You Don't Have to Do It All: Delegation Strategies and Support Systems for Working Moms - with Ashley Chang (part 2)

Leanna Laskey McGrath  0:04  

Welcome to The Executive Coach for Moms Podcast where we support women who are attempting to find balance and joy while simultaneously leading people at work and at home. I'm your host, Leanna Laskey McGrath, former tech exec turned full time mom, recovering perfectionist and workaholic and certified executive coach. 

Leanna Laskey McGrath  0:24  

Hi everyone. Welcome back to the show. Thank you so much for joining me today. I have part two of my conversation with Ashley Chang, CEO of Sundays, and she is going to be talking more about outsourcing, delegation and how we can do this whole working parenthood thing. I can't wait to hear her tips and tricks. If you weren't able to tune in last week, go back and listen to last week's episode, where we heard more about Ashley's story, her personal journey. She's just transitioned to being a new mom. She's got a almost four month old at home, and so I hope you'll go and listen to that. But welcome back, Ashley. 

Ashley Chang  1:10  

Thank you. I'm super excited to continue talking. 

Leanna Laskey McGrath  1:12  

Yeah, likewise. So when we left off last week, we started talking about the idea of delegation and thinking about, where am I most needed, and where can I maybe outsource or share the load with somebody else? And I think especially for high achievers, that can be really hard to do, because we think we need to do everything, and people don't do things my way or up to my standard, and so I'd just love to hear your thoughts on this and what you've learned and heard about in your conversations with parents. 

Ashley Chang  1:50  

Yeah, that is, like the thing that makes it so hard to be a working parent. I started Sundays just two years before started having my own baby, but just by researching as much as I could with parents I talked to, I think, like, 300 parents in the first couple months of building Sundays, and at first I was like, Oh, I'm gonna build an app, because that's gonna solve it for everyone. Like everybody just needs a new system. But the more people I talk to, the more I realize that there just isn't actually enough time in the day for all of the things that parents need to handle. And we call the company Sundays, because a lot of the parents I talked to, they had two working parents at home, and they're like, Well, I'm working all day, and I try to be present with my kids at night, and then we have this long family to do list that we end up doing on Sundays. And so our dream is that people get that time back to have quality time with their family, or just to relax on their own, which I know is really rare for parents, also. And so we started from that mindset. And then we also have our team, who are parents themselves, and they're the ones doing the support. So they're very cognizant of what does it take to run a family, what are the systems that you might have in place? And so now, how I think about it is that there are different recurring systems that happen, that you can really set yourself up for success by getting some of those in place. And that's where I've really been focusing my family delegation time in the last last few weeks. And then there's also just, like, one off things that come up, where you having like a trusted person who can dive in for you and understands where your family is coming from can also be really helpful.

Leanna Laskey McGrath  3:21  

Yeah, give me some examples of like, what are the recurring things that you see? 

Ashley Chang  3:24  

Yes, we call it, I kind of break it down into a couple buckets. We call it Life maintenance stuff. Still, that's like, making sure everyone went to the dentist this year, making sure your car oil got changed, things like that. Where, when you don't have a system for it, you have to just remember to do it every six months, and so figuring out, making sure that you have like, those reminders in place, and ideally someone who can actually get that booked for you, or maybe an online system or something like that. And then we also see things that happen on a more frequent basis, like meal planning, and then on a longer term basis. I think what's really interesting for families is that we're all experiencing these like recurring family things over and over again, like it was just Fourth of July, or every summer you do summer camp planning, or in the fall, you get Halloween costumes, and they are recurring events that you could approach the same way every time. But for a lot of families that we work with, they're so busy in the day to day that they don't have time to take their head out, to poke their head up and think about like, Okay, what's coming up in six weeks that, like, I could just do something quick for now and make it be more proactively prepared, instead of having that last minute stress that comes with it. 

Leanna Laskey McGrath  4:33  

Interesting. So tell me more about Sundays. What is your mission? Tell me all about it. 

