May 16, 2023 | Podcast, Your Business

How to Outsource Successfully and Confidently with Sadie Pestridge

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About the episode:

Today’s guest is someone I admire for so many reasons – Sadie Prestridge, the founder of Prestridge and Co., is here today to help you feel confident when it comes to making your first or next hire in your business. Something else that Sadie brings to the table is her knowledge of scaling your business while pregnant. She started her business in 2018 and was able to quit her full time job 3 months later (while pregnant) as she was fully booked and had surpassed her previous full time income. Beyond that, we’re chatting about the importance of communication, crafting long term relationships with your team members, and of course, the thing that has supported Sadie the most in becoming a prosperous empath. There’s something for everyone in this episode!

Topics discussed:

  • How Sadie scaled her business to $10K months while she was pregnant and what she learned along the way and would do differently 
  • The successful onboarding process that Sadie has created and how she helps her clients identify what they want and need support in
  • The impact of communication on the success of working with a VA agency like Prestridge and Co. 
  • Learning to confidently extend trust as a business owner and remembering who you trust is a choice 
  • What has supported Sadie in more effective communication as a CEO and a team leader 
  • What to do to craft a long-lasting relationship with your VA 
  • Making peace with clients who choose to end their working relationship with you 

About Sadie:

Sadie began her online business as an Executive Virtual Assistant in 2018, and now runs a team of highly-trained EVAs. In the beginning, still working her corporate job, Sadie quickly found her stride and was able to quit her full-time job only three months later. With her client roster full, she surpassed her previous income by June of 2019 and kept growing!

Training and building up a team of highly skilled women, Sadie created Prestridge and Co. to be a leading team that knows how to support and take initiative in leveling up business operations. Prestridge and Co. provide systems, structure, and day-to-day support that helps CEOs and Founders manage themselves, their busy schedules, and their visionary companies that are changing the world.

Connect with Sadie:

Episode Resources:

Click here for a raw, unedited transcript of this episode

Catherine A. Wood  10:17

 I’m so excited to have you on the podcast today.

Sadie Prestridge  11:12

Thank you. I’m so excited to be here.

Catherine A. Wood  11:14

I mean, I know that we tried to record this episode a couple of weeks ago, and I had some major tech challenges, which is like the bane of my existence as an online business owner. So I’m super glad that we rescheduled our episode, because as I was sharing before we started recording like, my energy was off and as an empath who talks about Empath entrepreneurship, like it’s kind of ironic to record an episode when I’m like, literally out of sorts. So thanks for your grace and rescheduling. And let’s just jump in. Because I have so many questions. I’m dying to ask you as much for like selfish reasons to help me and getting supported better, but also in helping our audience learn how to be supported better by their teams. So why don’t you just kick it off by sharing a little bit about who you are and how you got to be here?

Sadie Prestridge  12:06

Yeah, so I’m Sadie pressure edge. I am the CEO and founder of presaging co a virtual assistant agency. And I started out as a virtual assistant myself back in 2018, I took an online course, I was an executive assistant in corporate. And so it was very natural transition for me to go from corporate in person to virtual assistant online, kind of in the virtual space. And I quickly quit my job, I quit my job within three months of starting, but I was doing all of the things. I was a graphic designer, I was a Pinterest manager, I was a social media manager. And I had started it because I wanted to do the administrative support. So I was like, Man, how do I how do I move into that niche. And so in January of 2019, I found a six figure business coach who was looking for an executive assistant. And I applied and got the role. And I was able to niche into being an executive virtual assistant and all of 2019. And then in September of 2019, I got pregnant with our first little one. And I was like, Okay, how do I keep supporting all of these amazing women and the make time for being a mom and having a baby and all those things. And so, in January of 2020, I started presser Jenko, virtual assistant agency hired my first subcontractor trained her really well for four months. And then I had my daughter in May of 2020. And we were supposed to just kind of coast and be slow throughout the summer. But instead, we were in the middle of a pandemic, and people were coming online. And people were quickly noticing, you know, my agency and what we were doing. And so we quickly started hiring, we went from a team of one to a team of six over that summer, we hit our first 10k month in June, so a month after I had my daughter, and it just Yeah, and then by the end of the year, we had made six figures. So now we’re in 2023. I have a team of nine, fully in the CEO seats. I have a combination of executive VAs support vas, graphic designer, system specialists. And we’re just we’re really able to support those high level business owners with that VA support now and so that’s a little bit of how I got started, it was a whirlwind. I definitely wasn’t planning on becoming an agency owner or you know, leading a team or even just becoming a leader. I was really focused on supporting overwhelmed online CEOs with their business needs.

