6: How I Work with My VA: Systems and Strategy
8 Dec 2025 · 28 min
Jenny Blake delegates scheduling, purchases, research, travel, and miscellaneous tasks to a Zirtual VA. She uses email for requests, Evernote for reference, and Google Docs for collaboration, and stresses that clarity and timing matter most when handing off work.
Questions this episode answers
December 21, 2014
Zirtual — $200/month for 10 hours (as stated after two months of usage).
September 2016
Chapters
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Hi, I'm Jenny Blake, your host of the Pivot Podcast and author of the book Turn what's Working for your into what's Next, which comes out with Portfolio Penguin in September of 2016.
In this podcast I talk with peak performers to reverse engineer their most successful career. Pivots interview experts on what it takes to be agile in a rapidly evolving economy and open the kimono on what happens behind the scenes of my book and business. You can learn to capitalize on risk, fear and uncertainty as the doorways of opportunity. My promise is that you will leave every episode with practical tips, tools and tactics. For show notes from this episode, visit JennyBlake Me podcast.
If change is the only constant, then let's get better at it. Here we go.
You guys know me. I love systems. I love tools. I love anything that can help make our lives, businesses and just overall experience in a given day more efficient to free us up to do the things that really matter to us in our lives. So today I'm going to talk a little bit about the types of help that you could work with in your business. Or for some of you, you may be running your own business full time. For some of you this may be a part time. And so we'll talk just briefly about how to choose whether what you need is a VA or someone else. Then I'll talk about the five main categories of things that I have been outsourcing and delegating to my va. Then finally at the end, how to set up the flow, the workflow of everything. So once you know what you want to assign, which is half the battle, it also matters to have really good, strong systems so that you and your VA can communicate well. I will preface all of this by saying I'm not a super expert. It's not like I've been working with a VA for the last 10 years, but I am someone that cares deeply about finding the most efficient ways to do things. And so I noticed that even though there was a lot of supporting material online about how to work with a virtual assistant, I found that I really wanted to get clear on how this is going to work for me and not just what I was going to assign, but how to make sure that I would feel comfortable and feel confident, be able to trust in the whole system of everything. So I actually did spend quite a bit of time at the beginning trying to get everything right. And I can also speak from the experience of not quite knowing in the beginning if I would have things to delegate. I never really took the leap to hire a VA because I was never quite sure that I would have enough for them to do. And it really is true the adage that everyone kind of says that once you do hire someone, you'll notice that things will just start flying off your to do list and you'll want to give them even more and even more. So in a little way, it is kind of a leap of faith, no matter what at the beginning to say, I'm not 100% sure what you're going to be working on all the time, but I'm willing to start building the systems that kind of creates the container. It frees up the space for you to then figure out the next set of tasks and, and the next set after that. The first question, who do you even need to hire? In the last two and a half years of running my own business, I have worked with an intern of two different interns. I've worked with my right hand woman, kind of a strategic thought partner, operations person who is very savvy with WordPress and all of the online tools that I use. And then I dabbled with the idea of hiring a VA overseas. Never quite felt right, even as I went through the interview process. So I put that on hold. And then about six months later, which was just a few months ago, decided, okay, now or never, I'm going to at least give this VA thing a shot. And so I have been working with a Zirtual VA for two months. I pay $200 a month and that's for 10 hours. And I think their packages are a little different now. But the reason you might hire an intern would be and I'm always looking for a win win, no matter who I'm hiring. So people who might benefit from working with an intern, if you have content or aspects of the work that might be interesting to someone who's in college or recently graduated, they're looking for a resume builder. You can afford to pay them most likely hourly. And I found that when I worked with my interns, it was very good on a project by project basis. It wasn't like I was suddenly outsourcing every random task that I had under the sun. And partly I didn't feel right doing that. I didn't really want to say find me the nearest dry cle, you know, but I would assign things like helping me build the Makeshit Happen course or helping to run the community. And that worked really, really well. Then later, as I was moving the Makeshit Happen course online to be kind of an evergreen product that people could buy at any time. And I was doing much more strategic things in my business, like even launching the new website Jennyblake Me. That's when I brought on Melissa Ansman, who is just a brilliant right hand woman. She just launched her own site called LaunchYourself Co, I believe. And so she is really the one who's going to get in there with you, set the strategy, create a game plan, really feel like a true thought partner. And she has the tech savvy to back it all up. So Melissa was someone that I worked with when I could afford to pay her. And I had kind of big chunks of my most strategic work that I wanted to collaborate on and that I needed to get out the door and launch.
