Mary Ryan is a 2nd generation, seasoned executive assistant with nearly 15 years experience supporting c-level executives primarily in the tech industry. She currently supports the CEO of Stitch, a digital marketing consultancy.

mary ryan leader assistant podcast

In this episode, Mary talks about work / life balance, how to strengthen your relationship with your executive, setting and respecting boundaries, and more.


Empathy is being concerned about the human being, not just their output.

– Simon Sinek


Mary Ryan Leader Assistant Podcast - Headshot


Mary Ryan is a 2nd generation, seasoned Executive Assistant with nearly 15 years experience supporting C-level Executives primarily in the tech industry. She currently supports the CEO of Stitch, a digital marketing consultancy. She is a born and raised Hoosier from Indianapolis who has a deep passion for assisting, loves creating empathetic and fun-loving cultures in the workplace, and tends to be the ‘den mom’ of the office.

As a mom of two, wife, daughter, sister, and self-proclaimed work horse, multi-tasking is a superpower. But her ultimate joy professionally comes from helping others find happiness in the workplace through compassion, random dance parties, and encouraging a healthy work life balance.

Goody Gifting Platform


A special thanks to my sponsor, Goody!

If you send business gifts to employees, clients or sales prospects, Goody is a game changer. You can send one gift or hundreds at the same time, without ever worrying about shipping details. With Goody, your gift recipients provide all their shipping info, and they can even swap out your gift for another option if they prefer. It’s free to start gifting and you get a $20 credit when you sign up. Oh and if you mention you heard about Goody on The Leader Assistant Podcast, Goody will add an extra $10 credit to your account.

Go here to start gifting today!


To learn more about how you can join growth-minded Leader Assistants, check out our Leader Assistant Premium Membership for ongoing training, coaching, and community.

Leader Assistant Membership Circle Screenshot Welcome APR 2021


Download the first 3 chapters of The Leader Assistant: Four Pillars of Game-Changing Assistant for FREE here or buy it on Amazon or Audible.


Check out our constantly updated schedule of events for admins and assistants at Including our all-day, online leadership workshop at


Join the Leader Assistant Global Community here, or the Facebook Group here for bonus content and to network with other assistants who are committed to becoming leaders!


Subscribe to The Leader Assistant Podcast so you don’t miss new episodes!

You can find the show on Apple PodcastsSpotifyGoogle Podcasts, Pandora, and Stitcher.

Join my email list here if you want to get an email when a new episode goes live.


If you’re enjoying the podcast, please take 2 minutes to rate and review the show on Apple Podcasts here. Each review helps me stay motivated to keep the show going!


Mary Ryan 0:00
Hi, my name is Mary Ryan and here’s the leadership quote of the day. Empathy is being concerned about the human being, not just their output, and that is from Simon Sinek.

Podcast Intro 0:17
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident game changing leader assistants

Jeremy Burrows 0:31
The Leader Assistant Podcast is brought to you by goody. If you’re starting to think about holiday gifts for your team, like I am, goody is a game changer. They have amazing gifts that people will really love including brands that give back to charitable causes. As a longtime executive assistant, I’ve always been nervous about holiday gifting season. But thankfully, goody’s platform lets you send one gift or hundreds at the same time without ever worrying about shipping details. Can I get an amen? With goodyyour gift recipients provide all their shipping info, and they can even swap out your gift for another option if they prefer. It’s free to start gifting and you can get a $20 credit when you sign up. Oh, and if you mentioned you heard about goody from The Leader Assistant Podcast goody, we’ll add an extra $10 credit to your account. Go to to start gifting today. Hey friends, thanks for tuning in to The Leader Assistant Podcast your host Jeremy Burrows. Welcome to Episode 198. Today I’m very excited to be speaking with Mary Ryan. Mary is Executive Business Partner at stitch Mary. How’s it going?

Mary Ryan 1:49
I’m doing well today. How are you? Jeremy?

Jeremy Burrows 1:51
I’m hanging in there. What part of the world are you in?

Mary Ryan 1:54
I am in the fabulous and friendly midwest. I am just outside of Indianapolis, Indiana.

Jeremy Burrows 2:01
Awesome. And are you from that part,

Mary Ryan 2:03
born and raised move just over a county line. And that is as far as I went?

Jeremy Burrows 2:09
Nice. Nice. Tell us a little bit before we get into your career. Tell us a little bit about you personally, do you have kids pets hobbies?

