32:8 How to hire a virtual assistant - Lee Matthew Jackson
32:8 How to hire a virtual assistant - Lee Matthew Jackson

32:8 How to hire a virtual assistant

There comes a point in your agency when enough is enough. You cannot do everything and you realise you need outside help from a freelancer or virtual assistant. The thing is, you’ve heard horror stories from other agency owners and your last freelance experience was a nightmare.

Lee Matthew Jackson
Lee Matthew Jackson

There comes a point in your agency when enough is enough. You cannot do everything and you realise you need outside help from a freelancer or virtual assistant. The thing is, you’ve heard horror stories from other agency owners and your last freelance experience was a nightmare.

Lee Matthew Jackson - Trailblazer FM ™


Lee Matthew Jackson

Trailblazer FM ™

How do you find, select and onboard the right contractor for your agency? If you are struggling, this episode is for you.

  • Review
  • Where are the bottlenecks
  • What could be easily documented
  • What are you doing that you shouldn’t be
  • Plan
  • Write down key duties
  • Note skills you are looking for
  • Write a job description
  • Be realistic
  • Post
  • Post the position(s)
  • Give it time
  • Shortlist applicants
  • Interview
  • Provide a small easy task
  • Enrol
  • Start small
  • Provide documentation
  • Spend time with them
  • Build up their confidence
  • Lessons I have learned
  • Expect the first few days to be messy
  • Be patient before you rush to fire
  • Take responsibility
  • Replace if no improvement



Welcome to the Agency Trailblazer Podcast. This is your host Lee and today I’m going to share with you how to hire a virtual assistant, so stay tuned. But before we continue, this episode is kindly sponsored by Cloudways, my absolute favourite host on the planet. Be sure to check the link in the show notes for more information and the latest special offers. Right! On with the show. So let’s set the scene of the busy agency owner. Perhaps they have a few clients and a few projects all at the same time so that there is an awful lot of plate spinning going on. And when you own the business, be your solopreneur or be you have a team, you still have to wear all those hats and you have to cover multiple departments. So you might find yourself doing some admin one day you might find yourself going to a client visit to do sales another day.

You might find yourself doing some concept design the day after that, and then maybe that afternoon you’re back doing some code or you’re going to an exhibition or you’re on a call with the financial director or whatever is going on. It’s actually really stressful and there’s a whole load of things vying for your attention. Now we’re all aware of the fix and that is to hire a contractor of virtual assistant, get a freelancer or get an employee. And yet that seems to be easier said than done. You’ll have heard many horror stories of people who’ve had a terrible employee or a bad experience with a virtual assistant, or perhaps a freelancer has gone AWOL, mid project. All sorts can go on. And it can be really scary as a business owner going down that track, either you’ve been down that track before and you got burnt or you’ve heard of the horror stories from other people.

So how can you, knowing all of this and having all of this fear, now step tentatively out and reconsider getting in that virtual assistant or that freelancer. So in this episode I want to share with you the steps that I took to make sure that we got the right virtual assistant for our company and I’m going to break it down so that you can copy it. The same formula when finding contractors, freelancers, virtual assistants and employees for your agency. We’re going to go through reviewing, planning, posting your position, enrolling the person, the candidate as it were, and also sharing some of the lessons that I have learned along the way. So go ahead, grab a notepad on paper. Also note these bullet points along with the subtext will be in the show notes as well to help you as you plan. So let’s go. Step number one is to review your business and take a look at where the bottlenecks are.

In most circumstances, the bottleneck is probably, or possibly dare I suggest to you because I know I have been the bottleneck of my business. In fact, for most of my businesses, a lot of the book has stopped with me. I have kept control of specific tasks or actions that have required everybody else to wait on me. If I haven’t signed something off, then everything stops or everything draws to a halt. If I haven’t implemented something or done that one task that I want to keep under my belt, it slows everybody else down. So take a look. What are those things that you might be doing or holding onto that you don’t need to be doing and that could be supported by somebody else who also has specialist skills, who you can train and who you can ensure will do it the way that you want to.

I’ll share with you a couple of examples. One’s ridiculous. It was just simply setting up the development sites for our developers to work on. I had my own way. I had my own process. I like to know I’d got everything done just right and then I could hand everything over to them. But that was something that was super easy to document and have somebody else do. As long as that was checklisted out, somebody else could do that and I really had to let go. I guess that’s me moving from being the core developer to eventually growing a team and missing those things that I used to do because I’m now having to work more on the business rather than getting my hands on the code. Another example was me holding onto the social media. I felt like I wouldn’t be able to explain to somebody the sorts of messages that should be put out there and I felt like I had to control the entire conversation.

