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The Ultimate Guide to Hiring (And Keeping) a Virtual Assistant

So, you are thinking of hiring a Virtual Assistant to free up your time and increase your productivity?

Well, here is a really-quite-long article based on my book: The Fast Guide to Hiring (and Keeping) a Virtual Assistant.

It will help you find, hire and hang onto the best Virtual Assistant for you.

If you don't have time now then why not download the FREE 46 PAGE EBOOK version, which has all the information from this article and much, much more allowing you to access 100s of TOP TIPS, EASY LESSONS and FAQs. 

Firstly a brief introduction. My name is Thomas Smallwood, partner at HD Outsourcing. As I mentioned, I recently wrote a book on the subject of hiring Virtual Assistants.

So I am here to give you hundreds of top tips, form my own personal experience, to help you get on your way to increased productivity, more free time, a better work / life balance, more quality family time or whatever benefit you are looking to achieve by delegating key procedures and tasks to a virtual assistant. Now, without further ado lets get right into it...

1. What is a Virtual Assistant?

A Virtual Assistant is an independent contractor who remotely supports one or more clients by performing a variety of tasks; administrative, creative or technical.

A Virtual Assistant can revolutionise your time management, enable you to fully exploit your entrepreneurial side or simply create that perfect life balance you have been seeking.

2. Should I Use a Virtual Assistant?

Question: What is the most precious and un-renewable of resources?
Answer: Time.

You are, I am sure, aware of the Pareto Principle. You may have heard it expressed as the 80/20 rule, the Law of the Vital Few or The Principle of Factor Sparsity (thank you Wikipedia) but it is the Pareto Principle.  Essentially it states that; 80% of outcomes come from 20% of inputs”. In other words approximately 80% of your revenue will come from approximately 20% of your clients.

It has been exhibited to be true in a number of other fields, including time management, whether professional or personal in scope.

Whichever way you look at it - whether as a percentage of your time or your clients - you want to be concentrating on the 20% that brings the greater financial benefit or perhaps in a personal interpretation: the 20% that brings the greater feeling of mental wellbeing.

A Virtual Assistant is an ideal way of farming out that 80% and giving you the space to use all your powers on the 20%; the part you enjoy and excel at.

There is effectively no limit to how you can use a VA. If you are here it is likely you feel you are juggling a number of different projects or tasks within your personal or professional life. A VA can help you focus more clearly by unburdening you of many of these.

From personal administrative tasks that help you to optimize your time and make the most of your daily life, to taking on someone to help run your business, a VA can give you the freedom to really use time more effectively.

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A Virtual Assistant is a part time or full time extra pair of hands. Many individuals use a VA to run administrative aspects of their personal or professional lives. This can range from booking travel or finding a cleaner to online shopping or outsourcing aspects of their business like web site maintenance and online marketing.

Typical Business Services a Virtual Assistant Can Handle

For any business owner or entrepreneur a VA can bring extraordinary benefits. You know how much time you have to spend on uploading content to your website, building landing pages or managing your social media. It is all work that has to be done but eats into your time like few other things. And all this time could be spent honing your product or talking to potential partners or commercial leads. In short it is time that could be spent making or selling your product or service.

Below is a brief list of services, but in truth there is no limit. It is down to you and the kind of skills you require from a VA.

  • Office Admin (Minutes, File Management, etc.)
  • Diary & Calendar Management
  • Booking Travel
  • Data Entry
  • Preparing Presentations
  • Bookkeeping
  • Expense Management
  • Market Research
  • Outbound Marketing
  • Content Writing
  • Website Management 
  • Social Media Management
  • Recruitment

Typical Personal Services a Virtual Assistant Can Handle

If you have kids of school age, you will have realized now that your diary has quickly and rapidly filled up and you are struggling to find time for yourself or your own projects.

For a busy family a few hours of a VA’s time can make life a lot easier.; taking many day-to-day tasks off your hands and freeing up some quality family time.

Below are some typical personal services a VA can help with:

  • Booking Travel
  • Online Shopping
  • Gift research
  • Managing Home Services (cleaner / gardener etc.)
  • Diary Management

Skilled Virtual Assistants

There are also what might be deemed “skilled VAs”. This is not to denigrate the work of a “general VA” but to simply highlight that it is also possible to hire a VA with specific skills. There is of course a slightly higher cost associated with them.

