and burnout.

Over her 20+ years as an assistant, Annie has worked for boutique companies across multiple industries including accounting, marketing, nonprofit, and private wealth management. Working in a variety of settings has led to a diverse understanding of the assistant role and the many challenges that often come with it. Annie lives in Denver, Colorado where she enjoys green smoothies, her family, and an occasional evening of Latin dancing. To learn more about Annie and Whole Assistant, please visit

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Annie Croner 0:00
Hey guys, this is Annie Croner and today’s leadership quote comes from David Taylor clause. First be a leader of yourself. Only then can you grow to lead others.

Podcast Intro 0:16
The leader assistant podcast exists to encourage and challenge assistants to become confident game changing leader assistants.

Jeremy Burrows 0:31
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Annie Croner 2:35
Thank you so much for having me. i It does feel like forever ago and my company has changed so much what I provide for assistance has changed so much. And like thinking back to those early days, it’s just kind of fun to think how far things have come. I mean, COVID happened I had two babies, just a lot has happened in my life and world since then. And

Jeremy Burrows 2:57
so nothing much nothing much.

Annie Croner 2:59
It just still like forever ago and it feels like yesterday at the same time.

Jeremy Burrows 3:03
Right? Yeah, it’s been great because we you know, we’ve stayed in touch over the years. And you know, we connect whenever I’m in Denver, and yeah, it’s been awesome to watch. Watch from afar and watch the whole system. become whole, I’m gonna I’m gonna go there. Well, I

Annie Croner 3:20
have to say the same for you. I mean, you launched a book since then, you know, like episode 26 was really early on. And so like a lot has happened in your, in your world in your like sphere of influence, too. And it just I love that we get to come together and collaborate and have this discussion we’re gonna have so yeah, it’ll be fun.

Jeremy Burrows 3:40
Likewise. Yeah, it’s exciting. Awesome. Well, let’s jump in. Oh, actually, you know, the other thing I wanted to say that’s that’s fun about this conversation is I’m not going to simply interview you, Annie. I’m actually going to do that. Yes, of course, I want to hear hear all about what’s going on. But I’m then going to hand the microphone over to you and have you interview me because you actually have a podcast now since last time we talked. You didn’t have one and now you do. Called the whole assistant podcast. And we’ll hear more about that here in a second. But So yeah, those listening buckle up, it’s gonna be fun to have a conversation to a interview, if you will, for this episode. So let’s let’s jump right in. So Annie, tell us a little bit about your careers and assistance kind of give us the high level summary. I know people can listen to our last conversation on Episode 26, which is at leader Six. But for those listening who missed that episode, or are too lazy to go back and listen to what’s tell us about how you became an assistant and you know, give us the give us an overview

Annie Croner 5:00
Yeah, so I became an assistant, I actually started my administrative professional in college. And it’s partly what I did to pay the bills, I also waited tables, like most of us tend to do at some point. But I was a theater student, and I ended up working in the theatre office. And then after I graduated, I moved to Boston to start a theater with a group of friends. And just I met my mentor and, and I, in my role as a receptionist at the time, and I just saw how much respect my my boss at the time had with her executive, she was executive assistant to the CEO. And I just saw their relationship. And I’m like, That’s what I want. I want that mutual respect. I love that she was his true confidant, I love that she could also point out things to him that nobody else could, I love that she was kind of like the bridge between him and the rest of the company. And like, that’s what I want to be, I want to be that person that can like strategically partner with my executive to add value. And so 20 years later, here I am. And I started hold assistant, because I had this really kind of severe burnout. And I wanted to keep other assistants from that. And so that’s what I do, I coach assistants now to help them to avoid burnout, but also to level up and add value while remaining free from overwhelm. Because I’m sure you know, Jeremy, like we all contend to get overwhelmed from time to time, circumstances and whatever. So So yeah, that’s, that’s what I’m passionate about. I feel like, I feel like I just barely ended my career as an executive assistant, where I was supporting one high net worth person had been for the last five years. And I was kind of explaining to you Jeremy off offline, like off air, that I kind of worked my way out of a job. Like I have so many processes, processes and procedures, I found all the vendors to manage, like the various aspects of this person’s life. And then at the end, I’m like, Okay, well, I don’t really, like I don’t really have much more to contribute. So. So I now I’m coaching assistants full time, and I love it. It’s a lot of fun.

Jeremy Burrows 7:19
Wow, that’s great. And I love what you said about, you know, you unfortunately had that, that overwhelm and that burnout in your own story. And that’s what caused you to want to, you know, help other assistants avoid that. That’s really the same thing that happened to me in 2016. My executive was, surprisingly, and unexpectedly fired. And I realized I was burned out, he had burned out. And I was like, alright, what am I going to do? And, you know, the short version is, I realized that not only did I want to avoid making the same mistakes and burning out again, but I wanted to help other assistants and executives avoid the same mistake. So that’s I think that’s one thing that I’ve always appreciated about you is that you’re passionate about that same idea of, listen, you know, we only have one life, and we, we can be good assistance. If we don’t worry about self care, but we can’t really be great assistance, we can’t be leader assistance. If we avoid self care. And if we if we don’t pay attention to the fact that hey, you know, we’ve got to take care of ourselves, just like the quote that you said, that you read at the beginning of the episode. First, be a leader of yourself, only then can you grow to lead others. And so I think that’s one thing that I’ve always appreciated and respected about you. And we have that connection of like, we both burned out. And we both want to help those listening. Avoid the same mistakes.

