6 Interview Questions to Ask When Hiring a VA

Takeaways from the Youpreneur Summit (1)

Most people, as it turns out, have never had to hire or fire anyone. They’re not in that department.

But if you’re looking to hire some virtual support, whether you’re an entrepreneur, manager, CEO, or otherwise, you’re now in the position of making a big important hiring decision.

The best thing you can do is be prepared by arming yourself with the right questions and the right evaluation points to weed out anyone who isn’t a fit.

Be sure to review the candidate’s materials closely before you choose to take the next step and interview them, of course. The resume, cover letter, and any past testimonials should be able to tell you whether they have the skills to do what you need. The interview should be used to get a better sense of who the person is and whether you think they’ll be a good match for you long-term.

It’s a bit of a personality test mixed with a communications gauge and, of course, a gathering of the vibes. I’m all about the good vibes!

When you schedule the interview, pay attention to how the candidate answers your questions and how long it takes them to respond. I believe the interview starts the second they fill out your application and all of the communication from that point on is part of your evaluation process.

Try to conduct the interview using a video conferencing service like Zoom, Google Hangouts, or Skype. Notice if there is any pushback to this, whether it’s related to an unwillingness to try video or to a technological issue. Also, try to arrive to the interview right on time and see if the candidate is already there waiting for you.

Punctuality is paramount.

Once you get settled in with your notebook and pen (or Google Doc/Evernote notebook/Word doc), you can ease into the interview with some niceties, an explanation of whatever’s behind you, or a close-up of your hamster.

You set the tone of the interview and you have the opportunity to give your candidate a real first impression of who you are. Make sure it’s a positive one. They get to choose you just as much as you get to choose them.

Common interview questions include:

  • What do you see as your biggest strength?
  • What is something you’re working on? (A ploy to figure out someone’s “weaknesses” without saying it.)
  • Where do you see yourself in five years?
  • Why do you want this job?
  • What is your biggest professional achievement?

And so on.

There are also some questions that work specifically for virtual support and for finding candidates that help me find candidates that posses our six core values. In addition to sharing the questions and why they’re important, I’ll also share some positive qualities to pay attention to as well as some red flags.

Remember that none of these questions are make-or-breaks on their own. A candidate might show some signs of the red flags but still be a great fit. Instead, the answers to these questions are meant to provide some food for thought as you’re making your decision.

1. What’s your story?

I love starting an interview with an open-ended question, particularly this one. I’ll usually preface it by letting the candidate know I did, in fact, read their resume and cover letter. I’m not being a lazy jerk, but I love to hear about what they’re doing in their own words.

These kinds of questions allow your candidate to ease into the interview (after all, what they’ve been doing with their life thus far shouldn’t be a hard question to answer) and it gives you a peek into the way they speak and articulate themselves.

This question is actually SO open-ended that they can take it in a variety of different ways. Take note of which direction they choose to go. Do they tell you about the day they were born? What their family and growing up was like? Do they stick to the last few years of their professional life? Do they get choked up and confused?

Since strong communication skills are so important and should be evaluated throughout the entire interview, starting out with a longer, explanatory answer is useful. Plus, open-ended questions require a certain level of creativity and confidence.

It’s a simple question but can reveal a complicated set of traits and values about a potential hire.

Follow-Up Questions:

  • What was that like? I have interviewed some extremely interesting people with insane former job titles and experiences. It’s great to expand on certain areas of past experiences if you’re interested, whether it applies to the position or not. It’s another way to get the candidate to feel comfortable and engaged in the interview.
  • How did you find me? Sometimes people put a referral source on their application or cover letter and sometimes they don’t. It’s great to hear where someone came from so you can thank the connection or find out more.
  • What made you decide to apply for this position? Sometimes it will be obvious from the answer to the previous question, but if it’s not, this is a good thing to know.

Things to Pay Attention To:

  • Any mention of skills or experiences that directly relate to the job you’re hiring.
  • A conscious effort to tie in how they found you or what brought them to this point in their career.
  • Keeping it positive, even if they hated their last position. You don’t want someone who is a gossip or who goes around bad-mouthing employers. That could be you one day!

