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How to determine when it is time to hire a virtual assistant

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Sep 29, 2021
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Feeling like you could really use an extra pair of hands in your business? You’re not alone. 

Maybe you’ve thought about bringing on a virtual assistant. Knowing when it’s time to hire an employee is all about making the right decision at the right time to hire the right kind of talent for your needs. 

Keep reading for a close look at the kinds of tasks you can outsource to a VA, how to know if you’re ready to hire, and some virtual assistant discovery call questions you can use in your interviews.  

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What kinds of tasks can I outsource? 

Virtual assistants for coaches and knowledge entrepreneurs are able to take many routine (but necessary) activities off your plate. The key is to hire the right assistant so you can focus more of your time on marketing strategy, product development, and growth. Whether you’re a business coach or digital entrepreneur, there are a wide range of tasks you can outsource to a VA, including: 

  • Bookkeeping
  • Affiliate program management
  • Social media marketing
  • Blogging
  • Copywriting
  • Email marketing
  • Business administration
  • Video editing
  • Slide/presentation design
  • Podcast creation
  • Audio course editing

When is it time to hire an employee or contractor?

Crossing the threshold from a business-of-one to a business-of-many can seem like a big step. You might be worried that you’re expanding too quickly, or on the opposite end of the spectrum, that you’re holding back growth by not investing in your own company.

To allay your fears, here are three signs and symptoms that you could benefit from an assistant. 

Sign #1: You’re spending too much time on administrative tasks

Administrative tasks are a necessary evil, but they also expand to fill up almost any time you give them. From writing and responding to emails to calling prospects and scheduling appointments, routine activities eat up your precious time and distract you from doing the very things that could help you grow your business. 

By the end of the day, you’re probably exhausted and drained, like you’ve been spinning your wheels with nothing to show for it. 

Sign #2: You need skills that you don’t have

Some things (looking at you, taxes) take specialized, professional help to complete. Hiring an expert can get the task right and in a fraction of the time it would take you. This is a good place to start when you’re hiring help. 

But don’t stop there. Think for a moment about the projects you’re holding off on because you don’t have the right tool or experience. If you hire someone who can help  you complete those projects, you may be able to multiply your income — and more than pay for your VA.

Sign #3: You don’t have a healthy work/life balance 

Entrepreneurs often say they’d rather work 12 hours for themself than 8 for someone else. And many do. Like a frog in a pot, they don’t realize how busy they’re getting until it’s too late.

Sometimes we have to consciously create a healthier work/life balance. Yes, your business is like a baby or pet — needing your time and attention. But your life is also important. You need time to spend with family and friends, and time to pursue hobbies or just. do. nothing.

If you’re running yourself ragged trying to do everything, it may be time to hire help.

3 questions to ask yourself before hiring a VA 

It’s one thing to ask yourself, “When is it time to hire an employee?” and another thing to actually be ready to do so. Your finances, your workload, and your ability to delegate all come into play as well. 

Here are three questions to ask yourself if you’re serious about hiring a virtual assistant for coaches: 

What tasks do I want the assistant to be responsible for?

Before you decide to hire anyone, you need a clear picture of the tasks you want them to do for you. 

Look closely at the activities that need doing on a regular basis. What are they? Make a list. Then jot down how often they need doing and what level of clearance a VA would need to be able to do them. 

Keep in mind, you can hire specialists who do more than answer emails or schedule your podcast guests. You might prefer to have someone conduct your sales calls, run your tech, or do your marketing for you.

Kajabi Hero Caroline Onyedinma describes the difference like this: “If they are an assistant, they’re following your instructions as a digital doer. If they’re a strategist, you’re deferring to their professional experience and direction.”

What’s my budget? 

Think about the value of the work you’re wanting to hire out. What should it cost to hire someone for those tasks? Then look at your budget to determine what you can realistically afford.

If your budget is tight, consider starting small, finding someone to take on just 5 hours of work a week, so you can focus on a high-value, money-making activity without interruption. You can delegate more as your business grows.

Note: Check with your accountant to find the best way to set up your finances. Then take time to compare rates, so you can find an affordable, diligent contractor. 

Am I willing to let go and let them take over my responsibilities?

This can be harder than you might think. We typically like the way we do things and dislike it when someone tries to change things up. 

But when you delegate, those activities are going to be done differently. They may take on the personality of your assistant, not  you. And you have to be okay with that.

Your contractor or remote worker is willing and able to complete whatever tasks you want to assign. Focus on how much time it frees up, on the space it gives you to grow your business, create new courses or membership perks, and develop new marketing campaigns.