I had to control the imagery that went out and it had to be me that shed yield absolutely everything. And that was about four or five years ago when I met Sarah Moore and she started to help me see the need for other people to get involved. And still to this day I do find it really difficult to let go because I want to make sure the images are right and what we’re saying is on brand. But it is something that I’ve been able to relinquish a lot more of that control too and allow other people to listen to these podcast episodes within my team for example, and pull out quotes that they think are appropriate and create great content for our social media profiles. So those are two examples, but where are you becoming the bottleneck and you really do need to look deep. There are probably some very basic examples, but I imagine there are all sorts of areas in your business why you cannot progress.

You cannot get to the next level because there are bottlenecks. It could be you, it could be other people within your team who are holding onto, it could also be suppliers that you are already using and you might need to be replacing those as well. So take a look at those bottlenecks and also take a look at the activities that you are doing that could be easily documented. That’s the next element. What can be easily documented and then hand it off to other people. Even if you find something ridiculously easy and you can do the eyes shut, you are the owner, the director, the CEO, the founder or one of the key players within your business and your time is super expensive to have you working on things that could be easily documented and passed it to a lower paid, lesser skilled worker to be able to do it makes more sense because then you are afraid of with more time to do the highly valuable work that you do, which is focusing on the business and growing it.

So take a look. What are those activities that you are engaging with that you really don’t need to be doing? Again, back to social media, there was no reason I need to spend hours making images for social media when I could pay somebody else to help me with that. And again, that’s something I’m working on guys. And the final part of your review would be what are you doing that you shouldn’t be? And that’s not necessarily bottleneck stuff. And that’s not necessarily stuff that somebody else could do. It could actually be stuff that you’re just not qualified to do. Now, we talked in our managing your agency finances episode where you should be offloading all of that financial administration off to the experts and that is a very good example. If you are going crazy doing all of your invoicing, gear, bank reconciliation, your numbers, all of that sort of stuff.

If you’re taking all the time doing that and that is not your expertise, then you really should be looking for somebody to help you do that. They can do what might take you three days in maybe a couple of hours. So what are those things that you should not be doing that you can get an expert in to help you, even if that is only a few hours a week or a month of their time to get that thing done. It might cost you a bit of money, but it’s going to free you up the expert, the leader of your business to do the really, really important stuff. Okay, so next stage is to plan. We’ve ascertained that we have some needs, we understand where the bottlenecks are, we’ve focused on some of those things that can be very easily documented and we have also worked out those things that we shouldn’t be doing.

So this allows us to plan and the first step of plan is to write down those key, duties, those key roles that will need to be filled? Is that finance, is that basic development? Is that basic design, is that social media planning, whatever those are, make a list of those key roles that really should be covered by some form of external resource or a new employee or contractor, etc. Next you want to note down the skills that you are looking for. You have these key duties. What sort of person or people would you require and what skills would they have to be able to carry out those duties? So if you have somebody who’s going to be doing social media scheduling, what sort of experience would you like them to have had or what sort of skills would you like them to have or software should they have experience with?

For example, when we hired Nicole, I was really pleased that she already knew how to use Audacity and had tonnes of experience in Canva. That was essential for me as part of that hiring process and they were the tools I wrote down and the skills that I was writing down way before I even had her application. Then finally, once you have those duties and those skills, you want to write a clear job description so you are describing the role that you are looking to fill. It could be only a few hours a week or it could be a full time position, whatever that looks like. Describe that job, highlight the duties they’ll be carrying out as well as the skills that you are looking for. Now, the exercise here is really helpful because that allows you to be realistic. Are you actually looking for one person to do all of these things?

Is that realistic? Does that one person exist or perhaps are you looking for one, two or three people that might be able to do different elements of those different services that you are looking for? A lot of times the horror stories from freelancers or virtual assistants have actually come from a position where an agency owner has tried to find one person to do all sorts of jobs, and that’s just not reasonable. So be realistic is what you are looking for one person or more, and then make sure that you split that out. If you have to if you are looking for an audio editor and an artist, if that’s two different roles in your book, then make that two different roles and set some hours for those because you’re then going to take that onto the next step, which is to post, post. You want to post that position.

You have got all that information together. You have described the key duties and the skills I would recommend as well. You talk a little bit about your business, your ethos, etc, to attract the right people. So make sure you write that description in such a way that reflects your personality, but post out that position or those positions, and I would recommend check the show notes. There’ll be a few links to some online places. You can find contractors, freelancers and employees, especially in an industry such as ours. Once you’ve selected those platforms and posted out that job, all those jobs, then I would recommend that you give it time wait for at least a week. Many agency owners get to the point where they are desperate for a new employee, freelancer, etc, so they will post the job and then grab the first one or two people that apply.

