How to Find Your Perfect Virtual Assistant

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When you’re starting out with your business you’re doing it all; making phone calls, fulfilling orders, handling social media, accounting, making travel arrangements, and everything else in between. But one of the main reasons we take the leap into entrepreneurship is to have more time, not less. One way to achieve that without bringing on a full-time employee is to utilize the benefits of a virtual assistant. 

Think of a virtual assistant as an extra set of hands that works remotely to handle whichever tasks you assign them. Achieving success with this plan is going to depend on the work you put in on the front end with finding and training them to be an extension of yourself.




Rich: Jess Ostroff is a writer, a speaker, and proud Director of Calm. Her company, Don’t Panic Management, is the agency that embodies a people first approach to virtual assistant success. Since 2011 she has been making the best possible matches between chaotic, overworking entrepreneurs and focused, calm virtual assistants. Offering services that span form administrative assistants to marketing support, she finds deep joy in making a difference through service. It’s her goal to provide new, painless options for people to get work done as the future of virtual work becomes a reality.

When she’s not speaking, writing, or researching productivity hacks, you can find Jess trying new recipes, popping champagne, searching the next great music festival to attend, or playing with her labradoodle, Hummus. Jess, welcome to the show.   

Jess: Thank you so much for having me, Rich. I’m really excited to be here.

Rich: Now do you just love hummus, are you a vegetarian, what’s going on with that name?

Jess: I’m not a huge fan of hummus, actually, but it was one of those things when we were talking about getting a dog we were like, maybe we should name her something that’s related to things that we do. And both my fiance and I are musicians and we also love food, so one of the names was Spatula, Coda, we were kind of getting crazy with the names and then Hummus came up at some point during that time and it just kind of stuck. And she’s actually like an apricot/copper color so it worked out. She looks like hummus and she’s the best, and I’ve never met another dog named Hummus.

Rich: I’m sure Hummus is glad you did not name her Spatula, I’ll tell you that much. Although Coda is a cool name, I think that’s a good name for a black dog because I believe the Led Zeppelin album was a black album, right, the design on that?

Jess: Yeah. And I’ve also since then met a husky named Coda. I guess it’s an Alaskan or some kind of cold weather name, and so I’m glad we didn’t name her that either because then she’d have a twin.

Rich: Alright. Well thanks for coming on the show and talking dog names with us, this has been…no, I should probably start talking about marketing. So, Jess tell me how you got started in the VA business, the virtual assistant business. 

Jess: Sure. Well I graduated with a degree in marketing and international business and I knew I wanted to do something with that, but I didn’t want to do the traditional thing of going and working in an office, perhaps for an accounting firm or for an investment bank, which was what a lot of my fellow classmates were doing. I went to college in New York City at New York University and so it’s a big business capital, but I was just pretty bored by all of that and I sort of had an allergy to corporate America and I wanted to do something else. Which I’m sure a lot of your guests can relate to, a lot of your audience.

So instead of going straight into work I did an AmeriCorps program, which is like the Peace Corp but in America, and taught math and science to 8th graders for a year, which was completely different from what I had studied. I knew I didn’t want to do that either per se, but just having that experience opened up a lot of doors for me because I met a lot of new people, I dug deep into myself and into what I was capable of doing. It was definitely the hardest year of my life and the time when I kind of figured out what hard work looks like. And through that experience i learned that I wasn’t afraid of hard work and that I was willing to do whatever it took to build a life that I loved.  

And so, once I graduated from that program I got a job, it was really my first job out of college at that point, as a social media manager for a non-profit organization. But I quickly learned – and I did not learn this in the interview because I didn’t actually interview with the CEO –  but once I started working I found out that the CEO didn’t know what social media was. And so my whole job was basically trying to convince the higher powers that this was all a good idea. And that was not really what I signed up for. I thought I was going to be building these leadership programs for students and marketing them in high schools and making a difference for kids. And it turned out that I was bound by a lot of red tape – which can happen in non-profits in general – but having the added thing of trying to explain what social media was and why it mattered back then. This was 2009-10 and it was a little rough.

