Jacqueline Howard is a longtime Executive Virtual Assistant and homeschooling mom, so she has some great thoughts regarding working from home and more!

Jacqueline Howard Leader Assistant Podcast

Jacqueline and I talk about working remotely with kids in the home, how to stay connected with your executive while working from home, how to manage multiple executives, and more. Thanks for a great chat, Jacqueline!

Note: In this episode Jacqueline recommends the books Crucial Conversations and 48 Laws of Power.


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As a leader, the first person I need to lead is me. The first person that I should try to change is me.

– John C. Maxwell

Jacqueline Howard Leader Assistant Podcast

Jacqueline is a Pastors wife, Mother of 4 and a Virtual Executive Assistant. She has also homeschooled for the past 10 years and was the director and leader of a classical homeschool community. She currently partners with authors, publishers, and online course creators.


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Jacqueline Howard 0:00
Hi, I’m Jacqueline Howard and today’s leadership quote comes from John Maxwell. As a leader, the first person I need to lead is me. The first person that I should try to change is me.

Podcast Intro 0:15
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident game changing leader assistants. You’re listening to Episode 70

Jeremy Burrows 0:27
Hey everyone. Before we dive into the interview today, I wanted to share a note from our sponsor for this episode, life Squire was founded by a former executive assistant looking to create a healthier relationship between current assistants and their clients. They found their niche in placing assistants in positions where you and your executive can thrive. If you’re an executive assistant, they would love to help you can visit their website at lifesquire.com/leaderassistant. Hey, everyone, thanks for tuning into The Leader Assistant Podcast. It’s your host Jeremy Burrows. And today I am speaking with Jacqueline Howard. Jacqueline is a virtual executive assistant. She is a mom of a few we’ll get into that Oh mama for and she’s got her hands full. And she’s also homeschooled for the past 10 years. She currently partners with authors, publishers and online course creators, Jacqueline, how’s it going?

Jacqueline Howard 1:26
It’s going great. Thanks for having me.

Jeremy Burrows 1:28
Yeah, what part of the world are you in?

Jacqueline Howard 1:30
We live in Michigan, and we’re newer to this Michigan area. But we’ve been in Virginia for most of our married life.

Jeremy Burrows 1:37
Awesome. Well, why don’t we chat a little bit about your very first job and what you learned in that role that you still use today?

Jacqueline Howard 1:47
Well, that my very first job before you know taxes was babysitting. And what I learned from there is observing how the parents of the home did things and their preferences. And I tried to copycat that the best I could. And I also quickly learn if I make the kids happy, within the boundaries of the parents that I would have a promising opportunity to come back again and again. So customer service. Perfect. What

Jeremy Burrows 2:18
was your kind of first real tax job? And then how did you become an assistant,

Jacqueline Howard 2:24
my first tax job was actually working at a fast food place. And that lasted two weeks. Because I couldn’t stand the smell. And I honestly didn’t like the way they treated the customers. And I just couldn’t be on board with it. And so I left that. And then immediately after that, I got a job at a front desk of a hair salon. And I was I guess the assistant and I scheduled appointments, I occasionally would wash hair if they were backed up. And I just made the customers feel seen and you know, not just lingering around, I took care of them brought them drinks, made small talk stuff like that.

Jeremy Burrows 3:09
So what do you love about the role of an assistant?

Jacqueline Howard 3:14
I absolutely just love learning different kinds of businesses. So since I work virtually, some of my clients are authors, some of them are course creators, things like that. And I like that I get to learn different tech tools, different business models, different personalities. I love that basically, I’m always learning something new. And having to challenge myself to pivot a little bit all the time. I love that aspect. Like I’m not stuck. As one thing, you know, where I have to if I was an author, I always have to write or something like that. I get to do all of it. So that’s my favorite part about being an assistant.

Jeremy Burrows 3:57
So have you always been a remote virtual assistant? Or have you been in office assistant as well?

Jacqueline Howard 4:06
I actually have never worked outside of my home. I’ve always been virtual. Except for you know, when I was younger. But yeah, I’ve always been virtual. And I my only experience working in an office would be when I was in college, working at the hair salon or helping the like in the college admissions office, things like that.

Jeremy Burrows 4:28
Why don’t you share kind of maybe a con, to working remotely? What’s one thing that really you struggle with working remotely?