But I would encourage you to give it time, let a whole load of people apply and build up a list of applicants and then give yourself some time to shortlist all of those applicants. Take a look through, have a look at their qualifications. If you’re using something like Upwork, then take a look at their past experience, their record as well as the cover letter, etc. Are these the sort of people you’re looking for and if you find the sorts of candidates that you think you’re going to resonate with, then shortlist those applicants. Now, what I did with Nicole is I waited. I think we waited about 14 days in the end to make sure that we whittled it down to the last three so that we could interview those last three. That leads us to our next step, which is to interview those shortlisted applicants.

Interviewing techniques are a whole of the podcast in there. Other right, but what I would say is be yourself and see or whether or not in those conversations that you guys are resonate or click. That is like the most basic advice I could possibly give, but do you like each other? Do you get on well when you have a conversation? I think that is the most important thing ever. Anyone who works in our businesses are people that, first of all, I clicked with before anything else before I knew anything about their skills. I needed to know that I was going to get on with them, that I could have a good chat. I could have a laugh. I wasn’t going to run out of things to say. Nicole made me laugh multiple times in her interview and I already knew that she was going to be the person that I would hire as long as when we got to those skills conversations that she was able to demonstrate that she was skilled enough or she had the experience enough to fit the bill.

And even if she didn’t have quite as much, at least I knew and I’d got the impression that she was far more moldable and willing to learn and had a really good positive attitude. In fact, Nicole will be doing the transcription for this podcast episode she had been doing the past few transcriptions. So Hey Nicole, you are doing freaking awesome and I am so proud of you. And to wrap up the interview process, you can also provide them with some sort of small, easy tasks. This is something that they can go away and produce for you, but give a clear brief that tells them what you are looking for and then ask them to do it. So again, let’s use Nicole as an example. I asked for a magazine article layout. I gave her the copy, I told her the background and the general inspiration and she went away and within 24 hours she provided a design.

It wasn’t perfect by any stretch of the imagination, but the fact is that she was able to take a brief, she was able to follow instructions and she was able to demonstrate to me that she could come up with something. And I knew therefore at that point that this was the right candidate for this job. This was somebody who could take instructions and could have a go at things and learn and build up a good long term working relationship with. So now we are at the in role stage. You are going to bring the final chosen person or people into the fold into your business and I would encourage you to start small. The biggest mistake I made in the past when hiring people was to give them a desk full of work that they just had to get through. And this instantly led to stress and overwhelm.

I didn’t give them enough information and I would just get rubbish back. So I learned the hard way that you really do need to start small and I mean ridiculously small, set low expectations and get them used to just performing certain basic and simple activities to ensure that you all learn how to work together. Now I think I’ve mentioned it before on the podcast, but in most working relationships you’re going to have storming, norming, and then performing. So you’ve got the storming part, which is the initial part of the relationship where it’s a bit stormy, you’re learning how each other works, you’re getting a bit upset with each other falling out, cause you’re not quite sure how each other communicates. Then you’ve got the norming stage where you’re starting to understand how each other works, how to communicate better with each other.

And then finally you’ve got the performing aspect where you’ve nailed it. You both know how to work together, you know how to communicate to brief and you know what each other wants. And that’s where you’re really rocking it and performing well as a team. So start small, don’t throw everything at them, but give them something that they can reasonably achieve and then they can build upon and build their confidence. And you can go through that at storming, norming and performing on some of the basic, non-essential, non-important projects. Now with any of the tasks that you give them, I encourage you to provide documentation and if you’re now saying, Lee, I don’t have time to document everything that I do, that’s fine. I’ve got a hack for you. All you need to do is record yourself doing whatever it is and then give the video to your employee and ask them to watch the video and then take screenshots from that video and create a standard operating procedure from it that showcases exactly how they are meant to do something.

This is something that we do with Nicole and with all our employees. I will record what I do, I will ask them to watch that video, create the SOP, and then I’ll read through the SOP to make sure I am happy that they’ve captured all of the information that I’ve shared and that that flow works correctly. So it’s a two in one. You get to train and you get to create the document and you get to have the person who’s meant to be reading and consuming that really understand it because they’ve had to create the documents. There is a hack. That one was completely free. Actually, this entire podcast is completely free. So if you would like to support the show, check us out over on www.patreon.com/loveyouragency for ways that you can support the fantastic, the wonderful content that we are putting out into your ears.

That was an accidental segue. Slash plug. Did you see what I did there? Beyond documentation, I’d encourage you to spend time with them. So that means get to know them, have conversations, find out what makes them tick, what work they are enjoying. And again, another hack could be spending time with them, recording the call, showing them how you do some thing. This means you can send them the video and they can do that whole SOP thing. So you’ve spent time with them, you’ve shown them how to do something and now they’re going to create their SOP. And that is something that we did. We record nearly all of our meetings to make sure that we’ve got something that we can go back to and get some value from, create some documentation from. And then finally, I would encourage you to build that confidence. So over the next few days and weeks of their employment, tell them that they are good at what they do.

