The Art Biz ep. 59: My Best Practices for Working with an Assistant

Four and a half years ago I hired the best assistant I have ever had at Art Biz Success. She has been loyal, prompt, 200% dependable, and absolutely indispensable.

Art Biz Success Team at Biltmore
Mesa on the grounds of Biltmore in 2017.

She was 21 years old at the time—about to turn 22—and had just graduated early from college.

I hit the jackpot.

In this episode of the Art Biz Podcast, I tell you exactly how I hired the perfect person for my business at the time. I also going to give you the steps I put in place to make sure that we maintained a good relationship and that, above all, she enjoyed her position.

I’ll touch on the hiring process, setting up an assistant for success, working together, and keeping her happy.

I’ll also share my mistakes. I’m sure there are more that I’m unaware of, but I can tell you about those I know.

I’ll be getting a little vulnerable and a lot sentimental. I’m sharing the story because I don’t know of a single artist who wouldn’t like a little more help with their business. Perhaps you’ll benefit from my experience.

I’ll start at the beginning, when I first began looking for a new assistant in early 2016.

Music by Wildermiss

Writing the Job Description

[ Hiring tips ]

My primary criterion was that I needed to be able to trust someone to do the tasks without my having to micromanage. I needed (and still need) someone who pays close attention to detail.

Coors Western | Art Biz Success
After artist Stephanie Hartshorn gave us a private tour of Denver's prestigious Coors Western art show, Mesa and Stephanie have fun with the kiddy horses in one of the booths downstairs at the stock show.

I created a proper job description and ad. In it, I wrote these two sentences:

This is an administrative position. No art background is necessary, although we welcome creative thinkers and art appreciators.

I was trying to get across that I wasn’t looking for artists in this role. I asked applicants to submit the following via email:

  • Their resume in MS Word format
  • Their requested salary requirements
  • Two paragraphs about why they would be a good fit
  • Names and info for three references
  • A short video that told me a little about them: what they love and how it may help them in this role

I also gave them a precise subject line to use with their submission.

I was very specific because I planned on considering only people who submitted their application exactly as I wanted it. Again, I was looking for someone who paid attention to details.

Art Biz Success Team in Virginia
Taking a break at our workshop in Reston, Virginia in 2017.

Wading Through Applications

For the first time, I posted an ad to online hiring sites because I was being coached by a human resources expert who was a member of a mastermind group I belonged to back then.

These sites were a huge waste of time for me.

It's a trip to deal with some of the applicants on help wanted sites. Many seem to submit to anything and everything. Hey, I understand that you might be a little anxious about finding a job, but you'll never land a good position if you don't follow simple directions.

I somehow attracted an applicant who copied and pasted one of her previous applications and told me how much she had been wanting to learn about careers in the mortuary field. Hmmm. Mortuary business. Art Biz Success. No, not many similarities. No I am not the right person to teach you about the mortuary business. No, I won't consider you for a job that requires incredible detail. Good luck.

The request for a video with the application turned out to be one of the best things I did. It was important to me that even if they had never made and emailed a video in their lives, they would figure it out for a job they really wanted. That was the type of person I wanted on my team!

Art Biz Success Team
Mesa (r) quickly became indispensable. Here she is at Art Biz Breakthrough in 2016, right after she got a new job title. Left is Karin Olah, an incredible team member who came from Charleston each year to help us out.

Watching the videos is where it got pretty entertaining.

Some applicants gave me a show of their art on video. They sat in chairs and pulled out one canvas or drawing after another. Another wrote (I’m not kidding), “I don’t know how to make a video, but here are 25 photos.” To myself (picture gaping mouth): No, I'm not hiring you for your art. No, I didn’t ask you for a video because I wanted to see 25 different images. B-bye.

A few of the videos were perfectly acceptable.

Selecting The One

I narrowed down the applications first to those who submitted exactly as I requested, including one person whose video, blessedly, stood out among the rest. She wove together photos, video footage, and her voice—resulting in an engaging video that was actually fun to watch. I could tell that special care was put into its making.

Then I selected people to interview on a Zoom video call. Quickly I narrowed it down to 2 or 3 people to interview in person.

I ask finalists to take, at my expense, the Kolbe A Index test, which measures natural strengths. I'm looking for someone who has a high number in follow-through. That was Mesa.