Catherine A. Wood  14:39

So basically, what you’re telling me is that I can tell my husband that when we get pregnant, we’re gonna grow my business that

Sadie Prestridge  14:49

I would not recommend it. Oh, man, it was definitely a I made a choice, right. Like I could have said no to the clients and I could have put people on waitlist and like could have pushed them until I was done with my maternity leave. But it just I’m, I’m, I’m very much listened to my gut. And so it just felt like a gut thing of like, let’s do this. But it was messy, I came back fully from my maternity leave in August of 2020. And I had to take on some of those clients, because the systems and the scalability and everything weren’t there for me to be able to, like fully be in that CEO seat. So I had to take back clients and hire a nanny, and do like a lot of things support wise and systems wise to get it to where it is today. And I would totally do it again. But it was definitely it was definitely hard to do all of those things like to learn to be a leader, a mom, a CEO, you know, and deal with finances for a six figure business. And like all of those things were very new to me. It’s not a skill set that I had.

Catherine A. Wood  15:53

I mean, I can absolutely appreciate that. And there’s nothing like a beautiful bundle of joy to inspire you into Shen, but also into like strategic action, right, like I heard you say, following your gut, and and what is that quote, like? Taking messy, Imperfect Action, which actually is what I’d love to talk about next. Because, you know, most of the audience’s listening to this episode are likely ambitious empaths, who are driven by their heart and their sense of care and service and mission, and also highly ambitious. And something I really appreciate about ambitious impasse is that we can really struggle discerning the difference between perfectionism and excellence, and taking imperfect action, but being in motion versus trying to get things perfect. And that can be really challenging when it comes to getting supported, and allowing yourself to delegate and handoff responsibilities to others. So what? How do you onboard a client successfully? And how do you help a client be successful in delegating their work to you? I feel like that is a juicy question that my audience would absolutely love.

Sadie Prestridge  17:25

Yeah, and so something that I do differently, and I believe in is that we as entrepreneurs, CEOs, as women, we have to know what we want first. And so we need to be clear on the roll, we need to be clear on what we’re gonna delegate first. And so we always start with that. So we start with your systems first, what do you need your EPA to do? And what are the requirements? What are the systems? What are the trainings that we’re going to need for your EPA to do it well, and fully get it off of your plate? And so we’d like you to start there, like start to audit what you’re doing in your business right now? Is it making you money? Do you enjoy it? Is it a skill set that you can do? Is it taking you a long time? Do you not like it like thinking about all of those things? And start to write those pieces down? And then say okay, how long are those tasks taking me? Again, handoff, you can make a loom video or a video training of how you like you doing that task, step by step by step, and then link it to the here’s how to do the blah, blah, blah. And then when you bring on that VA, you say, Here’s the list of things that I need you to do with the video trainings that I need you to watch and make into a written standard operating procedure. And that’s going to give them that opportunity to slowly delegate those things. Well, because they’ve gotten it out out of them already of like, here’s how to do it. And then it gives that go ahead.

Catherine A. Wood  18:54

I just want to pause you there. Because I mean, you just shared so much gold, and I can appreciate how naturally it comes to you. And everything you just shared is not natural for empaths. Because I would I would assert because I would say for many of us and myself included, like we don’t always know what we want or need support in. And I mean in my coaching like what do you want that question is so confronting to people that I chat with. So for someone who’s so practiced in just doing things on their own, knows that they need to offload work and doesn’t even know where to start, like how do you help your clients identify what they want and need support in?

Sadie Prestridge  19:47

And so for us, I mean, I get on a call with them and we we walk through every single thing and I have a list of recommendations like taking getting getting you out of your inbox like how often are you Opening your inbox and spending 30 to 45 minutes in there. Because you’ve got, you know, networking emails and freebies that you’ve signed up for, and invoices and client questions. And all of that’s kind of jumbled. And so we kind of walk through each piece like the admin, the operations, the client experience, the social media, the blogs, the emails, we go bit by bit by bit, and see what for the client is going to make sense for them. Maybe they are a copywriter. And so it makes sense for them to keep writing their emails or writing their blogs, you know, and things like that. But also, we think about what’s going to make you money, and what’s going to keep you in your zone of genius, right, because I can guarantee none of us started our businesses to send out client contracts and make payments and deal with upset customers. We started our businesses because we wanted to help them with something like coach them, or write for them or strategize with them or consult with them. And so that’s what we focus on is like, what is your zone of genius? What are you What is the only thing that you can do, and then let’s talk about what else we can do, like pull off of your plate, and it might not just be a virtual assistant, it might be you need a graphic designer, or a project manager or a support coach, right. So we kind of we delve into all of that together, and we pull that out of out of our clients.

