5 Tips For Grooming the Perfect Assistant

5 Tips for Grooming the Perfect Assistant

5 Tips For Grooming the Perfect Assistant with Alissa Zimmerman

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All photographers have to start somewhere. Maybe you just picked up a camera for the first time and realized your passion for photography. Maybe you’ve been running a part-time studio out of your basement for the past three years and are bursting at the seams. Maybe you’ve been a professional full-time photographer with your own brick-and-mortar studio for 10 or more years and you’re ready to take your business to the next level.

At some point in the journey of the creative professional, we need to bring in another body, whether part-time or full-time. It is the most responsible decision to be made for future growth. Hiring and grooming an assistant is one of the most daunting tasks for creative business owners—our businesses are our babies, our livelihood. How can we possibly bring in some stranger to manage the back of the house so we can focus on doing the things that bring in money?

There is an art to grooming and managing the perfect assistant. Let’s be clear on what I mean by the perfect assistant. There is no such thing as perfect when it comes to an employee, but there sure as hell is a level of perfection for what you need to make your business more successful.

As the tables begin to turn for me, and I find myself in a position where I am looking to hire my first assistant, I have taken a great deal of time to reflect back on the top five most important elements of Sal’s training process that molded me into the person I am today and the key role I now play within our organization because of it. These tips can be used in any profession, and if they are practiced diligently, they can create the harmony you’re looking for.


There’s nothing more challenging or more important than being patient when training your new assistant. My first year working under Sal was, in retrospect, a complete waste of his time and money. I was not doing anything proactively, nor was he assigning me any high-level tasks. As the employer, you have to be mentally prepared going into this relationship that it will take 10 months to a year of shadowing and learning the business before your assistant is of any actual value to you or your company.

In the beginning, it’s important to set expectations. The first 90 days are meant for shadowing only—it’s a three-month window where you’re getting to know each other and figuring out if this person is the right fit for your company, as well as a time for your assistant to figure out if your company is the right fit for her. After that first 90 days, if you’re both still onboard, it’s off to the races. The following nine months are all about learning your organization and setting up processes together that make your workflow and life easier.

Will there be bumps in the road? Absolutely. If you are looking for a scenario where there will be no hiccups, you should probably abandon the idea of managing an employee. As an employer, you need to set expectations for yourself as well in order to make this a successful relationship.

Clear Direction 

As an employee, there is nothing more frustrating than trying to perform tasks with little to no direction. This vague type of management is only setting up your assistant for failure and creating an inevitable level of resentment between the two of you—ultimately leading to a complete failure in the role, whether your assistant ends up quitting or gets fired. All of this because of something that could have easily been prevented from the beginning.

Spend the extra five minutes to give clear direction in your tasks and what you’re expecting in the outcome so you’re not living in a constant state of unnecessary tension. This is especially critical in the beginning when training your assistant in how you expect things to be completed. If you decide to be half-assed in your task assignment details, you guarantee the same result from your assistant.


This is my favorite subject. It took me so long to understand how I went from a seven-year work history of job-hopping and being miserable as an employee to this career I have built for myself where I can actually envision a lifelong future.

Creating an environment where your assistant is accountable to you and your business at the end of the day is pivotal in the success or failure of this person. It is something that has to be established from the very beginning, or you will lose your very short window to build this foundation and run the risk of your assistant not respecting you as a leader.

Your assistant can be your best friend if that’s the relationship you want, but that person is still your employee and needs to understand that his job is to do what you tell him to do, and do it well. There has to be a certain level of fear in your assistant—a good assistant has to be afraid of disappointing you. If they don’t have that fear, their lack of performance will come out as complete disrespect, which ensures things will go bad.

Reward Based on Performance

I am a millennial, and understand my trophy generation all too well. Rewarding your assistant based on performance seems obvious, but it’s one of the most difficult things to execute. As business owners, it’s instinctual to want to give, give, give to make sure you’re keeping employees happy. At a certain point, you’ll realize the only thing you’re doing by rewarding these people regardless of performance is building entitlement and creating a nightmare employee.

I’ve watched too many people come through our organization who were rewarded with expensive gifts when there was nothing exceptional done to deserve any of it. Obviously those people didn’t last very long with the company. Who would stay once the work actually got challenging when they already got their Louis Vuitton?

Condition your assistant to understand that in order to receive any kind of reward, there has to be hard work that goes in first. It is your responsibility to train your assistant to be hungry in this dog-eat-dog world. There is nothing wrong with having ambition and drive to be the best; that should be something you’re looking for in assistants as you’re training them. The second you spot even a sliver of that competitiveness or hunger, embrace it.  

Get Them Vested in Your Business

When I look back on the past six years I have worked with Sal, I can point to one thing that has made my perspective change from this being a 9-to-5 grind to the most fulfilling career and most rewarding experience of my life.

Getting your assistant vested in your business in that first year is essential to molding her perspective throughout her time with you and your company.

Once you’re at the point in your business where you need to hire an assistant, you’re more than likely at a point of enormous growth, bigger opportunities and an endless supply of new and exciting projects. This is when you want to make sure to include your assistant. As an employer, you want to make your assistant feel like she has an actual impact on your business, that her voice matters to you.

It may seem insignificant, but it is exactly what made me into the employee I am today. Obviously, Sal is a bit of an exception when it comes to the number of new projects happening at any given moment, but I can look at every single company that exists today under the Salvatore Cincotta brand and say, with pride, that I played a huge role in building them all from the ground up. That alone makes me treat each of these companies as if they were my own.

If you find an assistant who can get to this point, the light bulb of perspective will click when that person realizes she gets to be a part of all of the rewards without any of the real financial risks.

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