Annie Croner 8:51
Yeah, definitely. Definitely. And there are some common pitfalls, right, like, there are some kind of things that most of us tend to do. One in particular, I think, you and I have spoken and we touched, we actually connected on this a while back about detaching your worth from your work. And I feel like if we can master that, like the world is our oyster. Yeah. Because then you can then you’re adding value from such a cleaner place than if you’re, if your self worth is all wrapped up into your role, right? Yeah. So I would love to hear your thoughts on that and like your experience with that and just kind of I’m just going to take over the interviewer role. Sorry. I would really love to hear your thoughts and your and your and your take on that. And I love it and riff about that a little bit. Yeah, no,

Jeremy Burrows 9:38
this is great. So yeah, so you know, detaching your worth from your work. I think my kind of the, if I go back to my last organization I was working at and my role supporting executives kind of in the middle I have that time I was there for 12 years. And in the middle of that time, my, my, actually my dad had this short version is had an emotional affair, lost his job losses, community lost, his friends lost everything. And I kind of saw that as like, Okay. And then he went, he went off the deep end, you know, depression and suicidal thoughts, and it was just a rough rough several years. And I, I remember thinking, okay, what can I learn from this scenario? And what, what I noticed was essentially, the short, shortest, obviously, there’s a lot of layers, but the shortest way to describe it is that my dad had placed his identity and his worth, in that job that he had in that role that he had, and when it was taken away, when he lost it, it was like his life hardly felt worth living. And so, you know, I’m sitting here looking at it my job at that prior organization, and I’m thinking, okay, am I doing the same thing, and I started seeing the similar tendencies. Seeing like, okay, you know, I’m actually putting a lot of my worth in my work. And so one thing I did was, I wasn’t great at it. And, you know, the next six years is when I kind of really just burned out and I went, work too hard. And, you know, I wrote a book, most of my book is about all that mess. But I remember having that in the back of my mind, okay, I can’t let this job in this role, define who I am, and really equal my worth as a human being. And so I used to almost like, tell myself, if I lose this job, it’s okay. Like, I would, I would just be like, if I get fired, or if I lose this job, it’s gonna be hard, but I’ll be fine. You know, and it was almost like a way for me to guard against what happened to my dad. And then unfortunately, you know, of course, I got in, I got the senior executive assistant role. And it was just like, I went to a whole nother level. And I was just working like crazy. And I burned out. So I, I wouldn’t, it was weird, it was like, I, instead of attaching my worth to my role at that organization, I started to attach my worth to the approval that I was getting from that executive. And if I didn’t get that approval, then, you know, I felt like I wasn’t worth it. And so that’s what drove me. And so I talked about this at a did an event in Orlando recently. And my whole topic was about detaching your work from your work. And one of the examples I shared was, you know, I essentially cared more about the approval of my executive than I did, my family. And, you know, obviously, this sounds obvious when you when you hear me say that out loud, that that’s a bad recipe. And so that, but that was my slow cooker recipe for burnout. And yeah, so anyway, that’s kind of a semi short version of it. I feel like

Annie Croner 13:41
I have a similar story. Like, you know, my, my, I’m not gonna go into my my story of burnout, because really dramatic, but I will say what led up to the burnout was people pleasing, and trying to make everyone in my life around me happy. And, and so like, I was in a failing marriage with a partner who was gaslighting. And like, there was a whole bunch of like, emotional abuse there. And I was in a location that I had only made one friend and five years, I was working a job that was really demanding drink, I was this EA to the CEO of a tax firm, during the middle of tax season. And I was trying to make everyone in my life happy. And what was so frustrating about it was that, like, if, if I got if I was able to actually accomplish making everyone happy, like I just still didn’t make me happy or fulfilled. And then, but more often than not, people still weren’t happy, because they’re people, they have their own interpretations of things. They have their own ways of viewing things. They have your own ways of thinking about things. And so really, what I was trying to do was to control them to feel some sort of inside thing in me that needed feeling instead of actually looking inward and focusing on what do I actually need here. I was trying to make everyone in my life happy. And then that led to a really intense like episode, like physically for me, to where it took me out of my job for a few weeks and like I was demoted. And all sorts of crazy things happened as a result, but like, and as I like, that, that entire next year, I lost everything, like, I lost, my mirrors got pushed on my job move back in with my parents, and it was like, rock bottom. But what’s great about it was that as I kind of built my life back up, I got to make intentional choices, because there was no other option. It was like, I feel like it was God’s grace for me, actually, because he’s like, Nope, we’re not gonna do that, you’re gonna look here, reset, like, she just kind of hit the cosmic reset button. And it was just like, No, we’re not even going there. And so grateful it happened, because now I’ve kind of set up systems for myself. And I’ve created boundaries for myself, and set parameters around my time and energy and like, really have been intentional about piecing my life back together. And now I know that my self worth comes from within and from God. And so like, instead of looking for, instead of looking to the all these outside people, my executive, my husband at the time, like everybody in my life that I was just trying to, like, take care of him. Like, I think we can all relate to this, right? Because it’s really easy if we’re not careful to slip into that as assistants because it’s literally our job to take care of people, and to make sure that they have what they need. So how do we do that, and not kind of slip into this pattern of like, people pleasing, which I define as like, making other people happy at your own expense, really. And it can be really hard and it does lead to burnout. 100% leads to burnout, because you aren’t actually taking care of yourself or like being intentional about what you pay attention to, and how you how you’re viewing how other people interact with you. It’s all about trying to control them to feel something inside of you.

