How to Hire a Personal Assistant for Your Art Business

Several years ago my business was really beginning to pick up and I was becoming overwhelmed with all of the minutia involved in running a business. I could never seem to get caught up on my email. I was travelling a lot and coordinating all of the travel arrangements was eating up precious hours out of my day. Bookkeeping and sales tax reporting were nearly impossible to keep up with. I was often working 9-10 hour days, six days a week (not to mention work I was doing at home).

Though I had recently hired a new gallery director to help manage the sales side of the business, it was increasingly clear I also needed to hire someone to work directly with me to help me manage my day-to-day affairs. Ironically, however, this was in the depths of the recession and I felt nervous about hiring an assistant. I wasn’t sure if business was going to continue to grow, and with a still-erratic cash flow I was worried about paying a new employee, even though I was only imagining the position as part time. I was also, honestly, worried about the extra tax filings I would obligate myself to with a new employee – would it be worth it for a part-time position?

I also suffered from (alright, let’s be honest, I still suffer from) a common small-business malady – the desire to do everything myself.

So, I resisted and procrastinated.

What finally caused me to break down and hire someone?  I had a conversation with my accountant one afternoon and he asked me why I didn’t hire a payroll service to take care of all of my payroll processing and tax filing. I replied that I probably couldn’t afford it, and that it probably wouldn’t make sense with such a small staff. He told me I would be surprised by how affordable it actually is and told me that I really couldn’t afford not to do it. He recommended a service – Compupay – and I gave them a call. I discovered that for a fee of about $40 + $3 per employee, they would take care of all of my payroll processing and tax filings. I could have kicked myself for all of the years I had been processing the payroll through Quickbooks and the hundreds of hours I had spent agonizing over ridiculously complicated payroll tax and employment insurance filings.

I immediately signed up for their services for my current employees and placed a help-wanted ad on for a personal assistant. I figured out what the position was worth to me at the time, which, honestly, wasn’t a lot of money, and listed a starting wage. I figured I had nothing to lose – the worst that could happen would be a complete lack of interest.

Within minutes of placing the ad, however, the resumes started pouring in. As I recall, within the first day I had nearly a hundred applications for the position. My problem wasn’t finding someone qualified to take the position, my problem was wading through the deluge of great candidates and having to decide on only one.

I finally pulled out three or four resumes that I considered interesting, called the candidates and scheduled interviews. I feel I could have hired any one of the interviewees and done very well, but one in particular, a young woman named Ashley, seemed especially organized, well-spoken and deliberate. After I completed the interviews I called Ashley back and hired her for the position.

Ashley hit the ground running and immediately took over some of the most laborious parts of my work. If I had at first been worried that I would have a hard time training her, I quickly discovered that she picked things up before I could even finish explaining. Not only did she get the hang of the job, she figured out better ways to organize things and found ways to expand her work, taking over even more than I had planned. Though I had initially imagined the position would be part-time, it almost immediately turned into a full-time position.

Having an assistant didn’t mean that I was suddenly working less, it just meant I was able to begin concentrating more on the big picture and big projects instead of getting caught up in the minutia.  I immediate felt the investment in an assistant was paid back in spades.

Ashley was with me for three years, during which time she completed a degree in accounting and recently moved on to a position in that field. Her leaving caused a momentary panic as I now had to worry about finding and training a replacement for someone who basically kept my entire professional life together. I was worried that I wouldn’t be able to find someone as organized or conscientious. I was afraid it would take a long time to train someone new to do all of the varied tasks Ashley handled with such aplomb.

These fears turned out to be unfounded, just as my initial fears of hiring an assistant had been. I recently hired Mj, and she seemed to almost seamlessly pick up right where Ashley left off.

When Should You Hire an Assistant?

So how does this apply to you? If you are a gallery owner or an artist, you should consider hiring an assistant if you find yourself getting bogged down in the details of your business. If there’s something you are doing that has become completely routine, consider hiring someone to take it over so you can concentrate on creating the most value with your skills and talents.

I waited too long. Looking back I realize I should have hired someone as soon as my time started being of more value to me than my money. This is a hard one to gauge. Remember, three years ago my business was still relatively young (just 7 years old) and the economy had just fallen off a cliff. The tendency to be conservative with finances was pretty strong.

If you are an artist and your work has begun to sell well, or you have increased the number of galleries you are working with and shows you are participating in, you will very quickly find value in having someone around to help you get your ducks in a row. You don’t have to hire someone full time at first – just 4-5 hours a week might be enough to take care of the busy work, especially if your assistant can devote their full attention to that work.

If you are a gallery owner or director your time spent working on marketing, advertising and customer relationships is your most valuable asset. You can’t afford to spend your time filing bills and calling copy machine repairmen or sorting through the spam in your inbox.

How do you Find Someone?