Mary Ryan 2:19
Yeah. So just the Summer I Turned fourty years old. And I have to say I don’t know if it’s like this for everybody. But it definitely was like a weird awakening. For me. I feel like I looked at my kids. My daughter who was 11 My son who is eight. And all of a sudden I blinked and they were self sufficient children and no longer needed me. I felt like my knees started to give out externally everything just went in a different direction. But at the same time, I found like this crazy peace in my life with where I’m at professionally where I’m at with my friends where I’m at with my family. And that was a really beautiful awareness to have. I married happily I’ve met him when I was 21 years old. And we have been married since 2009. Going strong, getting ready to do a kitchen renovation those so marriage, my marriage might hit some hiccups during that process. I’ve heard home renovation,

Jeremy Burrows 3:18
or sign up for some therapy just in case.

Mary Ryan 3:20
I agree it can be a little tough on a marriage. But he’s a pretty agreeable guy. So as far as the Reno goes, I’m hoping to have a little bit of more pull in those decisions. So that’s going that’s going well we love to travel. Spend a lot of time just getting out of Indianapolis, which I just said I love but also we like to just decompress and get away either with our close friends or family and like movies, a lot of movies, especially Marvel movies. Just saw what kind of forever it was amazing. And yeah, that’s in a nutshell.

Jeremy Burrows 4:02
Love it. Yeah, we just saw what kind of forever too, we enjoyed it very much. But we’ll not talk too much about it because I don’t want to, you know, put any spoilers or anything. Yeah. It was awesome, though. Nice, nice. Well, yeah, home renovation is fun and challenging. And you know, lots of ups and downs. And it takes longer than you think. And it costs more than you think. But if you get it done, if you get it done, then it’s awesome to enjoy it and see that oh, okay, we did this. Good luck to you on that. I appreciate that. So, okay, Mary. So tell us about your career. So how did you end up in the Administrative Professional executive assistant Executive Business Partner world?

Mary Ryan 4:44
Yeah. So, interestingly enough, and I say that sarcastically, I think most Administrative Professionals would tell you if you’re on a collegiate track, when you are meeting with your counselors and such there’s not really anybody that sits you down and says As one day, you could be an executive assistant. It is not typically on the chart of majors, concentrations, degrees, minors, you name it. And but my mother was an executive assistant. And I always loved what she did. I don’t know that I fully understood what she did, because it changed so vastly every day. But I never, I never saw her unhappy. And she and I are a lot of like, we’re busy bodies, we like monotony is like our worst enemy. So I love what she did. But like I said, when I went and met with, you know, the counselors and such, they, they really weren’t, that wasn’t anything they talked about, it wasn’t on the trajectory. So I ended up studying journalism, and just developed a really strong skill set and writing and communicating. And I’ve always been just empathetic as a person. I wrote for a while, but found myself in support roles. Even when I was at the magazine, I was the receptionist, doing freelance writing. And I was always looking for ways to help. And we had an executive assistant on staff. And I always kind of wanted to be doing what she was doing. But that wasn’t my job. And so I kept finding myself looking for assistant roles, roles with assistant in the title. As a people pleaser, that was the career path I followed for a while just entry level sales assistant media assistant, things like that, and really wasn’t quite sure how to break through to that next level up. So I went from a receptionist, to a sales assistant, and I wasn’t sure okay, how do I get to that exact level? How do I take this to the next level, and luckily, a friend of my husband’s father owned a business and was looking for an EAA. And it was entry level in regards to salary and responsibility. But it had that title, and I wanted that title. And I knew if I went in there and put in my time, it would help me build up my resume to a really good spot to then start doing this role, you know, professionally in supporting C suite in our city. And so that’s what I did, and ended up around 2009. Going into the tech industry, where I’ve pretty much stayed I went to commercial back to commercial real estate for a little while, but then ended up right back in tech. I think when you meet people that work in tech, they tell you, they never leave. And that’s for a reason. Because the culture is just amazing. The industry is ever changing. And it’s kind of like fly by the seat of your pants. Not not so much hair on fire, but it’s just it’s just like a nonstop thrill. And I love it. So I’ve been in tech for a while supporting C suite executives and most recently, my boss who His name is Michael, he’s wonderful. He was a CEO at our previous company that had been acquired and Michael wanted to be a CEO again. So he was getting ready to launch a startup. There are nine of us. But when he was getting ready to launch and he ended up going that way and like you’re going with me, and here I am. So there are nine of us it is gritty and crazy fast and we’re all wearing 17 different hats, but I wouldn’t have it any other way. So that’s where I’m at now is it stitch we’re a digital digital marketing consultancy, supporting Twilio, which is a CDP.