Catherine A. Wood  21:19

I mean, I appreciate that, like, I guess the visual that was coming to mind is like kicking the tires on all aspects of the machine that is your business, all the like, all the elements of the things that you do, the areas of business, the tasks you take on and, and discerning kind of opportunities for support in each.

Sadie Prestridge  21:39

Yeah. And then again, as your business grows, there’s going to be more things that pop up and things that we didn’t think about when we were initially bringing on the VA, but now you’re starting as soon as you start to delegate some of those things, you get kind of excited. You’re like, Oh, can I give you this? Can I give you this? What about this? Is this something you could take? And so then we start to build it out even further, once you actually get the VA in and start to get some of those things off your plate?

Catherine A. Wood  22:03

Are there any, like learned experiences over the years that you’ve noticed? Makes a client’s experience with your agency? Successful more so than others?

Sadie Prestridge  22:17

Yeah, I think communication is big. And trust is big. And it’s hard, right? Like we can all want to delegate and want to give up things in our business, but it’s also our business. And like we talked about, like the buck stops here. And so it can be hard to give it and then trust that they’re going to do it well. And also wait, right? Because what you don’t want to do is say, hey, I need you to go onboard my client. And then five minutes later, you’re like, well, they haven’t responded, I’m gonna do it myself, right? Like, we need to kind of sit with that. That feeling of uncomfortable? Like, are they going to do it? What are they going to do it? How is it going to get done? How do I communicate like what they did and didn’t do? And so the communication and the trust piece are big. I feel like the clients that have the most success with us are reaching out and saying like, This feels weird. Can you help me with this? Or is this a task my VA can take over? Or, Hey, it’s 2023. And we’re like thing, the world is weird. And things are changing. And I need to shift things in my business. Can you help me with that? Can we shift these VA tasks. And so that, for me is where success comes in, where we see things start to falter is they they don’t feel like they can come to us. And so they they get into like a six month or 12 month. And then we go into their renewal and they’re like, well, everything in my business has changed. And I don’t feel like I need this support anymore. It’s like, that should have been a conversation the minute you felt that way. So we could have adjusted.

Catherine A. Wood  23:46

I could not agree more. And those are such mindset changes, right? Like learning to trust your support, and communicate openly. Like they’re necessary business practices, but they’re also huge mind mindset shifts. So I’m wondering, how do you how do you coach your clients to communicate better and trust more, I’d love to share from my perspective, and I’d love to hear from yours.

Sadie Prestridge  24:18

Yeah, so it’s a lot of usually it’s a lot of back and forth. We do have like a welcome packet that helps, you know, tips and tricks and things for success. But something that I’m moving into doing is actually creating kind of a welcome sequence or almost, I mean, I could probably bundle it and sell it into a product. But what I want to do is give my clients almost like their own version of what we train our EAS on. So things like how to work successfully with your VA how to delegate with your VA five tips for success, how to allow your VA to start to step in and like manage and lead you. So I’m building out kind of a welcome sequence for those things. How to Prepare for your weekly call with your VA how How to, you know, once you’re fully into that COC how to stay there and not like get back into those tasks. So a lot of it’s going to just be training and how tos and our welcome packet explains it a lot as well. But I am building out more of a almost like a freebie welcome sequence for our clients coming in. But again, for me, it’s every quarter, we’re offering them coffee chats with me, so that we can delve into like, what’s going well, what’s not working, this is what your VA has come to me and said, we could use some support on we audit our clients call recordings so that we can see how they’re interacting with our team. And then we also audit like Slack and project management systems as well. Again, I’ll be able to quickly see if the client is commenting like, oh, I’ll just take this on myself, or like, Oh, this is too much of a pain to off, like off board, I’ll take it on, I’ll immediately reach out to them and say, Hey, let’s, let’s have a conversation and talk about some things that I’m noticing. And then I’ll coach them on just like a quick call.