Jeremy Burrows 17:07
Yeah, yeah. Yeah, one of my favorite quotes from Dorothy Sayers that I included in my book, she talks about how, you know, if the community as a whole is going to thrive, then the members of the community and I kind of use the parallel to career friends or you know, a company then, but basically, if the community is going to thrive, then we have to stop. The community members have to stop angling for applause. I love the term that she uses. Yes. And you know, I talked about like, oh, you know, when you’re in the office, and you run, get to fill up your water bottle, but you go the long way back to your desk, because you want to sum you want so and so to see that you’re like, busy and you’re working and you’re like, it’s like you’re you’re you’re angling for that applause and you know, the community doesn’t thrive, when that happens. And when it thrives, when, instead of angling for applause. The members seek to serve the work and do good work for the sake of, you know, producing good work, not for the sake of people pleasing and approval and all that. So what practically, though, Annie has helped you, you mentioned boundaries? What’s what’s one or two practical tips for those listening who are like, I’m burning out and I need to I need to do this. You’re right, amen. Keep saying this. But what do I do? Like practically speaking, you have boundaries? Like, what do I how do I set boundaries?

Annie Croner 18:49
This is a really good question. And it’s one we get hung up on a lot, because there are lots of misconceptions around boundaries. So I’ll break down like the two most common The first one is that boundaries has to be confrontational. Like most of us, when we envision setting a boundary, we envision merging into someone’s office and laying down the law. But that’s not actually what a boundary is. A boundary is a choice, that choice that we make, and how we decide to show up for ourselves every day. So for example, if you want to leave the office at five o’clock, and you’re just like, okay, at five o’clock, that’s when I’m going to leave and you have the discussion with your executive, maybe you’ve been working late, maybe you’ve just decided that you that you’re going to leave after your time is up five o’clock comes 530 Whatever it is, I’m out the door, and 530 rolls around. And you don’t honor that. Now there again, it’s it’s about showing up for yourself in that moment, right? If you actually don’t leave then what you’re saying essentially, is that your boundary isn’t exactly your boundary. So it’s more about how you decide to show up for yourself every The day and it may create a circumstance for somebody else. But then they get to decide how they show up for that. So it’s really about showing up for yourself every day, and then also recognizing that people are going to have the response to it. But I think the the person who has a hardest time holding the boundary is yourself. Because we have all this mind drama around what’s going to happen, like we’ve set this boundary. And now we are in now when it comes to holding it like another one is checking emails after hours, right checking, responding email after hours. So it’s like, your executive may write you an email, and you just feel like this urgent inclination to quickly respond. That’s training your executive, that you’re going to respond to emails after hours, and then we then we wonder why we’re getting burnout and having to work all these hours. Well, we train people on how we’re going to be treated with every interaction. So boundaries don’t have to be this like, really confrontational thing. It’s really more about how you’re deciding to show up for yourself.

Jeremy Burrows 21:01
Yeah, cuz it’s like, hey, you know, don’t don’t email me at eight o’clock on a Friday. Well, you can’t control whether or not they’re going to email you eight o’clock on a Friday, but you can’t control whether or not you’re going to reply to that email, or check your email at eight o’clock on Friday. So yeah, well, yeah.

Annie Croner 21:18
Yeah, yeah. It’s not about controlling other people. And I think often we think it is like, Oh, well, but what if, what if? What if? What if he calls me or whatever? Okay, well, he gets to choose how he shows up, but you get to choose how you show up for it. Yeah. Oh, so? Yeah.

Jeremy Burrows 21:33
Well, one thing I wanted to ask you about? So you know, we mentioned early on in the conversation, you’re a lots changed since we talked a few years ago on the podcast, and, you know, you recently left your assistant role. And you’re going all in on full time coaching assistants. So tell us a little bit about coaching. So what, I guess to two questions, one, why coaching, so for those listening, like, they’re thinking, like, I don’t need coaching? Or maybe I do, but why? Why would I? Why would I need coaching? And then two? Could you give us a little bit of insight on what a session might look like?