Jacqueline Howard 4:37
Yeah. I’d have to say even though I’m pretty introverted, I do like being around people a little bit and being able to read their body language and really sense how they’re feeling about things. And when you’re working remotely, you miss out on that element. You can pay attention to the tone of voice if you’re on a phone call, but that doesn’t happen often. And so that’s probably the biggest con, I feel like there’s a lot that you can catch from body language. I think when you’re in person with someone, you can decide how you’re going to ask a question or what angle you can approach the the question or proposal if you can read their body language, whereas virtually I have no idea, I just have this thing that I need to present to them. I just have to present it to them. And I can’t tell if they’re down that day or feeling great that day until we engage. And so that’s probably the biggest con for me.

Jeremy Burrows 5:37
Yeah, that makes sense. So what about some tips for people working from home, but maybe even specifically, advice for moms or dads that are working from home with kids in the house.

Jacqueline Howard 5:53
That’s like an ever evolving thing that you have to keep adjusting and fine tuning to figure it out. But I would say, make your expectations clear, and make them simple. And, if possible, have some sort of benefit or reward for set expectation. Even if it’s, I’ll be so proud of you, or I will appreciate what you’ve done. But I think a lot of times people, I mean, I know for myself, I get the most frustrated with my children, when I never set the expectation for the moment we’re about to enter or the place we’re about to go. And then they mess up. And then I’m frustrated. But the thing is, I never really let them know what was expected of them. So I think, in an overarching way, if you let your children know what’s expected of them, I’d like for everyone to be up by this time, and I need everyone to have breakfast by this time. And between this time in this time, there cannot be any noise. So here are this list of things you can do you know what I mean? Making it really, really simple and very clear what’s expected of them. And it minimizes the opportunity for chaos. Now, chaos still happens, because we’re human, but it significantly decreases the opportunity for the crazy.

Jeremy Burrows 7:12
Yeah, that’s we, we’ve been trying that out while we’re on lockdown and the whole COVID-19 thing. Basically a list of things, here’s here’s a list of things, you can do that or non screen. And here’s some list list of things you can do that are screen time. And just kind of like gives it a little bit more structure. And expectations, like you said, How do you feel valued? Or how do your executives make you feel valued, and part of the team even though your remote, two

Jacqueline Howard 7:47
big ways one is more ongoing. And one was like a one time thing that happened that really showed me that the executive valued me. So the ongoing way is just having weekly, like checking meetings, and where they just let me know, here’s big picture what’s going on in the company. And here’s, you know, what I need you to do, and even feedback when they say this isn’t working the way you’re doing this. And, you know, I’m able to ask questions and give feedback. And when they value my feedback, when I’m able to ask questions, and they value it. And mostly, when they use the term we instead of me or my, you know, when they refer to me as part of the team, and they say we have this going on this weekend we are launching this week, instead of you know, when they refer to their businesses, just their business. So little things like that. I’m like, yay. But another thing, I had one client, where, with this particular client, I’m more forward facing with his customers. And one particular male customer started getting inappropriate. Just in the email communication, and it just got out of line. And I was nervous because it’s like, okay, this is a lot of money, this person’s investing. I don’t, I just didn’t know how to essentially tell him like, you need to stop that. I can help you with this product, but you’re gonna stop talking to me this way. Right? And he was just, I don’t know, I was so uncomfortable. I didn’t know how to handle it without I just didn’t know what to do. So I went to the client, and I said, you know, here’s this person, I he’s taking things too far. I just want to help with this product. And he’s turning it into this other thing. And I don’t know what to tell him. I don’t know what to do. And really my hesitation with going to the client was I didn’t want to bother him with something because I’m supposed to be handling client thing. Customer stuff, right. So I was like, You know what, I have to interrupt you know what he’s doing and present this to him and I felt so so so appreciate Didn’t when he stopped everything he was doing. He completely, like cut off this customer, he’s like, You will not treat my system this way. Here’s all your money back, we will not do business with someone who thinks that this is appropriate. And he he completely just everything done. And he’s like, You never have to deal with someone treating you like that. If that ever happens again, you come to me and that person will not have you know, and I was just like, wow, I that’s the moment I knew that this person cared about me as a person more than he cared about the money that he could have made from this quiet. So those are ways I think that executives and leaders can make their systems feel valued when you stand up for them in ways that can impact your wallet even. And he was willing to sacrifice that for me. So that was incredible.

Jeremy Burrows 10:52
Wow. Yeah, that is incredible. It’s awesome. Yeah. What would you say to EAS, you know, virtual assistants or an office assistants, who manage multiple executives, or multiple clients, what’s something you’ve done to kind of keep on top of tasks and projects for multiple clients?