Catherine A. Wood  25:59

I love I love the multiple, like what I hear in your what you’re sharing is like there are multiple levels and layers of communication. So getting to audit calls, having weekly calls with their executive VA getting to have quarterly calls with you, like I just hear multiple opportunities for feedback. Yeah. Which I think is really is really useful because even creating the container to share feedback invites more of it.

Sadie Prestridge  26:26

Absolutely, yes. And we do see, send out a feedback form, which is more in depth on like, their support they’re getting from their VA. And then there’s a link there too, to book that call with me.

Catherine A. Wood  26:40

For for in my line of work from a mindset perspective, like a lot of the work I do with a lot of my entrepreneur clients is around like a mindset of trust and verify, like practice extending trust to support and then verifying that the work was to your standards, and that there weren’t any misgivings or errors or omissions because, you know, truly we have to extend trust, but trust is, is earned and developed over time and like, as an empath, I, for so many years in my own life, just gifted trust everywhere. And that was a hard learning that like trust isn’t does not have to be gifted to everyone I can, you know, I can be kind with everyone but who I choose to trust is is an honor for for myself and the person that I choose to be in that level of relationship with. So trust and verify is something that is huge in my work with clients. And then along with that, like expecting the best of people, like I noticed, working with leaders, like when we expect the best of our employees, we will receive the best in return. But if we’re you know, if we’re assuming that they’re going to mess up, or we expect that they’re mistrusting, like we’re, we’re, we’re putting out that energy, like we’re sending off that vibration. And so we’re creating, we’re creating, we’re literally creating the container to re perceive that experience, or behavior from other people.

Sadie Prestridge  28:28

Yeah, yeah. And something that is hard for business owners to wrap their mind around is like, wait, I just gave all of this to them. Because I don’t have the time for it. But now you want me to like check it and verify it and make sure it’s good. And so that can that can be hard to because they’re like, No, I’m, I’m hiring the support, because I want them to do the thing. I don’t have the time to check the work and do the thing. And so then maybe an error happens or it wasn’t done the way they wanted it to. And that brings that resentment and that frustration of like, well, I hired you to do it, why aren’t you doing it? Well, but it’s because they need to slow down and really work with their VA and partner with them and verify that things are going the way that they want them to go and the way that they would do that. And so that’s a really important piece of it, too, is trust, but verify.

Catherine A. Wood  29:18

And the communication piece that you shared. Like I think that that’s another just huge growth area for entrepreneurs because we can all learn to be effective communicators. Yeah. You know, like, I joke with my family about this a lot but like I grew up in a very conflict avoidant family. And so we didn’t have open conversations about things that weren’t going well in our, you know, in my sibling relationships or in the household or you know, with family money or the business like we didn’t talk about those things. So if I had no modeling of tough conversations as a child like how could I expect that when I am creating my business or starting to think about my family that I would have the skill set, if either someone else didn’t model it for me, or if I didn’t work with a coach, or do some type of educational learning that would give me that school that that skill set?

Sadie Prestridge  30:18

Yeah, yeah, absolutely. I mean, I’m the same way I was an executive assistant, I wasn’t a CEO in corporate or I didn’t have a role where there was a lot of like conflict or leadership. And so for me to step into that with the agency was like, just eye opening and raw, and I really had to learn not to enjoy conflict, but to be okay with conflict and to be able to lead and do some of those things. So it is it is hard, it’s hard to have those conversations. And I’ve had clients come to me and say, you know, it’s my fault. I didn’t, I didn’t want to have the hard conversation with her because I don’t like conflict. And so I get it. I wish there was more training and support out there around that piece. Like, the minute you start to bring in people, you need to be okay with some of that conflict for sure. Yeah.

Catherine A. Wood  31:05

And as Empath entrepreneurs, like, I noticed, there’s even like a tendency to be to, to withhold information, or withhold feedback or communications, because we don’t want to offend or hurt our employees, our teammates, like, we don’t want to hurt their feelings.

Sadie Prestridge  31:27

Yeah, and the thing too, is with contractors, right? Like, they don’t have to be here, they it’s a choice. And there’s a lot of things we can and can’t do. And so I know for me personally, that can feel hard to like, don’t want to have a hard conversation and make them feel unwelcomed or like, they don’t want to they don’t it’s not fun anymore. And they don’t want to be here, you know, and so some of that comes up to with that difference in the employee versus the contractor or the subcontractor, as well.

Catherine A. Wood  31:52

Well, so what what supported you, I think that this could be a really useful segue for our, our audience, like what has supported you in more effective communication as CEO, but also, for your employees? Like, what do you train them in to be able to collaborate and communicate more effectively with their partners and clients?

