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The Encore Entrepreneur



Episode 35: Hiring a Virtual Assistant: The Who, What, and When With Sadie Prestridge of Prestridge & Co

Hiring a virtual assistant can be tricky. If you’ve tried it, you know that things don’t always work out smoothly. There are a lot of misconceptions about when, why, and how to hire a virtual assistant.

In this episode, we have the pleasure of learning all about how to know when it’s the right time to hire a virtual assistant and how to go about getting yourself and your business ready to bring on a VA from Sadie Presteridge of Prestridge and Co.

Sadie also shares what the biggest mistake she sees business owners make when thinking about hiring a virtual assistant, the different types of help you might need, and more.

Connect with Sadie:

Website: https://prestridgeandco.com
On Instagram @prestridgeandco
Download her free resource: 172 Ways an Executive Virtual Assistant Can Support You

Episode Transcript:

[01:05] Carmen Reed-Gilkison: What is the who, what, and when of hiring a virtual assistant? We're happy to be talking to Sadie Prestridge, who will give us the lowdown.

[01:14] Deirdre Harter: Sadie began her online business as an executive virtual assistant in 2018, and now she runs a team of highly trained virtual assistants. 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 has surpassed her previous income by June of 2019 and has kept growing, training, and building up a team of highly skilled women. Sadie created Prestridge and Company to be a leading team that knows how to support and take initiative in leveling up business operations. Prestridge and Company provide systems, structure, and day-to-day support that help CEOs and founders manage themselves, their busy schedules, and their visionary companies that are changing the world. And Sadie, it all just sounds like a dream come true. So welcome.

[02:16] Sadie Prestridge: Hi. Thank you. I'm so excited to be here.

[02:19] Carmen Reed-Gilkison: We're super excited to have you here. And I know this episode is going to be so valuable to our listeners because a lot of people—you'll be able to speak to those because you know for sure—but there's a lot of misconceptions around when or why or how to hire a virtual assistant. So we'd love for you to tell us some of the things that you, maybe like, the biggest mistake you see people make or how people can know when it's time, would be a great thing to explain.

[02:48] Sadie Prestridge: Yeah. So the biggest mistake is not getting clarity around their needs with having a virtual assistant. A lot of people will just say, like, I feel like I need a virtual assistant, so I'll just go and hire one. And they don't know what they need them for, or maybe they actually need a graphic designer, or they need a project manager, or they actually need a business manager, but there's not a lot of knowledge for CEOs on the why. Like you said, the what, the how, the when, and the why of the virtual assistant. And so there's a lot of gaps in education for people hiring, so they need to get clear on what they actually need because it may not be a virtual assistant, or it may not be just a virtual assistant, right? Maybe they need some other players, too. And the same goes on the virtual assistant side. There's a lot of virtual assistants who don't know how to tell the CEO that that's not something they can do. They'll just say, oh, yeah, I can do that. And then they get into it, and they realize they can't. And so then the CEO is having to rinse and repeat over and over and over again because they didn't get clear on the rules that they needed.

[03:59] Deirdre Harter: Yeah, that's a great point, Sadie, and I know that we're talking about executive virtual assistants, and I think sometimes we just are tossing the name around. I need a VA. I need a VA. Yeah, exactly. In actuality, there are just, like anything else, any other professionals; everyone specializes in a different thing. And so that really speaks to knowing exactly what it is that you need first and then hiring the right individual for that role. And when it comes to working all that out, is that something that you help your clients with?

[04:34] Sadie Prestridge: We do. So because I've obviously been doing this for several years now. I really sit down with my clients and say; this is based on what I'm hearing in your business and where you're at and where you want to go. Here's where I feel like you need support and you need systems and processes. And I would recommend you hire a graphic designer, or you get some copy support, or maybe they have a mastermind, and they need some support coach. We go through all of those things and work through together what their needs are. And we also have a freebie that will help too. It's 172 ways an executive virtual assistant can support you. And in that welcome sequence, I actually have a training video that helps them start to get clarity around the tasks that they need for their specific business.

