Discovery Call Questions to Ask a Virtual Assistant

Discovery Call Questions for Virtual Assistants

Lessons from a Unicorn Digital Marketing Assistant who actually does the work:

You’ve decided you need help in your online business. You’ve collected applications and now you’re ready to set up interviews with potential virtual assistants.

Kudos, my business owner friend! This is a big step!

I know you can imagine the future when you’ve offloaded a mountain of marketing and admin tasks that are bogging you down. You need the help, like yesterday! So let’s find that perfect person to alleviate your burden.

If this is your first hire or you’ve made a wrong hiring decision in the past, you’re probably feeling nervous and wondering what questions to ask during the discovery call so you know you’re making the right choice for your team. 

Through the years of working with clients, coaching my students and biz peers, and hiring for my own team, I’ve found certain questions weed out those who are not a good fit and don’t have what it takes for the long-term team.

These discovery call questions assume you’re hiring a unicorn virtual marketing assistant, one who can perform a variety of marketing and admin tasks as a long-term teammate.

These are NOT the questions you would ask a specialized service provider, like a copywriter or ads manager who would work per project.

First off: always do a live interview. You’ll gain better insight and get a better vibe of each other chatting live.

Second off: write your questions down ahead of time so you are prepared and not forgetting anything. I recommend you start with this list of discovery call questions that I’ve already put in a printable PDF.

But these are the top four questions I would ask and the strategy behind them.

Let’s dive in.

Discovery Call Questions to Ask a VA

Hi, I’m Emily, a Digital Marketing Strategist & Consultant

I’ve been working as a freelance marketing assistant since 2009 and helped some pretty bit names behind the scenes, including Jennifer Allwood, Tracey Bellion, Wendy Batten, Miss Mustard Seed, Sage Polaris, Rachel Mazza, Meg Yelaney, and over 102 clients. My point is not to brag, but show I’ve been inside a mega ton of online businesses. Since I’ve always been in the trenches and booked out, I started sharing job leads and training with my friends and have built up a training side to my services with the Unicorn Digital Marketing Assistant School and the Digital Marketer’s Workgroup.

Now I’m in a privileged place to know what business owners are hiring for, looking for, and struggling with when it comes to VAs and teams. Basically, everyone is talking to me and spilling the tea about what’s working and not working. If I were on a season of Survivor, I would be the likable, social-gamed-up contestant who everyone is telling their immunity idol secrets to. (And maybe I’d have a shot of winning… if I could deal with low blood sugar, hangriness and not sleeping having my feather pillow?)

I’m here to pass on my discovery call questions and hiring suggestions so you can:

  1. Find the right teammate for your business
  2. Keep the dream team working with you
  3. Be that dream client for my digital marketing assistants
  4. Have a successful business that doesn’t stress you out and makes money


Let’s move on to this discovery call and how to find your dream hire, and we weed out the ones who don’t have what it takes.

Discovery Call Questions to Ask a VA

Here are four discovery call questions to ask a VA

(In addition to insight on their rates, work experience, and specific KSAs)

1) If you could take one work-related course to make yourself better what would it be?

Any good VA will already know what course that would be.

They’ll have their eye on their next skill-enriching course or advanced training because they are lifelong learners and truly embrace the growth mindset.

This shows whether they are passionate about their business and want to keep improving their skills.

It doesn’t mean you have to buy that course, unless it’s something to enhance your business, but this motivation is a positive sign they’ll learn what they need to do your tasks. 

VAs invested in their growth are in the long game.

Their answer will showcase if they have soft skills like being adaptable and eager to take on new challenges. It will demonstrate if they are serious about becoming a subject matter expert and if they will do what it takes to stay up-to-date and relevant in the skills they offer you.

Discovery Call Questions to Ask a VA

2) What kind of client do you work with best?

You need to be candid and honest with yourself here. You know what personalities you get along with and those you avoid. What has NOT worked for you in the past?

Established VAs know what types of clients they work well with. Get them to articulate this and ask yourself is this me?

Even if your candidate is a brand new virtual assistant, they know what types of people they resonate well with from past jobs. 

What comes to mind: micromanagers vs delegators, communication styles, neediness vs autonomy, focused vs scatterbrained, etc.

An example of what I coach my marketing students on is: I don’t work with clients who don’t take their business seriously. Those who do not respect my time or won’t put effort into creating the deliverables I need to do the job. It’s tough to be invested in their business if the client is not. 

On the flip side, opposites can sometimes be a good thing. If they are more organized and can help with your inbox or file management, it could be a good hire. 

The right personalities will make or break a team. 

This is a good point to ask about personality and work personality tests, like Kolbe or CliftonStrengths, to see if it’s a match or a balance and go into the working relationship with eyes wide open.

3) What accomplishment are you most proud of?

Here you’re looking for defining character traits based on their response.

Did they create something from nothing to achieve their goal?

Are they dependable, fast, problem-solving?

Are they creative?

Do they have the drive to finish despite challenges or at least give it their best effort?

Pull their story out and really listen. 

Even if the story is from their college years or from a past unrelated job, they’ll still have those traits today.

You can learn a lot about a virtual assistant’s character from their story.

It will give you insight into how they work, like to be rewarded, and what additional skills they’ll bring to the table.

4) What do you NOT want to do in my business?