Sadie Prestridge  32:16

Yeah, so I did for me, personally, it was one on one coaching. So I had a coach, up until just recently, where I did one on one support, and she think, thank goodness had a lot of that skill set. And so I could come to her and say, I’m having like this issue, like this person needs to go on maternity leave, or this person is unhappy, and this client is blocked, like whatever it was, and she would coach me through that and give me feedback on like, well, here’s how I would speak to that person, here’s what I would say. And then for me, it’s just been kind of like a rinse and repeat, like I’ve built built upon that. And for the most part, I have a lot of the same issues that come up when you have people and agencies and some of those things. And then on the team side, it’s a lot of resiliency training, we have like a whole resiliency toolkit that we give our VAs because again, it’s hard to step into someone’s business when there can be conflict, and the clients are stressed. Or they’re quickstarts. And they like they want to go Go, go, go go. And it can start to feel like you’re putting all of your energy into that person, and you’re not giving anything to yourself, and then you you reach burnout. So we do a lot of resiliency trainings, mindset trainings, also a lot of self care training, and how to make sure that you’re supporting yourself so you can support your clients. Well, that’s a big one. And also just time management, and thinking about what’s going to support you and your business and in your day to day. So you can go out and support your clients business in the same the same way. So show up both places well, because I have team members who will drop everything for themselves and their businesses and their lives and spend all of their energy on our clients. And that’s what we don’t want. We want a very well balanced VA and client.

Catherine A. Wood  34:04

I I know for me personally, like I have a lot of team members right now. And so I’m offering feedback a lot as well. And I’m constantly thinking like, how am I? How do I want to deliver this feedback? And over the years, it’s, I mean, first of all, it’s become so much easier, sharing feedback with practice. Like if I think about what it was like to offer feedback in year one versus now in year nine, like worlds worlds apart. So it really, and I would say one of the shifts that’s made it the easiest for me is assuming like, like honestly ownership like and what I mean by that is assuming I didn’t explain what I wanted sufficient for my team Remember to understand, or assuming that, you know, assuming that I contributed in some way, because I noticed when I can come from that place, like from that angle of, like, I can own this, I’m responsible for this. It allows for, like, whatever there is for me to communicate to be heard so much more from a place of collaboration, and partnership and co creation, and and looking for a creative solution versus, you know, versus putting out this energy that my my team member did something wrong, because that’s, you know, that’s not the culture I want. And I, and that is something that has been a golden lesson I’ve learned over the years.

Sadie Prestridge  35:55

Yeah, yeah. I love that. You know, we were talking briefly before, similar to that. And I think that that’s one of the things that I personally struggle with as an empath is, did I fail them? Like, do you know, is it me? Was it something that that I dropped the ball on? How can I support them better? And then after we’ve gone through that process, and things still aren’t feeling good? I struggle with that, like, Okay, well, then is it time to part ways because I’m so empathetic to them and like, feeling like maybe I just failed them in some way. And it’s not fair to let them go because I failed. And so that is something as a leader that I I struggled with and as an empath, it’s just, I think about it and relate to it too much of, you know, are they are they going through something or you know, and all those things that start to come up as a leader.

Catherine A. Wood  36:43

And I mean, I so appreciate you saying that. Like, as, as prosperous empaths like, we are so highly conscientious. We think things through so deeply. So anything we’re communicating to our team, right, we’ve likely already thought it through, up and down, left and right, talked with our coaches about it journaled about it had meditated about all the things. So whatever we’re articulating, is the result of extensive communication. And we don’t always trust our employees or our team members with our process. So what I’ve realized over the years is that like having a willingness to put my process on loudspeaker allows for more support and collaboration along the way. And it has people see me as more of a human versus, like someone who has everything has like their, you know, metaphorical shit together all the time, right. And because I don’t like I’m a human, I’m human, just like everyone. And I have like an example of this, because I did this just recently, like I, I run a mastermind, and I have a co facilitator in my mastermind, and she is a trained coach, we have many years of relationship. And there was a dynamic in our partnership that wasn’t working for me. And it was, it was making me uncomfortable, and I didn’t have a solution for it. And I, you know, the old me would have waited to communicate anything until I had the solution, right, which, again, leaves no space for collaboration and teamwork. And now, what I can do is I can actually just share my process, like, share what I’m noticing, share my frustration or my confusion about how we could do things differently. And it created this beautiful opening for deepening our relationship. And this is with someone who already have nine years of relationship with right so we already have a lot of practice and trust and that and still, you know, just like noticing that tendency that there’s always things we withhold sharing, and trusting people with so you know, again, human being. And she acknowledged me after that conversation, she said, Thank you so much for just sharing your process with me like it makes me feel more in partnership with you and like we’re going to work through it together. And it was so affirming for me to hear that like that. I don’t need to have all of my questions answered before I bring it to the people I trust my business with like, actually get to bring the concern and then trust that we will co create a win win, like CO create a solution that works for all of us.