So, I started looking for other opportunities. My first virtual assistant gig was for Jay Behr, who I know has been a speaker at your event and I know you know very well…

Rich: I’m a huge fan of Jay.

Jess: Yeah, he’s awesome. And he was actually my boss when I was doing an internship my junior year. I moved to Phoenix for a summer and worked with Jay in an office, which was funny, because when I actually reconnected with him he had left that agency and started his own thing. That was when he started Convince and Convert which is what he’s doing now. He needed a virtual assistant so he posted a tweet and I responded to that tweet and said, “I think I can do this.” I went through the interview process with him, I sent him this ridiculous email that was “7 reasons you should hire me”, and one of them was that I was a fellow tequila lover. 

Rich: He does love his tequila, doesn’t he?

Jess: I know, and I thought that was a good idea to mention in a formal job application. But it worked and started working with Jay about 10 hours a week. I was doing a lot of travel booking for him and researching things for blog posts. I remember I think I even sent a few faxes for him, which seems old fashioned.

Rich: Definitely dates you. 

Jess: Yeah, a little bit. And it really was such a great experience because I was able to sort of flex my detail oriented and organizational muscles while being at home. And figuring out my time in the workday and being able to get up at 7 or 8 and get my work done and then go to the beach, because I was living in LA at this time and I lived a mile from the beach so I would do my work in the morning and hang by the beach in the afternoon and it was awesome.

Jay also – as you know – is very well connected and was able to point me in the direction of some other entrepreneurs and business owners that needed support and it just kind of grew organically from there through word of mouth and through referrals. About a year and a half later I started Don’t Panic Management  because I had too much work to do on my own, I knew I wanted to hire people, and I wanted to basically just protect myself legally. Not knowing at the time that the business was actually a good idea.

Rich: So it sounds like you did a lot of different things for Jay, what typical jobs does a VA do for someone? 

Jess: Typically there are different kinds of VA’s. The one that you hear about most commonly I would say is your traditional Executive Assistant-type VA, and so they do things like schedule appointments, book travel, make sure that you have the notes that you need for meetings. Sometimes these VA’s will even sit in meetings and take notes for you and potentially create proposals from the meetings or create notes and upload those notes to a project manager tool, assign tasks.

Kind of behind the scenes administrative tasks, but there are also more skill-specific VA’s like content marketing VA’s, social media VA’s, podcasting VA’s, anything that you can think of today with relation to marketing execution and otherwise you can find a VA for. It’s really great because I’ve found that you might work with an agency that has really smart high level people that are great with strategy and ideas and making those ideas into a plan, but they don’t always want to or have the capacity to actually execute those ideas, and that’s what a VA is great for.

So they’ll take your strategic plan or your marketing system and actually put it to work. And what’ I’ve noticed, too, about VA’s is they don’t mind being behind the scenes and they don’t need any credit for it. And I think that’s one of the big differentiators between a VA and a marketing coordinator at an agency, or a marketing manager. Usually they are taking direction from those managers and those coordinators and making the plan happen. 

Rich: Alright so it sounds like this may be a good fit if we’re a busy entrepreneur or business owner or what have you, and the bottom line is, our plates are just too full. How do we decide what work we should continue doing, what work we may be able to automate and put computers or software to work, and which ones we should outsource to a VA?

Jess: Well that’s a great question because I have a little exercise for that that I call “The Life Audit”, and it’s basically as you would imagine an audit to be. It’s actually looking at everything that you do. There are a lot of people that I work with who  are so busy and so crazy all the time that they never stop to even think about what it was they just did for a whole day or a whole week. So this is something that I ask prospective clients to do when they’re not sure where to go is to sit down and get out a notebook or a spreadsheet and literally write down every single minute, every hour, all of the things that you’re doing. And that could include “walk Hummus”, or “drop my kid off at school”, or “make dinner”. Every single thing that you’re doing in a day for a week, I encourage people to write that down and be honest. Some people are like, “Oh, I checked Facebook for 2 hours, I don’t want to report that”. It’s like, no, nobody is going to look at this except for you so just write everything down.