Ashley Chang  4:38  

Yeah, we're practicing a potential new mission, but our mission right now is to make it possible to have both a meaningful career and the family that you want. And our new potential mission that we're thinking about is erase the motherhood penalty, meaning like that, it's possible to have the career that you want, that you're not dropping out of the workforce, that you're maintaining salary earnings that you would have if you didn't have kids, so experimenting with that phrasing instead, but really the same general concept behind it. And then what we really would love is to get more moms into leadership positions, whether that's executive roles at companies or starting their own companies and helping them be successful there. Because we think having moms in those positions of influence and representation is really how we can make more societal change and create a better working environment that's more flexible and supportive for moms.

Leanna Laskey McGrath  5:29  

I love that. We share that mission, for sure, because I think that I've always wanted more women in leadership roles and now being a mom and recognizing all of the unique strengths that we learned from motherhood. I think also having moms in leadership roles is so important as well, because, you know, I consult with different companies, and I was talking to this startup one time that it was all men and one woman on their executive team, and they had just never really, like, considered the challenges that a mom has, like, worked a full day before she even comes to work, you know, getting the kids ready and out the door and getting herself ready and making breakfast for everybody, and doing a workout or whatever, you know, all the things that you need to do before the work day even begins. But I think that whenever there are women in those positions, moms in those positions, even more moms in those positions where they can, like, talk about it, because I think whenever there's only one or two in the room, a lot of times it's like, oh, I have to, like, kind of compartmentalize and hide that part of me from all of these men, because it's kind of like their playground. But then whenever it's, you know, we have more seats at the table, so to say, then it's like, those are the conversations that we're having before the meeting starts. And then we start, you know, chatting with each other, and the guys start to hear that, and once everybody just kind of understands it, and it's more human, it's more real, then it's a lot easier to I think, like you said, make changes within organizations and make organizations more flexible and more human friendly.

Ashley Chang  7:14  

Yeah. And I think even just having like, one more person makes a huge difference in that situation when you're not the only mom or the only woman there, so one person at a time, and we take a very human first approach to everything we do, but we always celebrate even when we can get, like, one more mom on a leadership team or support them in feeling like they can push for that.

Leanna Laskey McGrath  7:35  

Yeah, so how do you do that? Like, what do you do that creates more moms in leadership positions. 

Ashley Chang  7:42  

Following up on kind of the types of tasks that we do. We really want to be partners with the families that we work with, and so one of our favorite things that we do is to do what we call like, a time and energy audit. I don't know if you've done this with your clients, but run through like, what is their typical day today? What's on their to do list that they didn't get to and then talk about, like, what's actually important to them, what needs to happen for either their family or their career, and then also how much energy do they get from it?. And then we try to sort those out and find, like, what are things that are really important but they don't give you energy, or they're not a great use of your time. So helping clients try to identify what is that best use of their time where they can really drive energy from it and help them be getting more of that time back by taking things off their plate. So we do a lot of the family kind of recurring tasks that I mentioned. We also will do one off projects, and then we also will get integrated on the business side too. So for a lot of the people we work with, if they've started their own business, probably similar to you, it's one long to do list that is like, work thing, family thing, work thing, the family thing. And so we try to take kind of the end of your to do a list away, essentially, so you can focus on, what are those, like, one or two top priorities where your brain is really special, and we can give you that power and time back.

Leanna Laskey McGrath  8:58  

Yeah. So it's basically you're providing an executive assistance and or personal assistance for the family as well as the business owner.

Ashley Chang  9:07  

Yeah, for a lot of clients, we'll work with them just on the family side. But then where we can, we love to work with business owners and families, because we think that that's really a place where we want to help push people forward. And we think that having even just, like, a little bit of support a lot of times, it's like one person who is on their own, and they're doing everything themselves, and so if we can give them time back to focus, they really can accelerate their business. And one thing I've noticed is, like, when you don't have as many admin tasks on your plate or things that take your energy away, you can actually get a lot more done because you're, like, enjoying the work that you're doing, too.

Leanna Laskey McGrath  9:44  

Doing, like, the high impact work that you actually enjoy. 

Ashley Chang  9:47  

Yeah.

Leanna Laskey McGrath  9:47  

Yeah. And so to kind of what we were talking about earlier, this idea of delegating the people who are able to delegate, and even in your own experience, because you also use a. Executive assistants, right? How do you trust them? How do you how do you, like, feel, okay? Like, okay. It's okay for them to do this work and it's okay for me not to do this work.