For example:

  • Graphic Design
  • Marketing & PR
  • Development
  • Extra Languages
  • SEO / SEM

The list of skills is of course endless and here the line between a VA and an outsourced skilled professional is blurred. If you need a VA who is going to do graphic design for 90% of the time, then you probably need a graphic designer, not a VA. Again this is not a problem but you need to adjust your budget and shift your expectations of the other tasks they may need, or indeed be willing, to do.

3. Where to Find a Personal Assistant

Recruitment Channels

There are basically three channels through which to find a great Virtual Assistant.

  • Online Marketplace
  • Virtual Staff Agency
  • Advertising Locally

Hiring Through a Marketplace

The most reputable freelancer sites can offer good candidates with a track record and reviews, but the worst will end up flooding you with hundreds of interested candidates that all look pretty similar on the surface but that in reality may or may not have satisfied customers behind them. This was my experience until I took matters into my own hands.

Recruiting Through an Agent

Agents can be split into two categories, those that take care of everything and request on-going subscriptions and those which simply request a one off fee.

HDO offers the former with elastic pricing models and tailored offers full time, part time and bespoke rates. The latter is obviously cheaper but with it come fewer guarantees.

Advertising Locally

This can be really successful but there is a big caveat attached to this recruitment method, because it is dependent on:

  • Having some local knowledge, such as the best (in terms of exposure and value for money) place to put an advert. For example I tried a few of locations including posting on University message boards and local job sites.
  • Being prepared to communicate directly with every single candidate and there are likely to be hundreds.
  • Assuming you do find the right avenues you will have to look at every single CV that comes to your inbox.

How to Write a Job Post

Here are my 8 top tips for writing a job post:

  • Write an interesting and attractive job title; (e.g. “Awesome Virtual Assistant & Content Writer wanted by US Digital Marketing Company”).
  • Be realistic in your requirements, demands or qualifications.
  • Be clear in your language and requirements and avoid jargon.
  • List the main (essential) skills / duties and the less important (desirable) skills / duties.
  • List the main duties first, before everything, clearly – to avoid time wasters.
  • Be ready to change your post on the fly. Think of it as a marketing campaign that needs to remain true but may need some optimization to get the best candidates.
  • Say a little something about yourself or your business.
  • Feel free to put an additional request (e.g. “When replying, please send me your LinkedIn profile”).

4. Assessing the Candidates

Stage 1: Sorting

Whether looking through profiles (if using an online resource) or by looking through CVs (if using a service provider) it is important to make a shortlist that requires more in depth assessment.

My advice, having done all of these, is always to use an experienced agency that can quickly narrow down the field in the first place but whichever way you do it there will probably need to be some email correspondence with the candidates, on your part or on the part of the VA agency.

If you manually do the sorting yourself then have some key criteria in mind that the candidates must fulfil (for example, the level of English required or experience as a content writer).

Whilst I am not of the opinion that that the scatter gun approach works, it is also true that spending a huge amount of time sifting through CVS or profiles trying to find the right person at this first stage is counter-intuitive.

A second stage will help you narrow the field down further.

Hiring a Virtual Assistant

Stage 2: Communicating

Using a two stage interview process enables you to narrow down a larger list by asking a few email questions. Again, as above, the agency may take care of this in which case you could request that certain questions be asked of the candidates.

My advice would be to limit these questions to a maximum of five. As in any interview I think there can be some basic ones, but a lot will be relevant to your job posting. My advice is to keep it to an absolute maximum of ten.

Here are some examples, but keep in mind that they may not all be appropriate. 

For instance many candidates will not have a LinkedIn profile, although I think it is fair to expect higher-qualified candidates with a specific skillset to do so. Not having a LinkedIn profile does not make them bad VAs.

  • What kind of Internet connection / speed do you have at home?
  • What are your principal methods of communication?
  • Have you done any specific training / have specific skills?
  • Can you send me your LinkedIn profile?
  • What are you plans for the next 3/5/10 years?
  • Have you ever failed at anything?
  • What are your strengths and weaknesses?
  • What is your typing speed?
  • Where do you read most of your news?
  • What is your preferred Social Network?
  • Do you have any tips or tricks for organising your time?

5. How To Interview a Virtual Assistant

Introduce Your Business

What may be obvious to you is not always obvious to others, so explain what you do and what your vision for your company / brand or project is.

Explain why your business requires the role of VA. Demonstrating the value of the VA is a good way to get candidates even more enthused for the role.

