How to tell if you’re ready to hire a Virtual Assistant


Email management – If you are spending up to 3 hours a day in email land, that eventually adds up to 15 hours a week or more. If you are checking your emails and responding to clients at all hours of the night and don’t even have a clue how much time is sucked into just email, that’s a red flag right there. This time could be spent elsewhere with the right system and person to manage it for you.

Calendar management – I really hope you are using some kind of calendar for your business. If you aren’t, you need one for planning and organization. If you are, it can be a royal pain in the (you know what) to manage it with small business orders, clients, requests, bookings or appointments. If you are spending up to an additional 3 hours a day on just calendar management that gets tacked onto your email management the next thing you know your 40 hour work week is spent with 30 hours of email and calendar management. “Hey Alexa, give me my time back!” “Humm, I don’t know that one?” She can’t. Go ahead, try it.

Hiring processes – You made it through your first few years as a successful business (Congratulations!) and now you are growing and need qualified candidates for these positions! Except, the responses are slim to none, they aren’t even close to being qualified and you don’t have a screening process. You can’t grow if you can’t fill positions and expand with qualified candidates. The right Virtual Assistant can use their marketing skills and systems qualifications to document and streamline this for you. Paired with Calendar and Email management, you’ll think you’ve landed a Magical Unicorn on your team!

Social Media scheduling and engagement – Small businesses, especially brick and mortar ones, are facing many challenges with the online world. Have you actually tracked how much time you spend on social media promoting and marketing your small business? Does this sound like you: creating graphics, engaging, trying to figure out how the hell to do a Facebook Ad only to end up discouraged and not meeting your expectations? Let’s not even mention the direct message cluster…you get my point. A Virtual Assistant who specializes in social media marketing, content creation and Facebook Ad services will take the pain away. Now, do me a favor, set a timer and get a realistic view on how much time you spend on social media. I’ll be here when you go into shock.

Reporting on KPI’s in the business – Successful businesses implement numerous reports. Yearly, quarterly, monthly, weekly, daily. If you are running and analyzing these reports on your own, you are really informed but also really wasting that precious time. As the business owner, you should be given an easy presentation to digest and make quick decisions with. A Virtual Assistant can run, prepare and present these to you and other stakeholders of the company. (By the way, as a business owner I would hope you know that a KPI is a Key Performance Indicator) If you are reading this and going cross-eyed, find a Virtual Assistant who specializes in it. Your business depends on it.


Work feels like Work (where did the fun go?) – This is basically a no brainer. With all the advances in technology and the fact that we haven’t gotten more time with it, you could work till your eyeballs pop out of your head and you’ve drunk a 6 pack of Red Bull. Small business owners typically start a business from a passion project. Now it’s “All work and no play makes Jack a dull boy” and you’ve lost interest in the passion that sparked it. No doubt the burden of administrative tasks above contributed to this in some way. “Here’s Johnny!”

Missing deadlines – If you are missing important deadlines for projects related to your business, then something has to change.

Creativity has lost its way – You can’t hide the fact that you are a creative Entrepreneur and a small business owner. Your craft got you here! However, all the burnout and overwhelm is hindering your creativity and you are struggling to find new ways to bring in business and connect with dream customers.

The flexibility factor is gone – Flexi—-what? When your work and business consumes you, you lose that precious flexibility factor you dreamed about when you started your business. Noone likes to tell someone they can’t do something because they have to “work” and face the confusing googly eyes that say “But aren’t you the boss?”


Sales are just not what they should be – So you finally ran those quarterly sales reports after spending hours to find out you barely made your goal and broke even. Now you have to analyze every nook and cranny to figure out what worked, what didn’t work and the entrepreneurial roller coaster ride sets in of ups and downs about your business feelings. Small businesses flourish on creativity, connections, great customer service as well as great products. This all leads back to the points above. Connect the dots, la la la la.

Customers are leaving bad reviews – You can’t control everything and there was that one time this irate customer was having an awful day. They slammed your business on social media, Yelp, Google and wherever else they could. They may even have called the local newspaper. (yikes!) The worst thing you can do is (try to) delete it and act like it doesn’t exist! A Virtual Assistant can take that weight off your shoulders, and you can partner with them to develop a plan for responding to these problematic reviews. Maybe the reviews are revealing the causes of low sales? A skilled Virtual Assistant can help with that, respond to them and help follow up as necessary to turn the bad into good.

Launching new products seems like it’ll never happen – You had a brain baby, started a project plan and got so busy with other tasks and issues that the product launch you’ve been planning keeps getting pushed further and further away. Or, you’ve never even thought of doing a new product launch. A Virtual Assistant with Project Management skills and background can give your business the edge it needs in accountability, managing teams, project planning and execution.


Family time is limited to small amounts – I really hope I don’t need to elaborate this one too much. You should not have to sacrifice your family values and time for your business.

Distractions are imperative – If and when you are trying to spend time for your self care and with family and your small business or work becomes a distraction, it’s a red flag.

Your health is suffering, you can’t do it all – The stress and burdens of owning a small business can take a serious toll on your body. If you outsource the mundane business administrative tasks to a Virtual Assistant you will free up valuable time for your family and health. Really though, who’s going to take care of your family and run your business if you’re not around?


Growth is happening but it’s just enough to break even – Your business is in the final stages of growth and survival. You’re making enough to break even but need to ramp up sales to turn a profit. This may be the time to invest in a Virtual Assistant so you can put that creative brain to work and make it happen.

You dread the idea of paying for employee expenses – Small business owners are faced with a ton of decisions and expenses when it comes to hiring employees. You’ve come to realize you need help, but the numbers and your gut can’t handle the thought of hiring another employee. That’s the beauty of a Virtual Assistant. They are also small business owners, or self employed and fund themselves, their equipment and insurances. It’s also considered a business service that can potentially used as a business expense when it comes time for tax season. Just for fun, a Project Manager’s salary can range between 50k and 60K a year in some areas. The Enterprise Retainer Package for AmbitiousVA that includes Project Management services is $1200 a month. That’s only 14k a year. (Without ad-ons)
To Recap 5 Key Warning Signs it’s time to Outsource for your small business are:
- You spend too much time doing administrative tasks
- You feel burnt out or overwhelmed
- You are not gaining more sales and new customers or getting bad reviews
- Your family says you work too much or you’re having health issues.
- You are growing but not enough to hire another employee
Take our Business Owner Assessment to see if you’re ready to hire a Virtual Assistant for your Small Business. It’s a scaled and scored assessment to help you decide if a Virtual Assistant is right for you and your small business. All assessments are scored and responded too individually with real human interaction!
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**This blog post was updated on 4/21/2021** I’m no longer offering Virtual Assistant Services and focus on Business Strategy and ClickUp Consulting.
In October of 2021 – AmbitiousVA rebranded to Anne Leah & Co., to serve a bigger purpose.
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