Don’t highlight the mistakes that they make. Yes. Do highlight them if it’s a serious mistake. I have had to point out with all of my employees at times what they have missed the mark. So they need to understand what the expectations are. But what I really try and do is push how proud or how pleased I am with specific things that they do. None of us want to work for us. We want to be able to work with people that appreciate our talent and that enjoy our work because that means we’re gonna enjoy our work. So for example, earlier, in this episode I told Nicole who is going to be transcribing this podcast, how proud I am of her, so it cost me nothing. That is just me sharing how I feel about a member of my team. You’ll have heard me mention on multiple other episodes, different team members within this company as I boast about the work that they do and that’s a culture that we apply internally as well.

We make sure that we give where credit’s due. We give people kudos. We lift people up, we encourage them and we say thank you for the amazing hard work that they’re doing. All right folks, we’ve gone through a review. We’ve gone through plan, through post and through in role, so I just want to share with you a few lessons I’ve learned and then we are going to wrap up this show. Lesson number one is to expect the first few days to be messy. You will probably have a complete horror show of a first few days and most of my employees have had a really rough few days where we’ve not really understood each other. I’ve probably given them too much work to start with, so it’s usually my fault and it’s just been a bit of a train wreck and they think they’re going to get fired and I think they might be terrible and it’s just all a bit of a mess.

So please expect that it’s probably gonna be messy. That leads me to the next tip, which would be to therefore be patient to expect that the first week or two is not going to be perfect and therefore be patient. Be conscious of that storming, norming, and performing relationship where you do need to get to know each other and that you did need to be reasonable and give them work that they can grow into rather than trying to throw everything at them. Leads me to the next one, which is to take responsibility. You need to take responsibility for your team and for the growth of your employees, your freelancers, etc. If they are struggling, that’s probably on you. You’re probably not explaining things enough. You’re probably giving them too much work. You’re probably expecting too much of them. So I would encourage you to take responsibility, take a step back and make sure that you’re really looking after them, making sure you’re starting small and making sure that you are building them up.

And then finally, if you feel you are and you’ve given it a few weeks, you do need to replace them if there’s no improvement. So yes, I’m going for the nice track here, but there is a point within a few weeks where it’s completely obvious you’ve done all the due diligence, you can possibly do fire them. I know it sounds awful, but you just have to let them go because you need to find somebody else that you can mould and build that relationship up with. Sometimes from an interview, we don’t always get it right and we do have to, again, take that responsibility, figure that this is not the right relationship. Let that person go so that they can be free to work in a place that they can thrive in and then find the next person. It could actually be one of the other people that you employed.

Now I do know a few agencies that will actually hire two people for the role and then select the one that works out best. I don’t like that personally. That feels a little bit competitive and I’d also kind of want to just keep them both cause I’m super nice but you know, do what you need to do, but just make sure that you respect the people that you are bringing onboard. Everything that we’ve shared today can apply to contractors, freelancers, employees, etc who are coming into your business. Let’s do the quick recap. You are first of all, gonna review. Look at those bottlenecks in your business, work out what can be easily documented and then you are going to work out as well what you shouldn’t be doing, especially if it’s things that you just can’t do very well. Next you are going to plan.

You’re going to write down those key duties. You’re going to note down the skills you’re looking for. You’re going to put out there a good well-written job description and you’re also going to be realistic with who you’re looking for. You might not be looking for one person, you might be looking for three. So be realistic. Then you’re going to post that position. You’re going to put it out in notebook or wherever you can to give it some time. Build a playlist of applicants, shortlist those applicants, interview them and give them some sort of easy task to gauge whether or not they can produce something from your instructions. Then from the final stage, you are going to enroll one of those people or two or have many you need and you’re going to start small. You’re going to start with a few easy tasks and you’re going to build up from that, providing them documentation and spending time with them using the hack that I shared of doing video calls, etc, and also you’re going to encourage and build their confidence.

And then finally we wrapped up with those lessons. All of the notes are in the show notes. Check that out over on agency trailblazer.com or if you’re listening on your podcast player, there is a link to take you to the full show notes. Don’t forget, this podcast is sponsored by Cloudways. Check them out over on www.cloudways.com. They are a phenomenal host that allow me to quickly scale up massive websites in our agency. If you’re not aware, I own another business and we power literally hundreds of sites around the globe with high traffic, so I make sure I rely on a good solid host like Cloudways. Check them out in the show notes with all of the other offers. Finally, don’t forget we have a free Facebook group. You can come and hang out with us over at www.trailblazer.fm/group and if we don’t see you in the group, we will see you in next week’s episode.


PodcastSeason 32

Lee Matthew Jackson

Content creator, speaker & event organiser. #MyLifesAMusical #EventProfs