Annie Croner 22:22
Yeah, so my wife would become a coach. Back when I was pregnant with my son, my first baby back in 2019, I hired a coach because I know myself. And I know that I was having a lot of anxiety about not working when I was on maternity leave. And I also knew that I would be totally wrapped up with this little baby. And I just wanted some help with my self care. And I wanted some help kind of reframing my relationship to work, and also kind of being intentional about my relationship as a mom then. And so I hired a coach, but I was really looking for a coach who had been an assistant before who was coaching about self care, you know, and I wasn’t finding it anywhere. And so I’m like, okay, so I ended up finding a coach who, I talked her into working with me, although she was working like with virtual assistants on certain them starting their business at the time, but I’m like, you used to be an executive assistant, can you help me? And she’s like, yes. And so she actually saw me all the way through COVID. Like, we had no idea what was coming at the time, she saw me through the birth of my son, through the first few months of COVID. And like juggling a baby and a full time job at home, like, while being sleep deprived, all the things. And I just found that experience so transformative. And like, that’s it like, I cannot, I cannot not become a coach. And I cannot not help assistants manage everything on their plate and remain free from overwhelming burnout. Like, I there is a way to do it. And I’m going to help assistants do it. So when when an assistant starts to work with me, we always do a values, a values assessment, so that we can get clear on what they’re valuing at that point in their lives, because values should shift and change over time. So we’ll get clear on what their values are. And then we’re going to create goals for our time together. And then from there, we just start taking action on the goals and I I’ve been trained as a mindset coach. So we deal a lot with thoughts that come up about inadequacy, lack of confidence. I can’t do this is too hard, or it won’t work for me. So we deal a lot with like that kind of way of thinking and we kind of flip the script, we work to flip the script. So I hope that answers your question, Jeremy. I hope

Jeremy Burrows 24:52
no, yeah, that’s great. What what’s maybe one tip or in sight that you give to your clients when when they say, How do I get confident? How do I get more confidence?

Annie Croner 25:09
Yeah, this one is, it’s hard because there’s like two types of competence, right? There’s like the type of confidence that comes from doing things a million times. And then there’s a type of confidence that comes innately that’s like, I have never done this before. But I can figure it out. And I’m sure I’m sure, like, I’ve got this, even if you’ve never done it before. So it’s just a matter of, I think, first of all, having them recognize what they’ve done a million times before. I think so many of us think that anybody can do our jobs, I think because it just is so innate, with most of us, like how we show up for our roles, how we break things down and into steps, how we conceptualize things, how we can see things 10 steps out. And, but common sense isn’t really common. And so it’s a matter of helping them see no wait, you know, your stuff, which is why you have a seat at the table. And you’re different, which gives your gift, which gives you your edge at that table, instead of like, I don’t belong here, you know, so it’s really about, like figuring out their unique skill set. And then how can we view that as an asset to my executive and organization, even though we just take it take those skills for granted? And once they can see that, then confidence automatically boost? In my opinion, I found was my people, what about you, because you coach to, like, what have you found to be really confidence boosting for your clients?

Jeremy Burrows 26:37
Yeah, I think, well, first of all, I think that’s great, great way to look at it. And, you know, I, I just, I’ve always respected you. But I think I think I respect you as a coach even more, just because you’ve just of how much work you’ve put into it, how much experience you’ve had with it now and how much even just training you’ve you’ve, you know, put yourself through the wringer. And so I really respect that, so props to you. I think, you know, when I, when I talk with clients, I talked with him the other day, and, you know, she was like, Hey, I, I just want to do more, I just want to do more. And I’m like, okay, you know, how was your last performance review? And oh, it was great, you know, what’s your executive thing? Oh, they think I do great. And, you know, I noticed it’s like, okay, well, what’s what’s causing you to want to do more and long story short, to kind of tie it back to what we were talking about earlier, it came down to the people pleaser mindset, and, and she was seeking the approval of her executive and what I see often in what I saw on my own, and still see in my own life, if you are, if you attach your worth to your work, or if you attach your worth, to the approval of your executive, for example, to get a little more specific, then you’re never going to, you’re never going to be satisfied, you’re never going to get enough approval if you the more approve, the more approval you get, the more you want. And so that’s what I find a lot where assistants are really crushing it, they’re, they’re doing a great job. They’ve taken a bunch of training, they’ve leveled up, they’ve automated things, they’re doing all this stuff, but they still feel like oh, I need to be doing more. And it’s, it’s, it just comes back to I don’t mean to sound like a broken record, but it keeps coming back to they’re attaching their work to their job as an assistant and, or the approval of their executive. And so what I tried to do is get to the root of okay, why do you feel like you need to do more? Why do you feel like you’re not worth it, or you’re not as good of an assistant as you need to be and all that. And then that kind of helps illuminate and, you know, uproot? What’s actually holding them back. And what’s keeping them from even just being content in their, in their role and in their work. So I don’t know if that helps answer your question.

Annie Croner 29:19
But no, it totally answers my question. And I feel like I’ve coached I’ve coached in similar situations where I actually I’ve been on Discovery calls before and I’m like, you don’t need a coach. I flat out told them like, You’re doing a great job. That’s all you need to hear. And that’s all you need to know like, you’re already doing all the right things. Yeah, I actually spoke at a for a company up in Seattle, and there was a gal there who I’d had that conversation with and, and, and I sought her out because I knew she was gonna be there. I’m like, Hey, how’s it going? She’s like, you’re the person who told me that I didn’t need a coach. I’m like, because you don’t. You still don’t you’re you know, everything’s like You’re doing all the right things. But I think sometimes, sometimes that’s all they need to hear, like, they just want, they just want to have somebody tell them that they’re doing a good job. But here’s the deal, you can provide that for yourself anytime. Right?