Red Flags:

  • Little or no experience working in an assistant capacity. Sometimes I get candidates who are overqualified for the position. They’ve had a ton of experience, but have been in more of a managerial level. Now, they might be starting a family or wanting a career change. But it’s a red flag because they may be too used to the power that comes with being the manager as opposed to the different power dynamic of being an assistant. Of course, this isn’t always the case. I have a great VA on my team who had been working on her own strategy business for years before she found Don’t Panic Management. She had done all of the implementation work before in other roles, decided to focus on the strategic side when she launched her company, but realized she preferred being in the weeds, doing the work. Her priorities had shifted, she was able to explain what she wanted at that point, so in this particular situation her experience was not a red flag at all.
  • Short, vague answers that don’t reveal anything particularly useful about the candidate’s experiences or their personality. This tells me that their communication skills may not be very strong or that they weren’t prepared for the interview. Look, everyone knows that when you’re an interview candidate you’re going to be put on the spot and it’s your time to shine in the spotlight. If you don’t have anything to say about yourself, well . . . I call bullshit! There are ways for candidates to figure out what they’re best at, what colleagues have said about their experiences of working with them in the past, and what makes them light up at the end of a hard day. There’s no excuse for not having prepared something interesting to talk about during an interview. While it’s not necessary for them to be great storytellers, being able to speak about themselves and their experiences is particularly important if you’re interviewing for a marketing-related position. Many marketing tasks require a level of creativity and storytelling, so it’s vital to look for this in the interview.
  • Of course, if the candidate doesn’t have the experience in the type of work you’re looking for, you should see that on their resume. Don’t schedule an interview with someone who has never done the type of work you need unless they’ve been specifically referred to you as someone who’s a fast learner!

2. Have you ever worked remotely before?

This question is so obvious I almost didn’t even write it down. But you’d be surprised by how many folks think they can work from the comfort of their own home and are quickly awakened by the rude and difficult truth that it’s not so easy.

If you’ve never worked remotely, you don’t realize how much discipline it takes. No one is watching over your shoulder making sure you’re getting your tasks done and no one is keeping you from turning on the TV or cleaning the dishes. No one is making you stick to a certain schedule or take a lunch break.

Oftentimes, unless you work in a shared co-working space or coffee shop, no one is there for you to talk to.

The lack of structure is a huge barrier for many people to overcome and they soon find that they’re not actually disciplined enough to make it work. They need the office environment with its accountability to be productive.

I’ve heard too many stories of work-at-home depression that comes from not recognizing how isolating it is before taking the plunge.

Follow-Up Questions:

  • What does a typical schedule or routine look like for you during your work day? You don’t want to make people feel defensive here or like one way is better than the other, so it’s a good idea to keep this question as open-ended as possible. Remember, unless you are hiring for an employee relationship, you can’t require your virtual support to work certain hours. Labor laws make clear distinctions between and employees and contractors. This question is meant to gauge their work style and give you a sense of whether or not it works with yours. For example, you might be an early riser who loves to watch three episodes of Gilmore Girls before you start your workday in New York. Someone in California who binge-watches Scandal in the afternoon and tends to work nights might be a great fit for you because they’d have their work completed and in your inbox at the end of their night on the west coast by the time you’re up and working on the east coast.
  • What kinds of technology do you use to communicate remotely? Ideally, you’re already on a video call with your candidate, but it’s important for you to know if they’ve had experience with other virtual communication tools such as Slack, Skype, Zoom, and Google Chats.
  • If they have worked remotely before: What are your biggest challenges working remotely? This can be hilarious. I’ve heard crazy stories about dogs, babies, and significant others, as well as yard work and demolition projects next door. But what you’re looking for here is a window into the personality of your candidate. Is it hard for them to get out of bed? To remember to eat? (I have both of these problems.) Or perhaps they’re challenged by separating work life from home life and they tend to work 12-hour days because the computer is right there. (I have this problem, too.) Digging deeper here gives you a sense of their vulnerabilities so you can be sensitive to them if and when you decide to work together. It also shows you how open and honest they’re willing to be in an initial conversation. You want to hear a tactful response, not an embarrassing one.
  • If they haven’t worked remotely before: What challenges do you foresee when it comes to working remotely? And they better have an answer here. If they’re like, “Weeeee I get to go to Starbucks four times a day and eat all the cheetos on my couch!” Then you know you’ve got a slacker on your hands. If they recognize, for example, that they’re an extrovert and will need to find some sort of co-working situation to make them successful, that shows you that they are self-aware and understanding that remote work can be tough depending on what kind of person you are.

Things to Pay Attention To:

  • Having remote experience is definitely a big plus, but it’s not necessary. You’ll have to decide how important this is to you, but keep in mind that you may want to provide some supporting resources for them if they have not worked in a virtual environment before.
  • Honesty about any challenges or potential setbacks.
  • Experience using technology to communicate virtually.

Red Flag:

  • No prior remote work experience is a red flag, but it’s not necessarily a deal-breaker. It’s more about the personality of the assistant and whether you’re willing to work with them on making sure they have the resources they need to be successful in a virtual environment.

3. Tell me about a time when you crushed it so hard at work that you wanted to go screaming from the rooftops about how much you rock.