[05:22] Carmen Reed-Gilkison: Awesome. I have a couple of things. One, before I forget to say, is that also they might not need full-time support, right? So a lot of people, they might be in a crunch time, and they're overwhelmed, and they're like, oh, my gosh, I need help. But maybe all they need is a contractor to come in and help for a certain amount of hours per month. That isn't a full-time kind of thing, right?

[05:43] Sadie Prestridge: Oh, absolutely, yeah. I don't have any of my…We work with six-figure business owners who have podcasts and summits and books and all kinds of things, and none of them have full-time support with anyone on my team. It's not a necessity.

[05:57] Carmen Reed-Gilkison: Yeah. And then my other question was, can you explain the difference between an Executive Virtual Assistant and a regular virtual assistant? And I know, obviously, that just like anywhere in the online space, people can put a label on themselves, and quality varies, but I'd love to be able to distinguish that for our listeners as well.

[06:15] Sadie Prestridge: Other people are going to have their opinions too, right? But my opinion is a virtual assistant is someone who needs more management. They're going to need you to say, I need you to do X, Y, and Z. I need you to do these things very specifically, and then the VA goes and gets them done and then comes back and says, okay, what else do you need? So they're more of a task doer, and they will need more management, either from you or a project manager or an OBM or someone. 

An Executive Virtual Assistant is your right hand. They are going to be wrangling you, your schedule, and your inbox. They're going to be proactive. They're going to be looking at your business holistically and saying, these are the things that I'm seeing that I need to take off of your plate, and they're going to be pulling those things from that person consistently. And I also get the question of, like, okay, well, that sounds like an OBM, but an OBM is there hiring. They're managing your team, they're managing your launches, your projects. An Executive Virtual Assistant isn't doing that. They are focused on you as the CEO and then doing those administrative and client support tasks.

[07:19] Deirdre Harter: All right, that's excellent. So I know as an entrepreneur, Carmen and I have had our share of tests and trials and working out for ourselves, building our team. And I think that a lot of CEOs, especially women who are solopreneurs, we are so used to handling everything ourselves, and it's a little bit difficult, and some of us have a little bit of control freakiness inside of us. And so, how—can you talk a little bit about how do we handle that challenge of letting someone else take control of the pieces of our business?

[08:01] Sadie Prestridge: Well, it's all about communication and clarity and collaboration. So you're going to get clarity around your needs. Your VA is going to create systems around those needs. You're going to approve the systems and processes, and then you're going to collaborate to get those things done and trust but verify for the first little bit, right? 

So trust them to do it. Verify that it's done in the way that you would do it, in the way that you're comfortable, and then allow them to take over that task and continue to do that in the different areas of your business until you've handed off everything that you're wanting to hand off. You guys are in a good flow. 

I usually say it takes about three months to really get into that flow. The first month feels really sticky, and you're like, why did I sign up for this? The second month, you're starting to see things come off of your plate. You're getting more space. The third month, you're like, this is amazing. What else can you take off of my plate? And then months, four, five, and six. You're really in a good flow and you're really able to be in your zone of genius.

[08:59] Carmen Reed-Gilkison: What you just said is gold about the three months. And the first month does feel sticky, and like, why did I sign up for this? And people don't realize that's going to happen. And that's one of the reasons why we really want to get this out there. So people do understand. And we've seen with clients and other entrepreneurs online that we've had discussions with where they may get into a situation where they are putting the cart before the horse, where they think that they need a VA, and maybe they do need one. But mostly, what they want is someone to do the thing for them because they don't want to figure out how to do it. And that doesn't work because then you're bringing in someone who also doesn't know how to do it because you aren't going to be able to teach them, and you're allowing them to come in and figure it out for you. So then they're not necessarily doing it the way that you would if you took the time to do that. I mean, there are so many nuances to this whole thing.

[09:53] Sadie Prestridge: Yeah, absolutely. There is a lot of back and forth. I get that a lot with clients where they're like, well, I just need someone to come in and take things off of my plate. But especially, like, let's talk about talking with your clients, right? Maybe they are emailing and they're having questions around your program. Your VA is going to have to ask you the question that that person is asking, and you're going to have to give her the answer, and you're going to have to do that for a few weeks or a month so she can understand how you would answer it. 