Ashley Chang  10:11  

Yeah. Well, we were just talking. I was telling you earlier that this is my first day having a nanny watch our baby. And so it's really interesting on the personal side, to figure out, like, how to build trust. And so I think there is some things that go into it, of just like understanding who that person is, making sure you're building, like, a good relationship with them, and checking, like, references, things like that, to make sure that, like, you feel good about the person that you're starting to work with. At Sundays, we always have clients do like chemistry calls with their EA to make sure that, we do a lot to try to find the right match for them right up front. But we think that, like nothing can really replace talking to that person and making sure that you click with them well. So we'll do that, and then once you decide, like you want to actually get started, I think there is a lot of trust building. So I think it's it is continuing to build, like that personal relationship, as well as as actually building out, like, what do you want to get done? A lot of people come to us and they're like, I'm so busy, but I don't actually know what I want to delegate yet. So going through some of those exercises to understand what are your top priorities, and what are things you can hand off. 

Ashley Chang  11:16  

And then I think starting slow and making sure that you have opportunity to give feedback. So I love to start with, like, something small, and then make sure that there's, like, a place to do a check in and say, walk me through where you are. Like, how did you think about doing this? And making sure we're kind of aligned on how we think about things, so that I can start to delegate more and more things, and then also just giving really frequent feedback and specific feedback. We have a lot of clients who are kind of afraid to give feedback, and so like, our team will do something for them, and they'll think they did a great job, but the client will be like, Oh, this like, missed the mark for me for certain reasons, and I'll just, like, do it myself. But if you actually want to build a relationship with this person, you need to tell them what they did that could have been done better to make something actually useful for you. So I think that feedback cycle and both sides being open to giving and receiving feedback is really, really important for both building trust, but also building something that's going to work for you long term. And it's actually giving you leverage.

Leanna Laskey McGrath  12:13  

Sure. Yeah, it's really making me think of like managing a team, and everyone listening to this is likely doing and also I was thinking about that a lot of times, people will say like, well, I'm too busy for coaching. And I say, Well, that means you need coaching. If you think you have enough time for coaching, you probably don't need coaching. But if you have too much on your plate and you feel like you know you're just drowning, then that's where coaching can help. And it sounds like, similarly, that's probably where an EA can help. Like, it feels like, oh, man, I'm too busy to even think about, what could I delegate? And how would I do this? And then training this person? And that's how you know you need someone.

Ashley Chang  12:56  

Yeah, totally. And it's really exponential, because it's like, every So, every time, like, for example, LinkedIn is our main marketing channel. So like, I do a lot on LinkedIn, and I still write all of my posts myself, but if I'm doing that myself every day, that means I'm spending like 45 minutes a day doing LinkedIn things. And if I can get someone else to do that, that's 45 minutes times, and I don't actually post every single day, but like, 360 days, or something like that. And so the time that you invest up front might only be like, maybe it would take me four hours, or even 10 hours something to onboard someone else to do some of those tasks, but I would actually get that time back within the first two weeks of someone doing it for me. So I think you're right, like being able to pause and take that step back and be like, Okay, why am I so busy? And what can I do to change that? And then I think also, when you're so busy, you're not necessarily able to do the most impactful things, at least that's the case for me when I'm so busy, when I'm like, my busiest, I'm like, Okay, did this, did this, it's just like a checkbox. It's not being really thoughtful about my business, and how can I grow it, or how can I make my family time more valuable, or things like that.

Leanna Laskey McGrath  14:05  

Yeah, absolutely. So you said you have had all these conversations with parents, so I'm curious, what were some of your biggest takeaways? You know, one of them that you said was that it's hard, it's hard for everybody, which I think everyone who's listening, who's a parent, would agree. But what else, like, what other takeaways did you have that kind of stood out to you?

Ashley Chang  14:25  

Yeah, I think another big thing is that, and the reason that we decided to go this human approach for Sundays is, like, every family is a little bit different. Like, I spent my early career building products people and trying to figure out, like, what's standard among 80% of people that we can build for.