Jeremy Burrows 8:39
Wow, so what was the what was the prior company with?

Mary Ryan 8:43
We were at love. Love is another digital marketing consultancy but partnered with Salesforce. So primarily supporting Salesforce customers to better utilize that platform and kind of switched spaces from CRM to CDP. Which is customer data platform. Sorry, tech, so many acronyms.

Jeremy Burrows 9:05
I can think of I was like, I think I know what that is. But there’s so many acronyms, so many acronyms. Sorry. Oh, good. So what is your least favorite part? You talked about how you always wanted this role and your mom was an assistant. What’s what’s maybe your least favorite part about being an assistant?

Mary Ryan 9:25
Oh, my least at like I can 100% Answer this with confidence. What I like doing least as an executive assistant, even saying it it makes my spine like an accordion is taking board minutes. I hate meeting and board meetings and taking minutes and I think there’s a couple of reasons why I think the pressure to not screw up. It’s like completely overwhelming. You’re like crap, what if I miss something? What if it was like the biggest part of the meaning but you zoned out for For a minute, you didn’t get it down. I just, I get so nervous that I’m gonna miss something. And then it’s just a snooze fest.

Jeremy Burrows 10:10
As much as I watch you tell us how you really feel,

Mary Ryan 10:14
which is I love the reportable and how the company is doing and all the successes. The All in favor, aye. And the all against is just not not where I thrive. So I would definitely, when we started having our board meetings, we probably asked my boss, if there’s a board secretary who could, who could fill that role to which he will say we are startup it is you and I will smile and do it anyway.

Jeremy Burrows 10:40
Nice. Well, you know, if it makes you feel any better, nobody reads the board minutes anyway. So,

Mary Ryan 10:45
you know, that’s what I need to channel next time I’m in there. I’m just gonna remember, Jeremy Burrows told me nobody reads these.

Jeremy Burrows 10:52
That’s my unprofessional non legal advice. Well, so tell us about work life balance. So how have you kind of, you know, working in the tech world can be pretty demanding and fast paced, and sometimes crazy. So how have you balanced and set set up boundaries? And yeah, yeah, not not burned out? Or if you did burn out, talk them walk us through that process? Sure. So

Mary Ryan 11:20
um, so there’s a few different things I’ve kind of implemented. For myself through the years to get to a place where I feel like I have, I am hesitant to use the word balance, because I feel like it’s never really balanced, right? Like, there’s never, there’s always going to be a lot of work or a lot of stuff at home. But I feel like I’ve done a good job of managing it, if you will, or we’re just trying to figure out how to persevere when things do get heavier on one thing or another, and not let it take me down with it. So the first thing I started doing, you, as you mentioned, was setting healthy boundaries. And I don’t draw just a line in the sand. I paint it with permanent paint on concrete. And it’s never coming off. Because no, no just has to be no. And, but I don’t mean that in an aggressive way. I just mean that in. If my kiddos have a plan, I have a daughter who has a reoccurring appointments on Wednesdays and they’re at two o’clock, at two o’clock on Wednesdays I am not available, period, the end. If, if there was a hell or high water situation where my boss absolutely needed me no matter what, I would find coverage, and I would give flexibility there absolutely. But I also have a boss who gives me on bridled space to take care of my family and things that home is needed. And I’m very lucky in that regard. And I understand not all Administrative Professionals have that. And it is definitely not something I take for granted. But I noticed myself as a professional, always setting these boundaries for my bosses, giving them an hour at lunch, giving them 15 minute buffers between meetings, giving them Fridays with no meetings, and I thought, why the heck can I not do that for myself? Like I’m doing this for another human being? Why can I not give myself those same respects or those same boundaries. And I thought I’m doing it, I am gonna do it. And so that’s exactly what I did. And what it’s done is it’s given me more time to stop and, and really just strategize or manage projects. You know, when I’m working day to day, we’re working on tasks for our boss and asks. And then you’re also sitting through, you know, various meetings and things like that. But what I found is I wasn’t really having time during the day to sit and strategize on how can I grow this role? How can what can I give back to the company? What other things can I take on? What do I want to take on? Just like the time we build up for our bosses, you know, they’re in back to back meetings all the time. But when are they really strategizing and trying to think about the company and growth and scale. And so I just started being more gracious to myself and my carpenter and said, Hey, take this time to kind of think through these things. So that was one of the things I did. Another thing really was, like, I found every day, I was just going downstairs and making lunch and just sitting at my computer by myself like for no reason. Like there was just no reason I worked for a moment. Why am I doing this? I don’t need to check emails, the world is not going to end. If I don’t stop and walk away from this computer for a minute and go eat quietly without looking at a monitor. Even if I’m looking at my phone or looking at a TV just not doing something work related for a minute. So I thought okay, I can get up and go sit and eat downstairs at the table, like I don’t need to bring it right back up here to this computer. And I started just eating lunch not at my desk, making myself do it and making plans with my friends even though it was a little bit out of my comfort zone when I’m sitting here in my PJs during the day working or my sweats, like saying, hey, yeah, let’s meet for lunch at this time. Let’s get out. Let’s do it, like taking the coffee date taking the lunch date. And I definitely was like loading those things on the way there. Because I’m just so comfortable sitting here. I think a lot of us have started to feel that way through the post pandemic world where we’re so comfortable being at home. But you know, I started saying yes to more of those things and stepping away for a minute, fully knowing. Even though in my mind, I thought things were going to catch on fire. They’re not roles are going to end everything was a new fine if I didn’t respond to something at one instead of new, you know what I mean? So giving myself some grace and being really firm with family time and things like that. Last thing I’ll add to that is I also have a spouse who knows that on Saturday, I might get a call at 5pm when we’re sitting at dinner. Yes, we eat dinner at 5pm sometimes four. Okay, I like to meet early, early to I like to you really early. And he’s very understanding though about knowing that this job is not going to begin at nine and into five ever by a longshot. That’s not the type of role I’m in. I know there are administrative roles that are that way mine is not one of them. There are times where my boss is traveling on a weekend or has a question in the evening. And I think the other thing with him just giving me that unlimited flexibility, as he knows that if I’m out for two hours in the morning, that when he texts me at 7pm That night, I’m not going to gripe and moan I’m going to happily respond to it because I’m on probably checking email anyways. And that that time it all comes out in the wash. It’s not a nickeled and dimed, you are out for 120 minutes on Tuesday to 10. So those 120 minutes have to be recuperated by the end of this payroll. Like, that’s not how we roll. And I was pretty open about that early on. I said, you know, I need you to trust me and trust that I manage my time well until I’ve given you a reason not to. And and he did. And here we are. It’s just a really mutual respect for each other and our families. And it’s helped me be able to manage those different time. Requests are time pressures through work and home.