And I think that's where clients start to get like, well, I could just be doing this myself. But what they are not realizing is by slowing down and allowing that teaching time to come into play, that person is going to—if you've hired the right fit, they're going to be able to start to take that off of your plate and start to work with your clients and answer those questions and go through the motions. But they need time to learn, right? 

It's just like a relationship. If you're dating someone, there's a process to dating someone. From going from dating to boyfriend/girlfriend to fiance to husband/wife, right? There's a whole process. It's the same in business.

[10:56] Deirdre Harter: Yeah, I think that is such a good point. And this process is the same for the most part for almost any team member that you're going to bring on. So it is really an evergreen process that you're talking about, and it's for anyone that you're going to bring in on your team that's going to be taking direction or learning from you as opposed to a consultant that already has expert knowledge that's going to come in. 

And so when we're thinking about, okay, I see the long term here. And that's, I think another critical piece of what you're doing, Sadie, is you're setting these expectations, and we like to do that too, that we always say that whatever you do today, you're not going to see the result and the benefit of it for 90 days at least. And so we have to be making decisions now and giving ourselves the runway so that we can get those things in place and let them run and let them sink in and gel up so that we can actually get the result that we're looking for.

[11:59] Sadie Prestridge: Absolutely. And I think it's a little bit of the VA or the team member also needs to have their own proven process for how they're going to step into a client's business. That's something that's really lacking in the VA space that I'm actually working on providing, is a lot of VAs don't know how to come into a client's business and go through those motions of, like, here's the tasks I'm going to do, here's how I'm going to set up the processes for how I do them. Here's how we're going to take them off your plate, yada, yada, yada. They don't know how to do that. And so they're looking for the CEO to tell them how to do it when to do it, and all of the things. And the CEO is like, well, I don't know, that's why I hired you. And so there is a missing piece there on both sides that we're working on helping with.

[12:44] Carmen Reed-Gilkison: That's such a good point. I mean, when you do hire someone, you're hiring someone to help you, and it's fine to even know that you've got that one-month period of time where you're going to have to educate them and work with them and hold their hand and all that, that's normal. But if the virtual assistant that you hired doesn't have leadership skills to be able to lead themselves, not even that she needs to lead the person who's hiring her. But that brings up a really good point. So I'm glad that you're working on addressing that because that is extremely important. So what would you say when someone is considering hiring a VA, or what signs are the signs that it's time to hire a VA? Like, is it certain tasks that need to be handed off? What's kind of the criteria?

[13:36] Sadie Prestridge: For me, personally, I like to see a client who's had really great marketing for a year. So they're able to easily bring on clients on board, do really great work, and offboard if that's their process. So their marketing is working really well for at least a year. Their referral program, or just their referrals in general, are coming through really easily. They're starting to kind of build that waitlist, and they're starting to want to scale. Maybe they're ready to create a group coaching program or a VIP day, or they're wanting to hire a subcontractor to take on some design work. Or some of those things are starting to happen, and they're realizing that they can't onboard clients, make sure invoices get paid, make sure contracts get signed, make sure that they get all of their deliverables and all of that stuff done. On top of starting to actually scale or think about scaling or think about growing these other things. And so what's happening is they're getting pushed out of their zone of genius, and they're getting stuck in the day-to-day. That's really when it's time to say, like, okay, I need to bring someone on. And even if it's just three to five hours a week, they're focused on client onboarding, client implementation, making sure that the deliverables are happening, and all of that client offboarding, invoicing payments, your inbox, and your calendar. Those are the basic things that a VA can step in and take off your plate that are going to make a really big difference if you're constantly bringing in a lot of clients.

[15:07] Carmen Reed-Gilkison: Are you ready to get the guidance you need to optimize your online business? We help ambitious female entrepreneurs cut through the online noise of too many options, too many tactics, and too many shoulds. Through our encore business incubator. Group program and our Empire Builder two-on-one laser coaching program, we teach you the right steps to take and in what order, so there's no more guesswork. And we teach you how to measure and track your progress so you can clearly see what's working and what's not. You are cordially invited to hop on a complimentary consultation call to discover if working with us is the next right step for you. Head over to encoreempire.com/consult to schedule your call now.