Sadie Prestridge  39:52

Yeah, and that’s a huge thing to think about when you’re hiring a VA or anyone in your business is it’s that Fear of like, well, what if and and what if they just say, You know what, this isn’t for me, and then you, you start to go down that rabbit hole, especially with a VA that you’ve given a lot of tasks like to, like, well, do I take those tasks back? Will I find someone else who can do the tasks? Well? How long will I have to do the tasks? Again? How do I take the tasks back? I haven’t done them in so long. And so a lot of that can start to come up and then you’re like, why would rather just sit with the uncomfortableness of whatever situation it is that’s making you either resent them or wonder if they’re doing a good job versus just having the conversation and being okay with if the end result is we’re not a fit anymore? So I think that’s really, really key when hiring.

Catherine A. Wood  40:44

Well, okay, so let me think like, most of the people who are tuning into this episode are have likely had a VA have had multiple vas, right? And like, we all hear experiences of yes, people kind of passing through vas. So I guess I just like, I’d love to kind of like dig into your brain a little more about, like, how, how can entrepreneurs make their next VA like their lifelong VA? Like, how can they set up that relationship? Which is a really like, crucial relationship in a business, but also for executives and leaders? Like how can they make it a truly long term relationship, if there’s anything more that you’d add that you haven’t already shared?

Sadie Prestridge  41:34

Yeah, so it’s two things, really, it’s actually both parties, it’s not just the CEO, the CEO needs to have some clarity around some of what they need done. And they need to have a job description. I don’t know how many times I’ve seen a Facebook post where I’m like, I need a VA, drop your email. And then there’s 100 comments, right? Like, the CEO is not gonna have time to go through all of those things. Or they did the other thing where they put their email, and said, like, email me your resume, right, and then it’s just like, blown up. And then again, the CEO is not going to have time to go through that. So very clear job description with an application, just Google Form is key there, and then you’ll, you’re gonna be able to go through the motions there. But on the VA side, that’s the, that’s the other part. Like, they also need to take some ownership there, they need to be able to come to the table, and say, like, based on what you’re telling me, based on what I’ve seen on like, socials, like they should audit their, their potential client before they get on a call. And they should be able to come to the table with like, here’s what I’m seeing that you need, based on what you’re telling me based on what I researched. And so it’s a part it’s a collaboration of like, this is what you, as a CEO, have told me that you need. And then this is also what I see that you have a need for. And then let’s partner and build out the systems and the tasks and the to dues and all of the things. And so it really goes both ways. And I think when the CEO is hiring, they need to be looking for that. Is the VA showing up with like, here’s how I can support you? Or are or are they saying what do you need, I’ll do whatever you want, because that’s, again, lacking clarity on the VA side, and then they’re, they’re picking up tasks that they don’t know how to do, or they’re like, I’ll figure it out on the fly, or it’s, they don’t actually enjoy it. And so then down the road, they’re like, Hey, I only really like to do these things for you. And you’re gonna have to find someone else to do these things, or they just experienced burnout in general, and they leave. And so if you’re looking to find someone long term, you’ve got to get clarity around what you want. You’ve got to create that application process. And you’ve got to make sure that when you’re hiring, those are interviewing those people. They’re actually saying, like, this is how I help people. This is what I can do for you. And they have a lot of clarity around those things. Because like I said, In the beginning, I was doing graphic design, I was doing copywriting I was doing social media management. I didn’t know any I didn’t have any I had no idea how to do those things. So it wasn’t doing them well. And it was stressful for me too. Because it wasn’t my zone of genius as a virtual assistant. And so that’s really key is getting clarity on both sides.

Catherine A. Wood  44:05

And I love I mean I totally hear that like knowing that what you need is what your support team is trained and and well resourced in and also has an interest for but the other piece is around like having a willingness to be proactive and looking at for both of for both people out here and what you’re sharing like on the CEO perspective, like constantly looking like how can I how can I offload this how can I delegate this, I feel like you’ll appreciate this I used to have this was a practice from my coach. And it was a post it note and the question on the post it note said how can this be the last time I do this?