Jacqueline Howard 11:15
I have to say that I two things. In when when I started having a lot of clients, I’m juggling juggling multiple things. Obviously, I’m still an assistant, but I no longer looked at myself as an assistant, I looked at myself as the CEO. And I said, Okay, as a CEO, how am I going to manage my different assets, right. And so I started reading books that are geared for, you know, CEOs and business owners, because it’s that same frame of mind that you have to have, I have to look at, like, each client is someone that is under my care. And it’s something that I want to see thrive and I want to see grow. So if you have a team, and you want to see a team member grow, how would you nurture them? How would you take care of them. And that’s exactly the same thing that I do for each client. And so I do that I look at myself as the SEO like, it’s like, almost have to play a little mind game with myself, but and I look at them as people that I’m managing that I want to see grow. And then I also do a lot of time blocking, I give a set amount of hours to each client, where I shut off everything else from everyone else. And I focused like deep, deep deep in that client’s business in the tasks I have to do for them. And even sometimes I’ll do a little extra this and that in their timeframe, new research or just ways to make their business run smoother, or to deliver a more elite client experience for their clients. So I focus on them before I move on to the next. So that’s one way that I manage them. Or sometimes depending on the level of the complexity of everything I need to do, I will have certain days that are devoted to certain clients, because not all of them need me to touch their business every day. So sometimes they’re blocked by days or half days, or sometimes it’s by a set amount of hours. And I have to say that’s the main thing. And then I of course, devote a lot of time to take care of myself. So I make sure that I’m exercising a lot, or not a lot, but regularly, that I’m sleeping well, eating well. And I’m looking at myself as the most valuable asset of those teams. And if I’m not taking care of, they can’t be well taken care of. So I’m making sure that I’m taking care of my, my mind, my heart, my body, and I’m able to perform at a higher level if I’m taking care of myself as well. Did that answer the question? Yeah,

Jeremy Burrows 13:48
that’s great. Very helpful. So you mentioned reading books that, you know, are kind of more SEO books, what’s one book or resource that you would recommend? Assistants read and I like that you said that because I’ve always thought you know, you should be reading as an assistant, you should be reading what your CEO or what your executive reads. Not just Yeah, you should also read things for assistance. But But yeah, you should also read things that your CEO reads. So yeah, any resource or book that you’d recommend?

Jacqueline Howard 14:21
Yeah, I could probably go on forever cuz I read I love reading. But I’ll give you one that’s really practical, Crucial Conversations. It’s tools for talking when stakes are high. And I think any and everybody who is a human being less interact with other human beings should read that book. And, you know, executives and executive assistants particularly, you should read it because there are a lot of times when stakes are high. Something fell apart. There was a misunderstanding or there’s a big meeting coming up with a you know, a big contract or something like that. And I think when people learn to communicate, clearly, effectively, kindly, respectfully, all those things, so many more like, things just run better. And so that’s one that I recommend to everybody, it’s helpful. And not everybody has had healthy interactions with leaders, and with teammates. And I think this, this helps balance out the scale. So you can give people a chance, instead of working out of past hurts or past assumptions or past behaviors, you know what I mean? And so that’s what I recommend. And then another crazy one, it’s almost not related. But if you I’m able to connect almost anything to what I’m doing. So 48 Law, Laws of Power by Robert Greene is another one. And it’s very fascinating, but I think all assistants should read that too.

Jeremy Burrows 15:53
Yeah, like the I haven’t read the complete, Crucial Conversations book, but I’m very familiar with it.

Jacqueline Howard 15:59
Yeah. Great. Excellent. Yeah.

Jeremy Burrows 16:03
So if you could snap your fingers and instantly give all assistants more of something, what would it be?

Jacqueline Howard 16:12
Confidence in their communication? I think a lot of things would be solved if people had confidence in speaking up for themselves. Confidence and speaking up when something isn’t right, you know, but I think the underlying thing is confidence. But I would hone in on the communication.

Jeremy Burrows 16:29
Talk about a little bit about leading yourself while working virtually. So. You know, you don’t necessarily have coworkers stopping by you don’t have you know, a lot of in person meetings or any in person meetings, how have you kind of developed yourself and made sure you said you read a lot so that yours is a big part of it. But any other thoughts on that?