Knowing what your virtual assistant doesn’t like to do is as important as knowing what they will do. 

Talk about what you need to be done and whether that’s in their wheelhouse or something they’d be willing to learn and do.

If you give them all writing tasks, and they hate writing … you’re setting both of you up for failure. 

New VAs may not know their likes and dislikes so they should be willing to do a variety. Give them various tasks and see where they shine. 

Established VAs know what they’ve enjoyed doing in the past. Many times, even if it’s a task they don’t like, they’re willing to do it for a while knowing you’ll hire more help and take it off their plate in the future. 

Aligning tasks your VA likes to do helps ensure they stick around. 

If my advice here about setting boundaries hit a nerve with you, here’s my advice about how to do just that.

As the client, you’re just as responsible for setting and enabling boundaries, and factors into teammate retention and workplace culture.

This episode of Unicorns Unite explains more: 

Listen on Apple Podcast or Spotify

Wanna attract and retain the best talent?
Are you a dream client and rewarding to work with?

Here are 5 Traits I coach my Digital Marketing Assistants to look for in their long-term clients:

This video will give you insight into what kind of clients virtual assistants and freelance marketers will stay loyal to. If you’re having problems with VAs quitting, definitely watch this! While you’re there, hit subscribe to my channel at @emilyreaganpr.

The Takeaway: be frank and honest, ask good discovery call questions, and listen.

As a business owner, these questions should help you decide if the candidate is a good hire for you. You also need to decide what tasks you want done. 

Every freelancer brings unique skills to the table, and the process of hiring shouldn’t be a dreaded process. 

Just be honest and frank about what you need done. Ask good questions and listen to the responses. 

Think long-term unless you’re hiring a specialist for a one-off project. You’re building a team and want people to stick around.

Feel free to add these discovery call questions to your interviewing repertoire. 

(Side note: Don’t shy away from hiring new VAs who lack experience. They won’t charge $75/hr and will still bring good ideas and skills to the table. They will gain experience and are a good choice as long as they have some tech skills and know the basics of online marketing).

Curious about starting your own service-based business from home?

This list is for you!

Grab my list of digital marketing-related tasks and services that online business owners are outsourcing and always need help with.

This is a goldmine of services you could be offering to your clients in your digital marketing VA business.

Where to Find a Virtual Assistant

You can submit your job via my hiring form at and I’ll share it with my Workgroup for free. You can also share your job opening in my free Facebook group here.

Download: More Discovery Call Questions to Ask a VA

I’ve put together a comprehensive checklist with 23 touchpoints and questions you can use for your next discovery call with a potential Unicorn Virtual Assistant or service provider. This will help you get clear about what kind of VA you need and who will be the best fit for your business tasks. I’ve designed this to help you create the best working relationship with your next team member. 

You got this! Stepping up as a business owner and learning to delegate as the CEO is a refinement process. Start now!

-Emily, Digital Marketing Consultant and Implementer

Emily Reagan is a mom of four, milspouse, freelance digital marketer and Virtual Assistant coach who has helped 400 go-getters, including military spouses, stay-at-home moms, and professional women learn in-demand skills and find flexible remote work as digital marketing assistants and specialists. She’s shared 2,000+ job leads with her freelance marketers & VA community.

Ask her any questions over on Insta @emilyreaganpr

“I help smart women learn the in-demand digital marketing strategies and profitable tech skills to get hired as a unicorn digital marketing assistant.“

3 ways we can work together:

Unicorn Digital Marketing Assistant School with Emily Reagan

1. Do you need to acquire digital marketing implementation skills and build your workflows so you can solidly put yourself out there for work? Check out the Unicorn Digital Marketing Assistant School. (It only opens once a year so jump on the waitlist now!… I also share job leads with my students so it’s a gateway for anyone who wants to build a freelance business that gives them flexibility and meaningful work). You can also choose to go through the self-study program now. Enroll here.

2. Already doing the work and have clients? But need more clients and a better referral network? Apply for our Digital Marketer’s Workgroup. This is a tight-knit community of freelancers like you, supporting each other. Plus I’ve shared 2000+ job opportunities with this community.

3. Need to hire a Unicorn Digital Marketing Assistant? Submit your job opportunity here. I’ll share with my workgroups totally free.

Further Reading:

All About Virtual Assistant Contracts

Hiring Your First VA: 3 Mistakes Small Business Owners Make

What Tasks Should You Give Your Unicorn Digital Marketing Assistant?

Why a Facebook Community Manager is Your Perfect First Hire

Yes, you really can work online.

Feeling overwhelmed and not sure how you can work from home and build your own online digital marketing business? Take a deep breath – you can do this. Start here with my list of 10 popular tasks that online businesses need help with the most!

These are the tasks that new clients are constantly asking for help with, and skills that they really need to find in a virtual assistant. Get access to this free download right now. Then make sure your own VA toolkit is up-to-date and relevant, and decide where you might need to invest in new growth and development for your biz.

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Meet Emily

Emily Reagan is a jill-of-all trades when it comes to digital marketing and techie skills. She’s worked as a behind-the-scenes digital marketing implementor and strategist for a decade for online biz owner clients.

She’s a mom of four, Air Force wife, and founder of the Unicorn Digital Marketing Assistant School, where she teaches smart women the in-demand, highly-coveted digital marketing skills to get flexible, online work.

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