Sadie Prestridge  44:48

Yes, that needs to be a t shirt.

Catherine A. Wood  44:51

It was so useful Sadie like yeah, right like as powerhouse women who are like skilled and being multi task oriented, like we don’t even know, half the things we do on a daily basis, right? Sometimes simultaneously. So having a willingness to look strategically and objectively like, How can I, how can this be the last time I do this, like, how can I offload this and this and this, and how can I train my VA in this and this and this, but from the VA perspective, and I think this is something that I’ve appreciated over the years also is like, looking like, How can I? How can I support more like, hey, offering suggestions, or recommendations or opportunities for more support, like, a couple months ago, even with my VA, like, I shared, I’m like, I don’t feel like I’m leveraging you as much as I could. Like, I could just have a conversation about everything that you do for your other clients. So I know, you know what other magic you have to share? Yeah, yeah. And it was so helpful. I didn’t know half the things that that they could do.

Sadie Prestridge  46:04

Yeah, and we do that in the agency, too. So every quarter, we have them fill out like a skills and proficiencies form to see if they’ve gotten any new certifications, or they’ve learned a new skill, or they know how to do something I didn’t know. And so we do, we do try to stay on top of that, too. Because yeah, skills change, people change and their desires for what they want to do in your business or in their own business change. And their family lives change to like, maybe they’ve had a couple of babies now, and they don’t want a business anymore, or they want to move on to something else. And there’s a lot of that happening, for sure. And I think that’s the thing that I enjoy about my agency is I’m helping CEOs ensure that they understand how like the type of support they need, why they want it, how to get things off their plate, like almost like a coaching piece. And then I’m also training VAs on the other side, to be really successful and understand what they want to do and how they want to do it. And then I get to bring them together and support both of them really well. And so that’s the fun piece for me for my agency is I get to be on both sides.

Catherine A. Wood  47:07

I mean, in half and getting to play that role. I also hear that you get to help your clients, like your CEOs remove the bottleneck that they can often be in the way of being supported. Yeah, yeah, exactly. Oh, man. Like taking so much from this conversation? Well, I mean, I feel like I think like the thing I’m curious about is how, like, what? I’m just Can you hear my dog snoring in the background?

Sadie Prestridge  47:47

No. I’m not listening. I’m listening for it.

Catherine A. Wood  47:52

I like just noticing through the microphone, but um, my fellow empaths. Um, I’d love to know, like scaling, right? Like, you scaled really quickly, you scaled? How many members are on your team now? We have nine, nine. Amazing. Congratulations. Thank you. So that’s a lot of those. That’s a lot of lessons learned to scale from one to nine. And hats to wear and growth edges to break through. What are some of your biggest learnings all in your journey.

Sadie Prestridge  48:36

So it’ll sound silly, but I have this kind of the quote that I say to myself to like, make me not burn it down. And it’s people come and people go, because that’s the hardest part for me is I’m so empathetic. And I like I build such a strong relationship with my people, that when they leave, it’s just like soul crushing. And especially if, right, they’re working with several of my clients, or whatever it is they’re doing, or they’re working, particularly for me, and they need to step out or they’re pregnant, and they have maternity leave or their own businesses have, you know, whatever it is. That’s been the biggest piece for me is people come and people go and I think that’s important for even just a solopreneur just hiring one person is that person’s not probably going to be here for the duration of your business or your life or their life or whatever, they’re going to get to a point where either their own growth has happened or something in their lives has happened. Or maybe they’re you know, shifting or whatever it is, and they may need to step out and we just need to kind of toughen ourselves to that and be okay with it. Because the thing that I have learned is even though people come and people go, people always bring the thing that I need in my business at that time. So they always helped me kind of step up, you know, up the ladder a little bit further. They’ve helped me get a little higher or scale a little more or make more money or streamline more or have provided some type of support and some type of way that’s helped me get where I, where I wanted to go. And so, for me, that’s the, that’s the biggest thing.