And then third, what kind of brought me to the VA was as I slowed things down in my business. Any of you who've been reading my blog will know it's been a transition year for me as I keep writing about. And so things slow down in my business. And at that point I wasn't doing any kind of big push. So the work really slowed down for me and anyone else that I had been working with, like Melissa. But what I started to notice was that there was plenty of that was still piling up on my plate that I didn't necessarily want to do. And so it just wasn't getting done. And that's when I had that coffee with Maren and I realized, okay, for $200, I'm willing to give this a shot. I'm gonna try this for one month and see how it goes. And after four days, four days, I was already texting my VA Stacy to say, I cannot live without you. I cannot believe there was ever a time that I lived without you. And thank you. You're a lifesaver. You're amazing. So I got quick as I kind of prepared for today's call. It's been nice because I've had some another month, really since the time that I wrote to everyone, I've had about a month to continue observing and noticing what works and what doesn't. And not only what the best things to delegate are, but the best way to do that. First, let's jump in with the broad categories of things that a person can delegate. Let me here's another caveat. This is for me personally, you may have totally different categories of things. I have a friend who is in graduate school who is assigning lots of things related to graduate school that I have really no need for. So you may have specific chunks that you notice or specific buckets. For me, it falls into five main categories. Scheduling, purchases, research, travel, and one offs. And I'm going to go through each one and give you some examples of each so that you can see how this might apply in your own life. What I encourage you to do, no matter what, is set up a spreadsheet for the next two weeks and start to note as you go through your day what are tasks that you could potentially be outsourcing to a va. So maybe, as I'm even saying, my experience on this phone call, maybe you're taking some notes in these five categories and then over the next two weeks you can continue to be an observer. And that also helped me hit the ground running when I did finally start working with Stacy, because I already knew at least the initial things that I wanted to delegate. So let's start off with scheduling. This is one of the ones. And let me also clarify, particularly with a company like Zirtual, they are really giving you a virtual executive assistant. They they're not assigning someone who is going to be the jack of all trades. Write your blog posts, know every last thing there is to know about WordPress and OptimizePress and Buffer and Tweetdeck and all these sophisticated tools that a lot of us use online, even though they feel intuitive to us. It's not that, I mean, you could potentially work with your VA and teach them some processes that you want them to follow, but in general, the way that they're trained through Zirtual is to be more of that executive assistant role. So a lot of the things that I'm going to focus on would really apply to anyone, whether you run your own business or you work for someone else. These are the personal tasks that tend to be really good for delegating. Scheduling is, I would say, a pretty huge bucket, and that can involve proactive and reactive scheduling. One of the first things that Zirtual even suggests is sharing your calendar with your va. And that's a good way for them to get to know you just as well as you get to know them. So they Start to understand your schedule and they will ask you through the intake process. How do you work? Do you have certain hours that you like things to be scheduled? What are your preferences? What kind of process do you follow? For me, I had a lot of little rules that I put out there. I said I generally keep my calls between 11 and 3pm I don't take calls on Monday and Friday. I would rather schedule a call two weeks out than put it on a day where I don't have any meetings unless it's a high priority call. Media takes top priority. You know, these things are lower priority. So you can make your own list of rules about scheduling that you probably already tacitly follow. They may not be an explicit rule that you've set, but yet you kind of know when you're working your schedule around. I'm not a morning person or maybe you are and so you want to optimize to your best energy windows. And as many of you know, I'm a big fan of chunking time anyway. I really believe in having meetings on one day and making sure that whatever your best energy window is, that that's generally free and clear so that you can do your most creative work. So when you have your VA help with scheduling, one thing you can start to do almost right away is loop in any emails that you have where the next step is to schedule a meeting. You can say, I'm CCing my V.A. stacy, who's going to help us schedule from here. Stacy will then. And now Stacy's going to be the catch all VA term. She's going to be like Siri, where I'm just for the purposes of this call, I'll just use her as an example. But she would then follow up with the person you're emailing with and by looking at your calendar, she'll take care of scheduling so that you can remove yourself from the equation. And that's really nice because that happens about five, five emails sooner than it might have if you