Jeremy Burrows 17:27
Yeah, that’s great. It’s very, it is hard, it can be hard to find executives who respect the boundaries, and you know, are flexible in those areas. So what I know there are probably some assistants listening like, well, that must be nice. Right? So what what would you say? Like how could those listening who are struggling in that aspect? Maybe strengthen their relationship with their executive in in that way of like, how do they stand up for the boundary? How do they convince the executive that the and persuade them that the boundaries are good?

Mary Ryan 18:06
Yeah. So for me, and I know, this isn’t going to be the case with everybody. It was about creating a personal relationship. And it also goes back to that leadership, quote, to empathy. I believe a boss or a leader is respectful of their employees time, or needs, if they genuinely understand or empathize with the ask. So for me when I was interviewing, for example, especially for the role I’m in now, a role I had been at Previously, I had a boss who, who didn’t know my children’s names after a full year. And I really struggled with that now just just to be impartial, my mother could care less if you knew her kids names. She was not that assistant, that was not a need for her. It was not a want for her. She came and did her job, went home and was fine with that. I need that personal relationship. It helps me better understand and proactively think for that leader. And I also think it helps gain the respect and understanding when you do have things come up. So when I was interviewing with my boss that I have now a couple years ago, I sat down with him and I said, Listen, I need to be really honest with you about something. I worked for somebody in the past who didn’t know my children’s names. It is not okay with me. I work with you and see you more than I see my family. And at the very least, I want you to know their names. You don’t need to know what the score of their soccer game was over the weekend. I Don’t expect you to know their favorite color. But I likewise would also love to know how your weekend was, I don’t need to know what you ordered at dinner. But I want to know you, I want to know your family, it’s important to me to have that kind of a relationship. And I know that that is not for everyone. And I respect that. But for me, I have found that it creates this profound level of a partnership, where you, you just have such a grace and understanding for one another, because you aren’t just supporting this person, they are your friend, they are your partner professionally. And I think it has just enabled us to have a level of understanding for one another, as we’ve got to know each other that we might not otherwise have, if there was not any substance to our relationship. And, and so I think that that has been really key, and having that kind of flexibility. Also, at the same time, early on in the interview process, I said, Hey, listen, I have two small children, they get sick, they catch every kind of crap you can think of at school, they’re involved in sports, sometimes they have extracurriculars after school. My My mom wasn’t able to attend those things. My parents were always really busy with work. And I said, I’m just that’s not the way that my family life runs. And it’s something that I need to be president, if you anticipate that being an issue. Now, I’m probably not a fit for you, I still think you’re a great person. But that’s okay, this just this role isn’t a fit for me. And I quit making interviews be a one way street, I quit thinking that I had to completely roll over on all of my belief systems and my core values just to get a job. And it might take you a little longer to find that right match. But they’re out there, they’re out there, and they’re looking for you too. And there are multiple compassionate leaders and people who are willing to work with you and be flexible, if you are not able to internally reset the boundaries in the role that you have. And I just started setting higher expectations for myself, purely based on the amount of time you spend in a career, you spend too much time working with someone for them to not be okay with you leaving to go get your teeth cleaned. Like that is that is a general human need. Like, your company’s paying for that insurance. But every time you go to make the appointment, they’re like, Oh, well, you’re going to miss this or you’re going to miss this. And, you know, as EAS we’re inherently people, pleasers anyways, we already feel bad that we’re missing time. And then to have somebody compact that to make you feel worse. They’re just, they’re good people out there. Sometimes you just have to find them. I don’t, I feel my heart breaks for the assistants listening who are like, but I have to keep this job or the economy’s really scary or things like that. There are 8 million roles out there hiring remotely. Take the call, take the call, see what’s out there or before you take a call, talk with your boss say, Hey, this is how I’m feeling. And if he’s like he or she is like, No, hey, this isn’t gonna work for me. Sorry, I can’t give you more flexibility. Well, there’s your cue to see what’s out there. There are good people in the world, and good people tend to find good people. So I think advocating for yourself is really important in that regard.