Catherine A. Wood  50:13

Honestly, I couldn’t agree more. Like, I really feel that for myself too. Because you know, as a coach, like I am in such intimate relationship with my clients. So when clients decide it’s time to complete, or they want to reinvent their relationship, or their, you know, they achieved what they came for, like, it’s, it can be really, really sad, like really heartbreaking. Like, actually, recently, I asked my coach, like, how do you do it? Like, how do you handle clients completing, and she said, something that I really appreciated. Which, honestly, I feel a little uncomfortable sharing, but, but I will since I started, but she’s, she’s like, you know, cat, like, most of the clients that I work with, stay for the long term. So typically, when a client chooses to complete, like, to some degree, it feels like it was it had come to a natural ending that relationship. And so so she was more, she’s more at peace with those clients who the relationship comes to a natural ending. And I really appreciated that reminder. And I tried to like I try to refrain because there are some clients, you know, who complete and, and I feel like there’s so much more for us to work on. And there’s so many more ways that coaching could support them and trying to remember like, well, first of all, this isn’t about me not to take it personally. But also, you know, how is this actually in service of me? And and what’s next for me? And how is this in service of who I’m becoming? That’s probably the reframe, that made the biggest difference for me, because people do always come and go, and sometimes we’re ready for them to go. And sometimes we’re not. And remembering how it’s in service of my future self, really helps me to kind of bless and release people. And the other thing that makes a difference for me personally, is realizing that the relationship, the reinvention of relationship is also possible, like, I may not be their coach anymore, but that’s not to say, I still don’t get to have a relationship with them, or, you know, who knows what’s possible in the future? Or how we could collaborate or, you know, like, so both of those make a difference for me?

Sadie Prestridge  52:42

Yeah, 100%. And for me, too, I’m very systems oriented. So I think about like, if it was maybe a bad release, or just what we parted ways, because it wasn’t a good fit for one of us or whatever. I just like to think about what can I put into place now to fix or help that in the future from happening again? You know, is it a backup VA so that there’s someone on standby if someone leaves or we have to release, so that helps me to like, kind of thicken my skin sort of to have kind of a plan or a backup or a process in place?

Catherine A. Wood  53:16

This has been so lovely. I mean, it’s been affirming for me and my own leadership, and the ways in which I’m allowing myself to be supported, but I think it’ll, it’s really useful for my audience. So I guess as we wrap, like, I have every expectation that people are going to want to reach out to you and follow you and continue learning from you or potentially hire you. So where would you recommend they check you out?

Sadie Prestridge  53:43

Yeah, so first thing is we do have a freebie and it’s 172 Plus ways an E, VA can support you. And so if you are like well, I’m ready to hire or I’m interested in hiring or hiring your agency, I would start with that, go grab that on my website, frustration And start there, there is a welcome sequence that follows it. And there’s some training videos in there where I talk about how to actually pull the tasks that you want someone to take off of your plate, we kind of go through that motion. So you’ll end it with a good list of things that a VA can take off your plate. And then I’m also over on Instagram, too, at pressuring CO as

Catherine A. Wood  54:19

well. Well, that sounds like an amazing freebie. Well done. Thank you. Thank you.

Sadie Prestridge  54:24

Yeah, I hope it’s super supportive, and it helps do it’s kind of a cheat for me because my goal is for them to go through that. And then when they get on the sales call, they’ve got that clarity of here’s some of the things that I would like someone to take off my plate.

Catherine A. Wood  54:39

And so as we wrap and, you know, I shared that this is a question I ask all my guests but truly like what has made the biggest difference for you and becoming a prosperous empath?

Sadie Prestridge  54:49

Yeah, definitely. For me, it’s learning those communication and leadership skills and as an empath, also knowing and learning that it’s not always me, right I like it’s not always it’s not always personal. It’s not always I did something or I’m, you know, I am a certain way like insert any bad word you can think of. Sometimes it’s just not a fit and it’s just not in both for clients and for team and so, for me, that’s been the biggest thing and that’s helped me scale and grow and be more prosperous. It’s just understanding as an empath. It’s not always me, right.

Catherine A. Wood  55:25

Pure gold. Thank you so much. This has been so I don’t know just like affirming and good from the soul.

Sadie Prestridge  55:36

Yeah, no, this was great. I feel like I need a warm cup of tea and just to go like, soak it all. And it was really fun.


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If you’re an ambitious empath, you probably feel the misalignment of hustle culture marketing almost daily. I know this was a huge problem for me early on in my business before I really gave myself permission to do things my way. With that being said, I’m so excited to have Sarah Santacrose on the show today. Sarah is the author of Marketing Like We’re Human, and it’s her mission to show how we, as prosperous empaths, can revolutionize the marketing industry.

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