Leanna Laskey McGrath  14:41  

Sure.

Ashley Chang  14:42  

And families do have that, but they also have, like, different things that are very particular about their family, that are really important to them. And so I think learning just like how personal family is and how you want the person who's helping your family to, like, really know your family. And it's not like, it's not just like, oh, I have a six year old and a five year old. It's like, I have a six year old who loves soccer, and that's the most important thing, but he hates broccoli. And then I have a five year old who is, like, very afraid of of starting school this year. And, like, just understanding, like, who are people as people, it's really important to building anything for families, is something that that was a big takeaway for me, and so that's why we're so focused on the human that goes into everything that we do.

Leanna Laskey McGrath  15:25  

Yeah.

Ashley Chang  15:25  

And then yeah, also, just like building, building the systems for things that you don't want to be thinking about, so that you actually can release some of that mental work. And thinking about ownership too. Because a lot of times people will approach delegation as like, handing things off, just like do the actual task, but they've done all of the pre thinking about it. I don't know if you, I'm sure you've heard of fair play, but there's kind of the concept of, like conceiving planning and then actually executing something and figuring out how to best hand off things at that conception phase, or in the planning phase, and not just at the execution phase, so that you're actually releasing the mental work of it, whether that's to your partner or to someone who you're bringing in to help you with it.

Leanna Laskey McGrath  16:08  

Yeah, I think that's really interesting, because my husband and I, for example, will say, like, what do you need me to do? And I'm like, I need you to think of what you need to do. I need to not just tell you what needs to happen. And I think that that is so common for women is like we're planning everything. It's a really heavy load to think about all the things that need to be done and plan everything out. And it's so nice to have people to execute. But sometimes we need help with the planning stage too.

Ashley Chang  16:41  

Yeah, it's super interesting. And I don't know that I have this nailed down, and especially in like, this early phase of parenthood, I feel like I want to know everything, even though I'm like. So for example, where my son, like, might start solids, not super soon, but in the next few months. I'm like, Okay, so like, how do we start solids? And then I've done a lot of the early research on feeding him and things like that. So I was like, Oh, my husband could research how to start solids and, like, have a plan for it, but then I'm, I'm not sure if I'm like, ready to let that go, but I still need to know it. So it's interesting to think about, like, how do you actually hand things off so that you feel comfortable with the results there? And what's the role of the other person potentially in, like, educating and bringing other person along with them too.

Leanna Laskey McGrath  17:22  

Yeah. I interviewed someone on the show a while back, and this is triggering the memory of it, Annemieke Rice was on here, and she was talking about how she and her husband are both tech executives and and she talked about that like, if you want a 5050, partner, if you want for both of you to be truly parents, then both of you have to own different things. And so they've broken it out that, like one of them, you know, whenever they were babies, like one of them owned sleep, and they, like, became an expert on all things sleep, they were the subject matter expert.

Ashley Chang  17:55  

Yeah. 

Leanna Laskey McGrath  17:55  

And then the other one was all things feeding and eating, and they were the subject matter expert on that, for example, you know. And then, kind of, as they kind of, as they grow, you know, different things become important. And I thought it was so fascinating, because I thought, like, I don't think I could not be a subject matter expert on everything. Like, I don't know how to do that. I don't know how to give that up. But I think if you really think about it, if you really want an equal partnership, then that really is a component to that. 

Ashley Chang  18:24  

Yeah, totally something I'm thinking of a lot about, and it's also been interesting for me, personally to just see it in fair play, I think Eve Brodsky talks about how, like, a lot of couples go into parenthood having very equal partnerships, and then becomes like this, very unequal distribution after babies enter the picture, and we're trying to, like, actively combat that and see, like, what are the things that we can do to change it. But I also recognize just like, different, maybe like, hormonal responses that we have when we actually, like, have a baby in our lives. And like, I think there are a lot of different like, mother instincts that go into things that my logical mind was like, oh, we'll just divide and conquer. And now I'm like, No, I feel, I have feelings about this.

Leanna Laskey McGrath  19:09  

Yeah, for sure. And I think it's important to honor all of that you know, and figure out what works best. And like you said, every family is different, but I think to your point, it's like each family needs to operate in the way that works best for them, that supports all of the members of the family.