Jacqueline Howard 16:54
Well, a lot of it is how I plan my week, I force myself to sit down on Sunday nights, and I plan out my week, I kind of like a budget, you know, you I tell my minutes where they’re going to go and what’s going to happen in advance. And so I don’t end up just wondering, Well, where did today go? What did I do, it’s all written down. And it’s all there. And I give myself grace, you know, because sometimes you just don’t get it all done. But at least if it’s written down, one, I’m holding myself accountable to keep plugging along at that goal for the day, and I don’t have a list of, I try not to ever have a list of 20 items, it’s usually five and under, right. And if you kind of plan your month out, and then break it down by weeks, it tends to work out that you don’t ever have to pile in 20 things in one day. So I plan out my week in advance, and I tell my time where it’s gonna go. And then I stick to it. And I also have online, like, I have an accountability partner, where we check in in the morning and Voxer. And we just tell each other these are the things I’m going to do today. And you know, and then we check in again, at lunch, how far are you on your thing? And then at the end of the day, we check in on each other and say, hey, the workspace over? Go be with your family? Did you meet your goals? You know, did you accomplish your task, and so I hold myself accountable. But I do use other people, because that’s important, because I can easily cheat myself. But I’ve learned that cheating myself just hurts me more than it benefits. Like, there’s no sense of lying to yourself that you’re accomplishing something and letting yourself cheat, you know. So those are the things I do I write it down, I plan an events in advance and I have someone hold me accountable. And so far, that’s been helpful. Because it’s so cool to see my planner and look back at all the things I was working on and go oh my goodness, I remember what I was scheduling out. I needed to learn this new online software or this platform or whatever. And I you know, chunked it out into little pieces in here I am I feel like I’m a master at this thing. So there’s a lot of reward of just being diligent. Am I tempted to scroll Instagram and stuff like that? Sure. But what I’ve done is I just I give myself 30 minutes a day for that. And I just it’s scheduled in, go scroll for 30 minutes, have fun. And so during that 30 minutes, there’s no shame. It’s my 30 minutes of Instagram, and I’m having a good time and then when it’s done, it’s done.

Jeremy Burrows 19:42
So let’s talk a little bit about the fun part of your role. What’s the biggest mistake you’ve made as an assistant?

Jacqueline Howard 19:50
Oh, my goodness. So one of my clients is an author and he’s kind of he you know, he’s pretty well known and he has like this email that he sends out every week. In this whole thing, and people look forward to this, it’s a thing. And my job, only job for this particular thing that he has is to schedule out, I have to write up a little email kind of like introducing the the article that he writes for them each week. And it’s not really a summary. But it’s like a one or two sentences of said day. And so and I have in it goes out every Wednesday at the same time. And for whatever reason, this particular week. Yeah. Have you ever had one of those days where you wake up, and in your mind, it’s a different day of the week, but it’s actually not that day. I woke up that day, and I was like, today is Wednesday. You know, I was just feeling Wednesday. And I don’t know why. But like, I just thought it was Wednesday. So I set everything up. And you know, and I ready to go. And then I like made my coffee I did my day. And I was like, why don’t have like 700 emails, like it was so weird. And then I see all the slack notifications from my client, like this is odd. So I look at it and like, Do you realize you sent the Wednesday email today? And I was like, Well, yeah. And they’re like, today is Tuesday. And I was horrified. I was horrified. And he was like, well, I need you to, I need you to like, fix it. I don’t like because, you know, he doesn’t know how to do it. So I was like, okay, and the first things first is I took complete ownership of it. I said, I am so sorry. I thought today was Wednesday, I’m going to fix this. And so I fixed the thing. And I emailed every single person that let me know, hey, the link isn’t working. Because the other thing is the links weren’t. Like everything was just

Jeremy Burrows 21:54
as they were like, because they weren’t published until Wednesday or something. And yes,

Jacqueline Howard 21:57
yes. And so then I emailed every single person, and I said, Hey, I’m sorry, this is my mistake. I thought today was Wednesday. And what was so cool, though, is everybody included, including this author, they were so gracious, like life happened, you’re not a robot, you’re a human being. And that’s what we love about you. And I was like, man, thank you, you know, and the, the all the customers and stuff. They were like, That’s so cool. You gave me an extra day, I thought today was Wednesday to that it was just they made it really light hearted. And so it was great. But it was I was so embarrassed, because I’m just like this really important person, and I’m over here messing this up. I did feel really sick to my stomach. Like while I was trying to fix my error. But as you know, the day went on, and everybody started replying, hey, no big deal. You know, it was kind of cool to hear from you guys on a Tuesday. And I don’t know, they the audience was great. The client was great. I just felt horrible, because like, I’m supposed to be the assistant, I’m supposed to have it together. So that was probably the most horrifying embarrassing thing that I have ever done. And he did say what I love to he said, he said this is important and whatever. But he’s like, we’re not curing cancer. So it’s okay. So it was cool.

