When Is the ‘Right Time’ to Hire a Virtual Assistant?

When is the ‘right time’ to bring on a remote assistant? I believe the ‘right time’ is a myth. Let me tell you why.

Typically, business owners judge when the right time is using 3 key resources: time, money, and stress level. For them, the illustration is as follows:

Time and money is pretty self explanatory. When you start your business there’s more time for strategic thought, since you often have little to no customers, and sometimes limited money.

As your business grows, you will naturally gain customers or clients and your available time will decrease while money increases. In regards to stress (for the purposes of this illustration): it is ‘low’ when you control your calendar and ‘high’ when your calendar controls you.

Let’s break down the thoughts entrepreneurs usually have at these three stages in the graph:


  • WHAT IT LOOKS LIKE: A lot of free time, low stress but also low money. You are doing all of the admin work yourself.
  • WHY START NOW: People usually miss the gifts of time and lower stress during the early stages. At this time you have the most mental capacity, due to lower stress, to do a proper/thoughtful hand-off. It also doesn’t have to cost an exorbitant amount of money to get started with an assistant. It’s why I don’t like VA models where clients are locked in to a certain amount of time. Needs change, new efficiencies are found. With ChatterBoss we’re an on-demand and dedicated service which means you can work with your assistant as much or as little as needed, and that’s why we’re the perfect partner to start with at this stage of the process!


  • WHAT IT LOOKS LIKE: There’s some money, some time and some stress but the entrepreneur is not too overwhelmed.
  • WHY START NOW: Balance between having free time to train an assistant and enough clients not to feel tight about paying for support.
  • WATCH OUT!!!: It’s extremely hard to pinpoint this time. Usually entrepreneurs have trained themselves to do it all on their own, and by the time they get to this stage they decide to keep going for as long as they can. Unfortunately, often until they get to the ‘it’s too late’ stage.


  • WHAT IT LOOKS LIKE: You have resources, but you’re drowning with no time and lots of stress. If a business owner hasn’t gotten the support they need by the time they get to this stage, it often looks like chaos as they try to manage too many things on their own. There are enough resources to pay for help, but an entrepreneur might be hesitant due to fear that it will take too long to train an assistant and they won’t have time for it.
  • WHY START NOW: You don’t have time, you’re stressed and you have resources to pay for help!!! Do it! Training might seem daunting but this is actually a great stage for it, because by this time you have plenty of tasks to start an assistant off with. An assistant can step in to watch you over a series of Zoom calls or prepared Loom videos and start taking things off your plate one by one while documenting your existing processes.
  • WATCH OUT: You are so desperate for help at this point that you might end up choosing the wrong partner to support you, which is costly and painful if you end up having to retrain a new person if the first partner didn’t work out. At this stage it’s also tempting to throw everything at once to your new assistant, but this is a mistake because it leads to errors and chance of miscommunication. Even at a time that you’re so busy, the better approach is to hand things off one at a time.

Ideally we would do everything in our personal and business lives at ‘the right time’. When it comes to getting admin support, tough, that ‘right time’ is wherever you are right now in your entrepreneurial journey because regardless of the stage there is always an administrative burden that should be handled by a professional.

What stage does it feel like you’re at today? Have you fallen victim to waiting until it’s the ‘right time’? If you’re an entrepreneur that is working with a VA, at which stage did you decide to start working with one? How did you get to your decision?

About us: ChatterBoss is a customer-centric remote executive assistant service that pairs best of class virtual assistants to busy entrepreneurs and business owners. If you’re interested in a complimentary consultation, email me at Valerie@chatterboss.com or text to 917–933–3682

Former Chief of Staff and Personal Assistant to A-List celebrities, C-Suite executives, and high-net-worth individuals. Founder of ChatterBoss.com

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