What do you think the biggest challenge would be in this role?

Back in April 2014 we wrote a piece outlining some of the questions I think it would be wise to ask a Virtual Assistant before you started working with them.  Since then we’ve been answering these questions so you’ve got an idea of my stance when it comes to work, and whether or not Time Saving Heroes might be the right solution for your business.

Today we’re looking at what the biggest challenge might be in a VA role.

Of course, it’s difficult to answer that question accurately right now without having a specific client in mind. However, there are some things that often come up when starting a new VA working relationship, so I’ll tackle those.

Feeling overwhelmed

Many clients get in touch with a VA because they’ve reached the point where they want to clone themselves. Essentially they have so much to do, and too little time to do it that they end up feeling completely overwhelmed.

Unfortunately, that feeling can last well in to a VA relationship with clients feeling so confused about what it is they want to achieve, and therefore unsure what they should be offloading to their new right hand woman.

It’s perfectly common, but it can take a little while to get over.  Personally I always sit down with a new client and ask them what their biggest problems are at the moment, and what it is they want to achieve.  We then start with that, and wait for everything else to naturally fall in to place.

Failure to delegate

The vast majority of my clients are microbusiness owners or sole traders. As a result they’re the only people that have ever worked in the business, and it really is like their baby.  It’s one thing recognises that they need help to take things to the next level, but it’s a whole other ball game actually getting to the point where help is accepted.

Many clients find delegating hard work, especially if they don’t have any real management experience behind them.  Problems can arise if they worry that they won’t get done, or that it won’t get done to a good enough standard.  Some even worry that they’re going to come across as being bossy if they keep putting demands on you (even though it’s your job).

Again, I always sit down and try to get to the route of the problem and ascertain why they’re reluctant to delegate work when they know they need to.  Talking through their feelings, potential control issues and what they’re worried about is a great way to get them to see the bigger picture, and start to resolve the barriers they’re putting up.

I’m 50% VA and 50% therapist most of the time.


Communication can be an issue in any relationship, but when you’re predominantly working in a virtual capacity it can all be made a lot worse.  Clients will always have a preference as to how they want to work, even if they don’t openly state it.

Conflicts can arise if they tell you to email them with everything, but then don’t respond to the emails because actually they’d prefer you to call.  Or vice versa.

Some clients really want someone to be in charge of them, but they don’t articulate that.  Which means you can spend a few weeks waiting patiently for them to get back to you, when in reality they need you to pick up the phone and nag them.

All new relationships take a while to settle down, and a good VA working relationship is no different. You have to take the time to get to know each other and find a way to work in harmony together.  Once that’s done, there really are no problems.



10 Questions to ask a Virtual Assistant BEFORE you hire them

If you’ve ever wished there were more hours in the day, or if you could clone yourself then it’s probably time you took on help.  For some people that might mean hiring staff, but not all businesses are in a financial position where they can handle that level of risk. Equally, some people really don’t want to deal with everything that having staff brings.

That’s where a Virtual Assistant can come in. No upfront costs, no training, no employee benefits, no need to find space for them or provide them with equipment, and you can be up and running within minutes.

However, we know finding the right Virtual Assistant isn’t always that easy.  It’s not a case of finding one online and saying “yeah, you’ll do”.  This person is meant to be your right hand (wo)man so you need to make sure you can work together. If you can’t, it doesn’t matter how good they are at their individual skills, it’s not going to work.

How do you find out though, at interview stage, if it’s a match made in heaven?  Whilst there’s no hard and fast rules, we’ve pulled together ** questions we think you should ask to find out more about your potential VA.

#1 – What are your core skills and services?

As with many roles, a VA doesn’t just do one thing, but equally that doesn’t mean they do all things brilliantly.

A good VA should have strong skills and extensive experience in admin settings, but they might also be proficient with social media, graphic design, website management, research, customer service, general organisation etc.

It’s important for you to know what they can offer, and what they might not be strong at so you can ascertain if they are right for your business needs.

# 2 – What’s your favourite way to communicate?

We all have a preference, for some they live on their phone, others are tied to their email. If you’re a phone person the last thing you want is to be forced in to emailing your VA if this isn’t natural of comfortable for you.

A good VA should be comfortable communicating whichever way feels best for you, but ask for clarification.

# 3 – What would you do if you realised you didn’t know how to do a task?

We all like to think we know everything, but the truth is, we don’t.  There might well be a time you ask your VA to do something they’re not able to do, which isn’t a problem; however, if they don’t handle it well it might be.

A VA that says “well, errr, I don’t know …” probably isn’t that experienced.  It’s happened to us all at some point, and there’s no shame in it.

# 4 – How do you manage conflicting deadlines, and what do you do if you realise you can’t meet them all?

Sometimes you take on work and suddenly realise there is no way you’re going to get everything done. We’ve all been there, and believe it or not, VA’s aren’t immune to this either. Whilst it might happen rarely, it is important you know what your VA would do if they were faced with it, and one of your tasks was going to get dropped.

# 5 – What do you think the biggest challenge would be in this role?

Every client brings their own challenges, and whilst no one wants to be potentially criticised, it’s also good to know your VA has given this particular relationship some thought.

A really good VA would already have highlighted potential sticking points, and will have come up with ways to handle them.

# 6 – You’re working on an urgent deadline, and your computer or internet crashes. What do you do?

Again, none of us are immune from the terrors of malfunctioning technology so it’s important to know what your VA would do if this happened whilst they were working on an urgent task for you.  Yes, they’re likely to have backups and contingency plans, but are they enough to make you feel happy should the need arise to use them?

# 7 – What are your schedule restrictions?

You might well want your VA to be available to you 24/7, but that’s unrealistic.  They are allowed a life too. Equally, you might want them to be able to respond to you during office hours, but is that practical if they have other clients?

They might be able to set aside specific days and times where they are open to your calls, or they may have a set turnaround time. Each VA works differently, and you need to make sure you’re happy working within their restrictions.

# 8 – Give an example of when you’ve proactively addressed a client’s needs

A good VA should do everything you ask them to, but an exceptional VA will do the things you don’t ask for. It can take a while, but if you have a good working relationship with your VA they will be able to anticipate your needs based on your previous requests and work habits.

# 9 – Have you ever challenged a client and suggested an alternative way of doing things?

We think one of the best things about a VA is that they’re not an employee.  They might be there to help you, but one of the best ways to do that is to bounce ideas around and provide suggestions.  They have their own experience, and they have no doubt worked within a wide number of businesses, and may have a few ideas you could benefit from.

A good VA won’t sit there and stay quiet.

# 10 – Have you ever sacked a client?

Sometimes relationships break down, and when this happens a VA is no longer effective.  It is a good idea to know if your VA has ever experienced this, and if so, what they did about it.  It will say a lot about them and their confidence.