stayed in the mix with it. Of course, there are online tools that you can send to someone else and have them book time with you. I've had mixed success with those, mostly because my weeks are very different. And so I kind of, I have tried those, but I realize that I really do want a human being who's looking at it saying, oh, Jenny's traveling the next day. Maybe I shouldn't schedule anything on this Tuesday because she leaves early on Wednesday. Things like that that these scheduling tools just weren't quite doing for me. That's A reactive scheduling request where people email or something comes in. Or you can even say, stacy, will you add a reminder to my calendar to do xyz? The other thing might be proactive scheduling. So, Stacy, will you reach out to this person and find a time for us to meet? Another good example is medical appointments. I have a template and these are all available on my website at jennyblake, Metoolkit. I have a template that is called my appointment tracker. It's all my doctors, their contact information, the last appointment that I had and the next one, you know, optometry appointment. Or can you. I have a thyroid doctor. Can you schedule the next thyroid appointment? And she can look in my tracker and see when the next one needs to be. Have all the info, call, get it done, put it on my calendar, and I don't have to touch it. That is really nice. And before we move on, I also want to say some of these things can seem really small. Like, oh, well, you know, that only would have taken me five minutes. It's no big deal. Why do I need to pay money for a va? What I'm finding is that really the minutes do make hours. And it's this sense of peace of mind that things are getting done even when I'm not there to do them. And I have been traveling a lot in the two months I've had various speaking engagements and personal trips. And it was really, really a huge relief to be able to email while I was in the taxi on my way to the airport and say, can you call and make such and such appointment and know that that was going to get taken care of. So it's not just the time that's the currency. It's also the trust that has been really a huge benefit. The next category that I really enjoy using a VA for is purchases. And that can be anything. I have these Paleo bars that I eat. It's from Steve's. It's called. What are they called? Paleo Crunch. Crunch with a K. They're really delicious. This is my little infomercial for these Paleo bars. But they're clean, they're healthy. They don't have all the random ingredients that most bars do, even the ones at Whole Foods. And so this is one of my specialty foods that I like to order online. An example of our purchase request. So in the beginning, you'll call your va, you'll give them your credit card information, and they store it in LastPass. It's a secure system on their end. It's not saved publicly anywhere. But once you give that to them once you can submit a request like, please log on to Steve's Paleo. Forget the name of his website, Steve's Paleo, create an account and purchase 20 bars under my personal credit card. And for all anyone who's curious, it's stevespaleogoods.com or Steve's Original. Anyway, so you can say, can you please create an account? And using my personal credit card, order this many, have them shipped to my home address.
You can even say things that you don't have the time to figure out, like, see if it makes sense based on shipping costs to do a double order. Now, what's cheaper to ship 15 bars or 30? That would be an example of a small purchase. Or something small, like creating an account when I recently moved last month as well. And that was a much bigger ordeal, as I'm sure you can imagine. And having a VA was priceless for that. And so I would say things like, can you research the cost of a mattress? Or can you. Can you give me a list of three mattress companies between these blocks of New York? And that brings me to the next category that is really helpful to have a VA for, which is research. I have had Stacy research so many different things for me, whether it's selling used clothing online, that kind of goes along with shopping and purchasing, but she could. She has also created E listings for me for things I wanted to sell. When my mom and grandma were in town, we were going to make a trip to Ikea because my new studio is basically an IKEA showroom. Gotta, you know, on a budget. So in New York, it's kind of a schlep. You have to take a ferry, basically take the subway to a ferry, then you take the ferry over to the Ikea in Brooklyn, and then you take the ferry back home. So an example, I was in the midst of signing the lease, doing coaching calls, running around, trying to get things done before my mom and grandma came into town. And even though this request would have taken me a few minutes, I emailed Stacy and I said, stacy, can you research the transportation? How do I get to IKEA from my apartment? Put it in the Evernote so that when my mom and grandma are here, we just look at it and know exactly what to do. And she put the subway directions that we needed, the ferry location, the ferry schedule, how much that would cost, and the hours that they ran. Very helpful. And again, I'll talk at the end about how the flow works. I know I just mentioned Evernote. I've talked about email I have a whole flow now of how things get assigned and processed, and so I will share that soon. But first, back to the uses. Anything that you can give clear instructions for.