10 virtual assistant discovery call questions 

So you’ve got the budget and the need. Now, you’re ready to hire the VA of your dreams. This is when the magic happens: you and your potential assistant on a call, talking about your business, asking discovery call questions that will give you a sense of whether they’re a good fit. 

Here are 10 virtual assistant discovery call questions you can ask

1. How did you become a virtual assistant? 

This is one of the most common virtual assistant discovery call questions, but it’s important to ask. Virtual assistants bring a range of expertise from their previous clients and employment positions. 

This question will help you learn about unexpected (but useful) skills they bring to the table, such as familiarity with a certain industry or speaking a second (or third) language. That may allow you to expand into new markets sooner than later.

2. How long have you been working as a virtual assistant? 

You may be speaking to people who have never worked as a VA before but are eager to learn. You also may be talking to people with years of experience. 

Don’t be too hasty dismissing new VAs, however. They may have prior experience that will make them especially valuable as your business scales. 

3. What are your areas of expertise?

Every virtual assistant has a unique set of skills and experiences. Some may be general VAs who perform a wide range of administrative tasks. Others may focus specifically on sales and marketing and be skilled in everything from lead generation to graphic design. 

Try to understand where their expertise lies so you know you’re hiring the right person for the job. 

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4. Which tools are you most familiar with? 

This question tells you how techy they are and how easily they’ll be able to learn your processes and systems. If you have specific tools you use or would like your VA to use (such as Kajabi), ask them if they have experience using that particular tool.

If they have experience using a variety of tools but not the one you’re most familiar with, it’s still worth giving them an opportunity to work with you. They can likely pick up and learn your preferred tool quickly with very little onboarding necessary.

5. What security measures will you be using? 

This question is particularly important if your virtual assistant will be handling sensitive client details or personal information. 

You want to ensure your business data, customer information, and website are safe from hacks and attacks. Some topics to discuss here might include

  • Their anti-virus and anti-malware programs, and whether they keep them up to date 
  • How they secure their wifi connection 
  • Whether they’ve enabled two-factor authentication on certain apps

6. What hours will you be working? 

Some virtual assistants need a flexible schedule that allows them to take care of children or aging parents. Others may be clocking in from the other side of the world. 

Ask yourself how important it is that they be available during your regular business hours. If you need to contact them often, it may be worth having someone located geographically closer. 

If a weekly virtual meeting is enough or you coordinate mostly in a project management app, the time differential may not matter at all. 

7. How do you prefer to communicate? 

It’s always refreshing when you find someone who likes to communicate the same way you do. Some people love chatting face-to-face in a Zoom meeting. Others are perfectly content to send a few messages over Slack.

Let your potential VA know how you prefer to communicate and verify they’re comfortable with it. The last thing you want is friction from a communication style mismatch. 

8. What is your availability like? 

Just because a virtual assistant works certain hours, doesn’t mean they’ll be working specifically for you during those hours. The best VAs have a full roster of clients and the tasks that you need done may be addressed between the needs of other clients. 

Tell the VA how many hours of work you’ll need from them each month and how those hours are distributed across the month. From there, you can ask about their availability to work within your schedule. 

Depending on how urgently your tasks need to be done, it may be worthwhile to hire a virtual assistant with less experience but a more flexible schedule. 

9. How do you prioritize your work? 

Good virtual assistants are organized and efficient. But if they have multiple clients, even the most efficient can get overwhelmed. This question helps you better understand how they prioritize their tasks and what happens if they’ve bitten off more than they can chew. 

Want more details about how they manage time? Ask them how they prioritize tasks, and what they do if they are unable to meet a deadline. 

10. Why did you apply to this job in particular? 

This tells you what the VA is looking to gain from working with you. Don’t expect them to be excited about routine data entry. But they should be enthusiastic about helping you get things done more efficiently, reducing your workload, or learning something new. 

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When is it time to hire an employee? 

When you’re ready on all fronts, hiring an assistant can unleash unprecedented growth. So how do you get started?

First, verify that you’re ready to hire. You’ve got the workload to justify hiring help. Financially, you can afford the help. And you’re ready and willing to delegate.

Then put out the word that you’re looking for help. Ask other business owners who they recommend. Do Google or LinkedIn searches. Or, post your job online.

Ask for resumes or have your applicants fill out a form with key questions about their skills, experiences, and work style. Screen the applications and try to find the top five who you’re interested in talking to. Then schedule an interview with each of them. 

The next task is to interview each person thoroughly and choose the one that’s the best fit for your current and future needs. Make sure they understand the job, your expectations, and the terms of their employment or contract.  

Your first hire is an exciting moment in your business. It’s evidence that your hard work is paying off. Don’t resist hiring help when you get to that point. This one step can remove the overwhelm and free you to continue growing your business. 

More resources


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