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The Ultimate Guide to Working With an Assistant If You’ve Never Had One Before

So you hired an what?!


At GYST we have the great privilege to work with lots of clients who have never worked with an assistant before. We love the chance to show busy people how much more time is available once they have a trusted partner, objective advisor and logistics coordinator (aka, an assistant) on their team, but we also know it is a big and sometimes scary step to take. We’ve created this guide to help ease first timer anxiety and to give you practical tools to build your relationship with your assistant strong from the start.


Preparation builds confidence heading into any new situation, especially in a new professional relationship.

Make your first shared to do list.

Spend a week jotting down every task you don’t want to do, or that someone else could do for you. Use those tasks to begin your first shared to do list. We suggest prepping this list on a Google Doc or on a Trello board for easy sharing.

Go into your first session with your new assistant armed with this list and highlight the tasks you need your assistant to handle right away. If your assistant is a keeper, she will use these tasks to learn more about your circumstances and preferences and come back to you with the next to do list herself. Not sure if a task falls within bounds? Just ask! Assistants are happy to suggest alternative solutions if a task is outside of their scope of work.

Here are the top five starter tasks we see most often:

  • Errands, think dry cleaning drop off and pickup, pharmacy runs, groceries, clothing returns, shoes to the cobbler, and anything you have to leave your house for that you’d rather just handled itself

  • Home repairs, finding, vetting and babysitting a handyman to come and deal with that leaky faucet, chipping paint, faulty light fixture, etc.

  • Scheduling, get those overdue doctor and dentist visits on lock, make sure you have a babysitter when you need one, get that vacation on the calendar at long last

  • Research, everything from new places for date nights to vacation destinations and excursions, if you are googling it between the hours of 11pm-3am – delegate now

  • Gifts, never miss a birthday or anniversary again, fork over the dates and let your assistant deal with the gift shopping and sending 

Grant access.

If your assistant will be coming and going from your home or office freely, get that key copied and ready to go, or have an extra on hand for your assistant to copy on her first day. How will you want your assistant to make purchases on your behalf? Here at GYST we have our Pyggy Bank program which allows assistants to make purchases without using their personal credit cards or petty cash. If you aren’t working with GYST, consider ordering your assistant a credit card in her name from your primary account. Petty cash works too, just make sure you’ve decided how you would like to be informed about expenses.

What tech tools and accounts will your assistant need access to in order to operate independently from day one? Make sure you know how to grant access or be ready to hand over your passwords so your assistant can grant herself access during your first session.

Here’s our starter checklist: Google or Outlook Calendar – Google Docs, Sheets – Your email, or set up email delegation 1Password, Dashlane or other password keeper Dropbox – Your to do list app of choice (try one of our favorites)

Share Info

Create an “About Me” doc that details your preferences, frequent associates and any other information that will give your assistant context to begin building a solutions framework for you. Here are three favorite questions from the GYST first session client interview to get you started: – Share any services you use on a regular basis including dry cleaners, laundry, housekeeping, pet services, childcare and babysitters, etc. (So that your assistant can handle scheduling and communications.) – Generally, would you rather save time or money? For example, if you need your dress for dinner downtown at the last minute should I get that faster by spending money on a taxi, or take an extra 20 minutes to take public transportation? (So your assistant can make the call you would make in urgent moments.) – How many options do you want typically? For restaurants, research, and everything in between. (So your assistant can give you enough, but not too much, information.)  


You should be prepared to spend the first hour of your first working session with your assistant uninterrupted and undistracted.

Orient your assistant to her surroundings and your circumstances.

Welcome your assistant to your home or office and show her around. Make sure your assistant knows where her work station will be, where the bathroom is, and where she can grab a glass of water. Introduce your assistant to anyone else working or living in your home, including any furry friends. Set your assistant up with the wifi password, a key, and share your “About Me” doc to review together. Invite your assistant to ask questions freely as you go.

Share your to do list and grant access.