I once read that many small business owners hire people they know to work in their business. I have certainly done that in the past, and several of my current and former employees have been family members. While that’s worked for me for those positions, I actually wanted to hire someone completely independent for the personal assistant position. I worried that a friend (or even a friend of a friend) would pose additional challenges if they didn’t work out. I wanted to feel like I could make a simple business decision about their efficiency and reliability, and not feel obligated to work with someone just because of a relationship.

CraigslistI am an fan of Craigslist has become the de facto source of classifieds. If you’ve ever bought or sold anything on the service, you know that they have a bare-bones interface that lends itself very well to the classified ad. Almost everything – create a listing or buying a used item, is free on Craigslist. A help-wanted add is one of only a few exceptions. There is (at the time of this writing) a $25 listing fee for job postings. I imagine this helps eliminate  spam and fraudulent job listings and provides one of the only sources of real income for the company.

Here’s the ad I placed in announcing the position when I was hiring a replacement for Ashley:

Scottsdale art gallery seeks full-time assistant for owner
Scottsdale art gallery seeks full-time assistant (35 hrs. per week) for owner. The ideal candidate will have strong writing/editing skills, excellent organizational abilities and be very comfortable with the computer (photoshop, some excel, data entry, blogging, social media). Position also includes, answering phones, managing communications with artists, order management, scheduling, travel booking/management, and occasional retail and customer service.

Schedule: 10:00 a.m. – 5:00 p.m., Tuesdays and Sundays off.

Try and be as specific as you can about the position so that you get the best possible candidates.

How Much Should You Pay?

You should pay your assistant what the freed up time is worth to you. The more you can pay, the better the candidates you will have apply. On the other hand, if you pay too much you’ll suddenly find that the money is worth more than the time and you’ll wish you were back to doing the work yourself.

I based my pay on an hourly rate – just a few dollars above minimum wage, but then I also include some performance based commissions on various special jobs and tasks (including art sales, since my assistant works in the gallery and helps cover the floor) that raises the total wage.

When advertising the position, I list only the base rate so the applicants wouldn’t have false expectations about the wage, but I then am able to pay more than the initially listed wage.

What Questions Should You Ask in the Interview?

Interviewing can be just as intimidating for the employer as  it is for the prospective employee. How do you find out if the candidate has the right skills? How do you figure out if they are honest? The stakes can feel pretty high. In just a few minutes of interviewing, you are trying to get to know someone who is about to become a virtual appendage in the coming months.

My approach has been to describe what I’m looking for, explain the position and then ask a prospective assistant to tell me why they feel they would be good at the job. I try to let the candidate do most of the talking.

Ask follow-up questions based on their assertions.

“I’m very organized,” says the applicant.

“Tell me how you used your organizational skills in a previous job.”

There are a lot of blog posts and online articles on how to interview – just do a Google search and you’ll find thousands of them. I’ve read a number of them, and some have been helpful. Most, however, seem to be geared more to HR directors who’s only job is to hire new people and who have to come up with creative new ways to torture applicants with silly questions.

“Ask your applicant why manhole covers are round” is a famous example. I guess it’s supposed to help you get into the mind of your applicant and figure out how resourceful and creative they are. I couldn’t ask a question like that with a straight face though, so I tend to stick to the basics.

How Do You Make a Final Selection?

In my last round of interviews, when seeking to replace Ashley, I interviewed five applicants. Of the five, four seemed extremely well qualified and interviewed well. In going back over my notes and the resumes, I felt I could pretty safely hire any one of the four. So how did I select Mj? I wish I could give you a formula I used, but truthfully, in the end it came down to a gut feeling. I liked Mj’s personality and confidence. Perhaps one day my instinct will lead me astray, but remember, you’re going to be working very closely with your assistant – it’s important to feel comfortable with them and I’ve found that instinct can be a better guide than logic in this arena.

The Paperwork

Once you’ve offered your assistant the job and they’ve accepted the position, you should discuss when they will start. Within the first day or two, it’s important to have them fill out all of the necessary (and mostly annoying) paperwork that will make them official. If you follow my suggestion above and have a payroll company take care of the payroll and tax filings, they will provide you with a new hire packet with all of the appropriate forms for your state. Those forms need to be completed within three days of the employee beginning work, so don’t procrastinate on this one.

Paying your Assistant and Filing Taxes

With a payroll service working for you, payday is easy. When I was dealing with payroll myself through Quickbooks, paydays seemed to come one right on top of the other. It seemed like I would just finish running all of the reports and filings and it would already be time to start the next. With a payroll service I only have to email my payroll manager the hours worked and bonus amounts and make sure there is money in the checking account to cover the payroll.

On payday, the paychecks are direct deposited into my employee’s accounts and I log in and print out a paycheck detail report.

Now that I use the payroll service I don’t even give tax filings a thought. The service handles everything and sends me occasional reports and forms for me to keep on file.