Explain the Role

  • It is really important to be clear as to what tasks the VA will be responsible for. A clear job description is helpful.
  • Give an outline of a typical working day.
  • Specify not only the number hours but also when the VA should be available (e.g. 9 to 5) and in which time zone this relates to.
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  • Explain how, and how often, you think you will communicate.
  • Explain which tools will be used for this and for lodging / recording work.

Work History

Ask the candidate to describe what experience she or he has that is relevant to the job description you outlined.

Do You Have Any Questions?

Ask the candidate if he or she has any questions about your business.

Further Questions

At this point I like to ask a couple of non job-related questions. You may have your own preference but I usually ask:

  • What they do outside work?
  • Do they have family?
  • Have you ever failed at anything?

This is not very scientific but the first two are designed to put the interviewee at ease and the third is more to understand what sort of person I am talking to. Are they humble, realistic, confident, cocky? Do they show resilience, for example in how they have tackled a failure?

Do You Still Want the Job?

It may seem silly but this is often overlooked. My final question is always, a version of this. After our brief discussion does the candidate think this is still a position that would be of interest?

Given my experience of VAs changing their mind after I had agreed to work with them and already lodged tasks, it is always worth asking this question.

Keep your ears open for any type of hesitation! 

6. How to Hang Onto Your Virtual Assistant

Build a Relationship

You cannot just hand over everything to a VA on the first day and expect stellar results. It takes time to train someone to work as you want and to build a relationship, but this kind of investment will repay great dividends.

It is important to remember that you need to get on with this person.

  • Cultural references and geographical aspects may not be obvious, so spell everything out clearly. Do you want the cheapest flight or the quickest flight to be booked?
  • Step-by-step guides will be massive boon. Yes they are time-consuming to compile but remember how important training is in any job. This is no different and the investment of time will be beneficial in the long run.
  • Once you are working together make time to review their work until you are happy with it and provide constructive feedback on how your VA can improve it.
  • If the work is not up to standard don’t huff and puff and redo it yourself. Provide constructive feedback explaining why it needs to be done the way you say. More often than not it is simply a misunderstanding.
  • Your VA is not sitting in the same office as you so it you can fall into the trap of not communicating but it is crucial to set aside time to do so.
  • Your VA may have worked in a totally different environment and may not be pro-active in alerting you when he/she hits some kind of obstruction in their work. Communication is vital in building a productive relationship.

Systems and Process, Systems and Processes…

Yes, I am probably repeating myself, but having systems and processes means the VA can work in an automated fashion and you will get the best out of them.

Set aside the time you need to educate this person to your systems and processes and then let them go. Time is Money.

  • Doubts as to what they should be doing will eat away at your time.
  • Questions as to what they should be doing will eat away at your time.
  • Waiting for tasks to be handed over will quickly eat away at your time.

Make sure you log how you do a task in as much detail as is possible. Then offload it. And repeat.

Entrepreneurs often ignore this as they work frantically, all hours, to build up their business but a VA is not automatically on your wavelength and does not have the intimate knowledge of your product that you have.

Having a detailed manual of your daily tasks will save you time and money and, importantly, it will increase the likelihood of your building a long and successful working relationship with your VA, which in turn will save you time and… ok, you get it.

What Kind of Work Should My VA Do?

As previously discussed, this depends very much on what you need and of course there is always an exception to every rule but in order to get the most out of your VA and to build and maintain a successful working relationship here are few pointers I would like to share:

  • Do hand over frequent repetitive time-consuming tasks to a VA.
  • o hand over simple tasks that are less frequent but you have done in the past.
  • Do not hand over tasks that are new to you (in other words things you have never done before). This is a generalisation and of course there can be exceptions but in the interests of always handing over work that can be fully explained it is a good rule.
  • Wait until you have a good relationship before handing over financial tasks such as paying invoices.
  • If you need your VA to make payments consider using a credit card with agreed weekly / monthly limit or use a platform such as mint.com

What Kind of Work Should My VA NOT Do?

I think this section is basic common sense and I debated with myself whether I should even include it. In the end I decided to do it so, at the risk of insulting my reader’s intelligence here is a short list of dos and don’ts around what you should not hand over to your Virtual Assistant.

Again, even in these cases, the below list is not made up of hard and fast rules. There will be exceptions. Perhaps after working with someone for a long time you will feel conformable handing over everything.