Jeremy Burrows 30:15
Yeah. Well, you know, the, and I think the reason there’s a desire is unfortunately, their work for executives or teams that that are vocal about it, you know, and so it’s, it’s always a fine balance, because it’s like, people say, Well, Jeremy, like, it’s good to have the approval of your executive, isn’t it good to, you know, get that affirmation from them? And I’m like, Yeah, that’s totally great. It’s great to have an executive that likes you. And that, you know, is thanks for doing a good job and all that. But I come back to there’s a quote from Dr. Timothy Keller, where he says that the main The problem is, and I’m going to mess up the exact quote, but basically says the problem isn’t that our hearts desire, bad things, it’s that our hearts over desire good things. So it’s not that like the approval from our executive is a bad thing. It’s when we make that the ultimate thing and when that’s what we attach our worth as human beings, to, that’s when we get messed up. That’s when that’s what holds us back from really being free to lead like we can, we could lead and can lead.

Annie Croner 31:30
I also feel like, there’s a difference between inserting yourself in your executive shoes and looking at things from his vantage point, and inserting yourself in his in your executives mind and trying to like figure out what he’s thinking about you and figure out like, all the things that way, right, it’s like, it’s like, when we’re inserting ourselves in our executives, shoes, and we’re trying to show up to create value, it can be really helpful to look at things from your executives vantage point of perspective, so that you can anticipate what they’re going to need next. So you can get a bird’s eye view and kind of point out holes. But then we kind of cross over to this dark side of like, oh, my gosh, I wonder what do you think and about me, he didn’t say thank you, the last year did this and that, or he was really short with me or whatever. And then we make that mean, something about us, too. It’s not just the accolades, like, we tend to, like, try and get up on our executives brain business. Instead of like, well, he’s in a place today, okay. You know, and just like leaving it that instead we’re like, oh, my gosh, what did I do? What did I say? What did I you know, it’s not, that’s not adding value. And so even that is like, we spend so much time and energy trying to figure out what he’s thinking from, like, a place of insecurity, instead of deciding that he can show up, however, he’s going to show up, and we can always show up and add value and be there.

Jeremy Burrows 32:55
Yeah. Yeah. It’s like, Oh, is that over analyzing? Right, you know? Yeah. Well said. Well, I think a good this has been fun conversation, I think a good segue. And I do want to let you kind of drill me with some questions. I think a good segue, though, would be I want to talk about automation. And you mentioned, you know, you’re leaving, you left your assistant role. And part of it was like, oh, you know, I set up all these systems and processes. And it’s like, you know, I kind of worked myself out of a job. So what was Was there some automation and AI involved? Was it workflows with Zapier? Or was there anything like that, that you use? Or if not, is there something to us now, that helps you with as far as automation and technology?

Annie Croner 33:42
Yeah, it’s funny that you asked that, because I was just having a conversation with Melissa peoples. And we were talking about what is it? It’s like, oh, chat, GPT GPT Oh, my gosh, it’s the most amazing thing ever. Like,

Jeremy Burrows 33:58
they just released a new version too. So yeah, so like,

Annie Croner 34:01
if you write a lot or anything like that is brilliant. Like, all you have to do is give it the themes, and then you have of course, have to go back and edit. But that is within one tool that I’ve used this week with a lot of my copywriting and stuff like that, but I think in terms of my executive, I really was big into Trello and I had things hit my board on automatic, like on repeat a lot like I had. So I had my Trello board, like lined up and you can go to my website, I actually have a free Trello training if you want to take it but on how to set up your board. But I use automation in my task management system and I would just have like every month but at the same time, you know expense reports will land on my to do list automatically. Or sell and like you know, credit card reconciliation with Lana and then quarterly same thing and then I had annual reminders my executive as well. So those like reminders that we’re reaping He on repeat, we just automatically man on my task list. Without even me thinking about it, which I love. It’s just it’s such a great, anything that you can do to streamline your life like that is just, I’m a fan of great. And I tried to get my executive into Trello is not wasn’t his jam, which I’m surprised about because he actually made most of his money by creating an app. And I’m like, he is gonna love this is not like that was not his jam. But like, we we cater to our executives and we go with their communication style. So I communicated mostly via email with him. But like, I do think that anything that you can do that way to streamline especially, I had tasks for like, I managed his entire estate and everything. So I had tasks when it was time to clean the windows and like all those things would like auto populate on my task list. Just streamlined everything. So anything you can do that way is awesome, because it’s just one and done. Yeah.

Jeremy Burrows 35:58
That’s great. And then, you know, as you’re now a podcast host whole system podcast, have you been able to embrace and utilize different automation for your workflow for the podcast?

Annie Croner 36:13
I mean, no, not yet. I would love to hear your automated screw your podcasts. Oh, my goodness. That’s a whole conversation in and of itself. Jeremy, for sure. I would love to hear. I would love to hear about that. Do you have do you have any podcasts like automations that you use?

