How To Know When You Need To Hire A Virtual Assistant

Hannah Hassler

Guest Author

Ex-English teacher, current VA, and aspiring podcast creator. She lives in Arizona and is passionate about taking the tangled web of ideas clients bring to her and turning them into succinct recaps that include actionable steps and bulleted to-do lists.

Entrepreneurs are used to handling a constant barrage of tasks on a daily basis, and it’s often something they pride themselves on. Wearing many hats comes with the territory, and there is seriously something so satisfying about knowing that you’re intimately invested in all aspects of your business.

At some point, however, you may find yourself showing up to black-tie event wearing last week’s unwashed night cap, and that’s not a good look for anyone. (Metaphorically speaking, of course. I’m sure you look great in yours!) Although this can be taken as a clear indicator that you need more sleep, it can also be a not-so-subtle hint that you really should think about getting some help.

And when the universe throws you hints, it’s usually wise to follow them.

Take the hint: Signs you need to hire a virtual assistant.

  • You’re normally on top of everything, but lately you feel frazzled and have been making mistakes.
  • Your business is starting to feel more exhausting than life-giving, and you find yourself fantasizing about throwing in the towel.
  •  You’ve put multiple AMAZING ideas on the back burner because there just “isn’t time” for them.

I know, I know – it’s all well and good to say that these are all “hints” and that you obviously need to hire help…but think of the cost, the training time, the possibility that they’ll make mistakes, create drama, or generally bring you more problems than results. How can you know that it’s really going to work out?

Where are the guarantees?

Well…they don’t exist. That’s just the honest truth. It would take you five seconds flat to find someone who could tell you a blood-curdling story about a terrible person they worked with that turned out to be a bad idea in every way possible. Horror stories abound, my friend.

So I guess that’s it then. If one person had a bad experience with something, it’s clear no one in the whole world should ever even consider attempting it themselves.

Clearly, I jest.

For everyone who has had a bad experience or walked away with a sour taste in their mouths, there is someone out there whose life and business were changed for the better once they decided to bring on help. It might be a scary step, but it can be exactly what you need to do to take things to the next level.

you need to hire a virtual assistant

Still not sure?

And just in case hints don’t do it for you, here are some serious reasons to think about taking the plunge:

  • You’re spending more time OUT of the genius zone than in it
  • Your business hasn’t grown in a while because you don’t have time to invest in scaling up
  • You’re spending an inordinate amount of time on some tasks simply because you don’t really know how to effectively do them
  • You feel stuck in a rut and are losing your rhythm
  • Your relationships are suffering, but there is no way you could possibly spend less time in your business

Any of these sound familiar?

If you’re running a successful business, there is going to come a point where you literally just cannot take on any more, do any more, or invest more of yourself. Now, if you’re already feeling the pressure and you KNOW this is you (or you’re using foresight to see that you’re reaching a growth area and this could easily be you in a few months), I would encourage you to start looking for a virtual assistant, social media manager, copy writer, or [whatever floats your boat here] today.

Download our Ultimate Guide to Delegating Here for More Tips & Tools on How to Delegate as a Solopreneur

Finding Help

Some things you can DO when you need to hire a virtual assistant:

  • Have a decent idea of what tasks you’d like done (start with the time-consuming stuff that is pulling you out of the genius zone on the daily).
  • Understand that you get what you pay for in this industry, and know that a higher price usually comes with the benefit of a huge amount of specialized talent + skill.
  • Connect with your network (lots of people you respect could probably recommend a great support person) or seek out a specialized group online (use Facebook’s group search function, or hop onto LinkedIn).
  • Be extremely clear in any online posts about HOW you want to be contacted, because there will likely be a huge response. You don’t want to drown in PM’s if you would have rather just sifted through some Google forms data at the end of the week.
  • Engage in some form of verbal communication when you’ve selected a few candidates you see potential in. If you’re bringing someone into your business, you want to feel really good about how you connect as humans. (Zoom is awesome for face-to-face contact!)

you need to hire a virtual assistant

And since you’re kind of sticking your neck out there, I’ll even throw in a few things you might want to avoid:

  • Don't ask for free “trial periods” or free work to be done on your behalf. (Unless you regularly give away your own products/services; then I guess it’s your call!)
  • Avoid asking for detailed project proposals and then never follow up or engage again.
  • Don't feel obligated to hire the first person/cheapest person/sweetest person if they don’t seem like a great fit.

Did you take action?

I feel like you should it, so I’ll wait right here.

And…you did it!

You knew what you were looking for (or at least a general sense of it), you asked around or posted in an online group, you interviewed a few candidates, and it’s easy sailing from here on out.


Right? (An echo chamber, uselessly repeating your own words back to you. Exactly what you were afraid of when you set out to hire help!)

Now Make it Amazing!

You’re not quite out of the woods yet, because the next couple interactions will really set the tone for your working relationship. Here’s how to nail the whole “someone works for me remotely” gig you just made happen:

Usernames and Passwords

  • Have a document listing usernames/passwords for any accounts you’ll need them to have access to.
  • Encourage them to access these accounts while you are on the phone with them, because many accounts have security features that will flag a new sign-in and require a passcode (i.e. Instagram requires a 6 digit authentication code that is texted to your phone).

If you are a solopreneur, it can be challenging to finally decide if you need to hire a virtual assistant. These hints will give you some insight and help you with the next steps.

Be Flexible

  • Come to terms with the idea that it probably isn’t going to be exactly the way you did it / always do it / would have done it. The point here is that YOU aren’t doing it, and that is a good thing. (Obviously crappy work is one thing; however, someone not choosing to utilize an Oxford comma probably isn’t worth losing sleep over. Or maybe it is. Personally, that might be my line in the sand.)
  • Be open to new ways of doing things – especially the things that were never even part of your genius zone to start with. (Psst. Isn’t that part of why you hired someone? Because if that isn’t your thing, why are you death gripping it so tightly and insisting it must be done exactly the way you learned how to do it in that blog article from 2011?)

Be Clear

  • Provide necessary materials in a timely manner so that projects can actually get done. (Nothing like having someone send you ALL. THE. THINGS. two hours before a deadline that’s been looming for two weeks. Don’t be that guy/girl/human).
  • Be honest if something just isn’t working for you. If you’re feeling stressed or frustrated by someone’s work style, they probably feel the same way about yours. Some people just don’t jive well, and that’s okay. (Not to get ahead of you, but read the next tip!)
  • Start out with a set time frame allocated as a “trial period” that entails specific tasks, due dates, and check-ins. If either of you aren’t happy at the end of things, it’s a natural stopping point where you can gracefully end the relationship. (This is NOT free…it’s just a time frame for expected services so you can get to know each other.)

And there you have it. Everything you need to know whether NOW is the time to bring someone new into your business.

Good luck! (And don’t forget to tell them they’re awesome when they turn out to be awesome!)

Some Resources

In case you actually didn't quite get around to doing it yet, here are a few active Facebook groups you're allowed to post hiring needs in:

Virtual Assistant Tribe Job Board

Social Media, Marketing, & PR Jobs

(I am a member of these groups - I do not run them, I am not an administrator, and I do not benefit from you using these links. I'm also not responsible for what happens to you if YOU use them, including and not limited to: substantial increases in time, money, health, and happiness.)

Of course, you can also work with Virtual A Team and reduce the unknowns and risk.