I offered her the job of my new administrative assistant. That title would change within 6 or 7 months, but that’s how we started out in early 2016.

By the way, Mesa hadn’t seen my ads. She came by word of mouth. It turns out that she was working as a barista at the café next door. Right. Under. My. Cappuccino-loving. Nose.

Art Biz Success Team
With Mesa at the airport on our way to the Art Biz Success workshop in Asheville in 2018.

Setting Expectations

The biggest mistakes I have made with contractors and assistants is that we didn't communicate our mutual expectations to make sure we were on the same page.

That’s totally on me. It was my responsibility, as the employer, not only to communicate my expectations, but to also ask my assistants about their expectations—and to be open to their feedback.

Now, with new hires, I lay out milestones for proficiency, which provides a marker to look at when it comes time for a performance review.

By this date, I expect you to be able to do [this or that].

Nobody can do their job well until it is clearly defined.

Before Mesa’s first day, I sketched out a series of regular performance reviews. I was determined to follow this wise advice: Hire slow and fire fast. In other words, take your time getting it right, but figure out early on if you got it wrong.

With performance reviews in place, I had an out should she not be the right fit.

After a couple of those reviews, I joked that I was a broken record. Here's what I repeated:

You're doing fantastic. Don't ever leave me.

That about sums up what I had to say to her.

And I rewarded her with frequent perks and regular raises. My mantra was simple: Keep Mesa happy. I’ll tell you how I tried to do that in a minute.

Art Biz Success Team in Seattle
Viewing the work of Carrie Yamaoka at the Henry Art Gallery, University of Washington in Seattle.

Training Properly

Most people hang onto the wrong employees or assistants because they dread searching for replacements. I know that was true for me. We know that not only is the search time-consuming, but that it will also take a lot of effort to teach that person how to do the job.

I have learned that it’s better to have no help at all than to invest in the wrong person for the job. Or to not do my part to make sure my team member receives proper training.

Don’t hire because you’re lonely or because someone else said that you should. Hire because you have specific tasks that someone else is actually better qualified to do than you—so that you can focus on the work in the studio and making important connections for your art business.

Temporary employees or interns often aren’t worth the trouble because of all the time you need to invest in training them. And then they’re gone. You have to start over again.

When you bring someone new onto your team, you must dedicate time and energy up front to training them. You have to help them succeed in their new position. This means blocking off time on your calendar to spend with a new assistant. It’s also possible that there are in-person or virtual trainings that could remove some of the weight from your shoulders.

When Mesa started, I sent her to Phoenix for a multi-day training for our customer management software. For too long I had been the software expert and I was ready to pass that baton to someone else. This was one of the wisest business investments I made.

Office Art at Art Biz Success
Some of the art in our former shared office. Artists: Carmen Mariscal, Lisa Jean Allswede, Lorraine Glessner, Dora Ficher, Maeve Eichelberger, Tina Mammoser, Natalya Khorover, Dianna Fritzler, Karin Olah, Jennifer Printz, and Liza Myers.

Communicating Openly

It’s vital to communicate with team members openly and professionally.

Art Biz Success Board Meeting Agenda in Notion
Our twice-weekly agenda in Notion for board meetings. Each item is a page of notes on that area of Art Biz Success.

Mesa and I shared an office for about 2 days a week before she moved away last year, so we talked regularly. I was so accustomed to having someone working next to me that I worried what a long distance relationship between us it might be like. (She said she wouldn’t move if I didn’t want her to, but it was I who had encouraged her to enjoy her youth. To be adventurous.)

At that point, we started our twice-weekly Zoom sessions, which we call board meetings.

Those meetings were repeated appointments on my calendar. We may have had to adjust the time on certain days, but they always happened. We used these meetings to review the status of every program and project on our plates—from online classes and students to private clients, newsletters, and new initiatives.

As an aside, we use the Notion app to organize everything. The board meeting agenda has a separate page for the status of each program and project.


Art Biz Success Team 2018
Mesa, me, and our learning consultant, Timeri Tolnay, at our 2018 Santa Fe workshop.

Mesa was in charge of organizing the board meeting agenda, but I had access to add things. I did my best to review the agendas in advance in order to cut down the length of the meeting. Nobody likes meetings that are longer than necessary.