  • Do be very thorough during the interview process to minimise risk of problems.
  • Do not hand over access to bank accounts.
  • Do not hand over your credit card details.
  • Do ask your VA to sign a Non Disclosure Agreement if handling sensitive data. This could also include work that you produce and monetise, for example
  • You can easily get carried away as your VA lightens your workload but I would suggest it is still best to hand things over slowly, monitoring the work. It only takes one small mistake / miscommunication to potentially damage your business. Doing something slowly and systematically will also ensure your VA understands everything better and does a better job, in the long run.

When Should My VA Work?

The hours your VA works are down to you. Many are happy for their VAs to work when it suits them, as long as the work gets done.

If there is a comprehensive task list backed up by clear instructions time zones do not necessarily need to pose a problem, although they can be tricky at least in the start up phase.

Personally I have had much more success with VAs in similar time zones.  There may also be time constraints based on communication, especially in the case of personal, rather than professional VAs.

Whatever your needs I think there is some best practice to guide you.

  • Your VA should work a standard number of hours (e.g. 10 hours per week / 40 hours per month).
  • Any overtime should be recognised and paid.
  • Even if you are happy for your VA to do their allotted hours when it suits them, it is best practice to start off with a structure, such as a 9 to 5 to ensure you build a strong relationship based on trust and regular communication.  This needn’t be forever but if you struggle to be online at the same time the process of on-boarding a VA will be longer.

How Should I Monitor My VA?

It is perfectly natural to be concerned as to what someone you pay is doing, however tracking time probably won’t be necessary if you have the right person. However to alleviate fears and ensure you grow a successful relationship it is important that you both gain each other’s trust.

In terms of monitoring or reporting, there is no definitive way this should be done. My friend likes to log tasks and communicate through the platform in which they are logged.

Others like to receive a short written report. I personally like to have a very short (virtually standing up) Skype call to run over tasks and potential problems. To begin with it can be daily and then of course as you both gain confidence it can be less frequent.

Here is an example of the agenda for my call, but it could easily be converted to another form of communication:

1. Very short feedback on open tasks from my side
2. Ask VA what actions they took during the day / week?
3. What came of these actions?
4. Ask VA if they encountered any problems?
5. Ask VA if there is anything they need to know from me

How Should I Reward My VA?

I am not going to get into the specifics of what you should be paying your VA (although I do touch upon it in Chapter 10) because it varies very widely, depending on how demanding the tasks you will hand over actually are, and to what extent the VA requires extra skills or to what extent he or she needs to think on his or her feet?

Beyond the hourly, weekly or monthly rate that you and your VA or Agency have agreed, it is wise to reward him or her based on performance and here are a few useful pointers:

  • If employing directly do consider offering a starting salary for between 1 to 3 months (probationary period), then offering a raise. This can increase motivation.
  • Do not imagine that because you pay someone they require no further motivation.
  • Do consider a raise based on performance if you believe it is warranted. It is a great way to motivate.
  • Regular raises in pay should be on an annual basis. Inform them of how often wages will be reviewed, so they are fully aware of the structure in which they are working.
  • Do consider inflation in your VA’s country as a guide to your annual raises.
  • In some countries it is customary to have a thirteenth wage. Essentially this is a bonus paid at Christmas / holiday time and amounts to an extra salary. Consider this when budgeting for your VA. It is not an obligation but remember you are trying to build a fruitful long term working relationship.
  • Do say thank you for the work they produce. Remember it’s saving you time and money.
  • Do say a “Power Thank You” when they perform beyond expectations and be specific in what you are thanking them for and what the positive consequences were (see How to Give a Meaningful Thank You, courtesy of Mark Goulston).
  • Do give them as much respect as you would any employee.
  • Do remember their birthday and send a small gift (chocolates for example).
  • Do consider they may be from a very different culture and the significance of certain actions may be interpreted differently.
  • Do consider promoting your VA. This may sound counter-intuitive but if you outsource certain aspects of human resources to your VA, such as finding a content writer for you, it may be worth considering making this into a form of promotion.

7. 10 Practical Examples of Work a VA Can Do. 

1. Researching and Editing Images

You are producing the content, reams of lengthy, well studied, keyword-rich articles it to sky rocket your business up the Google search results, but your audience wants images.

Attractive, relevant and well-researched images can make a huge difference to how sticky your content is and very importantly, how shareable it is. Tools like canva.com mean you can now also produce beautiful banners for your site, but it is extremely time-consuming.