Jeremy Burrows 36:30
Yeah. So I just found a new tool that uses some chat GBT open AI stuff. And it’s called swell AI. And I’m still they’re pretty new. And they’re updating the product pretty much every few days, it seems like so I’m still kind of figuring out exactly how I want to use it. But essentially, you can upload a podcast episode. You know, you can upload the mp3 or you can link to the to the Apple URL, RSS feed, whatever. And it will spit out within a matter of minutes. it’ll spit out a transcript of the podcast. Oh, wow. A summary. Like a short, like, you know, one or two paragraphs summary of the of the episode. It’ll spin, it’ll actually spit out an article written about the episode once and then it’ll spin and it’ll spit out like a LinkedIn post. And there’s, I think there’s one other thing that it does, but it creates all this content based on the episode. And I’m, I’m starting to use it, I’m starting to test it out. Um, my plan is to because I don’t have transcripts of my podcast, because in the past, it was like, $1 per minute just to be expensive. Yeah. And I’m like, I’ve turned it in. Well, this is 219 Episode turned 18. So 218 episodes, I’m like, that’s you do the math 30 to 45 minutes an episode. That’s a lot of money. So now, I will say the AI transcript is rough around the edges. And you know, there’s definitely some editing that could be done. But anyway, it’s, I’m all about repurposing the content that I’m already putting out, because I think that it can be consumed in different ways. Anyway, so I’m pretty excited about that. For the for the podcast, in an otherwise I’ve really, I’ve really, up until now, I haven’t used a lot of like aI automations. But I do have very simple workflows like, you know, or tools that I’ll use like Dropbox to save them. As soon as we’re done with this conversation. I upload it to Dropbox and make sure it’s backed up that way, if my computer crashes or something, I don’t lose anything. Yeah, I’ve got I use, like scheduling. So my podcast hosts my website, my community circle, has the ability to schedule out a schedule ahead posts. And so when I edit a podcast conversation, and I upload it, I go ahead and schedule it to publish at a certain date on my blog, scheduled to publish at a certain date on it, but so I don’t have to like, wait and do it on that day. And so those kinds of things are nice, too. But I’m excited about the swell AI tool. And I’ll definitely keep you posted as I figure out how to.

Annie Croner 39:28
Yeah, let me know that sounds awesome. Use it. So

Jeremy Burrows 39:32
yeah, go ahead. what other questions do you have for me

Speaker 1 39:34
I have a question for you. And this has actually come up several times, especially like I’m very active on LinkedIn. And this has come up in several LinkedIn conversations with people and people actually want. I’ve actually like, crowdsource podcast ideas. I just I’ll ask people to like so what do you what should I create an episode about and they actually brought up like, what do you do if you’re like an executive assistant to the CEO, and there’s nowhere to go? And like how do you create a path for success as an assistant? And I would love to hear your thoughts about this. And I would love to hear kind of your overarching, I have my own opinions about titles, but like, I’d love to hear your opinions about titles and career paths. And like, what do you do if you’re at the top? And you want to take your career to the next level, but there is nowhere to go in your organization? I’d love to hear what your thoughts on that are?