The meetings aren’t for me to tell Mesa what to do. I want anyone I work with to be invested in Art Biz Success. I want them to believe in what we are doing and that helping artists is rewarding.

To be invested in your position, you need to be part of the decision-making. I, as CEO, might know exactly what I want to happen, but most of the time it isn't critical how it happens. I'm more than okay with team members deciding how we'll get from point A to point B. I make a point to seek their opinions and listen to their ideas.

When edicts are handed from higher-ups, there is more resistance to the task. When team members are brought into the process, they are empowered in their positions. They become better employees.


When you hire correctly, provide proper training, give ownership, and communicate openly, you are more likely to trust that the job, whatever it is, will be done to your liking.

It should be noted that a good employee is not going to do the task exactly how you would have done them. As I said, the how is rarely critical. You have to be open to the fact that there is more than one way to finish the job, and that your way isn't the only way. All of these lessons in trust have taken me 3 decades to understand.

Trust starts with my clarity about the position and, again, my willingness to invest in training and providing the proper tools so that a team member can succeed. If she doesn’t succeed, I don’t succeed.

I've found that the more I trust someone, the more likely they are to come up with a better solution than what I had in mind. I love it when that happens! And I like to reward initiative.

Acknowledging and Rewarding

Mesa earned numerous raises during her tenure with me. By the fall of her first year, she had a new title to go along with that raise: Operations Manager. She had proven that she deserved that title. That she would do a better job than I at making sure every aspect of Art Biz Success ran smoothly.

Art Biz Success Team
Art Biz Success team in the fall of 2017. (l to r) Karen Olah, me, Debra DeVilbiss, Kristen O'Neill, Mesa Westlake, and Debby Williams. Not pictured: Cynthia Morris.

As a very small business, I can’t afford big benefits packages, so I made it a point to let Mesa know how important she was to me and to reward her whenever I could. I’m pretty sure that travel was a big perk of the job for her. In addition to her training time in Phoenix, she accompanied me to Asheville (twice), Santa Fe (twice), Scottsdale, Seattle, Reston, Virginia, and Lancaster, Pennsylvania.

Ceramics Smashing Party | Art Biz Success
In 2019 we were invited by Gail Frasier and Marilyn Brandenburger to an art destruction party. What other boss would give Mesa the chance to smash ceramics and tear up watercolors while on the clock?

We toured Biltmore (twice — once for the Christmas trees). We saw Taliesin West, Frank Lloyd Wright’s compound outside of Phoenix, experienced Amish country, and hung out at Seattle’s Pikes Place Fish Market.

When we traveled together, people often assumed we were mother and daughter, which was fine with me. If I had only been so lucky.

When Mesa lived nearby, we scheduled irregular field trips that were closer to home.

  • Attended art shows
  • Drove across town for the orchid show at the botanic gardens
  • Skipped out in the afternoon so I could show her the fairy gardens at my favorite nursery
  • Took a more than 1-hour roundtrip drive into the mountains for a favorite view and Mexican café
  • Had team holiday parties in Denver and Boulder. By the way … yes, you can have a party with just 2 people.

I also frequently took her out for lunch and coffee.

And now Mesa is moving on.

I’m a little heartbroken, but also very happy for her to continue growing professionally. And I’m kinda proud that I was her first full-time employer after college.

Honestly, I hope I spoiled her for other people. I hope she looks back later and says I was the best boss she ever had.

Yes, I made a lot of mistakes in the past, but I finally got it right.

Music by Wildermiss

Why I Love Systems So Much

I'm grateful that Mesa and I have dedicated so much energy to greasing our systems. All tasks are properly documented in our Notion app, and we've spent three weeks poring over them to make sure that someone else could take over the tasks.

THAT's why I love systems so much—because they help my business run (almost) on autopilot.

See The Art Biz ep. 78: How to Increase Your Productivity and Creativity with Art Business Systems.


In episodes 104-106 of The Art Biz podcast, I talked with artists who hired and had successful relationships with their assistants.

The Art Biz ep. 104: Trusting Another Artist to Help You Run Your Art Business with Angela Fehr and Robin Edmundson

The Art Biz ep. 105: How to Work Successfully (and Sanely) with a Relative with Trudy Rice

The Art Biz ep. 106: Learning How to Be a Boss with Ali Manning

This post was originally published on April 4, 2014. It has been updated with original comments intact.