There are number of royalty free image stock web sites you need to look through before you upload the chosen image and then play around with composition and fonts.

It is also an avenue that you can wander down and quickly get lost, forever tinkering. You are your harshest critic - you should be it’s your business - but it also means that sometimes you are never quite satisfied with what you produce. And so time flies.

Hand it over to your VA!

Produce a short document with guidelines, such as image types, minimum sizes to assure quality, banner proportions, fonts you like and let them get on with it.

2. Backlinking

This is a repetitive task. You need to contact hundreds of sites to ask them to add a link to your great article on the Fast Guide to Recruiting a VA but you just don’t have the time.

Hand it over to your VA!

Format the message you want to send. Research the articles yourself if need be, but hand over the repetitive task of outbound marketing to your VA.

3. Marketplace Listing

I recently spoke to a VA who comes from a background of Amazon sales. I mean how amazing is that? Moving your stock to an online marketplace is a chore, a time-consuming and utterly necessary chore and yet there may even be a VA out there for you with the ability to list on Amazon better than you.

Hand it over to your VA!

At the very least you can list a few yourself, to provide examples. And remember to meticulously record what you do for those all-important systems and processes that make the handover so much easier.

4. Social Media Scheduling

You want to post at the right time for the right timezone, with the right content and the right images, mentioning the right people.

But you then need to spend the time scheduling the Facebook and Twitter posts and matching each with the right image. It’s mind-numbingly boring, and although you know it’s important it risks getting neglected as you look to concentrate on the “bigger things”.

Hand it over to your VA!

Technically it’s not difficult, you just need a clear excel sheet which displays the when, what and where.

5. Customer Support

Say what? Yes, you heard right! A lot of what might be deemed first level customer support is about replying to standard queries with a standard resolution or response.

A knowledge base or FAQ section could probably answer most queries so…

Hand it over to your VA!

Prepare some canned responses, based on the major issues you repeatedly encounter and arm your VA with these, escalating any that don’t fit the criteria.

6. Finding an Apartment

You need to move. But it takes time to go through the listings and contact each one, ask a few questions and set up viewings that fit into your schedule.

Some may answer, others may not be available and will require a call back later on. Don’t miss out on the one you want.

Hand it over to your VA!

Your VA can call or email the landlords, ask a series of pre-defined questions, schedule the appointments that fit in with your diary.

7. Getting You More Exposure

You know you need to do it. You know you need to reach out to hundreds of influencers or journalists to try to pick up your product through a story but you are too busy refining your product to do this kind of repetitive outbound PR.

You know you should send a personal message when connecting on LinkedIn or attempting to engage with an influential journalist.

Hand it over to your VA!

Prepare your one hundred word pitch, perhaps refine it for different sectors and instruct your VA to find the right contacts and add a personal touch when contacting them.

8. Transcribing Audio

Stop, start. Stop, start, rewind. How long does it take you to transcribe your podcast, interviews or note down meeting minutes? And how much of that time could be better used in some more gainful employment?

Hand it over to your VA!

A job of a few hours that does not allow you to simultaneously build your business and operate in productive areas in which you excel should be given to a VA to perform for you.

9. Recruitment

As strange as it may seem if you are at the point of considering hiring a VA it is fair to say that once you have been working with one for some time, and once your VA understands your business, there are a number of elements of recruitment that you can pass on.

Wading through CVs and online profiles, checking portfolios and language skills is very time consuming.

Hand it over to your VA!

If you need to add more outsourced labour, or simply want someone who understands you and your business to narrow down a large pool of CVs, then get your VA to do it!

10. Booking Travel

You want to save every penny you can on your travel costs that can mount up over the course of the year. So you end up spending half a day changing dates, trying a different carrier, trawling through a huge list of hotels to save a few bucks. But consider this - how much do you pay yourself and shouldn’t your time be spent on bigger things that may bring some bigger ROI?

Hand it over to your VA!

Be clear in your criteria: “I want a 4 star hotel for 3 nights and I don’t want to fly after 7pm - please find me the 3 cheapest options? Done. How easy was that? Now you can concentrate on building your business!


Who are we?

HD Outsourcing is run by professionals with C-Level experience; individuals who have built up small companies and worked in some of the largest.  We understand the demands put upon Entrepreneurs and Small Business Owners because we have set up and managed start-ups, implemented processes and built technology solutions.

Our Clients.