Once you’ve got that, the easiest thing to start with is what things can you get rid of. And the way I do this is I ask myself is this something that’s important for the bottom line of my business, if not, get rid of it. Or is this something that I love, because I don’t think that just because you’re cooking dinner – that’s obviously not for the bottom line of your business – it’s something that is necessary or something that you love. And those things are ok to keep if you want.

So once you’ve gotten rid of the things that you shouldn’t be doing, which are things that shouldn’t be done at al such as checking Facebook for 2 hours – unless you’re a social media manager or a PR person – then comes automation, and this can be a little tedious but also really fun. I think putting processes in place around things that you’re doing everyday is really exciting because it kind of feels like you’re kind of manipulating time. You’re taking something that you do everyday or every week and getting it done for you.

So these are things like if you’re scheduling social media posts and you’re just doing them on the fly everyday, take an hour on Friday and schedule them for the following week. Or better yet maybe get someone else to write them for you and then all you have to do is approve them and get that person to schedule them for you. So think about those kinds of things that you can automate; reports for a social media or content tools are great things to automate.

For me as a business we send a lot of satisfaction check ins and those are usually emails, but the email itself could be automated and it could have a link to a survey that says, “How am I doing?”. You see this in big companies all the time, after you get off the phone with American Express or whatever, it automatically sends you an email that says, “Take this survey, how did this person do?” A lot of those kinds of things can be automated.

I wouldn’t automate anything that is sensitive in terms of information or time because you don’t’ want to worry about something going out without your knowledge. As with any tool there can be glitches. This happened to me recently with our Quickbooks software where we had our invoices that were all meant to be scheduled for the 1st of the month, and they decided to go out the month before on the 20th, so all of our clients were like, “Um, I just paid you, why are you sending me another invoice?” And it was one of those things where this was supposed to work, they tell us that this is going to work, but it’s not working. So  we actually took the automation off our Quickbooks invoices because that’s something that’s sensitive, we don’t want people to feel like they have to pay money in advance when we haven’t told them. So automation is great but I say to be cautious about the things that you want to automate and make sure  that they’re secure and safe.

And then after that you should be left with a list of things that you love that are necessary or that cannot be automated. And that’s where I say to create a new list and create 2 columns in that list. The first column will be “things for me to do” and the second column will be “things for someone else to do”. It should be easy for you to decide the things that you love to do, and those should definitely stay in your bucket. It should also be easy for you to decide what things are necessary for you to do, so what are the things that your unique value proposition requires.

So if you’re the CEO and you’re making connections and you go to conferences and you’re speaking on stage and you’re writing books, nobody else in your company can do that because you have that unique knowledge and you have that personality or whatever it is that got you onstage and with a publisher in the first place. So those are things that you should continue to do. 

There are also things that are necessary. Maybe you don’t love getting on business calls with prospective clients, but you’re a great salesperson and that’s what you should be doing because you’re great at it. So anything that you are uniquely qualified to do and anything that you love should stay in your bucket, and then really everything else should go out the door to somebody else. If you can’t find a way to automate it, that’s the time when you should start thinking about delegating it to an actual human being.

Rich: Ok, so let’s say we’ve got this list and we know what we might want to outsource, how do we actually find a VA? 

Jess: The first thing I always ask people to think about is what kind of person do you want, because VA’s are not for everybody. It’s possible that you may need an in-person assistant. You may not need them full-time, but you might need someone to pick up your dry cleaning, or bring stuff to the Post Office, or pick up your kid from school. Those are all things that Executive Assistants do, and if you find that you need more in-person tasks than tasks that can be done online,  you might need an Executive Assistant as opposed to the Virtual Assistant.

So think about that first, I know everybody wants to say that all their stuff can be done online these days, I think there are a lot of people that are trying to ride the wave of the future but aren’t quite there yet. So think about that first. And then how do you find one? Well once you’ve looked at your tasks list you should be able to see a pattern of the types of tasks. If they are traditionally bookkeeping or administrative level tasks, they you need an administrative VA. But if they are things like we were talking about before – scheduling social media posts, writing blog posts, producing my podcast – you might need more of a marketing VA.