Jeremy Burrows 23:19
How long have you been working with this client?

Jacqueline Howard 23:22
Two and a half years? Maybe? Yeah, like two and a half? Yeah, about two and a half years. So yeah.

Jeremy Burrows 23:29
How? How did you find your clients? You because you work for yourself? Right? You’re not part of a firm?

Jacqueline Howard 23:36
Yes, that’s correct. I work for myself. It’s I will call it an act of God. But I, I my very first client that I got, because I was homeschooling my children when I started working virtually. And I was I was leading a homeschool community. And it was a complex thing. So I was the director of the community and I hired teachers and I trained the teachers and provided supplies and on and on and on, I paid them and all these things. It was like a mini school, but it was homeschool. So they only came once a week, and whatever. So a part of that whole thing is I sent out, you know, weekly emails and you know, had like little staff meetings and all that stuff. And one of the dads in the groups. He had an online business, and he just kind of approached me because I you know, they’re in my community. They know me year after year, day to day, he’s just like, hey, you’re running this whole thing pretty well, and you’re not even breaking a sweat. Could you help me with my emails or something like that? And I was like, Sure, no big deal. And so I helped him out. And then like two weeks later, he’s like, Okay, you saved me this much time and I was able to do this big launch in this thing. Could you do this one more thing for me and like he kept growing and growing and growing. And I’ve, we still work together. We’ve been working together since 2015. So he then referred Me to the client I have now and several of my other clients, and then they refer me. And so it’s kind of, I’ve gotten all my clients through referrals. And so that’s why I say it’s an act of God like I

Jeremy Burrows 25:13
just keep doing good work. And yeah, word of mouth.

Jacqueline Howard 25:17
Yeah. Yeah. So that’s kind of happens. I mean, there’s occasional one or two people that find me on Instagram or Facebook, and they say, Hey, can you you know, but for the most part, I would say 95% of them are referrals.

Jeremy Burrows 25:29
So what would you tell an office EA, who is dreaming of becoming a VA, what’s one or two things you would tell them?

Jacqueline Howard 25:36
I would tell them to get familiar with online tech tools. And then I would tell them to learn to control yourself, discipline yourself, lead yourself, you know, because if you can’t get a hold of yourself, having all that freedom of no one watching over you all the time, and there’s no clocking in clocking out, there’s no one really, other than, if you don’t produce the work, there’s nothing to really hold you accountable, you’ll you’ll eventually drown, because procrastination will set in just different things like that. So I would say that, learn the tech tools, and learn to lead yourself.

Jeremy Burrows 26:19
So kind of along those lines, what makes an assistant a leader,

Jacqueline Howard 26:23
I don’t know if this is the right word, I’m pretty sure there could be a synonym, but being discerning a person who should know when to speak and when to be quiet. And who could know when to fight for something and when to let it go? You know, or when to, I don’t know, just having that wisdom. That’s not just being smart, not just knowing I know, just having that extra wisdom or instinct, or there’s just that extra something. I don’t even know if I have the right word. But just knowing when to be what that yeah, that makes a an assistant, a great leader.

Jeremy Burrows 27:05
Awesome. Well, Jacqueline, thank you so much for taking time out of your day to chat with us. What is something that we can do to support you? Or where can we find you online?

Jacqueline Howard 27:15
Yes, I am on everywhere online as the Jacqueline Howard, Instagram, Facebook and LinkedIn. And I would just love to connect with other assistants. And I just love to encourage other people. That’s like my favorite lesson, my little passion project. I just love to cheer people on. I want to see other people do well. And so find me connect with me. I want to cheer you on in what you’re doing. And if I can help with anything, I like to partner with other assistants just doing whatever. So yeah, find me in all those places, and I just want to connect, that’d be great.

Jeremy Burrows 27:53
Well definitely share those links in the show notes so people can reach out especially if they need somebody to cheer them on. Right?

Jacqueline Howard 28:01
Yes, absolutely.

Jeremy Burrows 28:04
Awesome. Well, yeah, yeah. Thanks again. And then hopefully we’ll talk soon and take care of your your large family.

Jacqueline Howard 28:13
Yes, absolutely. It was my pleasure being on your show and thanks so much, Jeremy.

Podcast Outro 28:30
You on Apple podcast. Goburrows.com


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