[15:59] Deirdre Harter: Yeah, that's really good. That's very clear because I think that's the time we go based on our feeling, like, when we feel overwhelmed, but it starts with us, we have to know where are we spending our time? And we have to be intentional about it. And, like you said, we have to focus in—I like to say we focus on the revenue line, like, stay close to the revenue line because it is a commitment. Even when it's a contractor, it's a financial commitment, and you want to be able to continue it because there's no point to go through the whole process of getting all the set up only to then be stressed about money or to say, oh, we're going to have to put this on the back burner for now. So I think that is a really great point. 

Can you give us any tips, Sadie, on what could they do? When they see it coming, they're like, okay, I'm getting close to the breaking point here, and I'm going to need to hire somebody. What can they do? Or what can they - maybe some kind of metrics, or can they prepare themselves in some way?

[17:08] Sadie Prestridge: Yeah, that's a great question. So they need to start doing time audits. So start to see where their time is going, how long it's taking them, and then start to audit that are those tasks making them money, like you said? Are they revenue-generating tasks, or are they things that they don't need to be spending their time on? 

I like to think about it in an hourly way, too. So if you're charging $200 an hour, do you want to be spending that time in your inbox, or do you want to be spending that time on a paying client? So thinking about that and then thinking about what systems and processes are you going to need for those tasks that you're wanting to hand off? And how can you start to create those? Can you make Loom videos and start to create a list of SOPs that you're going to want your VA to do? Because that's going to be the next step is the VA is going to come in and say, like, all right, well, what tasks you want me to do? How do I do them? And so if you've already got Loom videos lined up or you outlined your SOPs already, it's going to make it that much faster for that person to get in and start to do the work, which is really important.

[18:09] Carmen Reed-Gilkison: Yeah, I love that you started with time tracking because Deirdre and I are big fans of that. We will always do that because it's collecting data about what's going on in your business and where your time is going. And so, like, when you have a project or something that's outside the norm, let's say it's a project - like we did rebranding last year. So time tracking allows us to know how long did that project take us and how much of our time did that take us? So then, if we decide to do another big project down the road, we know what that is. And the same holds true with your day-to-day activities for you to know, where am I spending my time? Am I spending too much time in my email inbox, like you said, or monitoring my group or doing the things that someone else could do for you? I think that's such a good point.

[18:56] Sadie Prestridge: I will add to that it is something to think about. Like, the time audit will kind of be eye-opening because I get clients who are like, well, that task takes me five minutes, and that one only takes me ten minutes, and that one only takes me ten minutes, so I can just do them myself. It's like, okay, but now you've spent 30, 40, 60, 75 minutes on things because they added up. Those little two-minute tasks added up throughout your entire day, and you didn't even notice it. And so that's really important for that time audit is to see those little tasks start to add up too right?

[19:24] Carmen Reed-Gilkison: And it's also the context switching. So if you need focus time to create content or whatever you're doing, if you have a learning platform and you're creating lessons or whatever it is, to have to turn that part of your brain off, to go switch to do these other tasks, even when you do time blocking in your calendar, that can cause a problem. And I think people don't calculate that into it. 

The other thing that I was going to say is regarding SOPs or standard operating procedures; that's another thing that Deirdre and I do. And we also have recommended that clients, if they don't have them, they at least write down the steps, and then the new VA can come in and they can walk them through it. Like if you don't have them recorded, this is what we say. Sadie, you could tell me I'm totally full of baloney. But if they don't have a video recorded, but they have the steps, and they're working with the VA together, they can do it and record the video, and the VA can write the SOP at that point. Do you recommend that, or is that a good thing to say?

[20:25] Sadie Prestridge: Yeah, I think that's perfectly fine. But I think what you have to think about is not every single VA is systems-minded. They may not know how to write an SOP. They may not know how to think through a process from start to finish and give feedback and advice on things that could be added or taken away. So they may rely more heavily on the CEO to give them those steps. 