So we've talked about scheduling, purchasing, research. The next one is travel. Travel is a big one. I have not yet assigned booking an actual flight, partly because I am very particular. This is something I should just create some rules around and let go of it. That's the ideal state that great. So I'm picky about when I fly. So what, I should just know what my rules are like. I like to fly Virgin America. I like to leave within certain windows. I don't like to take. I will not take a red eye. You know, I could make all my rules and get assigned. So far I haven't assigned booking the actual trip, but you can certainly do that. Some things that I have assigned are booking my transportation to the airport. And I have set rules around that. Like three days prior. Can you call the taxi company, book a car? I like to get to the airport three hours early. Yes. Guys, I'm crazy, but I'm one of those people. I don't like anything to get in the way of me getting my flight. And so I'd rather get to the airport very early and have time to work. And I often get a lot done. So I can set a rule like that and then I'll say get. Then can you please log into TripIt, export a PDF of my entire trip, where I'm staying, when my flights are any confirmations, and put it in Evernote. And sometimes that's nice just to have it really quickly at a glance. Another example of how I've worked with Stacy for travel. I love yoga, as many of you know as well. And one thing that is challenging for me this year I traveled about 50% of the time I was away from home, away from New York. And so it's very important to me to try and keep as much of a routine and as much of my schedule I can when I travel. So this last recently I went to Nashville and New Orleans and I asked Stacey Stacy, can you please research on Yelp, the top three yoga studios in each city and the top three yoga teachers put them in a spreadsheet with a link to the schedule and how much they cost. And so Stacy created a spreadsheet that had for Nashville, three studios I should check out and a link to their schedule and their address and the same for New Orleans. And now we, we can add to the spreadsheet. So if I'm going For an extended trip in Southern California or some other US state for a speaking gig, she can just continue to add yoga studios. And it's nice for me because then I know it helps me with accountability. It's not just that, of course. Again, of course I can google it on my phone when I get there. But knowing that it's already in a list and she's already done the legwork of what are the three best rated studios on Yelp, I really have no excuse not to line something up when I get wherever I'm going. And she can also do the work of figuring out what's closest to my hotel or little logistical things that might just take me extra. The last category is one offs. One offs are what I refer to as just really random things that come up that you really can't even quite plan for. But things for me like because I moved, I missed two copies of my New York magazine subscription. Stacy, can you call and find out or get my accounts credited? I'm leaving for two weeks in December. Can you put my newspapers on hold through my online system? Things like all the apartment research. I actually this was great. I had her create and set up my Time Warner account so I didn't even have to do anything. Can you call the utility company, give them my account information, put it on my business credit card and make sure that I have lights and heat by the time I move in. And lo and behold, I did. And these are things that I did not have the time to even do or the space to think about because there was so much going on. So knowing that Stacy would wait on the phone with Time Warner, schedule my Internet installation, call the utility company again, just a huge sense of peace of mind that particularly with the move, I didn't have to do it all myself. And that was really, really nice. The other things I would say that tend to fall into one offs, I have started to work on teaching certain processes for WordPress again, more of the simple things. You can also work on any recurring tasks that you do. Or in my case, sometimes it's things like even setting up reminders. Can you remind me to do this? I talked earlier about selling things on ebay or researching consignment. It's a matter of looking at all of the areas of your life and then in a given day having the sense to really ask, do I need to do this or can I delegate this? And in a way I like that I have a 10 hour chunk because it does go in waves. I'm not always using the full 10 hours. But it encourages me to think, okay, I have 10 hours to fill. And that's in a way there are certain VA type task services where you get a different person each time and you pay more by the task. Fancy Hands is a good example of that. What didn't quite work for me there was I wanted consistency, I wanted someone to get to know me. And also many of the tasks I was assigning were over their 15 minute limit. And so I was having to spend five or six tasks just to get one thing done. What I love about having a VA is they can get to know you a little bit and there's trust that builds over time. So that allows me to feel comfortable going through my day thinking about, okay, what do I need to do next? Or what can I delegate? And probably pretty soon I would also ask my VA and I'll say, what do you do with your other clients? How can we work more efficiently together? The last piece of this is how. What are the processes? I am really big on smart systems and keeping things impeccably well organized so that everything is clear, it's easy to follow, it's easy to check in on, and everyone knows where to find things. Here's what's working for us. Requests happen through email. So anytime I have something new that happens through email, and initially I had tried to make that a reactive thing like labeling certain emails Stacy and then she would go in and check her folder and there they would be. That didn't really work, nor did putting them in Evernote. We found it's much better to just email each separate request and that way it also gets logged in their system on the back end as a ticket. Then once the request is logged, I use Evernote for reference. Evernote is anything that's kind of a static reference document, such as I have one note for JB account info. It's my accounts, whatever she would need to log in various places. Essentially I'm not giving her the password to everything under the sun that I have, but I have. When I know that I'm going to share an account with someone like a va, I do create a password for her to use. That's kind of common across all the things that she would log into. But for example, it's different than my Gmail password. And in some cases with Gmail and Calendar you can give delegate access. Same with PayPal, where they don't need to know your exact login, but you can give them delegate access.