Jeremy Burrows 23:41
Yeah, well said and you know, it is it is tough. It is a challenge to I talked with assistants all the time, who are who really struggle with looking outside the box that they’re working in and really thinking, Okay, this is all I’ve known for years. And there’s there can’t be anything out there. That’s, that’s better, you know? And then they put them Yeah, and, and that was me. And my last role was like, I didn’t know what was going on in the world other than my little, little bubble. And then, you know, but I put I got myself out in the world I networked I, you know, explored what was out there for our career. And, yeah, it’s there’s a lot of opportunities, and it’s not going to be easy, but it’s definitely worth the work and putting in the time and energy and effort to find somebody that you would enjoy working with.

Mary Ryan 24:40
Yeah, to find happiness. I mean, it’s it’s finding joy, you know, finding a positive relationship is his joy. Someone told me recently that sadness is the lack of is the lack of joy in that joy is the lack I have sadness. And I don’t know where they heard that or if someone you know, great whose name I don’t know said that. But I found it to be really profound. And I think there’s a lot of truth to that. And if you are sad in a role it is because you’re lacking joy. So you gotta find it. And you gotta get out there. It is overwhelming to see 900 people have applied for a role. Tell people right network network until you are blue in the face, I just reached out to a friend that I had known from high school to help get another friend and EA role. This was somebody that I met, it’s I mean, essentially, we’re 20 years ago. So these relationships, they come in, they come into play. So meet those people, add them to your LinkedIn, recruit, recruit, recruit people to your network, until you’re blue in the face, and then lean on them. Hey, remember, I met you at that networking event downtown. I noticed you know, somebody that works at this company think you could do an email introduction, I’m looking at a role there. It can be the most off the wall introduction ever, someone you don’t even know. But if it gets your resume from the bottom of the stack of 1000, up to the top score. Totally worth it.

Jeremy Burrows 26:16
Yeah. Awesome. Well, Mary, thank you so much for being on the show and sharing a little bit about your story and your career. And speaking of networking, how can people connect with you? If they want to reach out and say hi, yeah, absolutely.

Mary Ryan 26:31
I would love if anybody wanted to connect to LinkedIn, I’d be happy to speak further. Always happy to jump on a call and talk to anything and all things administrative professional, and I think I’m under Mary wall Ryan, which is my maiden name. And now my very last thing, yeah, I would love to connect and get to know people and grow our networks.

Jeremy Burrows 26:52
Perfect. Well, I will share your LinkedIn URL on the show notes at Thanks again, Mary. Best of luck to you and thanks for being on the show.

Mary Ryan 27:07
Thank you so much, Jeremy. Appreciate your time today.

Speaker 3 27:19
Please review on Apple podcasts.

Unknown Speaker 27:28


Download FREE Chapters