So there are a lot of different places you can look, Upwork is one that a lot of people use just for projects more so than ongoing VA services. I always recommend when you’re searching in those types of platforms, type in the type of VA that you want. So for example “podcasting virtual assistant” or “content marketing virtual assistant” or even just “admin virtual assistant”, because then you’ll be able to see the people that come up in those results are going to be the kind of people you want to start looking at. LinkedIn is an amazing platform for that as well. And then Google of course, you might have to weed out a little more by looking at Google.

But the best way that I’ve seen for you to find a VA is to ask your connections, ask your network, ask other people, other business owners or other managers that are similar to you and ask them what they’ve done. They might have a VA recommendation that they’ve used in the past or someone that they’re using right now.  Oftentimes VA’s are their own business and their own boss and they don’t work exclusively for one person or one company. So they will have oftentimes hours in their day or in their week to give to another client. And so if you ask a friend, “Who’s your VA, can I use them too?”, and then you give them 10 hours of work, then everybody wins because the VA gets more work, you get to share an assistant with a connection, and that secures the person for both of you.

What I’ve seen sometimes – not all the time – but sometimes individual VA’s have a hard time filling up their hours and then they have to stop being a VA, they have to go back to corporate or get a traditional 9-5 job because they just can’t sustain the work.

Rich: Sure. So if we’re doing this and maybe we’ve found one, how do you vet and onboard this virtual system?

Jess: So a lot of people think that working with a virtual assistant is like this turnkey solution, which is great, I think that would be awesome. I think that when you have certain tasks that are repeatable or that are pretty basic project-type tasks or data entry – things that are like that – it can be very turnkey. But if you’re looking for a VA to become a partner in your business, which I think are the best kinds of VA’s, you need to do a lot more work on the front end just like you would do when you’re hiring an employee. So you need to go through their LinkedIn profile,  you need to get a resume from them, get a cover letter. You don’t have to have a formal application process but you do need to at least get a resume and a cover letter.

Another thing that I like to do is ask for writing samples. A lot of what VA’s do is written communication, whether they like it or not. So get writing samples from your VA and see if their writing style and their attention to detail manifests itself in their writing sample.

And then of course do the interview. You can’t just rely on a resume and a good feeling, you have to do an interview. I always recommend doing a video interview not just an audio interview, and see the look on their face, see how they react to the questions that you’re asking. Ask them deeper questions, too; “What do you do to keep learning?”, “Tell me about a time when you knocked it out of the park at work”, “Tell me about a time that you made a mistake at work and how did you handle it”. Start to get deeper instead of those normal kind of strengths and weaknesses questions ro what are your hours. Try to get a little deeper with your VA because then you’ll start to see if you can actually see yourself working with this persona and actually making a connection with them.

And then once you’ve done the interview I would say have at least 2-5 applicants that you’re choosing from and give them a test project. For the test project I always recommend doing something that is related to the actual service that they’re going to be providing for you. So if you’re going to be hiring a podcasting VA, don’t have them do a calendar booking test project, have it be relevant to the work you’re doing. And if you can, give them all the same test projects so that you can rate them equally and have a rubric for how you’re going to score them.

I believe that the interview process starts with the initial contact. Did they address you by name? Did they spell your name right? Was their email warm and inviting and was it professional? Did they show up to the interview on time? Did they have problems with technology? Did they turn in their test project on time? Did they ask a lot of questions? Were the questions good questions or does it seem like they don’t really know what they’re doing? These are all things that you should be paying attention to throughout not only the sourcing of the VA, but then the interview process  and the testing project.

For me I think it’s always better to take the gut out of it in this process as much as possible because you might really like somebody and you might get a good feeling about them, but that doesn’t mean that they’re going to be able to do the work that you want. And I think that’s something that some people don’t think about that much and then they get upset when they have to train their VA’s. But if you had done the test project and had them do what you wanted them to do, you wouldn’t have to do so much training.