Some of the notes I have in Evernote are how to Documents, here's how to log into WordPress and add a new testimonial. Or here is how to log into WordPress or add someone to one of my courses. I have the account information like I said. I even have one that I asked her to create with all of my apartment information. The super, the landlord, the holding company, you know, everything I might ever need to reference. So the Evernote is as much for me as it is for Stacy. Things like addresses, people who I'm frequently mailing, or if I need to say I told my grandma I would help her order doggie bags from Amazon. Can you log in and send them to this address? That might be a request. Then in Evernote we also have things like travel itineraries and I try and name everything consistently. So if it's how to boom, boom, boom or reference, that would be reference would be processes like reference JB travel processes. You know, here's what to do when I have a trip coming up or reference responsibilities. Overall, here's everything I would love your help with. Then when it comes to bigger documents or collaboration, that's where Google Docs are great. Evernote is not really good with formatting or seeing when updates have been made. So for Google the things like the yoga studio spreadsheet that is a little more complex, that's really helpful for me. I have a lot of project plans like my moving checklist. I actually used my own template during this move recently and again that's available on the toolkit and so that is really helpful. Google is just great for tracking more complex complexity. And then I think that's basically it. So email captures the request, anything that will be referenced later or as a static thing goes in Evernote and then Google Docs is for the more complicated things. I would also say that like I said, sometimes we share access or she's a delegate to things like PayPal or other places. And then having.
Knowing that she has my credit card information, it's very easy to on a one off basis say oh here's this random thing I need to buy. Will you buy it with such and such credit card? Or can you make a dinner reservation or you know, whatever the kind of random one off request might be. That is the gist of how I work with my va. So just to recap, the five main categories are scheduling, purchases, research, travel and then one offs. And I would say again, track how you operate over the course of a given week and be an observer in your own life and work and start to imagine what you would delegate if you had the opportunity to do so. And then I would say there will be a certain point where you just jump in and you figure it out later and you can assess after a few months if you really aren't using it, then no problem, you can always downgrade your account or cancel it. But for me, I'm finding that it's opened up so much that I don't ever want to live without it if I can help it. The final thing that I would say are pitfalls. Some things to think about, the things that I've noticed for me that get in the way are a lack of clarity on my part, not being specific enough and not giving enough time on the lack of clarity piece. Sometimes we learn the hard way where I will submit a request and I'll get something back and it won't be complete in my mind or it won't be what I was looking for. That's, you know, as great as VAs are, they are not mind readers. And so that's when I realized, okay, I need to be clearer with what I'm asking for and how I want to see it back. And so at that point I can just write a follow up request. Okay, great, this is a great start. And what I'm also looking for is this. Or in some cases attaching a picture into Evernote wasn't working for me or a PDF because it was a pain to download it from my phone when I was out and about. So I would ask can you copy and paste all the text directly in next time? So little tiny things like that. But for the most part you'll get better too at providing the level of clarity and thinking through your task in advance of what will I want to see back and how do I ask for that? And then the second thing of not giving enough time. It's hard. Some things just are time sensitive. There are emergencies that crop up. There are last minute things. In general though, you know, I'm not paying for the highest account level that there is where I get, you know, split second 247 responses nor do I really expect that that's where it is important to be clear anytime you give a request. And this goes for really work in general. But what are you asking for by whom, by when and how will you know or what do you want it to look like? So it is good to say here's a task that needs to be done by Friday or this task I really need by tomorrow morning and just being clear of when you need that back and I try and if something's urgent or important, I'll put that in the subject line and same thing if it's low. So that's one good way to submit requests is to right from the get go in the subject line, say low, medium, high, or whatever nomenclature you want to use to convey the status of a request. All right. I think that's about everything I'm passionate about helping all of you be successful and set up your own systems and feel like you have what you need to go full speed ahead this next year. I know what it's like to be recalibrating, and I've been there. And I've spent so much time this year on building my own healthy habits around meditation and yoga, not drinking, and then in business getting the fundamentals down so that I can set myself up well in 2014. And I would just be honored to help any of you do the same. I wish you the happiest of holidays and I will look forward to keeping in touch and talking to you all again soon. Thank you so much for listening and have a great rest of your day.
Thanks so much for listening to this episode of the Pivot Podcast. To learn more and get in touch, visit JennyBlake me where I blog about systems at the intersection of mind, body and business. Or find me on Twitter @jennyblake. And remember, build first, then your courage will follow. Hasn't it always.
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