People experience a sense of accomplishment in different ways. For some, it could mean simply finishing a project on time and getting a thumbs up from a boss. For others, it could be helping to solve a conflict between coworkers. Still others might like to see their name emblazoned on a trophy for getting the most steps on their FitBit that month.

My absolute favorite answer ever to this question was one that we received from a potential assistant last year. It cracked us up then and continues to make us giggle every time we think about it.

It was this particular assistant’s first job out of college and she had been hired for a pretty standard assistant-type role. On one of her first days, the team asked her to make some coffee for a big staff meeting. Shockingly, she had never done this before and was panicked about what she would do.

Hiding in the break room, she frantically called her mom and asked her to walk her through the steps of making a pot of coffee. (Oh, if I had a dime for all the times I’ve called my mom to ask her how to do some adult-worthy task, we’d all be rich!)

She made the coffee and brought it into the meeting. She felt pretty good about her big accomplishment. But she noticed that while the team had all poured themselves a cup, no one touched their mugs after the first sip. And as she was cleaning up after the meeting, she found herself throwing away mug after mug full of coffee left by the team.

It was nice that they didn’t throw her shade for making a truly terrible pot of coffee.

That night, she went home, mortified, and made about a dozen pots of coffee, forcing a taste of each one to her roommate who gave her notes about what was wrong and what was right. She continued this process until she successfully made a normal-ass pot of coffee that she’d be able to recreate on the job the next meeting.

I love this story for a few reasons. One, it’s hilarious. I can just imagine her excitement when she gets the coffee going followed by her sad, sad disappointment when no one can stomach it. Two, it shows an eagerness to work hard to do a good job, no matter what the task is. And three, it shows resilience. Was she dissuaded by her poor coffee-making skills? Did she go cry in a corner, cursing her entire college education for not teaching her how to make one delicious godforsaken pot of coffee? No! She went home, turned on a coffee maker, and practiced until she got it right.

Hearing and understanding what makes an assistant proud can help inform how you reward them for a job well done. People need to feel appreciated in order to have job satisfaction, and as the manager, that part is on you.

On the other hand, if all they care about is public recognition and vacation time, you’ll know that you may not have the most humble assistant on your hand and they may not be the best fit.

Follow-Up Question:

  • What’s your favorite part of your (current or former) job? If you can get a straight answer here you’ll start to get to the core of what your candidate is all about. You’ll also be able to start to envision how they’ll be able to work for you. Do they love compiling spreadsheets? Awesome. Do they love color-coding the meeting schedule? Super awesome. Do they love picking out where they’re going to eat lunch each day? Maybe not as awesome, although finding and booking restaurants could be part of the job!

Red Flag:

  • If your candidate shares a time when they were awarded publicly for something they did and that’s the part that made them feel the most satisfied, you may be dealing with someone who is too praise-focused for a behind-the-scenes role. The reality of the virtual assistant experience is that it’s pretty un-glamorous. The type of people who thrive are the ones who don’t need a whole lot of direction or a whole lot of praise for their work. They are satisfied by simply delivering a good product on time, not being coddled with “this is awesome and here’s a prize”-type feedback. Now, this doesn’t mean you should stop giving just as much positive feedback, if not more, than negative, but you shouldn’t work with someone who can only feel good about their work when someone else recognizes it.

4. Tell me about a time when you made a mistake. What happened and how did you handle it?

I love this question because it’s another one that can go in a number of ways.

First, see how long it takes them to come up with an example. In my experience, the ones who are quick to pull something out of a hat are the ones who possess more attention to detail and are more eager to please. They internalize even the simplest of mistakes and work to remedy them as soon as possible.

Regardless of how long it takes for them to find an example, listen to the part about how they handled the mistake very closely. More often than not, especially in virtual assistant land, the mistake is not a big deal. It’s about how they handled it. Because let’s be honest: they ARE going to make mistakes. Everyone does. But you’ll need to figure out how they’ll make it right, especially if you’re not there to notice or reprimand them (because you’re so busy and all).

In the best scenarios, an assistant will not only tell you about the mistake, but they will have already fixed it and come up with a solution to make sure it doesn’t happen again.

In the worst scenarios, an assistant either doesn’t recognize the mistake or worse, hides the mistake, letting you find out about it later from a colleague, fan, or follower.

Ugh, I shudder to think about that, especially as someone who has experienced it firsthand.

This question helps you gauge whether you’re dealing with someone who could put you or your business in a compromising situation.

Follow-Up Question:

  • What did you learn from this experience? You want to get to the heart of whether this person is proactive about finding solutions even in the face of disaster. Can they keep calm, cool, and collected when something goes wrong? Do they do a healthy amount of reflection if and when something does go wrong (because it will) and then determine a system to make sure it doesn’t happen again?