You’ll want to talk to your accountant about this, but mine had me set myself up as an employee through the payroll service as well so that my personal tax filings would be easier.

Why I Hired a Real Assistant Instead of a Virtual One

I read a lot about small business owners who have hired virtual assistants – that is, someone who handles all of their work from a remote location via the internet. I find this concept intriguing and can see how technology would make this feasible, and even in some cases, preferable. For my situation, however, it works out far better to have my assistant physically present at the gallery. Because we are a retail operation primarily, it helps to have one more person on site to help handle phone calls and work with customers when we are busy. There are also tasks where I find it nice to be able to sit down together to figure out how to tackle a particular project.

I can see how a virtual assistant would work for many artists and gallery owners, however. If most of the work you would be having them do – inventory, email, website updates, etc. would be done on the computer anyway, it could easily work. You could manage your communication via email, Skype and Google Hangouts (chatting and video calls). A virtual assistant could be set up to share your email and manage your inbox. Travel arrangements are just as easily done from your assistants office as from your studio or gallery.

Training & Expectations

Before my first assistant began working for me, I sat down and created an outline of everything I wanted her to do in the position. I thought about all of the ways she could help me free up my time and listed them in as much detail as possible. When I recently hired Mj, I used the same list of responsibilities, but added to it everything that Ashley had taken over doing. It was amazing how much the list had grown from my initial expectations of what an assistant would do to what she actually ended up doing as she grew in the position.

Training was easier than I imagined it would be. With almost every task, I would simply explain what I was trying to accomplish, show her how I had been doing it and then let her run with it. In many cases I would often be pleasantly surprised to find out that very little training was required, and even more surprised to discover that my assistant was better at the job than I was and found easier ways to get the work done.

Here is a partial sample list of tasks that I have Mj take care of for me. This is what I emailed to her when I extended the job offer:


I would like to offer you the position we discussed last week in the interview. As I mentioned, Ashley, who currently holds the position, leaves at the end of this week, so I would love to have you start as soon as possible to have a couple of days of overlap. Let me know what’s possible (I understand you have to give consideration to your current employer).
To review the position.


Planning my national workshop schedule – including travel arrangements and booking the venue for workshops.

Researching artists in the area where I will be travelling and marketing the workshop to them via our email list and local art groups and art publications.

Sending out a series of emails to artists in the workshop area.

Managing registrations for the workshops – sending out workshop materials and instructions.

Coordinating images for our bi-monthly art catalog.

Coordinating images for our monthly ad in American Art Collector magazine

Managing inventory, processing orders, coordinating shipping.

Helping me manage email.

Answering calls.

Managing my calendar.

Editing and proofreading blog posts and marketing copy


Punctuality to schedule: Monday, Wednesday-Saturday, 10:00 a.m. – 5:00 p.m. (you can take 1/2 hour paid lunch)

Attire appropriate to a retail setting (business casual – more relaxed during summer months, but always appropriate for dealing with retail customers)

Your Life Will be Better and You’ll be More Productive when you Have a Personal Assistant Managing the Little (and Big) Things for You

You might say, “Jason, I’m a starving artist, I can’t afford to hire an assistant” or “my gallery is too young – I’m still in the stage where I have to do everything myself.”

That may be true, but I’ve always encouraged artists and fellow gallery owners to envision their art business as it can one day be if they work hard. Even if you can’t hire an assistant today, start thinking about how you could utilize an assistant when you are one day able to hire one.

Perhaps you have a friend, spouse or someone else who wants to help you with your business and would be willing to volunteer to take over some of the tasks that fill your day. You can apply many of the same principles in bringing in a volunteer that you would to hiring someone.

Business CardA Final Note

OLYMPUS DIGITAL CAMERAEven though this entire article has been about hiring a “personal assistant” – I don’t call Mj (or Ashley when she filled the position) my personal assistant. I don’t mind the title, I just don’t feel it accurately describes the position. On Mj’s signature line in her email and on her business card it lists her position as “Creative Director & Workshop Coordinator.” Although she does a lot more than this as well – I think this better describes the gravity of what she’s doing. I don’t really consider her an assistant, or secretary – in fact, most of the time I feel like she is so on top of what’s going on that she doesn’t really work for me, I work for her.

I also think that these titles give her more weight when she’s communicating with someone in my behalf. Someone communicating with Mj should believe that whatever they need help with, she has the authority to take care of it.

For an artist, I would think that “Business Manager” sounds pretty good for this kind of position.

What Do You Think?

Have I convinced you to hire a personal assistant? Do you already have one? If so, what advice would you give someone who’s considering hiring one for their art business? Have feedback about this article or questions you’d like to put out to the Reddot community? Please leave a comment below! Note that due to spam screening, we have to hand approve each comment and it can sometimes take up to 24 hours (usually less) for us to post your comment.

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