Jeremy Burrows 40:25
Well, yeah, this is good, good. Good stuff to chat about. More fun to chat about at happy hour, but you know. So I think that I’ll, I’ll take it from a couple different angles. So first titles, I was talking about titles. I know there was some recent hubbub about an article, I think it was the Wall Street Journal, talking about titles, or maybe it’s Bloomberg talking about assistants not wanting to be called assistants or something like that. And I’ll just say this, when it comes to titles and career paths, I don’t really care what my title is, I don’t really care what you call me, I don’t care if you call me an assistant, I don’t care if you call me a business partner, or Chief of Staff, whatever it is, what I care about are two things. One, the job description, aka what I’m actually doing, and to my compensation. So like, I care about what I’m doing and how much you’re paying me to do it. And if that, if that means, like, if I’m in a traditional organization that has a bunch of levels already planned out, and it means that I can’t make more money, unless I’m a Executive Business Partner three, or unless I’m chief of staff or whatever, then yeah, I care about title and I want to work my way up to that next title. But if it’s, if it’s an organization that doesn’t have any sort of career path, and I have to kind of self managed, and I have to figure it out myself and figure out okay, what’s the next step? How do I get this? How do I present a business case to make more money, and to have more bonus or more compensation, whether it’s, you know, PTO, or cell phone stipend or all the different things, then I don’t care as much about the title I care more about, okay, what is going to work for this organization for this team. And if that’s, you know, what, I can do this, this and this, look at the job description I was hired for, look at what I’m doing. Now, I don’t care about title, if you don’t have a, if the HR doesn’t, department doesn’t have a bucket for it, then fine, just pay me more. And I’ll keep the same title, you know, so I’m still an executive assistant, I’ve been at my company for I guess we’re going on, this is the seventh year now. And I was hired number one, now we have 110 115 people or so. And I’m still the only assistant I’ve not gone from like a administrative assistant, one, two administrative assistant to two administrators, you know, like, but I’m in a computer software AI company, that’s a startup that has, moves a lot quicker. And there’s a lot more fluid than maybe if you work at Google, or if you work it in a university or in the government or whatever. So, anyway, that’s, that’s kind of what I’ll say about that. And then as far as like, Okay, you a lot of people could look at me and say, Alright, you’re the executive assistant to the CEO. There’s no other assistants. So it’s not like I can say, Oh, I’m going to be the Director of administration. And I’m going to manage five assistants. And that’s my next step. Yeah. What’s the next step? Well, if, if I, let’s say, my company grows over the next, which hopefully does over the next few years, and we hire a few assistants, and whatever, okay, there may be an opportunity down the road where I could be more of a chief of staff where I’m managing a few assistants and, you know, on the board liaison, and all this stuff, which I already do a lot of that anyway, but then that’s one thing, but right now, it’s like, okay, there’s not, there’s not really a next step. So if if someone listening is in my shoes, then the questions that I asked myself, and then I would ask yourself, if you’re listening, you’re thinking, right on the EAA, the CL, there’s nowhere else to go. There’s three questions that I would ask. One is, do you really want to be an assistant still? Do you still want to be an executive assistant at a high level? Or do you want to move into operations or move in HR or move into product or move into, you know, finance, whatever. So that’s, that’s a question to ask yourself. And that’ll that’ll determine that’ll kind of help you guide you where you’re going to what you might do next second question is, okay. Are you enjoying it? Are you? Are you in a good place? Do you like the team? Do you like whatever? Is it simply you just want more money? Like, is it just about the money? Like, you’re just like, I need to pay my house off? I need to save more in my retirement. And I just want to make more money. Okay, that’s the second question. And then the third question is more of an open ended pushback, if you will, is okay. Is there something that I need? Am I bored? Essentially, am I bored? Or is there something outside of my day job, that I have interest in, that I could do maybe a hobby, maybe a hobby that turns into a side hustle, maybe just do straight into a side hustle, you know, maybe go back to school, maybe take a, you know, a class on pottery, maybe do some Latin dancing, you know, whatever it is? Like? Is there something outside of work that you could do? Because a lot of times, they’re like, they’re like, I’m just not challenged enough and whatever, and I get that. But could this be a really good opportunity for you to go back to school for you to learn the guitar for you to teach yourself how to, you know, how to bake, you know, all this kind of thing. And that can actually, oftentimes, I see with my coaching clients is, oftentimes that’s all they needed, they just needed something outside of work, to challenge them and to stretch themselves. And and that made it that made work more fulfilling, because they see that like, Oh, my life isn’t just this job. So those are kind of the three areas that I think through. And I really think that there’s a lot of opportunities to make more money without a title change. And even if you think you’re hitting that cap, if you’re in a booming industry, if you’re in a growing organization, that’s got a lot of revenue, and it’s, you know, that’s cashflow positive, and it’s, you know, maybe it’s a publicly traded company, the stocks been going up even in this rough macro environment over the last few years, then I think there’s actually a lot more opportunity than you think it may not be a salary bump, it may be equity, or stock compensation, and maybe bonus, you know, Spot bonus I talked to one of my clients went from, they did get a title change, they did get a promotion, and they got a spot bonus. And it was just like, oh, wow, this is awesome. Like, this is your salaries still the same for now. But you get the spot bonus, and you get the title change, and you can kind of work your way up to the next level. So anyway, those are kind of all the things I think about. When I think about titles, levels, am I hitting the hitting the cap? And then really, ultimately, for a lot of you listening? It’s simply you need to go to a bigger organization that has more of a career ladder, if that’s really what you want. And I do outgrow the organization.

Annie Croner 48:14
Yeah, it’s funny, because like, Y’all couldn’t see it, because this is a podcast, but like, I was literally nodding the entire time period. He’s talking like, yes, yes, yes. Because I think I have similar viewpoints, people get really caught up on titles. And I get it to a certain extent, like you said, if it affects your compensation, something like that, it makes sense. But like, most of us, a lot of us it doesn’t. And yet, we still get hung up on a title. And, you know, I think, in my last organization, I worked at it a VC firm. And there were eight people in the entire company. And my title was executive system, because there were two other managing directors other than my executive, and they had executive assistants. And each of our roles was vastly different. We each did vastly different things for our executive, I did a lot on the personal side on the on the state management side. And one was strictly business did a lot with Alta, the company I worked for, and the other one was managing this guy’s entire life. So it’s just like, it runs the gamut. And I think that’s what’s so great. And what’s so challenging about our roles is that the term executive assistant can apply to so to a vast array of different things right? But I didn’t get hung up on my title even though I’m like running my own tech is like it isn’t how tire world like I knew my worth. And like, there again, that outside thing didn’t really matter to me because I just knew I was just so focused on adding value and focused on on like taking a bird’s eye view and then getting down in the weeds of it and then taking them as I was I was calling instantly, like, going and taking, like, macro, micro, macro micro just constantly in and out, you know, to try and like streamline everything for him. So I think I and then I also took a class in finance. And then I took like a set of courses in project management because my executives brain is just so the theoretical that I thought it may be helpful to kind of have a framework in terms of project management, you know, just so that I could like, frame out the projects that were going on and everything like that for him and like a really calculated way. So I think there’s a way to stay engaged with your work, even if you’re kind of like, well, I’m bored. Well, don’t be bored, then. It’s like, yeah, pretty curious. Like, what what can you do that will still add value to him and I like, I’m all about the Latin dancing to, like, that’s my go to. So definitely take Latin dancing class, your personal life. And then also like, in your work life, ask if there’s anything that kind of piques your interest and just ask you, for your company will pay for it? Yeah, so I don’t understand this whole thing of being bored at work. Like, I don’t get it. Because there’s nothing we can do.