Ashley Chang  19:24  

I think that's one thing that's been really interesting with the families we work with, and a big learning is just, I think the happiest families are the ones who are like making intentional choices about how they want to balance family or work, or how they want to spend their time. I think that's the big difference that I see between families that are maybe it's really hard, but they're like, happy doing it, and then other families were like, it's really hard, and I'm drowning, and I I feel like this is unsustainable. So I think finding a way to make those choices just about what's most important to you and how you want to spend your time is really important. 

Leanna Laskey McGrath  19:57  

Yeah, I think that's a really important distinction the intentionality, because the thing that makes it even harder is when you're just going on autopilot, it's like you're running on a treadmill, and you don't even know where you're going or why you're going that way, and so it feels very purposeless, and you're doing all this work and it's hard, but when you make these intentional decisions, I think it's a constant exercise and course correction as well, of like, you know, oh, we're going in that direction. That's not the way we want to go. We want to move back here or whatever. But when you are thoughtful and intentional about it, I don't know, you're just more conscious. You're just more there with the experience, rather than like, the experience happening to you without you having any say in it.

Ashley Chang  20:43  

Yeah, totally. And I think that's a big thing that I actually see with a lot of moms who decide to leave corporate jobs and start their own roles, is like, they've been maybe, maybe, like, following a career trajectory that was kind of defined for them. But then once they have more time constraints and more things that are important in their lives, they're like, Okay, how do I actually want to define what success looks like to me? And how could I make this work versus being like, Okay, I'm going to be a VP of marketing, and then I'm going to do that for five years, and I'm going to be a CMO, and just opening up a whole bunch of different paths they could take. 

Leanna Laskey McGrath  21:16  

Yeah, well, I cannot let you go without you telling us, how can we do this better? We know it's hard. What have you learned through working with families? We talked about the intentionality. I'm just curious, like, what would you recommend? What can we do?

Ashley Chang  21:33  

Yeah, my favorite thing right now is, I think doing that, like time and energy audit on a regular basis, and identifying things that are taking up your time and energy that are not giving you energy, and then figuring out what of those things are recurring, and how can you get that off of your plate, whether that's like figuring out an app that's going to work for you, or figuring out a person who's going to help so everything from like meal planning to scheduling a dentist appointment to someone doing your laundry, things like that that are just like that you could possibly hand off to someone else. The next thing around that is onboarding people well. So I think I was telling you I made this whole like nanny long Apple note, of like, how we've been doing certain things with our baby, but giving people the context that they need to be successful, and then making sure you are giving them that feedback so that they can do well, and you are actually getting the outcomes that you want. Otherwise it's not worth your time to have someone else do it. And then my favorite thing right now that I'm trying to do is, like, have people push things to me so that I don't have the mental ownership of, like, the project management of things that are happening. So I have a person at Sundays who's like, helping me with meal planning, and every Monday, she's like, Ashley, here's your meal plan. I need you to, like, approve by Wednesday, or, like, tell me if I need to change things. And then she sets up a grocery order for me. And that, just like, not having to constantly remember that I need to do meal planning or I need to go to the grocery store is actually, like, an enormous lift, even if it's actually only taking her, like 20 minutes a week to do it, or something like that. But the constant, like everyday remembering is a lot. So if you can get people or systems who have that ownership and push things to you, I think that's my current biggest hack, too, to getting some time back.

Leanna Laskey McGrath  23:21  

Yeah, I love that so much, because I do, I think it's like we have this, like, running mental list, and that's a lot of times, what ends up taking us out of the present moment in those precious moments that we have with our kids, and then we're thinking about everything that we need to do, and, you know, something else pops in our head that's trying to steal our attention away from that little human right in front of us, and then we experience so much mom guilt about it, because we feel terrible that we're not spending enough time, and then not enough quality time, because we're always distracted, or, you know, remembering that we need to go and place a grocery order at the last minute, or whatever it is. So I love the idea of not having to project manage everything and outsourcing that part of it as well. 

Leanna Laskey McGrath  24:08  

So where would people go? Let's say that someone wanted to look into bringing an executive assistant on to help with some of these recurring tasks, or, you know, some of the things that you've talked about, where could they find you and tell us more about that?