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29 thoughts on “The Art Biz ep. 59: My Best Practices for Working with an Assistant”

  1. Alyson, I kinda feel like I should send a sympathy card for your loss. I know first hand how critical Mesa has been to your running a tight ship. What I know for sure is you had such a powerful process for hiring her, you’ll find another magically good fit. Not the same, but perfect for your next step. In the meantime, perhaps a pumpkin spice latte will soothe the pain… maybe by the gallon.

    I’m so proud of you, Mesa, for stepping into your own growth and personal power. You are creative and resourceful, joyful and compassionate, and such a risk-taker! Love how you stretch yourself! It was my honor to work alongside you, albeit distantly. Your loving willingness to help me through whatever glitches I created for myself 🙄 made all the difference! Good luck to you in your adventurous life! Much love ❤️❤️❤️

    1. Alyson Stanfield

      Debra: A sympathy card wouldn’t be out of place here. Ha! Yes, I know you understand. Thanks so much for writing this. 🧡

    2. Wow – thank you, Debra!! It was a pleasure getting to have you on our team. I’ve loved working with such fun, caring, and hard-working, successful women! I wouldn’t have had job security if it weren’t for those dang tech glitches 😉 Much love right back!

  2. I loved reading about all the steps you went through in hiring Mesa. It really worked because Mesa is amazing. I’m sad to see her go but very happy for her and her new adventures. You two we are so good together and the experience and knowledge she is taking with her after working with you it’s invaluable. It really is so important to have those systems in place.

    I spent some time with Mesa on several occasions in Golden, Asheville and Lancaster and just loved her. She was always prepared to answer any of my questions or to just sit have a drink and talk about life. Thank you for always responding to my emails and getting me to the right place.
    I’m sure this will be a big transition for both of you.

    Much success, Mesa! Wishing you the best!
    Alyson, you will be ok but I know how much you will miss her.
    Sending love to you both!

    1. Thank you, Dora! I couldn’t agree more – Alyson has prepared me so well for stepping out into a new challenge. I couldn’t have done it without all I have learned and experienced these 4.5 years! It’s been such a treasure getting to know you in person and online. xoxo <3

  3. Dear Alyson,

    I remember Mesa as being a caring, and professional assistant. She helped me with getting on board with clarity and enthusiasm.
    Wishing her all the very Best in her new job and in her life. I’m sure you’ll miss her, she is terrific!

    warm regards,


    1. Thank you for your kind words, Magdalena! I’ve been blessed to get to know and work with such amazing artists.

  4. Mesa – we met in person at Art Biz Breakthrough 2016 and since then in email over some event. You have always been so helpful, thorough and you shine in all you do. Very best of luck in your future endeavors!

    1. Thank you, Anita 🙂 Getting to meet the artists in person was always one of my favorite parts. Really appreciate your best wishes!

  5. Hi Mesa,
    I just want to leave a quick note to thank you.
    I got a hold of you guys when I was in a panic trying to resolve the correct way to credit my work.It was late in the day and the exhibit was due to begin the next morning. Mesa, you saved the day. You didn’t know, but you found out and got a hold of me.( it was a tricky one involving photography and mixed media, if you remember).
    Thank you girl!
    May your career always walk in the light,
    Annick Lemay.

    1. Annick, yes! I remember it. You are too kind but I’m certainly glad I could help when you needed it!! <3

  6. Yes, Alyson, you hit the jackpot with Mesa, but she did too. I really liked reading about your whole experience working together and all the effort you put in to making it an effective relationship. Since I know you both, it was fun to read all the details in your story.

    Alyson and Mesa, thank you for all the help you have given me over the years. It’s been a pleasure working with you both!

    1. Linda, I’m glad you enjoyed our story. And you’re right! I hit the jackpot, too. It’s been fun reminiscing on everything – a silver lining on this end of a chapter :(. So happy to have gotten to work with you.

  7. Hi Alyson,
    I had to write and tell you I teared up reading this and looking at the photos. What a beautiful way to honor a young person who came into your life. Too often we are not gifted with honoring or closing rituals in life. Doing this positively impacts both you and Mesa for the rest of your lives. A blessed, positive, leave-taking is so healing for younger women and all women actually.