That doesn’t mean that you don’t need to do any training, I think that you’re going to have to spend at least 5-10 hours in the first month with a VA teaching them how you like things and what your preferences are and why. Sometimes there are things that we do when we don’t really know why we’re doing them but we’ve always been doing them, and sometimes when you explain that to a VA they can say, “Hey, did you know about this other tool that might actually solve your problem in a more efficient way?”, or “Hey, did you know that you could not even do that step with the process and still get the same result?”

A lot of times VA’s come with their own set of knowledge, which is really valuable and it’s important to explain how you like things and have them listen, but also be open to hearing their feedback. Think about what you’re doing and see if there’s a better way. 

Rich: It sounds like there’s an investment, this isn’t – as you say – a “turnkey solution”. And speaking of investment, I know from reading The Four Hour Workweek all those years ago, there’s this expectation that I can get VA’s for $4-5 an hour if I go overseas. What are your thoughts on that, what should we be expecting to pay a good VA?  

Jess: So if you have those kinds of projects that are more repeatable and very basic, I don’t think there’s anything wrong with going to India or the Philippines and paying $4-5 an hour, having a clear set of guidelines and you should be able to find somebody that can do those things for you.

If you want – like I said earlier – more of a partner in your business, one that you can come to and ask, “Hey can you figure out how to get this banner up on my website?” or “Set up the lead page for me”, or “Hey, what do you think about this new speaking topic that I’m thinking about debuting?”, things like that are a little more subjective that you just want to bounce off somebody, someone who’s more versatile, someone who can do writing projects for you. That’s one of the things that becomes difficult if you go overseas with writing, just because of the language barrier. 

So I think it just depends on what the tasks you need are. But I would say in general if you want a U.S.-based or a European VA, you’re going to pay between $20-$60 and hour. For the most part, and that general range depends on their experience, how long they’ve been doing this, as well as what tasks they are doing.

So for example an administrative VA who is booking flights and setting meetings may cost $20 an hour, but a copywriting VA may cost $60 or more dollars per hour.  A lot of times VA’s will offer a blended rate, so if they’re doing 5 hours of admin work and 10 hours of writing work, they might combine that rate into $45 an hour or something like that.

But in my experience the best VA’s are a little bit more expensive, but again they’re very efficient so you’re not paying for hours that you don’t need and you’re getting clear and really great deliverables from them and you’re getting them on time. That’s one thing I’ve noticed sometimes that going overseas or going with somebody that you don’t have a personal recommendation from or a referral from, you just never know what you’re going to get. I think that’s why it’s scary for people to start working with a VA because they’re nervous. They say, “I’m going to send this assignment to somebody and I don’t even know if they’re going to do it right and I don’t know if I’m going to get it back on time.

You might feel that way in the beginning of any relationship, but you really shouldn’t feel that way ongoing. The person should be able to prove themselves to you, but that also comes from your effort up front in choosing the right person, doing the interview, getting recommendations from somebody, checking their referrals, and doing the test project.

Rich: Ok. Alright well this is definitely helpful and I’m sure a lot of people are now figuring what they’re going to be outsourcing to VA’s. If they want to learn more about you Jess, and your services, where can we send them?

Jess: Absolutely. So my company is called Don’t Panic Management, as you mentioned. The site is, and I also just launched a book and it’s called Panic Proof: How the Right Virtual Assistant Can Save Your Sanity and Grow Your Business, and I offer this step by step process that we talked about today. If you want to pick that up, go to And I’m on most social media platforms @JessOstroff.

Rich: Awesome. Jess, thanks so much for stopping by and sharing your expertise.

Jess: Thanks Rich, I really appreciate your time.


Show Notes:

Jess Ostroff helps entrepreneurs and small businesses find the right reliable, goal-oriented, and skilled Virtual Assistants to help their businesses grow. Head over to her website to find out how she helps to turn chaos into calm, and grab a copy of her new book.

Rich Brooks is the President of flyte new media, a web design & digital marketing agency in Portland, Maine. He knows a thing or two about helping businesses grow by reaching their ideal customers, and to prove that, he puts on a yearly conference to inspire small businesses to achieve big success. You can also head on over to Twitter to check him out, and he just added “author” to his resume with his brand new book!