Ashley Chang  24:27  

Yeah, so our website is withsundays.com W, i, t, h, and then the word Sunday is with an S. And we have our website kind of a breakdown of all the things we do, much more in depth than I was able to go over today, so people can find out more there. I'm also super active on LinkedIn. So if you look up Ashley Chang Sundays, there's a lot of Ashley Chang's out there, so you gotta have the Sundays part, but Ashley Chang Sunday is on LinkedIn. I am there, and I try to share a lot about what I'm learning. Well, as a new mom, and from all of the clients we work with for what works best.

Leanna Laskey McGrath  24:57  

I love it definitely. I think. Think it's something that everyone can check out. And how do you get started? I know you mentioned kind of an initial call to get to know the family. Is that how we get started? Or how would we go about that?

Ashley Chang  25:11  

Yeah, so on our website, the first step is you sign up, you put in a little bit of information about what you're looking for. And then we have used to be me doing every single call, but now we have another amazing teammate named Bethany who will do an intro call with you and learn about your family and what you're looking for, and tell you more about Sundays and in depth of like, how do we get started? What does onboarding look like? What are your goals? And we use that to figure out, like, who the best match on our team is. And if you're also looking for business support, we'll go a little bit more in depth about, like, business goals, expertise that you're looking for. And then, yeah, so we do that intro call. We use that to do a matching process that is pretty fun to meet our team and who we think will be the best fit. And then we'll share that with you. And then we have the opportunity to that chemistry call too. So you get to meet the EA, talk to them and make sure they seem like a good fit. And then we will get started with onboarding, and that looks a little bit different per client depending on where they are in their delegation process of working with someone else.

Leanna Laskey McGrath  26:11  

Okay, wonderful. And I love also that you are employing moms who are actually the EA's. So if people are interested in working for you, in becoming an EA, is this something that they would do part time, or kind of like on their own time? Or how does that work? 

Ashley Chang  26:30  

Yes, most of our team is part time, but we do look for at least 20 hours a week because we want to be highly involved with the clients that we're working for. So we need to have that level of responsiveness. And then we will always post the roles that we're hiring for on LinkedIn. And then also, we have a careers page on our website, so you can look there. We have almost 30 moms on our team now, which is so cool. And I think we also have just like a great culture, where people are always giving me tips about things I can do better as a parent. So it's fun to see kind of moms from all over the country coming together.

Leanna Laskey McGrath  27:06  

I love it so much. I love your mission. I love the idea of, you know, supporting women to get more moms into leadership positions and eliminate the mom penalty. So I'm so happy that you have created this. Thank you for for creating this for for women and moms, and I know it's gonna help so many people, and good luck to you with your your little one. I'm thinking, like, I want you to come back in a year or two and like, report back on how you're, like, living and breathing this so like, how you how you have been doing it.

Ashley Chang  27:41  

Yeah, everybody keeps asking, and I'm like, I'm actively figuring it out as fast as I can. I think it's gonna always feel like that. So I will. I would love to chat again in a little bit and tell you if I've discovered anything new.

Ashley Chang  27:55  

Wonderful. Well, thank you so much, Ashley for being here and sharing all this wonderful information with us. I've really enjoyed our conversation. 

Ashley Chang  28:02  

Thank you so much. This was really fun.

Leanna Laskey McGrath  28:05  

All right, thanks everybody for tuning in, and we will see you all next week. Bye. 

Leanna Laskey McGrath  28:10  

If you're loving what you're learning on this podcast, I'd love to invite you to check out The Executive Mom Reset. It's my six month coaching program for ambitious, success driven, career focused women who are ready to stop surviving and start thriving. Together, we'll tackle the stress, guilt and overwhelm that come with being a high achieving executive mom. You'll learn how to set boundaries, prioritize what truly matters, and build the confidence to show up powerfully at work, at home, and for yourself. Head on over to coachleanna.com right now to schedule a free discovery call. We'll spend an hour talking about where you are now, what you want to create, and how I can help you get there, because every woman deserves to live the life of her dreams. Let's create yours together.