    It also is good for your readers to see how truly amazing many gen z women are. I have seen Gen Z folks and millennials often disparaged in art marketing circles lately because they don’t buy art in the “traditional” way. Therefore they are judged as being less than. Which is such a huge misperception imo. So glad women like Mesa are our future.
    Anyway, I admire what you have done here.

  8. Oh Alyson! What a journey. It was fabulous to read! I love the fact you were super specific with the application process.

    I know that Mesa has been such a support to you and your business and it will be a great loss. Over the years I have emailed Mesa with tech questions which she answered and solved promptly and professionally. Mesa, I wish you all the very best as you venture out and Alyson, I hope you find the replacement you need to continue the fabulous work you do.

    xx Trudy

    1. Thank you, Trudy!! I will really miss everyone. It’s always a joy to hear from you and it’s so special to have two of your beautiful pieces that you’ve gifted me <3

  9. You have both set the bar high for each other!

    Mesa, beyond your being thorough, timely and knowledgeable, it is your kindness that I want to honor. I enjoyed interacting with you both online and in person and you were always so kind. I wish you the best of luck in your new endeavors.

    1. Karen, wow, thank you! It means so much to hear that. I’ve really enjoyed getting to know you and am sad to be leaving the Art Biz Success team and all of our amazing artists.

  10. I’m so sorry to hear that Mesa won’t be your “right hand woman” any longer! Although I am excited for her to have the opportunity for new adventures. Please pass along my best wishes to her. She was always such a welcome, smiling, happy soul when she stopped into the boutique.

    If you are looking for someone to fill Mesa’s spot (which I am guessing you are), I hope you are able to find one quickly that will fulfill your every expectation. Of course, you will never truly “replace” her!

  11. Mesa, I want to wish you the very best as you move on in life. I can’t imagine Alyson without you, but I am certain your shared affection will remain despite the change of scenery and jobs.

    We corresponded rarely and met once (or was it twice). I was always impressed by your professionalism, compassion, and cheer.

    Take care and stay happy!

  12. Alyson, I thoroughly enjoyed reading the story and seeing the photos of Mesa and you. As Debra said, I’m sure you’ll find the next right person.

    Mesa, we didn’t have occasion to communicate frequently but when we did, your professionalism, enthusiasm, and friendly manner always left me feeling valued. It was great to finally get to meet you in Asheville in 2018.

    It was also a joy to hear and see Alyson express what a fantastic support system you were.

    I look forward to hearing about your next adventure.

    With sincerest best wishes,


  13. What an incredible tribute…to both of you. To the creation of an enthusiastic, powerful and incredibly successful working partnership. I enjoyed listening and looking at all the images. I also appreciate (as always Alyson!), how you broke down the process, the possible stumblingblocks, and clearly outlined an effective process…a system…for this whole endeavor. Mesa, best wishes on your new adventure. Alyson, sending’ve launched one from the nest. Letting go and allowing another to fly is difficult but also a beautiful thing.

  14. Best Wishes and Good Luck to Mesa in all your future endeavors! Thank you again for purchasing a print from me (a gift for your grandmother I believe?) last year, it lifted my spirits tremendously that you reached out. Thank you for your work with Art Biz and I’m certain you will do good things whereever you go in life. -Lin Price

  15. Thank you for taking such good care of me all these years. Congratulations on your successes in Golden and on the successes to come. Thank you for making ALL of us feel special and welcome at AB events. Thank you for setting such a good example of grace under pressure and joy in humanity.

    ONWARD! XOXOX Gwen Meharg

  16. Hi Alyson,
    I thoroughly enjoyed listening to this podcast from the beginning to the end. I felt the feeling of connection throughout. It’s so lovely! Mesa, and I have exchanged a few emails since the time I joined ACSS, and I can tell that she is beautiful inside-out.

  17. Pingback: Learning How to Be a Boss with Ali Manning - Art Biz Success

  18. Pingback: How to Work Successfully (and Sanely) with a Relative with Trudy Rice - Art Biz Success

  19. Pingback: Trusting Another Artist to Help You Run Your Art Business with Angela Fehr and Robin Edmundson - Art Biz Success

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