Also, I have a program that we use called Tango, and it will, I don't know if you've heard of this, but it will screen record as you're going through a process and it will take screenshots of every single process. So it will create a guide for you. And then you could pair that with a Loom video too, so that will help as well. But just something to think about is not every single virtual assistant is capable of being able to take that and make it into something.

[21:17] Deirdre Harter: So that brings up another thought for me, Sadie, is the way that you work with potential clients coming in, do you have some onboarding material or questions they can go through or how do you find out about their business? Or is it really up to the CEO to come in and to say, okay, here are the areas that I have, and here's what I need? Do they have to be that clear or is that something that you help walk them through?

[21:44] Sadie Prestridge: That's a great question. So we always start with a system set up in some way, shape, or form with our clients because they don't have systems and processes or Loom videos or things like that. So they're trying to get themselves out. So we have a system specialist, like a tech VA, on the team that will go through and automate and create all of those SOPs, and then we bring on the VA, and she's focusing on the actual work. But we do, we go through, we have a conversation, and we have them fill out questionnaires and things too, but we go through, and we talk about what they have in their business, right? So they'll say, I do a monthly blog, and I have a podcast, and I have a YouTube channel. And so we'll start to gather everything that they have. I do a webinar once a month, and then we already have a lot of templates and processes for those things. And so we'll say, this is what we suggest. And then, we work with them to customize it for them. And then our system specialist obviously goes out and creates it and maps it and gets it all ready for our virtual assistants to take over the actual task. Yes, we do go through and do a comprehensive overview of their business and where they want it to go. Maybe they're like, in six months, I want to start doing webinars, so we can start to pre-plan the system for that and get them ready for it.

[22:56] Carmen Reed-Gilkison: That's excellent. It sounds really comprehensive and it sounds like the guidance that so many entrepreneurs need out there. Because I know that being a solopreneur, which is the segment of the population that we work with the most, there's so much going on, and it helps to have someone on your side. Like Deirdre and I, we say we're the guides on the side or their silent business partner, and we need to cultivate those kinds of relationships and hire those kinds of people in our businesses when we're solopreneurs because we don't have all the answers. And to get that guidance, it's just a huge relief off your shoulders to know that you've got someone there who can guide you through using their expertise and let you see things that you wouldn't see otherwise.

[23:43] Sadie Prestridge: That's really the benefit of an agency too, at least in my case, is I'm training your VA. I'm hiring all of the VAs. They're going through all of my processes and my requirements, and my system specialist is trained by us. And so the clients coming in and they're like, I've never hired a VA or I've hired one and it hasn't worked out. I'm taking all of that off of their plate and let's say a year from now, their VA needs to go on maternity leave or they quit and they decide to do something else. Like, I'm the one that's going to put someone else in place, I'm going to go out and hire more people. They don't have that worry. Like, they're always going to be covered and there's like an entire team of us. I have a team of ten that's going to be supporting them on the backside and supporting their VA too. And that's a really important thing to think about if you're hiring a solo VA versus an agency.

[24:32] Deirdre Harter: That is a huge benefit, Sadie. I know that we have done our share of looking for people, finding people, putting them in the roles, and figuring out it wasn't right. There was so much I mean, it was valuable as lessons learned, the time and energy that it took to do that until we finally got it right, all of that time can be spent on doing those things that generate the revenue. Right?

[24:59] Sadie Prestridge: Yeah, absolutely. Our clients, we've had VAs leave, obviously, and there's no stress. They're like, oh, totally fine. I know you've got somebody else who can pick it up and keep doing it. And that's the risk of hiring a solo VA is maybe they didn't get all those systems and processes created. And so now you're starting completely over and now having to hire someone else and hope that they will do all of the creation of the systems. Whereas for us, that's a requirement. We're checking it, we're making sure those things are getting done, and we're making sure that as new things come up, those systems and processes are created, too. So there is definitely a big difference between hiring a VA, like, “off the street,” and then going with the virtual assistant agency.

[25:43] Carmen Reed-Gilkison: Definitely. And we've heard I'll share a nightmare story where she had a VA and the relationship ended, but the client was one of the people who was not, she didn't take the time to learn her processes first, and that VA had done everything for her for like six months or longer. And when she left, it wasn't a good situation, and she left and did not transfer the intellectual property back to the client, which was a big bummer. 