Red Flag:

  • A lack of acknowledgment of the mistake. This really aggravates me and ties into the entitlement issue that a need for praise often indicates. The best virtual assistants take ownership for a mistake even if they know it’s not their fault. That’s because it’s their job to keep projects moving forward and make things right for their client, no matter what. If you don’t get the sense that this candidate would be willing to fall on their sword for you, you may not be working with someone who will be a good long-term fit. (But, for the record, just because they will fall on their sword doesn’t mean you should ever let them. Everyone needs to own up to a mistake when they make one—even you!)

5. Let’s say we started working together today. One year from now, what do you think I’d have to say in a testimonial about you?

This question tests your candidate’s appetite for forward-thinking reflection. It also sets the expectation that you do intend to measure the success of the relationship over time and that it’s something they’ll need to work on with you.

You want to see the wheels turning here. Taking a pause to think about this one is totally fine. This is the question that reveals what they really think about themselves and their work.

Follow-Up Questions:

  • What have other people said is their favorite part about working with you?
  • Are there things that you’ve done to make sure you’re performing well at your job? This follow-up is more relevant for people who have worked as a virtual assistant before. Since virtual assistants are responsible for growing and maintaining their own client base, it’s important for them to be checking in and making sure their clients are happy. You’ll want to be giving feedback and having review meetings as the manager, of course, but it’s great when you can see an assistant taking the initiative to ensure that they are providing a great service.

Red Flags:

  • If they give vague and vapid answers like, “I’m really nice,” or they can’t be specific about the kinds of things that you’ll love about working with them, they may not be confident in their abilities, they may not be a very good communicator, or it might be a combination of the both.
  • On the contrary, if they’re saying things like, “I’M GONNA CHANGE YOUR LIFE, YO!” then they may be overly confident and you really don’t want that either. The balance is in the humility. Confidence without cockiness. It’s a delicate line to walk, but you’ll be able to see the signs throughout the interview and decide accordingly.

6. What do you do to keep learning?

Perhaps my favorite question of all time, this one teaches you about whether or not your candidate is that master of curiosity. That Google-queen who we all covet.

Most commonly, I’ll get answers like, “I read a lot,” or, “I listen to a lot of podcasts.” This is great if you can dig deeper into what types of content they consume. Romance novels and the Welcome to Night Vale podcast are all well and good for their entertainment value, but a perfect answer involves something about seeking answers and gaining knowledge simply for the sake of it. It shows you they have an active mind and that personal growth is important to them.

Follow-Up Question:

  • What are your favorite TV shows/movies/books/podcasts? If you have time, seeing if you have any common ground in the types of media you like to consume can be a great way to build rapport with your candidate. Ultimately, commonalities can also help us trust each other, kickstarting that deeper connection which leads to a long-lasting relationship.

Red Flag:

  • If the person you’re interviewing doesn’t have any hobbies or doesn’t seem excited to talk to you about their interests and knowledge, they may be fine to do menial and very objective tasks, but they may not be what you need to help you grow your business. That is completely up to you. The type of work you need done COULD indeed be perfect for a simple, quiet person. But in my experience, you want someone with life in their eyes, someone who craves knowledge, who loves solving problems, and desires growth.

No one question should be the crown jewel of your interview. Make sure you take notes throughout your interview, record it if you can, and take a holistic look at your candidates’ answers before you make a decision.

Remember, you don’t have to choose just one candidate at this point. If possible, depending on your timeline, you’ll be able to pick your top two or three candidates and have them do a test project for you. Then you’ll be able to make an educated choice about which one is best for you.

I’ll be discussing some strategies for assigning and evaluating test projects, so keep an eye out for that blog post coming soon!

Editor’s Note: This post is an excerpt from the book Panic Proof: How the Right Virtual Assistant Can Save Your Sanity and Grow Your Business. Grab your copy on Amazon today! 

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Jess Tyson, CEO & Director of Calm

Jess is the founder and proud Director of Calm at Don’t Panic Management. (And yes, she invented that title because that’s what you do when you’re the boss!) She wrote the book on how building a successful relationship with a virtual assistant can make all the difference in helping business owners get to the next level. Her life is often a whirlwind of wrangling her toddler, speaking at conferences (virtual and beyond!), researching productivity hacks, and meticulously making matches between overworked entrepreneurs and focused virtual assistants. Jess's first book, Panic Proof: How the Right Virtual Assistant Can Save Your Sanity and Grow Your Business is available now: panicproofbook.com

  • Current location: Redding, CT
  • Go-to Karaoke song: “Hand in My Pocket” by Alanis Morissette
  • Favorite kind of cheese: Aged Goat Gouda
  • Beverage of choice: Champagne
  • Pronouns: She/Her/Hers
  • Superpower: Delivering miracles, especially when all hope is lost.

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