Jeremy Burrows 51:17
Yeah, and I will say that there’s there definitely plenty of people listening who are in tough situations. You know, single mom, who has been in this organization for a while, and there’s, there’s kind of a recession, macro market environment going on. And, and jobs are tough. And it’s, it’s a, it’s a big, you’ve got benefits, and you know, you’ve got insurance for your kids. And, you know, there’s, it’s a big jump, you know, I’m not saying it’s easy to say, Okay, this job, doesn’t have any room for me to grow, I’m just gonna go find another one. But I think that there are definitely opportunities to find that next opportunity while you’re while you’re still doing your job. And I think that people don’t, people still are pretty one one track minded, or however you say that where it’s like, I have one job. And that’s my option. And I think that the world has changed to where multiple streams of income is becoming more and more, not only necessary. But actually, there are more and more opportunities and ways that you can create multiple streams of income for you and your family. And so, I think that is where a lot of assistants who are worried about titles can and should, in my opinion, put their energy toward and instead and you can, you can work hard at presenting a business case for a raise and negotiating your your worth at your current job, maybe a title, title bond, if that’s what’s your organization needs to get you into the next salary band. But you can also work toward how can you make money outside of your, your day job, and so that you’re not so reliant upon? You know, you don’t have all your eggs in one basket?

Annie Croner 53:23
Yeah, that’s a really good point. I do think that when we think outside the box, and that way, the whole world opens up for us, there’s like a whole world of opportunity. And so it’s a really creative way of thinking that I would encourage every everybody who’s listening right now to really consider like, hey, wait a minute, like, I do feel kind of stuck in my position, I don’t want to leave because of X, Y, or Z, I have a really good job overall, and just kind of feel like, they just can’t sit still on my kind of twiddling my thumbs here. Like, you can look for opportunities in your organization to add value. Like if there’s a project that interests you, you can speak up if, like, you can also look for another stream of revenue for you, whatever that is. And I would challenge you to also think about like a stream of revenue that does not require a whole lot of time to manage as well. Right? Yeah. Like like really get creative and how you’re thinking about this because there are ways like a portfolio life right Jeremy so like, I think that you’ve done a really great job of that in your life with your full time job and the book and like all these like, supporting our broader student community. And I think I think that we can all kind of take like a page from from what you’re doing and actually ask ourselves, okay, what can is there somewhere else in my life that I can add value to were people that people will pay me for?

Jeremy Burrows 54:48
Yeah. It can be as simple as okay, what are people asking me for? What what are people coming to me for help with and that could be or, you know, what, what, what some people think, are or what you think, is obvious, is extraordinary to other people. And so, and I think that, you know, that’s one place to start. And it could be as simple as, you know, I’ve helped so many assistants, or I’ve helped so many of my colleagues set up a Trello board, or I’ve helped so many colleagues figure out how to set up their outlook settings in a certain way, that’s way more efficient. You know, what if I put together a little ebook on how to do that? And, you know, I sold it for 1520 bucks, and I sold a, you know, coaching session where I walked through how to do it. And, you know, there you go, like, there’s a, there’s a little revenue stream that you who knows what could happen with with it, you know?

Annie Croner 55:56
Yeah, exactly. Exactly. I love that out of the box thinking. And this has been such a fun conversation. I also wanted to add, maybe we can do it again. And like two years, Jeremy, yeah, there

Jeremy Burrows 56:05
you go two, three years, every two years or revisit. So what So what is the best place for people to reach out to you for my listeners, and then we can flip? Yes, I

Annie Croner 56:15
definitely want to give to my audience too. So you can reach out to me on LinkedIn, I’m very active on LinkedIn, at any dark corner on LinkedIn. Or you can email me Annie at hole And I just love to connect with other assistants, you know, so whether it’s through through LinkedIn, or via email, or, you know, I also am coming out with a new freebie for my website. And it’s going to be a work boundary work boundaries inventory. So if you really want to deep dive into your work boundaries, and you really want to ID and create clear boundaries for yourself, please check that out as well. And that’ll be up on my website by the time this podcast goes live. So So yeah, please, please check that out. And yeah, I just want to be a resource for you. I want to be here for you. So feel free to reach out to me anytime. And for my listeners, I’m sure you’re all familiar with Jeremy. But for those of you who aren’t please Jeremy, can you please share how they can get in contact with you and how they can learn more about you?

Jeremy Burrows 57:23
Yeah, I think the simplest place to go is just leader And check out the podcast. The book, I also have a workbook, a digital PDF workbook, or a Kindle version, as well. But that goes along with the book. So that if you want to lead a book club, with your team at your organization, or if you want to gather a few assistants, for assistant friends together and do a little book club, that workbook is a good companion guide to go with that. So leader should be able to find everything of course LinkedIn as well. And hope you leave a nice review for Annie’s podcast, the whole system podcast on Apple podcasts and then while you’re there, hop over to mine and do the same.

Speaker 1 58:14
I don’t think actually left my website If you want to work founders inventory by the way, sorry about that. But yeah, no, please check out Jeremy’s book. I read it and it’s really good. It’s a great resource to have on hand and for sure do book club about it because it’s really a great a great thing to talk about too. Thank you so much, Jeremy for this conversation.

Jeremy Burrows 58:37
Yeah, thank you Annie and appreciate you taking time out of your busy schedule and with your family and everything to chat with me and I’m excited to share our conversation with with the world.

Annie Croner 58:49
Yeah, me too.

Unknown Speaker 59:00
Please leave a review on Apple podcasts.

Unknown Speaker 59:10


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