So it's really important that when you're bringing someone on, it's your stuff, you know how to do it, and you retain access to it. And then going with someone, an agency like yours, Sadie, where it's all professional, and you're not worried about this one person off the street, is definitely something that helps give some confidence in the process.

[26:37] Sadie Prestridge: Absolutely. Yeah. And to that point where the VA didn't transfer things, that is my biggest beef. Like, if we get into a client's account and we see the copywriter owns everything or the project manager owns all of the documents, we're immediately making a note, and we're transferring everything. Because I'm a huge advocate that it's your business. You're paying these people, they're your assets, and you should own them at all times. It shouldn't be, “Well, when I offboard, I'll give it to you.” It's like, no, we're going to own it from the start, so we don't have to worry about that. So that is something that I am of stickler on.

[27:11] Carmen Reed-Gilkison: Yeah. And I think it's a poor business practice to do it. Any other way, so I'm glad to hear that. A question I have is when would someone consider hiring an Executive VA versus a regular VA?

[27:24] Sadie Prestridge: A lot of that has to do with personality, I feel. I think some business owners need that control of giving that to-do list, and there are other business owners who are more comfortable allowing the VA to actually lead and allowing them to take some of those reins. And it's not to say that you couldn't hire a VA, and they couldn't grow into the EVA space for you. It really just depends on the type of person that you're hiring and your own personality and how you like to be a leader, too, right?

[27:57] Carmen Reed-Gilkison: Yeah. That's awesome. Everything you've shared is so valuable. I hope everyone's getting a lot out of this. If you had one tip, to give someone—a parting tip—what would you have to say?

[28:10] Sadie Prestridge: I would say that it's scary to hire and to hand things off. Your business is your baby, but it's worth it. It's worth it to be uncomfortable. It's worth it to get into that sticky situation. And it's a relationship, right? Sometimes they don't work out, and you learn from it. So I would just say if you're feeling like you're ready to hire, don't let the fear and the unknown of hiring someone stop you. Really just dive in, get the clarity that you need, interview some people, and bring someone on. It's absolutely life-changing. 

[28:44] Deirdre Harter: And that goes for every part of our business, Sadie, that's such good advice. We get out of our comfort zones all the time because we can see what's on the other side of it. And this is no different.

[28:55] Sadie Prestridge: Absolutely. Yeah. As an agency owner, I've hired dozens of people. I've had people quit. I've had to release people. And I always say this; people come and people go. I always say that in my brain. Starbucks doesn't have longevity. Virtual businesses don't always have longevity. But I will say every single person that I have hired has either taught me something or has given me the next step up to where I want to be. And so that's really important to me is people come, and people go. But you learn something, they leave you with something, or they help you get one more step closer to your overall goal.

[29:32] Carmen Reed-Gilkison: I think that's such a great way to frame it, and it's such a good mindset. You have the CEO mindset by doing that because some people might not be able to extract that out of the situation, but you're doing that. Tell us where people can connect with you and learn more about Prestridge & Company.

[29:52] Sadie Prestridge: So you can always go to our website, prestridgeandco.com. I'm very heavily on Instagram, and my Instagram handle is @prestridgeandco. So you can find me over there and go through my reels or my Instagram stories or just DM me. I would love to chat if anybody has any questions.

[30:09] Carmen Reed-Gilkison: Thank you so much. It's been a delight having you on, and the information you've shared is just extreme value.

[30:17] Sadie Prestridge: Oh, thank you. I've really enjoyed chatting with you both.

[30:20] Deirdre Harter: And thank you, Sadie, for what you are bringing into the entrepreneurial space to help empower CEOs and solopreneurs and helping them reach their next level, because what you're doing is really, really integral to helping them grow.

[30:34] Sadie Prestridge: Thank you. Yes, I'm very passionate about it, and I can't wait to keep growing and supporting various CEOs.

[30:41] Carmen Reed-Gilkison: Yeah. Congratulations on all your success.

[30:44] Sadie Prestridge: Thank you.

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