Your relationship with your new assistant is just like any other, it needs strong communication, clearly defined expectations, and a good, strong start. At GYST, we’ve spent time and energy analyzing and building a program around the first client/assistant meeting because we know how critical those first moments are to ensuring both parties feel confident moving forward together. Whether you are working with a GYST assistant or an executive assistant at work, here are our five tips for getting started in the right direction.


First session interview

Your assistant should begin your first session by briefly interviewing you to understand your overall priorities, preferences, and preferred communication style. By sharing general guidelines, your assistant will be able to apply them to many scenarios, saving you both from answering essentially the same question again and again. 5 starter questions to answer for your assistant:


What is the best way to get in touch with you for a question? (Text, email, call?)

What method of payment should be used to make purchases on your behalf? (Petty cash, credit card?)

How should your assistant generally prioritize tasks if given a laundry list? (In order of family, personal, work?)

Do you prefer economy of time or economy of resources if both can’t be accomplished? (Uber is more expensive, but gets the job done faster than the subway…)

When your assistant arrives for the day and is heading out at the end of it, what do you expect? (An email rundown? A quick chat? Don’t forget to put the dogs in the crate?)


A day in your life

Give your assistant a sense of what it’s like to be you, share your output level from 9-5, your work expectations, your home routine, etc. This will help your assistant put herself in your shoes and make better decisions overall about how best to support you. Your assistant should apply this context when considering the best ways to present information, the best times to catch you with questions, and will help her proactively find ways to be more helpful to you.


Delegate A and Z

When delegating a new task or assigning a big project to your assistant, share A, the current state of a project (even if it’s a disaster!), and share Z, your ideal outcome when the project is done. Then step back and trust your assistant to get you from A to Z, prompting any necessary decisions and asking any pertinent questions along the way. If you can’t trust your assistant to figure out the best way to negotiate the litany of logistics between A and Z, you don’t have the right assistant.


For example:

A: I need to plan a bachelorette party for my sister in two weeks and haven’t even started. I want to spend $500 total, there will be 10 people.

Z: I want a classy girl’s night out for my sister and our friends to remember forever, where nothing goes wrong and there is nothing for me to prep and coordinate the night of.  


Try your assistant’s shoes on for size

When you ask your new assistant to complete a task, imagine what questions you might have if you were in their shoes. Try to provide all necessary information to complete the task. For example, if you’ve asked your assistant to “cancel my cable,” be sure to share your current provider and your account number. An experienced assistant will have these questions, but information from you is always appreciated.


Be generous with feedback

If your assistant does something well, take a moment to share with her exactly why you were so pleased with the result. The more specific you can be, the better. For example, if your assistant wrote a very clear email, and the specific reason it was so easy to digest was because the main points were bulleted, tell her the bulleted format is clutch! Any assistant worth your time and money will take that feedback and never send a parenthetical email again.

Be sure to share constructive feedback if something isn’t quite right. The chances are your assistant isn’t aware of your preference and is doing the best she knows how. Explain why you’re  asking for the adjustment to give your assistant further context. For example, if your assistant wrote a lengthy, parenthetical email, you can share how difficult it is for you to read and process information presented that way because you are trying to read and respond quickly from your iPhone screen while dashing to your next meeting. Suggest a different way, and let your assistant apply your feedback and do better next time.


Practical advice on how to get it done.
For personal assistants, by personal assistants.