Share the materials you’ve prepared, including your starter to do list, and grant access to any relevant accounts. Spend time reviewing the to do list together and share details so your assistant has the info she needs to get started. Decide together how you will maintain an ongoing, shared task list moving forward. Any good assistant will come armed with their own questions too, so plan to spend time answering those. Set communication guidelines.

During your first session make sure your assistant knows how to reach you during business hours, outside business hours, over the weekend and in case of emergency. The most common reason work from your assistant doesn’t end up in your inbox on time is because he or she runs up against an unforeseeable stuck and can’t find you to get a quick answer and keep moving. If you would rather not be disturbed during certain times of day tell your assistant upfront so she is aware and can work around your preferences. Once you’ve set these guidelines your role is to be responsive as you’ve indicated you will be. Your assistant will learn how to build a solutions framework for you over time, but make it your goal to be as responsive as possible especially at the start of your work together. You should discuss with your assistant how you will get updates about tasks and projects. Should your assistant send you a quick recap email at the end of each working session? Will you keep track yourself via your shared to do list? Make sure you both know how you will be staying on the same page moving forward. Get started.

The most important part of your first session is to identify your top 3-5 tasks and set your assistant free to get them done that very first day. If you’ve got the right assistant she will be eager to start and show you what she’s capable of. Give her all of the information she may need to get moving and then watch your to do list disappear.


As you and your assistant get more comfortable with each other and settle into a regular rhythm here’s how you can keep the relationship strong and productive. Set a regular in person session.

Even if your assistant manages work independently and you no longer need to be in the same room together, it’s critical to have regularly scheduled time you are both in the same room (or on a video call) with undivided attention. This serves as your steady touch point to answer and ask questions and share information about a new or complicated task or project. Feedback

Provide your assistant specific and timely feedback about the work she is producing on your behalf. Applying the usual workplace rules about positive reinforcement and constructive criticism to your working relationship with your assistant will help her continue to learn how to serve you best. Point out when something is done exactly the way you like and mention areas for improvement as much as possible.


We asked our team of New York City’s best and most trusted assistants to share words of encouragement and any advice they would give clients who are working with an assistant for the very first time, and here’s what they had to say:

“CONGRATS! You’ve taken the first step towards freeing yourself to focus on what matters most. Be proud.” – Brooke Stone, Founder and CEO, GYST “Ask for what you want clearly and directly.” – Jenna Sofia, GYST Assistant

“Whatever you think you have to do yourself, you don’t. Most everything can be delegated to a trusted partner.” – Taylor Presley, Digital Marketing Manager

“Clients should ask their assistant to describe tasks they’ve managed for other clients to get an idea of what the assistant is fully capable of up front.” – Cameron Berne, Client Experience Director, GYST “Don’t apologize for not being able to do something yourself – that’s what we are here for!” – Rachel McPhee-Benson, GYST Assistant

“Let it go. You deserve to pursue things that are really important to you so see working with an assistant as an investment in your freedom! Let your assistant hold your hand and be your guide in creating a flow and in helping you with tasks that are taking up too much of your time.” – Esther Robles, GYST Assistant

“Trust your assistant is capable of more. Give them tasks and sprinkle a little extra on to see how far they can go. Often they have areas of interest and skill sets you don’t even know about yet.” – Ashley Weatherspoon, Employee Experience Director, GYST

“Do you from the start. Let your assistant be the one to adapt to you, not the other way around.” – Alli Trussell, GYST Assistant

“No need to feel embarrassed or self-conscious, you are letting someone into a vulnerable part of your life but we are professionals and have seen and heard it all.” – Travis Brown, GYST Assistant

Armed with our guide and the wisdom of NYC’s most trusted assistants, we are wishing you a long, happy and productive relationship with your assistant. As our Founder Brooke would say “Go spend time on what matters most!” And if you haven’t quite managed to hire your own assistant quite yet, try one of ours.

Originally published on Thrive.

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